EP3713539A1 - Selbstinvertierender inverser latex mit alkylpolyglycosiden als invertierungsmittel, verwendung davon als verdickungsmittel und diese enthaltende kosmetische zusammensetzungen - Google Patents

Selbstinvertierender inverser latex mit alkylpolyglycosiden als invertierungsmittel, verwendung davon als verdickungsmittel und diese enthaltende kosmetische zusammensetzungen

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Publication number
EP3713539A1
EP3713539A1 EP18826410.5A EP18826410A EP3713539A1 EP 3713539 A1 EP3713539 A1 EP 3713539A1 EP 18826410 A EP18826410 A EP 18826410A EP 3713539 A1 EP3713539 A1 EP 3713539A1
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EP
European Patent Office
Prior art keywords
equal
weight
less
water
composition
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Application number
EP18826410.5A
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English (en)
French (fr)
Inventor
Miruna BODOC
Georges DACOSTA
Jérôme GUILBOT
Aurélie PIERRE
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Societe dExploitation de Produits pour les Industries Chimiques SEPPIC SA
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Societe dExploitation de Produits pour les Industries Chimiques SEPPIC SA
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Publication of EP3713539A1 publication Critical patent/EP3713539A1/de
Withdrawn legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C09K23/56—Glucosides; Mucilage; Saponins
    • 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
    • A61K8/345—Alcohols containing more than one hydroxy group
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04—Dispersions; Emulsions
    • A61K8/06—Emulsions
    • A61K8/064—Water-in-oil emulsions, e.g. Water-in-silicone emulsions
    • 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
    • A61K8/60—Sugars; Derivatives thereof
    • A61K8/604—Alkylpolyglycosides; Derivatives thereof, e.g. esters
    • 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
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/8141—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • A61K8/8158—Homopolymers or copolymers of amides or imides, e.g. (meth) acrylamide; Compositions of derivatives of such polymers
    • 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
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
    • C09D133/24—Homopolymers or copolymers of amides or imides
    • C09D133/26—Homopolymers or copolymers of acrylamide or methacrylamide
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C09K23/017—Mixtures of compounds
    • C09K23/018—Mixtures of two or more different organic oxygen-containing compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C09K23/16—Amines or polyamines
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/10—General cosmetic use
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/48—Thickener, Thickening system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/14—Preparations for removing make-up
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
    • 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
    • A61Q19/008—Preparations for oily skin
    • 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
    • A61Q19/04—Preparations for care of the skin for chemically tanning the skin

Definitions

  • Self-invertible inverse latex comprising, as an inverting agent, alkylpolyglycosides, its use as a thickening agent, and cosmetic compositions comprising
  • the invention relates to self-reversing inverse latexes comprising, as an inverter agent, a surfactant composition comprising alkyl polyglycosides, the use of said self-reversing inverse latexes as thickeners used to prepare cosmetic, dermocosmetic, dermopharmaceutical and pharmaceutical formulations, as well as formulations.
  • Cosmetic, dermocosmetic, dermopharmaceutical and pharmaceutical compositions comprising polar phases, for example aqueous alcoholic or hydro-alcoholic phases, frequently require the use of rheology-modifying polymers to increase their viscosity of said polar phases, and more generally to give them a uniformity. specific rheological behavior.
  • rheology modifying agents which can be used for the preparation of these compositions, mention may be made of synthetic polymers such as, for example, linear or branched, crosslinked or non-crosslinked anionic or cationic polyelectrolytes or ampholytes, two physical forms, the powder form and the liquid form.
  • the said cosmetic, dermocosmetic, dermopharmaceutical and pharmaceutical compositions are generally in the form of aqueous gels, hydro-alcoholic gels, hydro-glycolic gels, emulsions or microemulsions or nanoemulsions of the water-in-water type.
  • the surfactants of oil-in-water type are added at the end of the polymerization step. Their addition is intended to modify and adjust the hydrophilic-lipophilic balance of the water-in-oil emulsion comprising the polymer (also called "inverse latex") so as to obtain a mixture which, once added in a polar phase as for example water, will change direction of emulsion to pass from the water-in-oil form to the oil-in-water form, allowing then to contact the previously prepared polymer with the polar phase to thicken.
  • the crosslinked and / or connected polyelectrolyte polymer deploys in said polar phase and forms a three-dimensional network allowing the polar phase to swell, which manifests itself by an increase in the viscosity of this phase.
  • polar The mixture comprising the "inverse latex" and the oil-in-water type surfactant is called the self-invertible inverse latex and said oil-in-water type surfactant is called "inverter" or "inverter agent”.
  • Inverter agents commonly used for the preparation of self-reversing inverse latices are oil-in-water surfactants which have a sufficiently high HLB (Hydrophilic Lipophilie Balance) value to make it possible to prepare oil-in-water type emulsions. in-water stable, generally greater than 9 and less than 16. They generally comprise a hydrophilic portion consisting of a chain of ethylene oxide units and a part consisting of a hydrocarbon-based aliphatic chain of hydrophobic nature.
