Composition and method for caring for keratin materials
A composition with hexapeptides, dipeptides, laminaria digitata extract, and polyhydroxy acids addresses skin aging by boosting collagen IV production, improving skin elasticity and firmness.
Patent Information
- Application Number
- PCT/CN2024/075954
- Authority / Receiving Office
- WO · WO
- Patent Type
- Applications
- Current Assignee / Owner
- Filing Date
- 2024-02-05
- Publication Date
- 2025-08-14
AI Technical Summary
Existing cosmetic products are inadequate in effectively resisting skin aging, as they fail to boost collagen production, which decreases with age, leading to thinning of the dermis.
A composition comprising hexapeptides, dipeptides, laminaria digitata extract, and polyhydroxy acids is formulated to enhance collagen IV production, addressing skin aging.
The composition effectively boosts collagen IV production, providing anti-aging benefits by enhancing skin elasticity and firmness.
Smart Images

Figure PCTCN2024075954-FTAPPB-I100001 
Figure PCTCN2024075954-FTAPPB-I100002 
Figure PCTCN2024075954-FTAPPB-I100003
Abstract
Description
COMPOSITION AND METHOD FOR CARING FOR KERATIN MATERIALSTECHNICAL FIELD
[0001] The present invention relates to a composition. In particular, the present invention relates to a composition for caring for keratin materials. The present invention also relates to a non-therapeutic method for caring for keratin materials.BACKGROUND ART
[0002] Human skin is constituted 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 mainly constituted of fibroblasts and an extracellular matrix (ECM) . This extracellular matrix is constituted of various macromolecules responsible for the mechanical strength of the skin, its suppleness, its tonicity and its elasticity, and also for physiologically important functions (hydration, thermoregulation and regulation of the permeability of the skin) . These macromolecules include, in particular, collagens, elastin and glycoconjugates (glycoproteins and proteoglycans) .
[0004] Collagens represent 70%of the proteins of the ECM. Naturally, collagens are constantly renewed, but this renewal decreases with age, which leads to thinning of the dermis.
[0005] A wide variety of cosmetic products have been used to care for the skin, for example, to resist the ageing of the skin by boosting of the production of collagens. However, some cosmetic products on the market are not satisfying on resisting skin ageing.
[0006] Thus, there is still a need to formulate a composition for caring for the skin, which can effectively resist skin ageing.SUMMARY OF THE INVENTION
[0007] An object of the present invention is thus to develop a composition for caring for the skin, which can effectively resist skin ageing.
[0008] Another object of the present invention is to provide a cosmetic process for caring for the skin.
[0009] The inventors have now discovered that the composition in the present invention can effectively resist skin ageing.
[0010] Accordingly, in a first aspect, the present invention provides a composition comprising:
[0011] (i) at least one hexapeptide;
[0012] (ii) at least one dipeptide;
[0013] (iii) laminaria digitata extract; and
[0014] (iv) at least one polyhydroxy acid.
[0015] The inventors have found that the composition of the present invention can effectively resist skin ageing by boosting the production of collagen IV.
[0016] In a second aspect, the present invention provides a non-therapeutic method for caring for keratin materials, comprising applying the composition according to the first aspect of the present invention to the keratin materials.
[0017] In a third aspect, the present invention provides a use of the composition according to the first aspect of the present invention for providing anti-aging effect on keratin materials.
[0018] Other subjects and characteristics, aspects and advantages of the invention will emerge even more clearly on reading the description and the examples that follow.DETAILED DESCRIPTION OF THE INVENTION
[0019] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by those skilled in the art the present invention belongs to. When the definition of a term in the present description conflicts with the meaning as commonly understood by those skilled in the art the present invention belongs to,the definition described herein shall apply.
[0020] In that which follows and unless otherwise indicated, the limits of a range of values are included within this range, in particular, in the expressions "between... and... " and "ranging from... to... " .
[0021] Moreover, the expression "at least one" used in the present description is equivalent to the expression "one or more" .
[0022] Throughout the instant application, the term “comprising” is to be interpreted as encompassing all specifically mentioned features as well optional, additional, unspecified ones. As used herein, the use of the term “comprising” also discloses the embodiment wherein no features other than the specifically mentioned features are present (i.e., “consisting of” ) .
[0023] Unless otherwise specified, all numerical values expressing amount of ingredients and the like which are used in the description and claims are to be understood as being modified by the term "about" . Accordingly, unless indicated to the contrary, the numerical values and parameters described herein are approximate values which are capable of being changed according to the desired purpose as required.
[0024] For the purposes of the present invention, the term "keratin materials" is intended to cover human skin, mucous membranes such as the lips. Facial skin is most particularly considered according to the present invention.
[0025] All percentages in the present invention refer to weight percentage, unless otherwise specified.
[0026] According to the first aspect, the composition of the present invention comprises:
[0027] (i) at least one hexapeptide;
[0028] (ii) at least one dipeptide;
[0029] (iii) laminaria digitata extract; and
[0030] (iv) at least one polyhydroxy acid.
