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WO2016180979A1 - Composition comportant des dérivés d'acide salicylique et un solvant particulier - Google Patents

Composition comportant des dérivés d'acide salicylique et un solvant particulier Download PDF

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Publication number
WO2016180979A1
WO2016180979A1 PCT/EP2016/060912 EP2016060912W WO2016180979A1 WO 2016180979 A1 WO2016180979 A1 WO 2016180979A1 EP 2016060912 W EP2016060912 W EP 2016060912W WO 2016180979 A1 WO2016180979 A1 WO 2016180979A1
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Prior art keywords
compound
formula
carbon atoms
composition according
composition
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PCT/EP2016/060912
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English (en)
Inventor
Magali Szestak
Chantal JOUY
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L'oreal
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Publication of WO2016180979A1 publication Critical patent/WO2016180979A1/fr

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A61K8/342—Alcohols having more than seven atoms in an unbroken chain
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A61K8/368—Carboxylic acids; Salts or anhydrides thereof with carboxyl groups directly bound to carbon atoms of aromatic rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37—Esters of carboxylic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/39—Derivatives containing from 2 to 10 oxyalkylene groups
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom

Definitions

  • composition comprising salicylic acid derivatives and a particular solvent
  • the present invention relates to a composition, preferably a cosmetic composition, comprising certain salicylic acid derivatives, and at least one particular compound promoting the dissolution of these said derivatives.
  • these salicylic acid derivatives correspond to at least one compound of formula (I), at least one of the salts thereof of formula (II) or a mixture comprising at least one compound of formula (I) and at least one compound of formula
  • bioavailability means the molecular penetration of the active agent concerned into the live layers of the skin and in particular of the epidermis. It will be sought for the penetrated concentration to be as high as possible, so as to increase the amount of active agent reaching the live layers of the skin.
  • dissolved form means a dispersion of the derivatives according to the invention in a liquid, in the free molecular state, in particular in non-complexed form. No crystallization of the salicylic acid derivatives according to the invention is visible to the naked eye or under cross-polarized light microscopy.
  • the object of the present invention is, precisely, to propose a novel galenical formulation of the salicylic acid derivatives according to the invention that enables the abovementioned drawbacks to be overcome, and thus enables these compounds to be incorporated in a long-lasting dissolved form.
  • This novel galenical formulation of the salicylic acid derivatives according to the invention makes it possible especially to improve the efficacy of the active agent for the treatment of keratin materials such as the skin.
  • the compositions according to the invention make it possible especially to formulate salicylic acid derivatives in a dissolved form in a high content, without using large amounts of glycols in the composition.
  • This novel galenical formulation of the salicylic acid derivatives according to the invention makes also it possible in particular sensory properties experienced ( a touch or feeling with better freshness, penetration, sliding or softness, and/or less greasy) in the application on keratin materials such as the skin of said formulation.
  • the inventors have in fact discovered, unexpectedly, that the combination of at least one salicylic acid derivative (a) as defined below, compounds of formula (I) and/or compounds of formula (II), with at least one compound (b) as defined later, makes it possible to improve the solubility of these salicylic acid derivatives and/or salts thereof while at the same time avoiding their recrystallization, especially after storage for 2 months at room temperature (25°C) and/or at 4°C and/or at 45°C.
  • novel galenical formulation comprising the combination of at least one salicylic acid derivative (a) as defined below, compounds of formula (I) and/or compounds of formula (II), with at least one compound (b) as defined later, makes it possible especially to improve sensory properties experienced in the application on keratin materials such as the skin of said formulation, in particular makes it possible a touch or feeling with better freshness, better sliding or softness, and/or less greasy.
  • composition especially a cosmetic composition, comprising:
  • R independently denotes a saturated or unsaturated and linear or branched alkyl radical comprising from 12 to 20 carbon atoms, it being possible for said radical R to comprise one or more ethylenic unsaturations, and
  • Cat+ represents an organic or inorganic cation or a mixture of organic or inorganic cations which makes it possible to achieve electrical neutrality of the compound of formula (II) or of the mixture of compounds of formulae (I) and (II), b) at least one compound chosen from:
  • glycols chosen from pentylene glycol and hexylene glycol
  • - fatty alcohols comprising a branched and/or unsaturated hydrocarbon-based chain containing from 8 to 26 carbon atoms
  • R1 COOR2 and R10R2 in which R1 represents a fatty acid residue comprising from 8 to 29 carbon atoms and R2 represents a branched or unbranched hydrocarbon-based chain, containing from 3 to 30 carbon atoms, and in which R2 represents a hydrocarbon-based chain of 4 to 30 carbon atoms when R1 represents a fatty acid residue comprising from 8 to 14 carbon atoms,
  • a subject of the invention is also a process for preparing such a composition, comprising the following steps:
  • step 1 of said process is performed by heating to a temperature of 40-60°C, preferably at 70°C, with stirring (for example magnetic stirring), especially for about 10 minutes. More particularly, the step of said process is likewise performed at a temperature of 40- 60°C.
  • compositions comprising at least one compound of formula (I), at least one salt thereof of formula (II) or a mixture comprising at least one compound of formula (I) and at least one compound of formula (II):
  • the compounds of formula (I) and the salts of formula (II) are cosmetically acceptable.
  • the term "cosmetically acceptable compound” is intended to denote any compound suitable for the topical administration of a composition in which it is present.
  • a cosmetically acceptable compound is preferentially a compound which has no odour or unpleasant appearance, and which is entirely compatible with the topical administration route.