  • HLB Hydrophilic Lipophilie Balance
  • Ethoxylated fatty alcohols whose aliphatic hydrocarbon chain contains from 8 to 14 carbon atoms and the number of ethylene oxide units of which is between 5 and 40, for example lauryl alcohol ethoxylated with 7 moles of ethylene oxide (INCI name: Laureth-7), or tridecyl alcohol with 6 moles of ethylene oxide (INCI name: trideceth-6);
  • Ethoxylated sorbitan esters whose aliphatic hydrocarbon chain contains from 12 to 22 carbon atoms and the number of ethylene oxide units of which is between 5 and 40, for example 20 molar ethoxylated sorbitan oleate; ethylene oxide sold under the trade name Montanox TM 80, or sorbitan laurate ethoxylated with 20 moles of ethylene oxide sold under the trade name Montanox TM 20;
  • Ethoxylated alkylphenols for example ethoxylated nonylphenols and ethoxylated octylphenols; or
  • Ethoxylated castor oils for example castor oil ethoxylated with 40 moles of ethylene oxide sold under the brand name SIMULSOL TM OL 50.
  • the invention relates to a water-in-oil emulsion (E) comprising for 100% of its mass:
  • (a 2 ) - Optionally of a proportion greater than 0 mol% and less than or equal to 70 mol%, of monomeric units derived from at least one monomer chosen from the group consisting of acrylic acid, methacrylic acid, itaconic acid, maleic acid, 3-methyl-3 - [(1-oxo-2-propenyl) amino] butanoic acid, the carboxylic function of said monomers being in acid form, partially salified or totally salts and / or from among the group consisting of (2-hydroxyethyl) acrylate, (2,3-dihydroxypropyl) acrylate, (2-hydroxyethyl) methacrylate, (2-hydroxyethyl) acrylate, 3-dihydroxy propyl) or vinyl pyrrolidone;
  • the sum of the molar proportions of the monomeric units (ai), (a 2 ) and (as) is equal to 100%; b) - from 5 wt% to 50 wt%, more particularly from 5 wt% to 45 wt%, and even more particularly from 5 wt% to 40 wt%, of a fatty phase consisting of at least one oil (H ), and c) - from 1 wt.% to 50 wt.%, more preferably from 5 wt.% to 45 wt.%, more preferably from 5 wt.% to 40 wt.%, and d) - from 0.5 wt.
  • % by mass at 10% by weight more particularly from 0.5% by weight to 8% by weight, and even more particularly from 0.5% by mass to 7% by weight of a water-in-oil emulsifier system (Si), and e) - from 2% by weight to 10% by weight, more particularly from 2% by weight to 8% by weight and even more particularly from 4% by mass to 7% by weight of an oil-in-oil emulsifier system (S 2 ).
  • water comprising for 100% of its mass, at least 50% by weight of a composition (C e ) comprising for 100% of its mass:
  • n represents an integer greater than or equal to 1 and less than or equal to 6, or a mixture of said diluents, e 2 ) - a proportion greater than or equal to 20% by weight and less than or equal to 80% by weight of d a composition (C e 2) comprising for 100% of its mass:
  • composition ((3 ⁇ 4) comprising:
  • composition (C 2i ) consisting of a mixture of compounds of formulas (llh), (III 2), (II b), (II U) and (lll 5):
  • composition (C 22 ) consisting of in a mixture of the compounds of formulas (IV1), (IV 2 ), (IV 3 ), (IV 4 ) and (IV 5 ):
  • R23 represents the n-octyl radical
  • G23 represents the remainder of a reducing sugar
  • t represents a decimal number greater than or equal to 1.05 and less than or equal to 5.00
  • said composition (C23) consisting of a mixture the compounds of formulas (V1), (V2), (V3), (V 4) and
  • composition (C 24 ) represented by the formula (VI):
  • composition (C 24 ) consisting of in a mixture of compounds of formulas (Vh), (VI2), (VI3),
  • compositions (C21), (C22), (C23), and (C 24) are equal to 100%; b2 b 3) - a proportion greater than or equal to 10% by weight and less than or equal to 40% by weight of a composition (0 2b 3) comprising for 100% of its mass: e 2 p3i) - A proportion greater than or equal to 30% by weight and less than or equal to 50% by weight of a composition (C 3 1) represented by the formula (VII):
  • R 31 represents the n-hexadecyl radical
  • G 3 1 represents the remainder of a reducing sugar and x represents a decimal number greater than or equal to 1, 05 and less than or equal to 5.00,
  • composition (C 3 1) consisting of a mixture of compounds of formulas (VI), (VII2), (VI l 3), (VI l 4) and (5 VII):
  • composition (C 3 2) represented by the formula (VI II):
  • R 3 2 represents the n-octadecyl radical
  • G 3 2 represents the remainder of a reducing sugar
  • y represents a decimal number greater than or equal to 1.05 and less than or equal to 5.00
  • composition (C3 2) consisting of a mixture of compounds of formulas (Vllh), (VI I I2), (I3 VII), (VII U) and (VI II 5):
  • crosslinked polymer denotes, for the polymer (P), a non-linear polymer which, when added to water, is in the state of a three-dimensional network insoluble in water. water, but inflatable with water and leading then to obtaining a chemical gel.
  • the term "salified" indicates that the strong acid function present in the monomer is in an anionic form associated in salt form with a cation, especially the alkali metal salts, such as sodium or potassium cations, or as nitrogen base cations such as ammonium salt, lysine salt or monoethanolamine salt (HO-CH 2 -CH 2 -NH 4 + ).