[0031] Hexapeptides
[0032] The composition of the present invention comprises at least one hexapeptide.
[0033] Preferably, the hexapeptide is any type of hexapeptide containing the sequence-Glu-Glu-Met-Gln-Arg-Arg-.
[0034] More preferably, the hexapeptide is selected from those of formula (I) : R1-Glu-Glu-Met-Gln-Arg-Arg-R2 (I)
[0035] wherein
[0036] R1 is selected from H, a polymer derived from polyethylene glycol, a non-cyclic aliphatic group, alicyclyl, heterocyclyl, heteroarylalkyl, aryl, aralkyl and R5-CO-, wherein R5 is selected from H, a non-cyclic aliphatic group, alicyclyl, aryl, aralkyl, heterocyclyl and heteroarylalkyl;
[0037] R2 is selected from the group consisting of–NR3R4, -OR3, -SR3, wherein R3 and R4 are independently selected from H, a polymer derived from polyethylene glycol, a non-cyclic aliphatic group, alicyclyl, heterocyclyl, heteroarylalkyl, aryl and aralkyl; and
[0038] R1 and R2 are not amino acids.
[0039] As used herein, the term "non-cyclic aliphatic group" includes linear (i.e., straight and unbranched) or branched, saturated or unsaturated hydrocarbyl groups such as alkyl, alkenyl and alkynyl. The non-cyclic aliphatic group may be substituted (mono-or poly-) or unsubstituted.
[0040] As used herein, the term "alkyl" includes both saturated linear and branched alkyl groups, which may be substituted (mono-or poly-) or unsubstituted. The alkyl group is bound 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 preferably from 1 to 12, yet more preferably 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.
[0041] As used herein, the term "alkenyl" refers to a group containing one or more double carbon-carbon bonds, and which may be linear or branched and substituted (mono-or poly-) or unsubstituted. Preferably it has 1, 2 or 3 double carbon-carbon bonds. Ifmore than one double carbon-carbon bond is present, the double bonds may be conjugated or not conjugated. 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, yet more preferably 2, 3, 4, 5 or 6 carbon atoms. The alkenyl group is bound to the rest of the molecule by a single bond. The term "alkenyl" includes, for example, vinyl (-CH2=CH2) , allyl (-CH2-CH=CH2) , prenyl, oleyl, linoleyl groups and similar.
[0042] The term "alkynyl" refers to a group containing one or more triple carbon-carbon bonds and which may be linear or branched, and substituted (mono-or poly-) or unsubstituted. Preferably the alkynyl group has 1, 2 or 3 triple carbon-carbon bonds. The triple bonds may be conjugated or not conjugated. 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, yet more preferably 2, 3, 4, 5 or 6 carbon atoms. The alkynyl group is bound to the rest of the molecule by a single bond. The term "alkynyl" includes, for example and not restricted to, ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, pentynyl, such as 1-pentynyl, and similar. The alkynyl group can also contain one or more double carbon-carbon bonds, and alkynyl groups include, for example and not restricted to, but-1-en-3-ynyl and pent-4-en-1-ynyl groups, and similar.
[0043] The term "alicyclyl" is used herein to cover, for example and not restricted to, aliphatic cyclic (alicyclic) groups such as cycloalkyl or cycloalkenyl or cycloalkynyl groups. The term "alicyclyl" refers to 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 that they are not aromatic. More specifically alicyclic groups contain three or more, from 3 to 24, from 3 to 12, or from 6 to 12, ring carbon atoms. The alicyclic group may be a monocyclic, bicyclic, or tricyclic ring system and the rings may be, for example, fused or linked by a single bond or a linking group such as a methylene or other alkylene group. The alicyclic group may be substituted (mono-or poly-) or unsubstituted. In one embodiment, the alicyclyl group is a 6 to 12 membered ring system which consists of carbon atoms and optionally contains one or two double bonds.
[0044] The term "cycloalkyl" refers to a saturated mono-or polycyclic alkyl group which may be substituted (mono-or poly-) 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, yet even more preferably 3, 4, 5 or 6 carbon atoms. The cycloalkyl group is bound to the rest of the molecule by a single bond, Cycloalkyl groups include, for example and not restricted to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, methyl cyclohexyl, dimethyl cyclohexyl, octahydroindene, decahydronaphthalene, dodecahydrophenalene and similar.
[0045] The term "cycloalkenyl" refers to a non-aromatic mono-or polycyclic alkenyl group which may be substituted (mono-or poly-) 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, yet more preferably 5 or 6 carbon atoms. The cycloalkenyl group is bound to the rest of the molecule by a single bond. Preferably the cycloalkenyl group contains 1, 2 or 3 double carbon-carbon bonds. Ifmore than one double carbon-carbon bond is present, the double bonds may be conjugated or not conjugated. Cycloalkenyl groups include, for example and not restricted to, the cyclopent-1-en-1-yl group and similar.