  • a compound according to the invention, a mixture of compounds according to the invention or a composition comprising one or more compound ⁇ ) according to the invention is employed topically, i.e; by application at the surface of the keratin material targeted, said keratin material preferably being the skin of the face and/or body and more particularly the skin of the face and/or neck.
  • the radical R independently denotes, in the formulae (I) and (II), a saturated or unsaturated and linear or branched alkyl radical which comprises from 12 to 20 carbon atoms, preferably from 14 to 18 carbon atoms, in particular 14, 15, 16, 17 or 18 carbon atoms, preferably from 14 to 16 carbon atoms, and which may comprise one or more ethylene unsaturations.
  • the radical R of the compounds according to the invention does not comprise an ethylenic unsaturation.
  • the radical R of the compounds according to the invention comprises at least one ethylenic unsaturation, preferably one, two or three ethylenic unsaturations.
  • the radical R of the compounds of the invention comprises from 14 to 18 carbon atoms, preferably from 14 to 16 carbon atoms, and comprises one, two or three ethylenic unsaturations.
  • Cat+ represents an organic or inorganic cation or a mixture of organic or inor- ganic cations which makes it possible to achieve electrical neutrality of the compound of formula (II) or of the mixture of compounds of formulae (I) and (II).
  • Cat+ can be mono-charge or multi-charge.
  • Cat+ represents a mono-charge cation or a mixture of mono- charge cations, preferably a mono-charge cation.
  • Cat+ represents an inorganic cation.
  • alkali metal cations such as sodium or potassium salts, alkaline-earth metal salts, such as calcium, strontium or magnesium salts, or also transition metal salts, such as copper, zinc, iron or manganese salts.
  • Cat+ is chosen from alkali metal, alkaline-earth metal and transition metal salts.
  • Cat+ is chosen from the group consisting of sodium, potassium, calcium, strontium, magnesium, copper, zinc, iron and manganese salts.
  • Cat+ represents the sodium salt.
  • Cat+ represents an organic cation
  • Cat+ may denote the cationic form of triethanolamine, monoeth- anolamine, diethanolamine, hexadecylamine, N,N,N',N'-tetrakis(2-hydroxypropyl) ethylenediamine or also tris(hydroxymethyl)aminomethane.
  • Cat+ is an organic cation or a mixture of organic cations chosen from:
  • R 1 ; R 2 and R 3 which may be identical or different, denote a saturated linear alkyl radical comprising from 1 to 12 carbon atoms and L denotes a saturated linear divalent hydrocarbon-based radical comprising from 1 to 6 carbon atoms.
  • the Cat+ cation represents the cationic form of an amino acid of L or D form and preferably the cationic form of lysine, arginine, alanine or tryptophan, more preferentially of lysine.
  • Cat+ represents a quaternary ammonium N + R 1 R 2 R 3 -L-C0 2 H, in which:
  • Ri , R 2 and R 3 which may be identical or different, preferentially represent a saturated linear alkyl radical comprising from 1 to 4 carbon atoms and in particular repre- sent a methyl radical; R 1 ; R 2 and R 3 are preferably identical; and/or
  • L preferably denotes a saturated linear divalent C C 4 hydrocarbon-based radical, in particular a divalent -CH 2 - radical.
  • Cat+ preferably denotes a quaternary ammonium N + R 1 R 2 R 3 -L-C0 2 H salt, in which R 1 ; R 2 and R 3 are identical and denote a saturated linear alkyl radical comprising from 1 to 4 carbon atoms and L denotes a saturated linear divalent C C 4 hydrocarbon-based radical.
  • R 1 ; R 2 and R 3 are identical and denote a methyl radical and L denotes a divalent -CH 2 radical.
  • Cat+ represents a sodium salt or the cationic form of lysine, preferably the cationic form of lysine.
  • the present invention relates to the use of a compound of formula (I) or of a mixture of compounds of formula (I).
  • the compound of formula (I) denotes the compound
  • a composition according to the invention is anhydrous and comprises at least one compound of formula (I) as defined above, preferably compound ( ⁇ ').
  • the present invention relates to the use of a compound of formula (II).
  • the compound of formula (II) is chosen from compounds (A), (B), (C) and (D) below:
  • the compound of formula (II) is (A).
  • the compound of formula (II) is (A) and Cat+ is chosen from an alkali metal salt, preferably a sodium salt, and the cationic form of an amino acid of L or D form, preferably the cationic form of lysine, and preferably represents the cationic form of lysine.
  • the compound of formula (II) denotes the compound (E) and/or (F):
  • the present invention relates to the use of a mixture of compounds of formula (II).
  • the mixture of compounds of formula (II) com- prises at least one compound possessing at least one ethylenic unsaturation, preferably at least one compound comprising an ethylenic unsaturation and at least one compound not comprising an ethylenic unsaturation.
  • the present invention relates to the use of a mixture of compounds of formula (II) comprising at least one compound not comprising an ethylenic unsaturation, at least one compound comprising an ethylenic unsaturation, at least one compound comprising two ethylenic unsaturations and at least one compound comprising three ethylenic unsaturations.
  • these compounds contain a radical R bearing the same number of carbon atoms.
  • the compounds of formula (II) according to this embodiment may be chosen from compounds (A), (B), (C) and (D) indicated above.