  • the strong acid function of the monomer containing it is in particular the sulphonic acid function or the phosphonic acid function.
  • Said monomer is, for example, partially or totally salified styrenesulphonic acid or, for example, 2-methyl 2 - [(1-oxo-2-propenyl) amino] 1-propanesulphonic acid partially or totally salified.
  • the monomer having a strong acid function is 2-methyl-2 - [(1-oxo-2-propenyl) amino] -1-propanesulfonic acid, and more particularly the sodium or potassium salt.
  • said crosslinked polymer (P) is derived from the polymerization for 100 mol%:
  • said crosslinked polymer (P) is a crosslinked homopolymer of 2-methyl-2 - [(1-oxo-2-propenyl) amino] 1-propanesulfonic acid partially or totally salified.
  • said crosslinked polymer (P) is a crosslinked copolymer of 2-methyl 2 - [(1-oxo-2-propenyl) amino] 1-propanesulfonic acid partially or totally salified and of at least one monomer selected from acrylic acid, partially or fully salified methacrylic acid, (2-hydroxyethyl) acrylate, (2,3-dihydroxypropyl) acrylate, (2-hydroxyethyl) methacrylate, hydroxyethyl), (2,3-dihydroxypropyl) methacrylate and vinyl pyrrolidone.
  • the water-in-oil emulsion (E) as defined above comprises from 20% by weight to 80% by weight and more particularly from 30% by weight to 80% by weight of said polymer ( P).
  • said polymer (P) is a crosslinked copolymer, it is particularly derived from the polymerization, for 100 mol%,
  • At least one diethylenic or polyethyleneic crosslinking monomer (AR), in the definition of the water-in-oil emulsion (E) which is the subject of the present invention, is meant a monomer especially chosen from ethylene glycol dimethacrylate. diethylene glycol diacrylate, ethylene glycol diacrylate, diallyl urea, triallylamine, trimethylol propanetriacrylate, methylenebis (acrylamide) or a mixture of these compounds, diallyoxyacetic acid or a salt thereof, such as diallyloxyacetate; sodium, or a mixture of these compounds.
  • the crosslinking monomer (AR) is chosen from ethylene glycol dimethacrylate, triallylamine, trimethylol propanetriacrylate and methylenebis (acrylamide).
  • the crosslinking monomer (AR) is used in a molar proportion of less than or equal to 0.5%, more particularly less than or equal to 0.25% and most preferably less than or equal to 0.1. % it is more particularly greater than or equal to 0.005 mol%.
  • crosslinked polymers (P) which are mentioned in the context of the present invention, there is more particularly: - A homopolymer of 2-methyl-2 - [(1-oxo-2-propenyl) amino] 1-propanesulfonic acid partially or totally salified in the form of sodium salt or ammonium salt, crosslinked with triallylamine and / or methylenebis (acrylamide);
  • a crosslinked copolymer of 2-methyl 2 - [(1-oxo-2-propenyl) amino] 1-propanesulfonic acid (y) partially or totally salified in the form of sodium salt, and acrylic acid (e) partially or totally salified as sodium salt in a molar ratio (g) / (e) greater than or equal to 40/60 and less than or equal to 90/10.
  • oil By oil, the definition of the water-in-oil type emulsion (E) which is the subject of the present invention is intended to mean the oil (H) in particular:
  • Linear alkanes comprising from eleven to nineteen carbon atoms
  • Cycloalkanes optionally substituted with one or more linear or branched alkyl radicals, - Mineral white oils, such as those sold under the following names: Marcol TM 52, Marcol TM 82, Drakeol TM 6VR, Eolane TM 130, Eolane TM 150,
  • Hemisqualane or 2,6,10-trimethyl-dodecane, CAS number: 3891 -98-3
  • squalane or 2,6,10,15,19,23-hexamethyltetracosane
  • hydrogenated polyisobutene or hydrogenated polydecene
  • Z 1 and Z 2 identical or different, represent a linear or branched alkyl having from five to eighteen carbon atoms, such as dioctyl ether, didecyl ether, didodecyl ether, dodecyl octyl ether, dihexadecyl ether, (1, 3-dimethylbutyl) tetradecyl ether, (1,3-dimethylbutyl) hexadecyl ether, bis (1,3-dimethylbutyl) ether or dihexyl ether.
  • R" 2 represents, independently of R "i, a hydrocarbon-based chain saturated or unsaturated, linear or branched having from one to twenty-four carbon atoms, for example methyl laurate, ethyl laurate, propyl laurate, isopropyl laurate, butyl laurate, 2-butyl laurate, laurate of hexyl, methyl cocoate, ethyl cocoate, propyl cocoate, isopropyl cocoate, butyl cocoate, 2-butyl cocoate, hexyl cocoate, methyl myristate, ethyl myristate, propyl myristate , isopropyl myristate, butyl myristate, 2-butyl myristate, hexyl myristate, o
  • said oil (H) is chosen from:
  • Emogreen TM L15 Mixtures of alkanes and isoalkanes and cycloalkanes marketed under the names Emogreen TM L15, Emogreen TM L19, Emosmart TM L15, Emosmart TM L19, Emosmart TM V21, lsopar TM L or lsopar TM M;
  • the emulsifier system (Si) of the water-in-oil type consists of either a single emulsifying surfactant or a mixture of emulsifying surfactants. provided that said mixture has a sufficiently low HLB value to induce the formation of water-in-oil type emulsions.