[0046] The term "cycloalkynyl" refers to a non-aromatic mono-or polycyclic alkynyl group which may be substituted (mono-or poly-) 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, yet even more preferably 8 or 9 carbon atoms and is bound to the rest of the molecule by a single bond. Preferably the cycloalkynyl group contains 1, 2 or 3 triple carbon-carbon bonds, conjugated or not conjugated. Cycloalkynyl groups include, for example and not restricted to, the cyclooct-2-yn-1-yl group and similar. Cycloalkynyl groups can also contain one or more double carbon-carbon bonds, including, for example and not restricted to, the cyclooct-4-en-2-ynyl group and similar.
[0047] As used herein, the term "heterocyclyl" or "heterocyclic" refers to a hydrocarbon ring system of 3 to 10 members, wherein one or more of the atoms in the ring or rings is a heteroatom (i.e., not a carbon atom) . Thus "heterocyclyl" or "heterocyclic" refers a cyclic group in which the ring atoms consist of carbon and one or more heteroatoms. To satisfy valence, the heteroatom may be bonded to H or substituent groups. Preferably from 1, 2 or 3 of the ring carbon atoms are heteroatoms. Each heteroatom can be independently selected 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 (mono-or poly-) or unsubstituted. The heterocyclyl group may be a monocyclic, bicyclic, or tricyclic ring system and the rings may be, for example, fused or linked by a single bond or a linking group such as a methylene or other alkylene group. Nitrogen, carbon, or sulfur atoms present in the heterocyclyl radical may be optionally oxidized and the nitrogen atom may be optionally quaternized. The heterocyclyl radical may be unsaturated or partially or fully saturated. The heterocyclyl radical may be aliphatic or aromatic. In one embodiment, the heterocyclyl is aliphatic (also known as heteroalicyclyl) and is a 3 to 10 membered ring system where the atoms of the ring or rings consist of carbon atoms and from 1 to 4, or 1, 2 or 3 heteroatoms. In one embodiment, the heterocyclyl group is a 6 to 10 membered ring system where the atoms of the ring or rings consist of carbon atoms and from 1 to 4 heteroatoms and where the ring system optionally contains one or two double bonds. In one embodiment, the heterocyclyl is aromatic (also known as heteroaryl) and is a 6 to 10 membered ring system where the atoms of the ring or rings consist of carbon atoms and from 1 to 4, or 1, 2 or 3 heteroatoms. The greatest preference is for the term heterocyclyl to refer to a ring of 5 or 6 members. Examples of saturated heteroalicyclyl groups are dioxane, piperidine, piperazine, pyrrolidine, morpholine and thiomorpholine. Examples of aromatic heterocyclyl groups are pyridine, pyrrol, furan, thiophene, benzofuran, imidazoline, quinoline, pyridazine and naphthyridine.
[0048] The term "aryl group" refers to an aromatic group which has from 6 to 30, preferably from 6 to 18, more preferably between 6 and 10, yet even more preferably 6 or 10 carbon atoms. The aryl group can comprise 1, 2, 3 or 4 aromatic rings, which may be linked by a carbon-carbon bond or fused together and includes, for example and not restricted to, phenyl, naphthyl, diphenyl, indenyl, phenanthryl or antranyl among others. The aryl group may be substituted (mono-or poly-) or unsubstituted.
[0049] The term "aralkyl group" refers to an alkyl group substituted by an aromatic group, with from 7 to 24 carbon atoms and including, for example and not restricted to, - (CH2) 1-6-phenyl, - (CH2) 1-6- (1-naphthyl) , - (CH2) 1-6- (2-naphthyl) , - (CH2) 1-6-CH (phenyl) 2and similar.
[0050] The term "heteroarylalkyl" refers to an alkyl group substituted by a heteroaryl (also known as aromatic heterocyclic) group 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 from 1 to 3 heteroatoms. Heteroarylalkyl groups include, for example and not restricted to- (CH2) 1-6-imidazolyl, - (CH2) 1-6-triazolyl, - (CH2) 1-6-thienyl, - (CH2) 1-6-furyl, - (CH2) 1-6pyrrolidinyl and similar.
[0051] As is understood in this technical field, there may be a certain degree of substitution of the aforementioned groups. In particular, there can be substitution in any of the groups identified above where it is explicitly stated. The substituted groups (radicals) referred to above are groups (or radicals) which are substituted in one or more positions available by one or more substituents. Preferably substitution is in the 1, 2 or 3 positions, more preferably in the 1 or 2 positions, yet even more preferably in the 1 position. Suitable substituents include, for example and not restricted to: C1-C4 alkyl; hydroxyl; C1-C4 alkoxyl; amino; amino-C1-C4alkyl; C1-C4 carbonyloxyl; C1-C4oxycarbonyl; halogen such as fluoride, chlorine, bromine and iodine; cyano; nitro; azide; C1-C4 alkylsulfonyl; thiol; C1-C4 alkylthio; aryloxy such as phenoxyl; -NRb (C=NRb) NRbRc; wherein Rb and Rc are independently selected from H, C1-C4 alkyl, C2-C4 alkenyl, alkynyl, C3-C10 cycloalkyl, C6-C18 aryl, C7-C17 aralkyl, heterocyclyl of 3-10 members or protective group of the amino group.