  • a mixture of at least 4 compounds of formula (II) is used, denoted compounds (1), (2), (3) and (4), in which:
  • radicals R of each of the compounds (1 ), (2), (3) and (4) denote a linear hydrocarbon-based radical comprising from 14 to 18 carbon atoms, preferably from 14 to 16 carbon atoms and more preferentially 15 carbon atoms, and contain the same number of carbon atoms in each of the compounds (1), (2), (3) and (4); and
  • the proportion of compound (1) ranges from 0.001 % to 5%, preferably from 0.5% to 1 %,
  • the proportion of compound (2) ranges from 20% to 45%, preferably from 30% to 35%,
  • the proportion of compound (3) ranges from 5% to 35%, preferably from 15% to 25%,
  • the proportion of compound (4) ranges from 25% to 50%, preferably from 35% to 40%, the percentages being by mass, relative to the total weight of the mixture of compounds (1), (2), (3) and (4).
  • the mixture of compounds (1), (2), (3) and (4) denotes the mixture of compounds (A), (B), (C) and (D) and more preferentially the mixture of compounds (A), (B), (C) and (D) for which Cat+ is chosen from an alkali metal salt, preferably a sodium salt, and the cationic form of an amino acid of L or D form, preferably the cationic form of lysine, and preferably represents the cationic form of lysine.
  • the present invention relates to the use of a mixture of compounds of formula (I) and of compounds of formula (II), especially as defined previously.
  • the compound of formula (I) preferably denotes compound ( ⁇ '):
  • compound (II) preferably denotes compound (E) and/or (F):
  • a composition according to the invention comprises water and comprises at least one compound of formula (I) and at least one compound of formula (II) as defined above, and preferably comprises compound ( ⁇ ') and compound (F) or compound ( ⁇ ') and compound (E).
  • the compounds of formula (I) may be obtained in 2 or 3 steps starting from compounds A2 and B1 illustrated in the synthetic scheme below.
  • Compound A2 with x representing an integer between 1 and 9, may be obtained by synthesis in 8 steps starting from compound A1 (Chem. Pharm. Bull., 2001 , 49, 18-22).
  • Compound B1 may be obtained in four steps starting from 3-butynol, as de- scribed in Chem. Pharm. Bull., 2001 , 49, 18-22.
  • Compound B2 may be obtained by Wittig coupling between compounds A2 and B1 in the presence of butyllithium in an apolar solvent such as hexane, for example, at room temperature, under an inert atmosphere.
  • apolar solvent such as hexane
  • Compound G may be obtained from compound B2 by reaction with BBr 3 in di- chloromethane, for example, followed by treatment with sodium hydroxide in a protic solvent such as ethanol.
  • x represents an integer between 1 and
  • compound G obtained includes 1 , 2 or 3 unsaturations (compound G corresponds to the mono-, di- or tri unsaturated compounds of formula (I)).
  • a saturated radical M is preferentially used and the double bond introduced during the Wittig reaction is reduced by catalytic hydrogenation, for example using Pd/C in a protic solvent, it being possible for this hydrogenation to be performed either on compound B2 or, after the reaction with BBr 3 /NaOH, on compound G. 2: Preparation of the compounds of formula (II)
  • a mixture of compounds of formula (II) for which R denotes a linear C 15 hydrocarbon-based chain presented below may be obtained in 2 steps starting from the ana- card ic acid mixture.
  • Anacardic acid is a mixture of four 6-15 alkylsalicylic acid compounds: 6- pentadecylsalicylic acid ( ⁇ '), 6-[8(Z)-pentadecenyl]salicylic acid ( ⁇ '), 6-[8(Z),-1 1 (Z)- pentadecadienyl]salicylic acid (C) and 6-[8(Z),1 1 (Z),-14-pentadecatrienyl]salicylic acid (D'), of formulae:
  • the anacardic acid mixture may be obtained from raw or natural starting material, known as CNSL ("Cashew Nut Shell Liquid"), ex- tracted from the cashew (Anacardium occidentale) nut shell, generally containing from 60% to 80% of anacardic acid.
  • CNSL Cashew Nut Shell Liquid
  • This isolation of the anacardic mixture may in particular be performed according to the method described in J. Agric. Food Chem., 2001 , 49, 2548- 2551 .
  • compound ( ⁇ ') described above in the description, for which R denotes a saturated linear C 15 chain may be obtained by catalytic hydrogenation of the anacardic mixture of compounds A', B', C and D'
  • the salts of formula (II) may be obtained by adding one equivalent of the sali- fying compound to compound (I) or to the mixture of compounds (I).
  • the salts of formula (II) may be obtained by adding one equivalent of the salifying compound in the form of an aqueous solution to a solution in an alcohol, such as isopropanol, of compound (I) or of the mixture of compounds (I).
  • the salts of formula (II) are isolated by evaporation of the solvent.
  • Compound(s) a) are present in a total content of compounds (I) and/or (II) ranging from 0.01 % to 30% by weight, better still from 0.1 % to 10% by weight, more particularly from 0.2% to 8% by weight and in particular from 0.5% to 5% by weight, relative to the total weight of the composition.
  • composition according to the invention comprises at least one compound that promotes the dissolution of at least one compound of formula (I), of at least one salt thereof of formula (II), or of at least one mixture comprising said compound of formula (I) and said compound of formula (II) according to the invention, this or these compound(s) defined in b) being chosen from:
  • glycols chosen from pentylene glycol and hexylene glycol
  • - fatty alcohols comprising a branched and/or unsaturated hydrocarbon-based chain containing from 8 to 26 carbon atoms
  • R1 COOR2 and R10R2 in which R1 represents a fatty acid residue comprising from 8 to 29 carbon atoms and R2 represents a branched or unbranched hydrocarbon-based chain, containing from 3 to 30 carbon atoms, and in which R2 represents a hydrocarbon-based chain of 4 to 30 carbon atoms when R1 represents a fatty acid residue comprising from 8 to 14 carbon atoms,
  • the lipophilic derivatives of amino acids are especially C6-C22 N-acylamino acid esters. These derivatives are especially those described in patent application EP 1 269 986.