  • emulsifying surfactant of the water-in-oil type mention may be made, for example, of saturated or unsaturated aliphatic, linear or branched, aliphatic carboxylic acid esters having from 12 to 22 carbon atoms optionally substituted with one or a plurality of hydroxyl groups, and more particularly anhydrohexitol esters chosen from saturated or unsaturated, linear or branched aliphatic anhydro-sorbitols and anhydro-mannitols and carboxylic acids containing from 12 to 22 carbon atoms which may be substituted with one or more hydroxyl groups.
  • the emulsifier system (Si) of the water-in-oil type is more particularly chosen from the group consisting of sorbitan laurate, by example that marketed under the name Montane TM 20, sorbitan palmitate, for example that marketed under the name Montane TM 40, sorbitan stearate, for example that marketed under the name Montane TM 60, sorbitan oleate, for example the one marketed under the name Montane TM 80, sorbitan sesquioleate, for example the one sold under the name Montane TM 85, sorbitan trioleate, for example the one marketed under the name Montane TM 83, sorbitan isolaurate, sorbitan isostearate, for example that marketed under the name Montane TM 70, mannitan laurate, mannitan oleate, or a mixture of these est
  • y 2 represents an integer greater than or equal to 2 and less than or equal to 50
  • Z 4 represents the hydrogen atom, the methyl radical, or the ethyl radical
  • Z 3 represents a radical of formula (XV):
  • y ' 2 represents an integer greater than or equal to 0 and less than or equal to 10, more particularly greater than or equal to 1 and less than or equal to 10 and Z' 2 represents a radical of formula (XV) as defined herein above, with Z 2 'identical to or different from Z 2 , or the hydrogen atom.
  • a water-in-oil emulsifying surfactant of formula (XIV) which can be used to prepare the emulsifier system (Si)
  • a water-in-oil emulsifying surfactant of formula (XIV) which can be used to prepare the emulsifier system (Si)
  • said emulsifying system comprises:
  • (S 2 ) oil-in-water type comprising for 100% of its mass, at least 75% by weight of said composition (C e ) as defined above.
  • said emulsifier system (S 2 ) of oil-in-water type is the composition (C e ) as defined above.
  • diluting agent of formula (I) is meant in the definition of said emulsion of water-in-oil type (E) object of the present invention, including glycerol, diglycerol, triglycerol or hexaglycerol.
  • said diluting agent is characterized in that in formula (I), n represents an integer greater than or equal to 1 and less than or equal to 3. According to a very particular aspect, n is equal to to 1.
  • said water-in-oil emulsion (E), as defined above, is characterized in that, in formulas (III), (IV), (V), (VI ), (VII) and (VIII), G21, G22, G23, G24, G31 and G32, which are identical or different, represent, independently of one another, the remainder of a reducing sugar chosen from glucose, dextrose, sucrose, fructose, idose, gulose, galactose, maltose, isomaltose, maltotriose, lactose, cellobiose, mannose, ribose, xylose, arabinose, lyxose, allose, altrose, dextran and tallose. Said remains of a reducing sugar G21, G22, G23, G24, G31 and G32, which are identical or different, are more particularly chosen from the residues of glucose, xylose or arabinose.
  • said water-in-oil emulsion (E) as defined above is characterized in that in the formulas
  • said water-in-oil emulsion (E) as defined above is characterized in that in formulas (III),
  • said water-in-oil emulsion (E) as defined above is characterized in that in the formulas (III), (IV), (V) and (VI), r, s, t and u, respectively, represent, independently of one another, a decimal number greater than or equal to 1, 05 and less than or equal to 2.5; this decimal number is in this case often less than or equal to 2.0, and for example greater than or equal to 1, 25 and less than or equal to 2.0.
  • said water-in-oil emulsion (E) as defined above is characterized in that in the formulas (VII) and (VIII), said remains of a reducing sugar G31 and G32 represent the same residue of reducing sugar chosen from the rest of the glucose, the rest of the xylose and the rest of the arabinose, and most particularly represent the rest of the glucose, or the rest of the xylose.
  • said emulsion of water-in-oil type (E) as defined above is characterized in that in the formulas (VII) and (VIII), said remains of a reducing sugar G31 and G32 are identical and represent the rest of the glucose.
  • said water-in-oil emulsion (E) as defined above is characterized in that in the formulas (VII) and (VIII), x and y respectively, represent a decimal number greater than or equal to 1, 05 and less than or equal to 2.5; this decimal number is in this case often less than or equal to 2.0, and for example greater than or equal to 1, 25 and less than or equal to 2.0.
  • Said emulsion of water-in-oil type (E) object of the present invention is prepared by the implementation of a method called "inverse emulsion polymerization", well known to those skilled in the art, and which includes the following steps :
  • a step a) of preparing an aqueous phase comprising water, the water-soluble monomers and optionally the crosslinking monomer (AR), as well as commonly used additives, for example sequestering agents such as ethylene diamine tetra acetic acid. its sodium form, or the penta-sodium salt of penta acetic acid diethylenetramine (marketed under the brand name Versenex TM 80)
  • SA crosslinking monomer
  • a step e) of initiating the polymerization reaction by introducing into the emulsion formed in c), a free radical initiator and optionally a co-initiator; then let it unfold,
  • the polymerization reaction of step e) is initiated by a hydrogen sulfite ion generating pair (HSO3).