[0052] Preferably, in formula (I) , R1 is selected from H, a polymer derived from polyethylene glycol with a molecular weight comprised between 200 and 35000 Daltons and R5-CO-, wherein R5 is selected from C1-C24 alkyl, C2-C24 alkenyl, C2-C24 alkynyl, C3-C24 cycloalkyl, C5-C24 cycloalkenyl, C8-C24 cycloalkynyl, C6-C30 aryl, C7-C24 aralkyl, 3-10 membered heterocyclyl ring, and a heteroarylalkyl containing from 2 to 24 carbon atoms and from 1 to 3 heteroatoms, wherein the alkyl group has 1 to 6 carbon atoms. In one embodiment, R1 is selected from H and R5-CO-, wherein R5 is selected from C1-C18 alkyl, C2-C24 alkenyl, C3-C24cycloalkyl or selected from C1-C16 alkyl, C2-C18 alkenyl, C3-C7 cycloalkyl. The R5-CO-group includes alkanoyl groups such as acetyl (CH3-CO-) , which is abbreviated herein as "Ac-" ) , myristoyl (CH3- (CH2) 12-CO-, which is abbreviated herein as "Myr-" ) and palmitoyl (CH3- (CH2) 14-CO-, which is abbreviated herein as "Palm-" ) . In one embodiment, R1 is selected from H and acetyl, tert-butanoyl, prenyl, hexanoyl, 2-methylhexanoyl, cyclohexanecarboxyl, octanoyl, decanoyl, lauroyl, myristoyl, palmitoyl, stearoyl, oleoyl and linoleoyl. In one embodiment, R1 is selected from H and R5-CO-, wherein R5 is selected from C1-C16 alkyl or C2-C18 alkenyl. In one embodiment, R1 is selected from H, acetyl, myristoyl or palmitoyl.
[0053] Preferably, in formula (I) , R2 is selected from-NR3R4, -OR3, and-SR3, wherein R3 and R4 are independently selected from H, a polymer derived from polyethylene glycol, C1-C24 alkyl, C2-C24 alkenyl, C2-C24 alkynyl, C3-C24 cycloalkyl, C5-C24 cycloalkenyl, C8-C24 cycloalkynyl, C6-C30 aryl, C7-C24 aralkyl, 3-10 membered heterocyclyl ring, and heteroarylalkyl containing from 2 to 24 carbon atoms and from 1 to 3 heteroatoms, wherein 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 one embodiment, R3 and R4 are independently selected from H, a polymer derived from polyethylene glycol with a molecular weight comprised between 200 and 35000 Daltons, methyl, ethyl, hexyl, dodecyl and hexadecyl. In one embodiment R3 and R4 are independently selected from H and C1-C16 alkyl. In one embodiment R3 is H and R4 is selected from H and C1-C16 alkyl, including methyl, ethyl, hexyl, dodecyl and hexadecyl. In accordance with one embodiment, R2 is selected from-NR3R4 and-OR3 wherein R3 and R4 are independently selected from H and C1-C16 alkyl. In one embodiment, R2 is selected from-OH, -NH2and-NHR4 where R4 is C1-C16 alkyl. R4 can be C6 alkyl, i.e. –C6H13, or C16 alkyl, i.e. -C16H33.
[0054] More preferably, R1 is selected from H and R5-CO-, wherein R5 is selected from C1-C18 alkyl, C2-C24 alkenyl, C3-C24 cycloalkyl; and R2 is-NR3R4 or-OR3 wherein R3 and R4 are independently selected from H and C1-C16 alkyl. In an exemplary embodiment, R3 is H and R4 is selected from H and C1-C16 alkyl; for example, R2 is selected from-OH, -NH2 and–NHR4 where R4 is C1-C16 alkyl.
[0055] Even more preferably, R1 is selected from H and R5-CO-, wherein R5 is selected from C1-C16 alkyl or C2-C18 alkenyl; and R2 is-NR3R4 or-OR3 wherein R3 and R4 are independently selected from H and C1-C16 alkyl. In an exemplary embodiment R3 is H and R4 is selected from H and C1-C16 alkyl; for example, R2 is selected from the group consisting of-OH, -NH2 and-NHR4 where R4 is C1-C16 alkyl.
[0056] Even more preferably, R1 is selected from H and acetyl, tert-butanoyl, prenyl, hexanoyl, 2-methylhexanoyl, cyclohexanecarboxyl, octanoyl, decanoyl, lauroyl, myristoyl, palmitoyl, stearoyl, oleoyl and linoleoyl; and R2 is-NR3R4 or-OR3 wherein R3 and R4 are independently selected from H and C1-C16 alkyl. In an exemplary embodiment, R3 is H and R4 is selected from H and C1-C16 alkyl; for example, R2 is selected from-OH, -NH2 and-NHR4 where R4 is C1-C16 alkyl.