  • N-acylamino acid ester(s) are generally of formula II:
  • n is an integer equal to 0, 1 or 2
  • R'i represents a linear or branched C 5 -C 2 i alkyl or alkenyl radical
  • R' 2 represents a hydrogen atom or a Ci to C 3 alkyl group
  • R' 3 represents a radical chosen from the group formed by a hydrogen atom, a methyl group, an ethyl group and a linear or branched C 3 or C 4 alkyl radical,
  • R' 4 represents a linear or branched Ci to Ci 0 alkyl or C 2 to Ci 0 alkenyl radical, or a sterol residue.
  • the group R'i(CO)- is an acyl group of an acid chosen from the group formed by capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, behenic acid, linoleic acid, linolenic acid, oleic acid, isostearic acid, 2-ethylhexanoic acid, coconut oil fatty acids and palm kernel oil fatty acids. These fatty acids may also contain a hydroxyl group. Even more preferably, it will be lauric acid.
  • the -N(R' 2 )CH(R' 3 )(CH 2 ) n (CO)- part of the amino acid ester is preferably chosen from the following amino acids: glycine, alanine, valine, leucine, isoleucine, serine, threonine, proline, hydroxyproline, ⁇ -alanine, aminobutyric acid, aminocaproic acid, sarcosine, or N- methyl-B-alanine.
  • the part of the amino acid esters corresponding to the group OR' 4 may be obtained from alcohols chosen from the group formed by methanol, ethanol, propanol, isopropanol, butanol, tert-butanol, isobutanol, 3-methyl-1 -butanol, 2-methyl-1 -butanol, fusel oil, pentanol, hexanol, cyclohexanol, octanol, 2-ethylhexanol, decanol, lauryl alcohol, myristyl alcohol, cetyl alcohol, cetostearyl alcohol, stearyl alcohol, oleyl alcohol, behenyl alcohol, jojoba alcohol, 2-hexadecyl alcohol, 2-octyldodecanol and isostearyl alcohol.
  • amino acid esters may be obtained in particular from natural sources of amino acids.
  • the amino acids originate from the hydrolysis of natural plant proteins (oat, wheat, soybean, palm or coconut) and then necessarily lead to mixtures of amino acids that subsequently need to be esterified and then N-acylated.
  • the preparation of such amino acids is more particularly described in patent application FR 2 796 550, which is incorporated herein by reference.
  • amino acid ester more particularly preferred for its use in the present invention is isopropyl N-lauroylsarcosinate of formula:
  • CH 3 CH 3 such as the product sold under the name Eldew SL-205 by the company Ajinomoto.
  • amino acid esters that are preferably used for the purposes of the present invention, and the synthesis thereof, are described in patent applications EP 1 044 676 and EP 0 928 608 from the company Ajinomoto Co.
  • An isosorbide ether may especially be dimethyl isosorbide; in particular, use will be made of dimethyl isosorbide sold under the name Arlasolve DMI by the company Uniqema.
  • the glycols according to the invention are chosen from pentylene glycol and hexylene glycol; the glycol is preferably pentylene glycol.
  • the fatty alcohols comprising a branched and/or unsaturated hydrocarbon-based chain containing from 8 to 26 carbon atoms may be chosen from cetyl alcohol, stearyl alcohol and the mixture thereof (cetylstearyl alcohol), octyldodecanol, 2-butyloctanol, 2- hexyldecanol, 2-undecylpentadecanol, oleyl alcohol or linoleyl alcohol.
  • the fatty alcohols comprising a branched and/or unsaturated hydrocarbon-based chain containing from 8 to 26 carbon atoms may be chosen especially from octyldodecanol, 2-butyloctanol, 2-hexyldecanol and 2-undecylpentadecanol.
  • the fatty alcohol containing from 8 to 26 carbon atoms is octyldodecanol or 2- octyldodecanol sold under the name Isofol N/F by the company Sasol.
  • R1 COOR2 and R10R2 in which R1 represents a fatty acid residue containing from 8 to 29 carbon atoms and R2 represents a branched or unbranched hydrocarbon-based chain containing from 3 to 30 carbon atoms, and in which R2 represents a hydrocarbon-based chain of 4 to 30 carbon atoms when R1 represents a fatty acid residue comprising from 8 to 14 carbon atoms may be chosen from: Purcellin oil, isononyl isononanoate, 2-ethylhexyl palmitate, 2-octyldodecyl stearate, 2-octyldodecyl erucate or isostearyl isostearate; hydroxylated esters, for instance isostearyl lactate, octyl hydroxystearate, octyldodecyl hydroxystearate, diisostearyl malate or triisocetyl citrate; fatty alcohol
  • the oils v) are chosen from: isononyl isononanoate, isopropyl palmitate, 2- ethylhexyl palmitate, and mixtures thereof.
  • Isononyl isononanoate is sold under the name Isononyl isononanoate DUB INN by the company Stearineries Dubois.
  • 2-Ethylhexyl palmitate is sold under the name 2-Ethylhexyl palmitate (DUB PO) by the company Stearineries Dubois.
  • Isopropyl palmitate is sold under the name Isopropyl palmitate (DUB IPP) by the company Stearineries Dubois.
  • said compound(s) defined in b) are chosen from:
  • the ingredient that promotes the dissolution of said compounds a) defined above is isopropyl N-lauroylsarcosinate.