  • a hydrogen sulfite ion generating pair HSO3
  • the cumene hydroperoxide -metabisulphite couple sodium Na2S2C> 5
  • the cumene hydroperoxide-thionyl chloride (SOC) pair at a temperature of less than or equal to 10 ° C, if desired accompanied by a co-initiator polymerization agent such as, for example, azo bis (isobutyronitrile) and then conducted almost adiabatically to a temperature greater than or equal to 50 ° C, or by controlling the temperature.
  • reaction medium resulting from step e) is concentrated by distillation, before the implementation of step f) ⁇
  • reaction medium resulting from step e) or step f) is atomized in a suitable installation.
  • the aqueous phase prepared in step a) may comprise chain reducing agents, intended to reduce the length of the polymer chains formed and to increase the rate of branching on the polymer, to modify the rheological properties.
  • chain reducing agents suitable for the process as defined above mention may be made of methanol, isopropanol, butylene glycol, 2-mercapto ethanol, thioglycolic acid, formic acid or its salts.
  • composition (C e ) included in the emulsifier system (S2) of oil-in-water type is prepared according to a process comprising the following steps:
  • G represents the residue of a reducing sugar, with a molar excess of a mixture of alcohols of formula (II):
  • Stage A) is generally carried out in a reactor in the presence of an acidic catalyst system, by controlling the stoichiometric ratio between the two reactants, and more particularly by introducing a molar excess of the mixture of alcohols of formula (II) under mechanical stirring under predetermined temperature and partial vacuum conditions, for example at a temperature between 70 ° C and 130 ° C and under a partial vacuum between 300 mbar (3.104 Pa) and 20 mbar (2.103 Pa).
  • acidic catalytic system strong acids such as sulfuric acid, hydrochloric acid, phosphoric acid, nitric acid, hypophosphorous acid, methanesulfonic acid, para-toluene sulfonic acid, trifluoromethanesulfonic acid, or ion exchange resins.
  • the process as defined above may further comprise neutralization, filtration and bleaching operations.
  • the subject of the invention is also the use of the water-in-oil emulsion (E) as defined above as a thickening and / or emulsifying and / or stabilizing agent for a topical cosmetic, dermopharmaceutical or pharmaceutical composition.
  • E water-in-oil emulsion
  • said use consists in thickening polar phases such as, for example, aqueous, alcoholic or hydroalcoholic phases or polar phases comprising polyols such as glycerol.
  • polar phases such as, for example, aqueous, alcoholic or hydroalcoholic phases or polar phases comprising polyols such as glycerol.
  • said use consists in stabilizing an oil-in-water or water-in-oil type emulsion, conferring a homogeneous appearance to said emulsion during storage under different conditions, and more particularly to ° C for a period of at least one month, more particularly at 4 ° C for a period of at least one month, and more particularly at 45 ° C for a period of at least one month.
  • said use consists in stabilizing solid particles in topical cosmetic, dermopharmaceutical or pharmaceutical compositions.
  • These solid particles to suspend can take different geometries, regular or irregular, and be in the form of beads, beads, rods, flakes, lamellae or polyhedra. These solid particles are characterized by an apparent average diameter of between one micrometer and five millimeters, more particularly between ten micrometers and one millimeter.
  • the solid particles that can be suspended and stabilized by the water-in-oil emulsion (E) as defined above in topical cosmetic, dermopharmaceutical or pharmaceutical compositions there are micas, iron, titanium oxide, zinc oxide, aluminum oxide, talc, silica, kaolin, clays, boron nitride, calcium carbonate, magnesium carbonate, magnesium hydrogencarbonate, inorganic colored pigments, polyamides such as nylon-6, polyethylenes, polypropylenes, polystyrenes, polyesters, acrylic or methacrylic polymers such as polymethyl methacrylates, polytetrafluoroethylene, crystalline or microcrystalline waxes, porous spheres , the selenium sulphide, zinc pyrithione, starches, alginates, plant fibers, Loofah particles, sponge particles.
  • micas such as nylon-6, polyethylenes, polypropylenes, polystyrenes, polyesters, acrylic or methacrylic polymers such as polymethyl methacryl
  • the subject of the invention is also a topical cosmetic composition (F) comprising for 100% of its total mass between 0.1% and 10% by weight of the water-in-oil emulsion (E) as defined above. and a topical pharmaceutical composition (G) characterized in that it comprises, as a thickening agent, for 100% of its total mass between 0.1% and 10% by weight of the water-in-oil type emulsion ( E) as defined in one of claims 1 to 8.
  • compositions (F) and (G) means that they are implemented by application to the skin, hair, scalp or mucous membranes, that it is is a direct application in the case of a cosmetic, dermocosmetic, dermopharmaceutical or pharmaceutical preparation or an indirect application for example in the case of a body care product in the form of textile or paper towel or products sanitary preparations intended to be in contact with the skin or the mucous membranes.
  • compositions (F) and (G) are generally in the form of an aqueous or hydro-alcoholic or hydro-glycolic solution, in the form of a suspension, an emulsion, a microemulsion or a nano emulsion, whether of the water-in-oil, oil-in-water, water-in-oil-in-water or oil-in-water-in-oil type.