[0057] Even more preferably, R1 is selected from H, acetyl, myristoyl or palmitoyl; and R2 is-NR3R4 or-OR3 wherein R3 and R4are independently selected from H and C1-C16 alkyl. In an exemplary embodiment R3 is H and R4 is selected from H and C1-C16 alkyl; for example, R2 is selected from the group consisting of-OH, -NH2 and-NHR where R is C1-C16 alkyl.
[0058] Most preferably, the composition according to the present invention comprises hexapeptide with the sequence of Ac-Glu-Glu-Met-Gln-Arg-Arg-NH2, which is also named as acetyl hexapeptide-8.
[0059] Advantageously, the hexapeptide is present in the composition of the present invention in an amount 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.
[0060] Dipeptides
[0061] The composition of the present invention comprises at least one dipeptide.
[0062] For the purpose of the present invention, preferably, the dipeptide is selected from those with formula (II) :
[0063] wherein
[0064] n represents 0, 1 or 2,
[0065] R1, and R4, independently from each other, represent H, optionally substituted C1-C6-alkyl,
[0066] R2 represents H or optionally substituted C1-C6-alkyl,
[0067] R3 represents C1-C12-alkoxy, C1-C12-alkylamino, optionally substituted aryl-C1-C6-alkylamino, optionally substituted heteroaryl-C1-C6-alkylamino, optionally substituted aryl-C1-C6-alkoxy or optionally substituted heteroaryl-C1-C6-alkoxy and
[0068] R6 represents H or amino, as racemates or pure enantiomers, as well as the salts thereof.
[0069] Substituents of the optionally substituted alkyl residues and of the groups containing these residues are, e.g., halogen, amino, guanidino, hydroxy, C1-C6-alkoxy, C1-C6-alkylthio, carboxy, carbamoyl, optionally substituted phenyl, optionally substituted benzyl, imidazolylmethyl, indolylmethyl and cyano.
[0070] Substituents of the optionally substituted aryl and heteroaryl groups are, e.g., halogen, C1-C6-alkyl, hydroxy, C1-C6-alkoxy, C1-C6-alkoxycarbonyl, CN, amino, C1-C6-alkylamino, di-C1-C6-alkylamino, aminocarbonyl, C1-C6-alkylaminocarbonyl, di-C1-C6-alkylaminocarbonyl, C1-C6-alkylthio, C1-C6-alkylsulfoxyl, C1-C6-alkylsulfonyl, optionally substituted benzyl, optionally substituted phenyl, optionally substituted phenoxy or optionally substituted phenylcarbonyl, whereby the above mentioned aromatic rings may be substituted with 1 to 3 identical or different substituents selected from the group comprising halogen, cyano, C1-C6-alkyl, C1-C6-alkoxy, hydroxy, amino, C1-C6-alkylamino, di-C1-C6-alkylamino and C1-C6-alkoxycarbonyl.
[0071] “Halogen” means fluorine, chlorine, bromine and iodine, fluorine and chlorine being preferred.
[0072] Preferably, in formula (II) , R1 represents H, R2 represents H or methyl, R3 represents phenyl-C1-C6-alkylamino and n represents 0 or 1, R4 represent H or C1-C4-alkyl, R6 represents H or amino.
[0073] More preferably, the composition according to the present invention comprises dipeptide with the sequence of H-Beta-Ala-Pro-Dab-NH-Bzl, which is also named as dipeptide diaminobutyroyl benzylamide diacetate.
[0074] Advantageously, the dipeptide is present in the composition of the present invention in an amount ranging from 0.5 ppm to 200000 ppm, preferably 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.
[0075] Laminaria digitata extract
[0076] The composition of the present invention comprises laminaria digitata extract.
[0077] Laminaria digitate is a brown alga rich in iodine and sodium, dark brown in color and large in size. 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 and Russia and Brittany.
[0078] Laminaria digitata extract is preferably obtained by leaching with water, filtration and concentration by reverse osmosis.
[0079] As an example of commercial products of laminaria digitata extract, mention can be made of that sold under the name of PHYCOJUVENINE DIG ALG147 by the company CODIF.
[0080] Advantageously, laminaria digitata extract is present in the composition of the present invention in an amount ranging from 0.0001wt. %to 20 wt. %, preferably from 0.0001 wt. %to 5 wt. %, more preferably from 0.001 wt. %to 0.1 wt. %, even more preferably from 0.002 wt. %to 0.05 wt. %, most preferably from 0.005 wt. %to 0.02 wt. %, relative to the total weight of the composition.
[0081] Polyhydroxy acids
[0082] The composition according to the present invention comprises at least one polyhydroxy acid.
[0083] The term “polyhydroxy acid” here means an organic compound which has at least one carboxyl group and a plurality of hydroxy groups. The number of carboxyl groups in the polyhydroxy acid is not limited, but one or two carboxyl groups are preferable, and one carboxyl group is 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 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 more preferable.
[0084] The above organic compound may be aliphatic or aromatic. In other words, the polyhydroxy acid may be selected from aliphatic polyhydroxy acids and aromatic polyhydroxy acids. It is preferable that the aliphatic polyhydroxy acid be selected from sugar acids.