  • composition according to the invention comprises (a) at least one compound of formula (I)
  • Isopropyl N-lauroylsarcosinate, pentylene glycol and/or dimethyl isosorbide will be advantageous for dissolving large amounts of compound of formula (I), which may be greater than or equal to 25% by weight, preferably greater than or equal to 30% by weight percentage of compound(s) of formula (I), preferably compound ( ⁇ '), present in a formulation containing only these said compounds (b) as defined above.
  • Isopropyl N-lauroylsarcosinate, pentylene glycol and/or dimethyl isosorbide will be advantageous for dissolving large amounts of compound of formula (I), which may be greater than or equal to 0.5% by weight, preferably greater than or equal to 5% by weight percentage of compound(s) of formula (I), preferably compound ( ⁇ '), present in an anhydrous composition according to the invention as defined above.
  • composition according to the invention comprises:
  • composition according to the invention comprises:
  • the compound(s) defined in a) are present in a total content of compounds (I) and/or (II) ranging from 0.01 % to 40% by weight, in particular from 0.1 % to 10% by weight, more particularly from 0.2% to 8% by weight and in particular from 0.5% to 5% by weight, relative to the total weight of the composition.
  • the ingredient(s) that promote the dissolution of the compound(s) defined in a) may be present in a content ranging from 0.01 % to 99% by weight, particularly ranging from 0.1 % to 20% by weight and more particularly from 1 % to 15% by weight relative to the total weight of the composition.
  • the mass ratio of said compound(s) that promote dissolution defined in b) relative to the compound(s) defined in a) of formula (I) and/or of formula (II) present in the composition according to the invention is generally greater than or equal to 2, for example ranging from 2.5 to 40 and preferably ranging from 5 to 20.
  • composition is anhydrous, and said compound(s) defined in b) are chosen from:
  • glycols chosen from pentylene glycol and hexylene glycol, preferably pentylene glycol, and mixtures thereof.
  • composition according to the invention is anhydrous, comprises as compound(s) defined in a) at least one compound of formula (I), preferably compound ( ⁇ '), and said compound(s) defined in b) which are chosen from:
  • glycols chosen from pentylene glycol and hexylene glycol, preferably pentylene glycol, and mixtures thereof.
  • composition comprises water, and said compound(s) defined in b) are chosen from:
  • - fatty alcohols comprising a branched and/or unsaturated hydrocarbon-based chain containing from 8 to 26 carbon atoms, preferably octyldodecanol,
  • R1 COOR2 and R10R2 in which R1 represents a fatty acid residue comprising from 8 to 29 carbon atoms and R2 represents a branched or unbranched hydrocarbon-based chain, containing from 3 to 30 carbon atoms, and in which R2 represents a hydrocarbon-based chain of 4 to 30 carbon atoms when R1 represents a fatty acid residue comprising from 8 to 14 carbon atoms, preferably isononyl isononanoate, isopropyl palmitate and/or 2-ethylhexyl palmitate,
  • composition according to the invention comprises water, comprises as compound(s) defined in a) compound ( ⁇ ') and/or compound (F) or compound (E), and said compound(s) b) are chosen from:
  • - fatty alcohols comprising a branched and/or unsaturated hydrocarbon-based chain containing from 8 to 26 carbon atoms, preferably octyldodecanol,
  • R1 COOR2 and R10R2 in which R1 represents a fatty acid residue comprising from 8 to 29 carbon atoms and R2 represents a branched or unbranched hydrocarbon-based chain, containing from 3 to 30 carbon atoms, and in which R2 represents a hydrocarbon-based chain of 4 to 30 carbon atoms when R1 represents a fatty acid residue comprising from 8 to 14 carbon atoms, preferably isononyl isononanoate, isopropyl palmitate and/or 2-ethylhexyl palmitate,
  • compositions used according to the invention may comprise a physiologically acceptable medium, i.e. a medium that is suitable for the topical administration of a composition, i.e. that is compatible with human keratin materials such as the skin, the scalp, the hair and the nails.
  • a physiologically acceptable medium i.e. a medium that is suitable for the topical administration of a composition, i.e. that is compatible with human keratin materials such as the skin, the scalp, the hair and the nails.
  • compositions preferably cosmetic compositions, comprise a physiologically acceptable medium.
  • a physiologically acceptable medium is preferentially a cosmetically acceptable medium, that is to say a medium which is devoid of unpleasant odour or appearance and which is entirely compatible with the topical administration route.
  • the term "keratin materials” means the skin, of the body, face and/or area around the eyes, the lips, the nails, mucous membranes, the eyelashes, the eyebrows, bodily hair, the scalp and/or head hair, or any other area of bodily skin. More particularly, the keratin materials according to the invention are the scalp, the hair and/or the skin.
  • the keratin materials according to the invention are the scalp and/or the hair.
  • the keratin material according to the invention is the skin.
  • skin means all of the skin of the body, and preferably the skin of the face, neckline, neck, arms and forearms, or even more preferably still the skin of the face, in particular of the forehead, nose, cheeks, chin and area around the eyes.
  • the compound of formula (I) and/or of formula (II) is advantageously present in the compositions in accordance with the invention in a dissolved form.
  • the composition according to the invention may be intended to be administered topically, that is to say by application at the surface of the keratin material under consideration, such as the skin under consideration.
  • composition of the invention may be a cosmetic composition (i.e. intended for cosmetic purposes) or a dermatological composition.
  • the composition is a cosmetic composition and even more preferentially a cosmetic composition for topical application.