  • compositions (F) and (G) as defined above can be packaged in a vial, in a device of the "vial” pump type, in pressurized form in an aerosol device, in a device provided with a perforated wall such as a grid or in a device provided with a ball applicator (called “roll-on").
  • compositions (F) and (G) also comprise excipients and or active principles usually used in the field of formulations for topical use, in particular cosmetic, dermocosmetic, pharmaceutical or dermopharmaceutical, such as thickening surfactants and and / or gelling agents, stabilizers, film-forming compounds, hydrotropic agents, plasticizers, emulsifiers and co-emulsifiers, opacifying agents, pearlescent agents, superfatting agents, sequestering agents, chelating agents, antioxidants, perfumes, preservatives, conditioning agents, whitening agents for hair and skin discoloration, active principles intended to provide a treatment action with respect to the skin or the hair, sunscreens, mineral fillers or pigments, particles providing a visual effect or intended for the encapsulation of a exfoliating particles, texture agents.
  • cosmetic, dermocosmetic, pharmaceutical or dermopharmaceutical such as thickening surfactants and and / or gelling agents, stabilizers, film-forming compounds, hydrotropic agents,
  • foaming and / or detergent surfactants that can be associated with the water-in-oil emulsion (E) in the said compositions (F) and (G) as defined above
  • foaming surfactants may be mentioned. and / or anionic, cationic, amphoteric or nonionic detergents.
  • foaming and / or detergent anionic surfactants that can be combined with the water-in-oil emulsion (E) in said compositions (F) and (G) as defined above, mention may be made of alkali metals, alkaline earth metals, ammonium, amines, or aminoalcohols of alkyl ether sulfates, alkyl sulfates, alkylamidoether sulfates, alkylaryl polyethersulfates, monoglycerides sulfates, alpha-olefin sulfonates , paraffin sulfonates, alkyl phosphates, alkyl ether phosphates, alkyl sulphonates, alkylamide sulphonates, alkylaryl sulphonates, alkyl carboxylates, alkyl sulphosuccinates, alkyl ether sulphosuccinates, alkylamide sulphosuccinates, alkyl
  • alkylbetaines may be mentioned, alkylamidobetaines, sultaines, alkylamidoalkylsulfobetaines, imidazoline derivatives, phosphobetaines, amphopolyacetates and amphopropionates.
  • foaming and / or detergent cationic surfactants that can be associated with the water-in-oil emulsion (E) in said compositions (F) and (G) as defined above, there may be mentioned in particular the derivatives of quaternary ammoniums.
  • foaming and / or detergent nonionic surfactants that can be associated with the water-in-oil emulsion (E) in said compositions (F) and (G) as defined above, mention may be made more particularly alkylpolyglycosides having a linear or branched, saturated or unsaturated aliphatic radical containing from 8 to 16 carbon atoms, such as octyl polyglucoside, decyl polyglucoside, undecylenyl polyglucoside, dodecyl polyglucoside, tetradecyl polyglucoside, hexadecyl polyglucoside, 1-12 dodecanediyl polyglucoside; ethoxylated hydrogenated castor oil derivatives such as the product marketed under the INCI name "Peg-40 hydrogenated castor oil”; polysorbates such as Polysorbate 20, Polysorbate 40, Polysorbate 60, Polysorbate 70, Polysorbate 80, Polysorbate 85; coconut amides;
  • thickening and / or gelling surfactants that can be associated with the water-in-oil emulsion (E) in said compositions (F) and (G) as defined above
  • fatty esters of possible alkylpolyglycosides alkoxylates such as ethoxylated methylpolyglucoside esters such as PEG 120 methyl glucose trioleate and PEG 120 methyl glucose dioleate respectively marketed under the names GLUCAMATE TM LT and GLUMATE TM DOE120
  • alkoxylated fatty esters such as PEG 150 pentaerythrityl tetrastearate marketed under the name CROTHIX TM DS53, PEG 55 propylene glycol oleate sold under the name ANTIL TM 141
  • fatty chain polyalkylene glycol carbamates such as PPG-14 laureth isophoryl dicarbamate marketed under the name ELFACOS TM T21 1, PPG-14 palm
  • thickening and / or gelling agents that can be combined with the water-in-oil emulsion (E) in said compositions (F) and (G) as defined above, include copolymers AMPS and alkyl acrylates whose carbon chain comprises between four and thirty carbon atoms and more particularly between ten and thirty carbon atoms, linear terpolymers, connected or crosslinked with at least one monomer having a function strong, free, partially salified or totally salified acid, with at least one neutral monomer, and at least one monomer of formula (XVII):
  • R'3 represents a hydrogen atom or a methyl radical
  • R'4 represents a linear or branched alkyl radical containing from eight to thirty carbon atoms and n represents a number greater than or equal to one and less than or equal to fifty .
  • thickening and / or gelling agents that can be associated with the water-in-oil emulsion (E) in the said compositions (F) and (G) as defined above
  • thickening and / or gelling agents that can be associated with the water-in-oil emulsion (E) in the said compositions (F) and (G) as defined above
  • polysaccharides composed of saccharide derivatives, such as sulphated galactans and more particularly carrageenans and agar, uronans and more particularly alginines, alginates and pectins, heteropolymers of oses and uronic acids and more particularly gum xanthan, gellan gum, exudates of arabic gum and karaya gum, glucosaminoglycans.