[0085] Examples of the polyhydroxy acid include, dihydroxy propanoic acid such as glyceric acid; trihydroxy butanoic acid such as erythronic acid and threonic acid; tetrahydroxy pentanoic acid such as ribonic acid, arabinoic acid, xylonic acid, and lyxonic acid; pentahydroxy hexanoic acid such as allonic acid, altronic acid, gluconic acid, mannoic acid, gulonic acid, idonic acid, galactonic acid, and talonic acid; hexahydroxy heptanoic acid such as glucoheptanoic acid, galactoheptonic acid; tartaric acid; lactobionic acid, maltobionic acid, and mixtures thereof.
[0086] It is preferable that the polyhydroxy acid is in the form of a lactone. The lactone ring of the polyhydroxy acid in the form of a lactone may be saturated. Examples of the polyhydroxy acid include, gluconolactone, ribonolactone, and mixtures thereof.
[0087] Preferably, the polyhydroxy acid is selected from lactones with 2-6 hydroxyl groups.
[0088] Advantageously, the polyhydroxy acid is selected from lactones with 2-6 hydroxyl groups and 3-8 carbon atoms.
[0089] It is more preferable that the polyhydroxy acid be gluconolactone, which has the following structure.
[0090] Advantageously, the polyhydroxy acid is present in the composition of the present invention in an amount ranging from 0.5 wt. %to 20 wt. %, preferably from 1 wt. %to 15 wt. %, more preferably from 2 wt. %to 10 wt. %, even more preferably from 3 wt. %to 8 wt. %, relative to the total weight of the composition.
[0091] Niacinamide and / or derivatives thereof
[0092] Preferably, the composition of the present invention comprises niacinamide and / or a derivative thereof.
[0093] Niacinamide, also called Vitamin B3, is a compound of the following formula:
[0094] Niacinamide derivatives that may be mentioned include, for example, nicotinic acid, nicotinyl alcohol, nicotinuric acid, niconityl hydroxamic acid, nicotinic acid esters such as tocopherol nicotinate, amides derived from niacinamide by substitution of the H of-CONH2, products from reaction with carboxylic acids and amino acids, esters of nicotinyl alcohol and of carboxylic acids such as acetic acid, salicyclic acid, glycolid acid or palmitic acid.
[0095] Mention may also be made of the following derivatives: 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.
[0096] Advantageously, niacinamide and / or a derivative thereof is present in the composition of the present invention in an amount ranging from 0.5 wt. %to 20 wt. %, preferably from 1 wt. %to 15 wt. %, more preferably from 2 wt. %to 10 wt. %, even more preferably from 3 wt. %to 8 wt. %, relative to the total weight of the composition.
[0097] Aqueous phase
[0098] The composition of the present invention may comprise an aqueous phase.
[0099] Preferably, the aqueous phase comprises water.
[0100] Advantageously, water is present in the composition of the present invention in an amount ranging from 50 wt. %to 99.99 wt. %, preferably from 70 wt. %to 99.99 wt. %, more preferably from 80 wt. %to 99.6 wt. %, relative to the total weight of the composition.
[0101] Optionally, the aqueous phase comprises an organic solvent miscible with water (at room temperature 25℃) 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.
[0102] Advantageously, the aqueous phase is present in the composition of the present invention in an amount ranging from 60 wt. %to 99.99 wt. %, preferably from 70 wt. %to 99.99 wt. %, more preferably from 80 wt. %to 99.6 wt. %, relative to the total weight of the composition.
[0103] Additional cosmetic active ingredients
[0104] The composition of the present invention may comprise an additional cosmetic active ingredient in addition to the cosmetic active ingredients as defined previously.
[0105] The skilled in the art can adjust the type and their amount of the additional cosmetic active ingredients based on the final use of the composition according to the present invention.
[0106] Additional adjuvants or additives
[0107] The composition of the present invention may comprise may also contain conventional cosmetic adjuvants or additives, for instance fragrances, chelating agents, preserving agents and bactericides, surfactants, thickeners, pH regulators, and mixtures thereof.
[0108] The skilled in the art can select the amount of the additional adjuvants or additive so as not to adversely impact the final use of the composition according to the present invention.
[0109] According to a particularly preferred embodiment, the present invention provides a composition comprising, relative to the total weight of the composition:
[0110] (i) from 2 ppm to 500 ppm of acetyl hexapeptide-8;
[0111] (ii) from 10 ppm to 1000 ppm of dipeptide diaminobutyroyl benzylamide diacetate;
[0112] (iii) from 0.002 wt. %to 0.05 wt. %of laminaria digitata extract;
[0113] (iv) from 2 wt. %to 10 wt. %of gluconolactone; and
[0114] (v) optionally from 2 wt. %to 10 wt. %of niacinamide.