  • composition especially means a substance or a preparation intended to be brought into contact with the various superficial parts of the human body, in particular the epidermis, the bodily-hair and head-hair systems, the nails, the lips and the oral mucous membranes, with a view, exclusively or mainly, to cleansing them, making them more attractive, fragrancing them, modifying their appearance, protecting them, keeping them in good condition, or correcting body odours.
  • the composition according to the invention may be in any galenical form conventionally used for topical application.
  • compositions according to the invention may be anhydrous.
  • anhydrous composition means a composition containing less than 2% by mass of water, or even less than 0.5% of water, and especially free of water, the water not being added during the preparation of the composition but corresponding to the residual water provided by the mixed ingredients.
  • compositions according to the invention may be solid, in particular in wand or stick form.
  • solid composition means that the measurement of the maximum force measured by texturometry during the penetration of a probe into the sample of formulation must be at least equal to 0.25 newtons, in particular at least equal to 0.30 newtons and especially at least equal to 0.35 newtons, assessed under precise measurement condi- tions as follows.
  • compositions according to the invention may comprise water, and may thus be aqueous.
  • compositions according to the invention may be in the form of aqueous solutions, aqueous-alcoholic solutions, oil-in-water (O/W) emulsions, water-in-oil (W/O) emulsions or multiple emulsions (triple: W/O/W or 0/W/O), aqueous gels, more particularly an oil-in-water emulsion.
  • O/W oil-in-water
  • W/O water-in-oil
  • aqueous gels more particularly an oil-in-water emulsion.
  • compositions comprise an aqueous phase.
  • the aqueous phase of said compositions contains water and generally other water-miscible or water-soluble solvents, which are additional and different from the compounds b) according to the invention as defined above.
  • These additional water-soluble or water-miscible solvents comprise short- chain, for example C1 -C4, monoalcohols, such as ethanol or isopropanol; diols or polyols, such as ethylene glycol, 1 ,2-propylene glycol, 1 ,3-butylene glycol, diethylene glycol, di- propylene glycol, 2-ethoxyethanol, diethylene glycol monomethyl ether, triethylene glycol monomethyl ether and sorbitol.
  • Use may be made especially of propylene glycol, glycerol and/or 1 ,3-propanediol.
  • the composition according to the invention has a pH ranging from 3 to 7.
  • the pH of the composition ranges from 4 to 6.
  • the amount of water is not limited, and may range from 10% to 99% by weight, preferably from 20% to 80% by weight and more preferably from 40% to 75% by weight relative to the total weight of the composition.
  • composition according to the invention may also comprise at least one oil, which is an additional oil different from the compounds b) according to the invention as defined above.
  • additional oils include: - hydrocarbon-based oils of plant origin, such as liquid triglycerides of fatty acids containing from 4 to 10 carbon atoms, for instance heptanoic or octanoic acid triglycerides, or alternatively, for example, sunflower oil, corn oil, soybean oil, marrow oil, grapeseed oil, sesame seed oil, hazelnut oil, apricot oil, macadamia oil, arara oil, castor oil, avocado oil, caprylic/capric acid triglycerides, for instance those sold by the company Stearineries Dubois or those sold under the names Miglyol 810, 812 and 818 by the company Dynamit Nobel, jojoba oil and shea butter oil;
  • esters and ethers especially of fatty acids, for instance the additional oils of formulae R1 COOR2 and R10R2 in which R1 represents a fatty acid residue containing from 8 to 29 carbon atoms and R2 represents a branched or unbranched hydrocarbon- based chain containing from 3 to 30 carbon atoms, for instance Purcellin oil, isopropyl myristate, 2-octyldodecyl stearate, 2-octyldodecyl erucate or isostearyl isostearate; hydroxylated esters, for instance isostearyl lactate, octyl hydroxystearate, octyldodecyl hydroxystearate, diisostearyl malate or triisocetyl citrate; fatty alcohol heptanoates, octanoates or decanoates; polyol esters, for instance propylene glycol dioctanoate,
  • hydrocarbons of mineral or synthetic origin such as volatile or nonvolatile liquid paraffins, and derivatives thereof, petroleum jelly, polydecenes, and hydrogenated polyisobutene such as Parleam oil;
  • additional fatty alcohols containing from 8 to 26 carbon atoms for instance cetyl alcohol, stearyl alcohol and the mixture thereof (cetylstearyl alcohol), 2-butyloctanol, 2- hexyldecanol, 2-undecylpentadecanol, oleyl alcohol or linoleyl alcohol;
  • silicone oils for instance volatile or non-volatile polymethylsiloxanes (PDMS) with a linear or cyclic silicone chain, which are liquid or pasty at room temperature, especially cyclopolydimethylsiloxanes (cyclomethicones) such as cyclohexasiloxane; polydimethylsiloxanes comprising alkyl, alkoxy or phenyl groups, which are pendent or at the end of a silicone chain, these groups containing from 2 to 24 carbon atoms; phenylsilicones, for instance phenyl trimethicones, phenyl dimethicones, phenyltrimethylsiloxydiphenylsiloxanes, diphenyl dimethicones, diphenylmethyldiphenyltrisiloxanes or 2-phenylethyl trimethylsiloxy silicates, and polymethylphenylsiloxanes;
  • PDMS volatile or non-volatile polymethylsiloxanes
  • hydrocarbon-based oil means any oil mainly comprising carbon and hydrogen atoms, and possibly ester, ether, fluoro, carboxylic acid and/or alcohol groups.
  • the composition according to the invention may comprise substances that are solid at room temperature (25°C), for instance fatty acids comprising from 8 to 30 carbon atoms, such as stearic acid, lauric acid, palmitic acid and oleic acid; waxes such as lanolin, beeswax, carnauba wax or candelilla wax, paraffin waxes, microcrystalline waxes, ceresin or ozokerite, and synthetic waxes such as polyethylene waxes and Fischer-Tropsch waxes.