  • thickening and / or gelling agents that can be associated with the water-in-oil emulsion (E) in said compositions (F) and (G) as defined above, mention may be made of cellulose cellulose derivatives such as methyl cellulose, ethyl cellulose, hydroxypropyl cellulose, silicates, starch, hydrophilic derivatives of starch, polyurethanes.
  • stabilizing agents that can be combined with the water-in-oil emulsion (E) in said compositions (F) and (G) as defined above include microcrystalline waxes, and more particularly ozokerite, inorganic salts such as sodium chloride or magnesium chloride, silicone polymers such as polysiloxane polyalkyl polyether copolymers.
  • solvents that can be associated with the water-in-oil emulsion (E) in said compositions (F) and (G) as defined above, mention may be made of water, organic solvents such as glycerol, diglycerol, glycerol oligomers, ethylene glycol, propylene glycol, butylene glycol, 1,3-propanediol, 1,2-propanediol, hexylene glycol, diethylene glycol, xylitol, erythritol, sorbitol, water-soluble alcohols such as ethanol, isopropanol or butanol, water mixtures and said organic solvents.
  • organic solvents such as glycerol, diglycerol, glycerol oligomers, ethylene glycol, propylene glycol, butylene glycol, 1,3-propanediol, 1,2-propanediol, hexylene glycol, diethylene glycol, xy
  • thermal or mineral waters that can be associated with the water-in-oil emulsion (E) in said compositions (F) and (G) as defined above, include thermal waters or Mineral having a mineralization of at least 300 mg / l, in particular Avene water, Vittel water, Vichy basin water, Uriage water, Roche Posay water, the water of the Bourboule, the water of Enghien-les-Bains, the water of Saint-Gervais-les Bains, the water of Néris-les-Bains, the water of Allevard-les-Bains, Digne water, Maizieres water, Neyrac-les-bains water, Lons le Saunier water, Rochefort water, Saint Christau water, Fumades water and water water water of Tercis-les-bains.
  • thermal waters or Mineral having a mineralization of at least 300 mg / l in particular Avene water, Vittel water, Vichy basin water, Uriage water, Roche Posay water, the water of the Bourboule, the water of
  • hydrotropic agents which can be associated with the water-in-oil emulsion (E) in said compositions (F) and (G) as defined above, mention may be made of xylenesulfonates and cumenes. sulfonates, hexyl polyglucoside, 2-ethylhexyl polyglucoside, n-heptyl polyglucoside.
  • emulsifying surfactants examples include nonionic surfactants, anionic surfactants, cationic surfactants.
  • emulsifying nonionic surfactants that may be combined with the water-in-oil emulsion (E) in said compositions (F) and (G) as defined above, include esters of fatty acids and sorbitol, as products marketed under the names MONTANE TM 40, MONTANE TM 60, MONTANE TM 70, MONTANE TM 80 and MONTANE TM 85; compositions comprising glycerol stearate and ethoxylated stearic acid between 5 moles and 150 moles of ethylene oxide, such as the composition comprising stearic acid ethoxylated with 135 moles of ethylene oxide and glycerol stearate.
  • alkylpolyglycosides comprising a linear or branched, saturated or unsaturated aliphatic radical containing from 14 to 36 carbon atoms, for instance tetradecyl polyglucoside, hexadecyl polyglucoside, octadecyl polyglucoside, hexadecylpolyxyloside or octadecylpolyxyloside, eicosyl polyglucoside, dodecosyl polyglucoside, 2-octyldodecyl polyxyloside, 12-hydroxystearyl polyglucoside; linear or branched fatty alcohol compositions, saturated or unsaturated, and comprising from 14 to 36 carbon atoms, and alkylpolyglycosides as described above, for example the composition
  • anionic surfactants that can be associated with the water-in-oil emulsion (E) in said compositions (F) and (G) as defined above, mention may be made of glyceryl stearate citrate, cetearyl sulphate , soaps such as sodium stearate or triethanolammonium stearate, N-acyl derivatives of salified amino acids, for example stearoyl glutamate.
  • emulsifying cationic surfactants which may be associated with the water-in-oil emulsion (E) in said compositions (F) and (G) as defined above, include aminoxides, quaternium 82 and the surfactants described in WO96 / 00719 and mainly those whose fatty chain comprises at least 16 carbon atoms.
  • opacifying and / or pearling agents which may be associated with the water-in-oil emulsion (E) in said compositions (F) and (G) as defined above, include palmitate of sodium, sodium stearate, sodium hydroxystearate, magnesium palmitate, magnesium stearate, magnesium hydroxystearate, ethylene glycol monostearate, ethylene glycol distearate, polyethylene glycol monostearate, polyethylene glycol distearate, fatty alcohols having from 12 to 22 carbon atoms.
  • N-acyl derivatives As examples of texturizing agents that can be associated with the water-in-oil emulsion (E) in said compositions (F) and (G) as defined above, mention may be made of N-acyl derivatives. amino acids, such as lauroyl lysine marketed under the name AMINOHOPE TM LL, octenyl starch succinate marketed under the name DRYFLO TM, myristyl polyglucoside marketed under the name MONTANOV TM 14, cellulose fibers, cotton fibers, chitosan fibers, talc, sericite, mica.