[0115] According to a most preferred embodiment, the present invention provides a composition comprising, relative to the total weight of the composition:
[0116] (i) from 5 ppm to 50 ppm of acetyl hexapeptide-8;
[0117] (ii) from 25 ppm to 100 ppm of dipeptide diaminobutyroyl benzylamide diacetate;
[0118] (iii) from 0.005 wt. %to 0.02 wt. %of laminaria digitata extract;
[0119] (iv) from 3 wt. %to 8 wt. %of gluconolactone; and
[0120] (v) optionally from 3 wt. %to 8 wt. %of niacinamide.
[0121] Galenic form and method
[0122] The composition of the present invention is in the form of emulsion, cream, lotion, or hydrogel, and can be sued as toner, lotion, light cream, nourish cream, sleeping mask, or eye cream.
[0123] The composition of the present invention can be used for caring for keratin materials. In particular, the composition of the present invention can bring benefits on skin radiance, forehead wrinkles, small folds on nasolabial zone and ptosis of the lower part of the face.
[0124] According to the second aspect, the present invention provides a non-therapeutic method for caring for keratin materials, comprising applying the composition according to the first aspect of the present invention to the keratin materials.
[0125] In some embodiments, the present invention provides a non-therapeutic method for anti-aging of keratin materials, comprising applying the composition according to the first aspect of the present invention to the keratin materials.
[0126] In particular, the keratin material is the skin, especially the facial skin.
[0127] In a third aspect, the present invention provides a use of the composition according to the first aspect of the present invention for providing anti-aging effect on keratin materials.
[0128] In particular, the keratin material is the skin, especially the facial skin.
[0129] EXAMPLES
[0130] The examples that follow are given as non-limiting illustrations of the present invention.
[0131] Main raw materials used, trade names and suppliers thereof are listed in Table 1.
[0132] Table 1
[0133] Invention Examples 1-2 and comparative examples 1-4
[0134] Compositions of invention examples (IE) 1-2 and comparative examples (CE) 1-4 were prepared based on the amounts of ingredients given in Table 2. The amounts are given by weight of each active ingredient relative to the total weight of the composition.
[0135] Table 2
[0136] Compositions of invention examples 1-2 represent compositions according to the present invention.
[0137] Compositions of comparative examples 1-2 does not comprise at least one polyhydroxy acid.
[0138] Composition of comparative example 3 does not comprise laminaria digitata extract and at least one polyhydroxy acid.
[0139] Composition of comparative example 4 does not comprise laminaria digitata extract.
[0140] Preparation process:
[0141] The compositions listed above were prepared as follows: adding acetyl hexapeptide-8, dipeptide diaminobutyroyl benzylamide diacetate, laminaria digitata extract (if presents) , niacinamide (if presents) , and gluconolactone (if presents) slowing into water with stirring under room temperature to obtain a homogeneous mixture.
[0142] Evaluation
[0143] The effect of compositions prepared above on production of collagen IV was tested as follows.
[0144] 1) cell inoculation:
[0145] Fibroblasts were revived, and when the laying rate reaches about 60%, the cells were seeded into 6-well plates and cultured overnight in an incubator with CO2 (37 ℃, 5%CO2) .
[0146] 2) Solution preparation:
[0147] The working solutions were prepared according to the test groups listed in Table 3.
[0148] Table 3
[0149] 3) Administration:
[0150] 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 corresponding concentration of active ingredients in culture medium was added to each well for the testing sample groups.
[0151] 4) UVA irradiation: all groups except for the blank control group were subjected to UVA irradiation. After irradiation, they were placed in an incubator with CO2 (37 ℃, 5%CO2) for further cultivation.
[0152] 5) Immunofluorescence detection and gene expression detection were performed.
[0153] Improvement rate and upregulation rate were calculated according to the following equations:
[0154] Improvement rate (%) = (the testing group-NC group) / NC group*100%
[0155] Statistical analysis was conducted by t-test method, as compared with the BC group, significance is represented by#, p-value<0.05 is represented by#, p-value<0.01 is represented by##; as compared with the NC group, significance is represented by*, p-value<0.05 is represented by*, and p-value<0.01 is represented by**.
[0156] The PCR data of collagen IV were summarized in Table 4.
[0157] Table 4
[0158] It can be seen from Table 4 that composition of invention example 1 shows better boost effect of the production of collagen IV as compared with composition of comparative examples 1 and 3.
[0159] It can be also seen from Table 4 that composition of invention example 2 shows better boost effect of the production of collagen IV as compared with compositions of comparative examples 2 and 4.