  • fatty substances may be chosen in a varied manner by a person skilled in the art so as to prepare a composition having the desired properties, for example in terms of consistency or texture.
  • the composition according to the invention is a water-in-oil (W/O) or oil-in-water (O/W) emulsion.
  • W/O water-in-oil
  • O/W oil-in-water
  • the proportion of the oily phase of the emulsion may range from 1 % to 80% by weight and preferably from 5% to 50% by weight relative to the total weight of the composition.
  • the emulsions generally contain at least one emulsifier chosen especially from amphoteric, anionic, cationic and nonionic emulsifiers, used alone or as a mixture, and optionally a co-emulsifier.
  • the emulsifiers are chosen in an appropriate manner according to the emulsion to be obtained (W/O or O/W emulsion).
  • the emulsifier and the coemulsifier are generally present in the composition in a proportion ranging from 0.3% to 30% by weight and preferably from 0.5% to 20% by weight relative to the total weight of the composition.
  • emulsifiers For W/O emulsions, examples of emulsifiers that may be mentioned include dimethicone copolyols, such as the mixture of cyclomethicone and dimethicone copolyol sold under the name DC 5225 C by the company Dow Corning, and alkyl dimethicone copolyols such as the lauryl methicone copolyol sold under the name Dow Corning 5200 Formulation Aid by the company Dow Corning, and the cetyl dimethicone copolyol sold under the name Abil EM 90® by the company Goldschmidt.
  • dimethicone copolyols such as the mixture of cyclomethicone and dimethicone copolyol sold under the name DC 5225 C by the company Dow Corning
  • alkyl dimethicone copolyols such as the lauryl methicone copolyol sold under the name Dow Corning 5200 Formulation Aid by the
  • emulsifiers examples include nonionic emulsifiers such as oxyalkylenated (more particularly polyoxyethylenated) fatty acid esters of glycerol; oxyalkylenated fatty acid esters of sorbitan; oxyalkylenated (oxyethylenated and/or oxypropylenated) fatty acid esters; oxyalkylenated (oxyethylenated and/or oxypropylenated) fatty alcohol ethers; sugar esters such as sucrose stearate; and mixtures thereof, such as the mixture of glyceryl stearate and PEG-100 stearate.
  • the composition may be an aqueous gel, and may especially comprise common aqueous gelling agents.
  • the composition according to the invention may also contain adjuvants that are common in cosmetics or dermatology, such as gelling agents, film- forming polymers, preserving agents, fragrances, fillers, UV-screening agents, bactericides, odour absorbers, dyestuffs, plant extracts, cosmetic and dermatological active agents, and salts.
  • adjuvants that are common in cosmetics or dermatology, such as gelling agents, film- forming polymers, preserving agents, fragrances, fillers, UV-screening agents, bactericides, odour absorbers, dyestuffs, plant extracts, cosmetic and dermatological active agents, and salts.
  • the amounts of these various adjuvants are those conventionally used in the field under consideration, for example from 0.001 % to 20% of the total weight of the composition.
  • a subject of the invention is also a cosmetic treatment process for caring for, making up and/or cleansing keratin materials, especially the skin, comprising the application to said keratin materials, especially the skin, of a composition according to the invention as described previously.
  • Said cosmetic treatment process for caring for, making up and/or cleansing the skin is non-therapeutic.
  • a subject of the invention is also a cosmetic process for preventing and/or treating the signs of ageing of the skin, comprising at least one step of topical application to the keratin materials, such as the skin, of a composition according to the invention as described previously.
  • the signs of ageing of the skin to be prevented and/or treated in the cosmetic process according to the invention may be chosen from wrinkles and fine lines, and/or for combating wizened, flaccid and/or thinned skin.
  • a subject of the invention is also the cosmetic use of a composition according to the invention as defined previously, for caring for, making up and/or cleansing keratin materials.
  • the invention relates to a cosmetic treatment process for caring for, making up and/or cleansing keratin materials, especially the skin, comprising the topical administration, to an individual, of a composition as defined previously.
  • the amounts of the ingredients are expressed as weight percentages.
  • This compound is weighed out and placed in a hermetic pillbox.
  • solubilizers 10 ml of solubilizer are placed in a beaker and the compound of formula (I) is added mg by mg. The suspension, optionally brought to 70°C, is stirred by magnetic stirring for 30 minutes.
  • the insolubility of compound (A) in the solubilizer is characterized macroscopically by a precipitate or a cloudy solution, and microscopically by the presence of birefringent crystals of geometric form.
  • solubilizers are isopropyl N-lauroylsarcosinate, dimethyl isosorbide and pentylene glycol, which made it possible to dissolve more than 25% by weight of compound of formula (I) (the rest of the solution being constituted of the solubilizer).
  • Example 2.2 Tests of solubilization of a salicylic acid derivative of formula (I) or of formula (II) in a composition comprising water Protocol:
  • solubilizer 10 ml of solubilizer are placed in a beaker and compound ( ⁇ ') or compound (F) is added mg by mg.
  • the suspension optionally brought to 70°C, is stirred by magnetic stirring for 30 minutes.
  • isopropyl N-lauroylsarcosinate does indeed make it possible to dissolve a compound of formula (I), compound (A), in a composition comprising water, unlike ethanol for which the composition has a cloudy solution at 24 hours, with the presence of birefringent crystals of geometric form.