Claims
1.A composition comprising:(i) at least one hexapeptide;(ii) at least one dipeptide;(iii) laminaria digitata extract; and(iv) at least one polyhydroxy acid.2.The composition according to claim 1, wherein the hexapeptide is selected from those of formula (I) : R1-Glu-Glu-Met-Gln-Arg-Arg-R2 (I)whereinR1 is selected from H, a polymer derived from polyethylene glycol, a non-cyclic aliphatic group, alicyclyl, heterocyclyl, heteroarylalkyl, aryl, aralkyl and R5-CO-, wherein 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, wherein R3 and R4 are independently selected from H, a polymer derived from polyethylene glycol, a non-cyclic aliphatic group, alicyclyl, heterocyclyl, heteroarylalkyl, aryl and aralkyl; andR1 and R2 are not amino acids.3.The composition according to claim 2, whereinR1 is selected from H and R5-CO-, wherein R5 is selected from C1-C18 alkyl, C2-C24 alkenyl, C3-C24 cycloalkyl; and R2 is-NR3R4 or-OR3 wherein R3 and R4 are independently selected from H and C1-C16 alkyl,preferably, R1 is selected from H and R5-CO-, wherein R5 is selected from C1-C16 alkyl or C2-C18 alkenyl; and R2 is-NR3R4 or-OR3 wherein R3 and R4 are independently selected from H and C1-C16 alkyl,more preferably, R1 is selected from H and acetyl, tert-butanoyl, prenyl, hexanoyl, 2-methylhexanoyl, cyclohexanecarboxyl, octanoyl, decanoyl, lauroyl, myristoyl, palmitoyl, stearoyl, oleoyl and linoleoyl; and R2 is-NR3R4 or-OR3 wherein R3 and R4 are independently selected from H and C1-C16 alkyl,even more preferably, R1 is selected from H, acetyl, myristoyl or palmitoyl; and R2 is -NR3R4 or-OR3 wherein R3 and R4are independently selected from H and C1-C16 alkyl.4.The composition according to any of claims 1-3, wherein the hexapeptide is present in an amount 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.5.The composition of any of claims 1-4, wherein the dipeptide is selected from those with formula (II) : whereinn represents 0, 1 or 2,R1, and R4, independently from each other, represent H, optionally substituted C1-C6-alkyl,R2 represents H or optionally substituted C1-C6-alkyl,R3 represents C1-C12-alkoxy, C1-C12-alkylamino, optionally substituted aryl-C1-C6-alkylamino, optionally substituted heteroaryl-C1-C6-alkylamino, optionally substituted aryl-C1-C6-alkoxy or optionally substituted heteroaryl-C1-C6-alkoxy andR6 represents H or amino,as racemates or pure enantiomers, as well as the salts thereof.6.The composition of claim 5, wherein R1 represents H, R2 represents H or methyl, R3 represents phenyl-C1-C6-alkylamino and n represents 0 or 1, R4 represent H or C1-C4-alkyl, R6 represents H or amino.7.Composition of any of claims 1 to 6, wherein the dipeptide is present in the composition of the present invention in an amount ranging from 0.5 ppm to 200000 ppm, preferably 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.8.Composition of any of claims 1 to 7, wherein laminaria digitata extract is present in an amount ranging from 0.0001wt. %to 20 wt. %, preferably from 0.0001 wt. %to 5 wt. %, more preferably from 0.001 wt. %to 0.1 wt. %, even more preferably from 0.002 wt. %to 0.05 wt. %, most preferably from 0.005 wt. %to 0.02 wt. %, relative to the total weight of the composition.9.Composition of any of claims 1 to 8, wherein the polyhydroxy acid is selected from aliphatic polyhydroxy acids and aromatic polyhydroxy acids, preferably selected from lactones with 2-6 hydroxyl groups and 3-8 carbon atoms, more preferably the polyhydroxy acid is gluconolactone.10.Composition of any of claims 1 to 9, wherein the polyhydroxy acid is present in an amount ranging from 0.5 wt. %to 20 wt. %, preferably from 1 wt. %to 15 wt. %, more preferably from 2 wt. %to 10 wt. %, even more preferably from 3 wt. %to 8 wt. %, relative to the total weight of the composition.11.The composition according to any of claims 1 to 10, further comprising niacinamide and / or a derivative thereof, wherein the niacinamide 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 a mixture thereof; preferably said niacinamide and / or a derivative thereof is present in an amount ranging from 0.5 wt. %to 20 wt. %, preferably from 1 wt. %to 15 wt. %, more preferably from 2 wt. %to 10 wt. %, even more preferably from 3 wt. %to 8 wt. %, relative to the total weight of the composition.12.The composition according to any one of claims 1-8, further comprising water, preferably in an amount ranging from 50 wt. %to 99.99 wt. %, preferably from 70 wt. %to 99.99 wt. %, more preferably from 80 wt. %to 99.6 wt. %, relative to the total weight of the composition.13.The composition according to claim 1, comprising, relative to the total weight of the composition:(i) from 5 ppm to 50 ppm of acetyl hexapeptide-8;(ii) from 25 ppm to 100 ppm of dipeptide diaminobutyroyl benzylamide diacetate;(iii) from 0.005 wt. %to 0.02 wt. %of laminaria digitata extract;(iv) from 3 wt. %to 8 wt. %of gluconolactone; and(v) optionally from 3 wt. %to 8 wt. %of niacinamide14.A non-therapeutic method for caring for keratin materials, comprising applying the composition according to any of claims 1 to 13 to the keratin materials.15.A use of the composition according to any of claims 1 to 13 for providing anti-aging effect on keratin materials.
Citation Information
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