  • isopropyl N-lauroylsarcosinate does indeed make it possible to dissolve a compound of formula (II), compound (F), in a composition comprising water, unlike dipropylene glycol for which the composition is solid at 24 hours, with the presence of birefringent crystals of geometric form.
  • Example 3 Anhydrous composition according to the invention
  • a skincare composition having the following composition was prepared:
  • Caprylic/capric acid triglycerides 70/30 C8-C10 qs 100
  • Dioctyl carbonate (Cetiol CC® from Cognis) 30
  • composition is stable and homogeneous and free of birefringent geometric crystals after storage for 2 months at 4°C and 45°C.
  • This composition may be applied regularly to facial skin to care for the same, especially in order to attenuate the signs of ageing of the skin.
  • Example 4 Skincare composition according to the invention
  • a skincare composition (oil-in-water gel emulsion) having the following composition was prepared:
  • Compound ( ⁇ ') is dissolved in isopropyl N-lauroylsarcosinate, with magnetic stirring, while heating to 70°C.
  • This solution B2 is clear and free of crystals.
  • This solution B2 is then added to the fatty phase B1 of the formula heated to 70°C.
  • the aqueous phase A is heated to 70°C.
  • the emulsion is prepared using a rotor-stator stirrer by pouring the fatty phase into the aqueous phase.
  • composition is stable and homogeneous and free of birefringent geometric crystals after storage for 2 months at 4°C and 45°C.
  • This composition may be applied regularly to facial skin to care for the same, especially in order to attenuate the signs of ageing of the skin.
  • This composition may be applied regularly to facial skin to care for the same and allow good sensory properties experienced in the application on keratin materials such as the skin of said formulation, in particular a touch or feeling with better softness, and/or less greasy.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
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  • Emergency Medicine (AREA)
  • Dermatology (AREA)
  • Cosmetics (AREA)

Abstract

L'invention concerne une composition qui comporte : a) au moins un composé de la formule (I), au moins un de ses sels de la formule (II) ou un mélange comportant au moins un composé de la formule (I) et au moins un composé de la formule (II) ; b) au moins un composé choisi parmi : des dérivés lipophiles d'acides aminés, des éthers d'isosorbide, des glycols choisis parmi le pentylène glycol et l'hexylène glycol, des alcools gras présentant une chaîne hydrocarbonée ramifiée et/ou insaturée contenant de 8 à 26 atomes de carbone, des huiles des formules R1COOR2 et R1OR2, et des mélanges de ceux-ci. Son utilisation est indiquée pour le soin, le maquillage et/ou le nettoyage des matières de kératine, en particulier de la peau.
PCT/EP2016/060912 2015-05-13 2016-05-13 Composition comportant des dérivés d'acide salicylique et un solvant particulier WO2016180979A1 (fr)

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Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0928608A2 (fr) 1997-12-25 1999-07-14 Ajinomoto Co., Inc. Composition cosmétique
EP1044676A2 (fr) 1999-04-16 2000-10-18 Ajinomoto Co., Inc. Composition contenant des substances huileuses
FR2796550A1 (fr) 1999-07-21 2001-01-26 Asepta Lab Preparations et applications d'esters de n-acylaminoacides
FR2826273A1 (fr) * 2001-06-26 2002-12-27 Oreal Composition contenant des derives d'acide salicylique et des derives lipophiles d'acide amine
EP1269986A2 (fr) 2001-06-26 2003-01-02 L'oreal Compositions comprenant un composé de faible solubilité et un dérivé lipophile d'acide aminé, utilisations et procédés correspondants
WO2007093375A1 (fr) * 2006-02-16 2007-08-23 Dsm Ip Assets B.V. Compositions nutraceutiques et pharmaceutiques atypiques et leur utilisation dans le traitement, le co-traitement ou la prevention d'affections inflammatoires
WO2015071374A1 (fr) * 2013-11-13 2015-05-21 L'oreal Utilisation comme agent déodorant d'un dérivé salifié d'acide salicylique, seul ou en mélange

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0928608A2 (fr) 1997-12-25 1999-07-14 Ajinomoto Co., Inc. Composition cosmétique
EP1044676A2 (fr) 1999-04-16 2000-10-18 Ajinomoto Co., Inc. Composition contenant des substances huileuses
FR2796550A1 (fr) 1999-07-21 2001-01-26 Asepta Lab Preparations et applications d'esters de n-acylaminoacides
FR2826273A1 (fr) * 2001-06-26 2002-12-27 Oreal Composition contenant des derives d'acide salicylique et des derives lipophiles d'acide amine
EP1269986A2 (fr) 2001-06-26 2003-01-02 L'oreal Compositions comprenant un composé de faible solubilité et un dérivé lipophile d'acide aminé, utilisations et procédés correspondants
WO2007093375A1 (fr) * 2006-02-16 2007-08-23 Dsm Ip Assets B.V. Compositions nutraceutiques et pharmaceutiques atypiques et leur utilisation dans le traitement, le co-traitement ou la prevention d'affections inflammatoires
WO2015071374A1 (fr) * 2013-11-13 2015-05-21 L'oreal Utilisation comme agent déodorant d'un dérivé salifié d'acide salicylique, seul ou en mélange

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Title
CHEM. PHARM. BULL., vol. 49, 2001, pages 18 - 22
J. AGRIC. FOOD CHEM., vol. 49, 2001, pages 2548 - 2551
J. AM. MOSQUITO CONTROL ASSOCIATION, vol. 25, 2009, pages 386 - 389
PROCEEDINGS OF THE INSTITUTION OF CHEMISTS, 1961, pages 81 - 85

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