  • amino acids such as lauroyl lysine marketed under the name AMINOHOPE TM LL, octenyl starch succinate marketed under the name DRYFLO TM, myristyl polyglucoside marketed under the name MONTANOV TM 14, cellulose fibers, cotton fibers, chitosan fibers, talc, sericite,
  • deodorant agents that can be combined with the water-in-oil emulsion (E) in said compositions (F) and (G) as defined above include alkali silicates, salts zinc such as zinc sulphate, zinc gluconate, zinc chloride, zinc lactate; quaternary ammonium salts such as cetyltrimethylammonium salts, cetylpyridinium salts; glycerol derivatives such as glycerol caprate, glycerol caprylate, polyglycerol caprate; the 1, 2 decanediol; 1,3 propanediol; salicylic acid; sodium bicarbonate; cyclodextrins; metallic zeolites; TRICLOSAN TM; aluminum bromohydrate, aluminum chlorohydrates, aluminum chloride, aluminum sulphate, aluminum and zirconium hydrochlorides, aluminum and zirconium trihydrochloride, aluminum zirconium tetrachlorohydrate , aluminum and zirconium
  • oils that can be associated with the water-in-oil emulsion (E) in said compositions (F) and (G) as defined above, mention may be made of mineral oils such as paraffin oil, petrolatum oil, isoparaffins or mineral white oils; oils of animal origin, such as squalene or squalane, vegetable oils, such as phytosqualane, sweet almond oil, coconut oil, castor oil, jojoba oil, olive oil, rapeseed oil, peanut oil, sunflower oil, wheat germ oil, corn germ oil, soybean oil, cottonseed oil, alfalfa oil, poppy oil, pumpkin oil, evening primrose oil, millet oil, barley oil, rye oil, Safflower oil, sayoulier oil, passionflower oil, hazelnut oil, palm oil, shea butter, apricot kernel oil, calophyllum oil, sysymbrium oil, avocado oil, calendula oil, oils derived from flowers or vegetables ethoxylated vegetable oils; synthetic oils such as
  • fatty acids such as glycerol triheptanoate, alkylbenzoates, hydrogenated oils, poly (alpha-olefin), polyolefins such as poly (isobutane), synthetic isoalkanes such as isohexadecane, isododecane, perfluorinated oils; silicone oils such as dimethylpolysiloxanes, methylphenylpolysiloxanes, amine-modified silicones, fatty acid-modified silicones, alcohols-modified silicones, alcohol-modified silicones and fatty acids, modified silicones, polyether groups, modified epoxy silicones, silicones modified with fluorinated groups, cyclic silicones and silicones modified with alkyl groups.
  • oils is meant herein the compounds and / or the mixtures of water-insoluble compounds having a liquid appearance at a temperature of 25 ° C.
  • waxes that may be associated with the water-in-oil emulsion (E) in the said compositions (F) and (G) as defined above, mention may be made of beeswax and wax carnauba wax, candelilla wax, ouricoury wax, Japanese wax, cork fiber wax, sugar cane wax, paraffin waxes, lignite waxes, microcrystalline waxes, lanolin; ozokerite; polyethylene wax; silicone waxes; vegetable waxes; fatty alcohols and solid fatty acids at room temperature; glycerides solid at room temperature.
  • waxes is meant in the present application the compounds and / or mixtures of compounds insoluble in water, having a solid appearance at a temperature greater than or equal to 45 ° C.
  • Examples of active principles that can be associated with the water-in-oil emulsion (E) in said compositions (F) and (G) as defined above, include vitamins and their derivatives, in particular their esters, such as retinol (vitamin A) and its esters (retinyl palmitate for example), ascorbic acid (vitamin C) and its esters, ascorbic acid sugar derivatives (such as ascorbyl glucoside) tocopherol (vitamin E) and its esters (such as tocopherol acetate), vitamins B3 or B10 (niacinamide and its derivatives); compounds showing a lightening or depigmenting action on the skin, such as w-undecelynoyl phenylalanine marketed under the name SEPIWHITE TM MSH, SEPICALM TM VG, the mono ester and / or the glycerol diester of w-undecelynoyl phenylalanine, the w-undecelyn
  • SURVICODE TM anti-aging photo active ingredients
  • the active ingredients protecting the integrity of the dermal-epidermal junction
  • actives enhancing the synthesis of extracellular matrix components such as collagen, elastins, glycosaminoglycans
  • assets acting favorably on chemical cellular communication such as cytokines or physical ones such as integrins
  • active ingredients that create a sensation of "heating" on the skin such as activators of cutaneous microcirculation (such as nicotinic acid derivatives) or products that create a sensation of "freshness" on the skin (such as menthol and derivatives)
  • the active agents improving cutaneous microcirculation, for example the venotonic ones
  • draining assets decongestant active ingredients such as extracts of ginko biloba, ivy, horse chestnut, bamboo, ruscus, holly, centalla asiatica, fucus, rosemary, willow; tanning agents or skin browning agents, for example dihydroxyacetone (DHA),
  • antioxidants that can be associated with the water-in-oil emulsion (E) in said compositions (F) and (G) as defined above, mention may be made of EDTA and its salts , citric acid, tartaric acid, oxalic acid, BHA (butylhydroxyanisol), BHT (butylhydroxytoluene), tocopherol derivatives such as tocopherol acetate, mixtures of antioxidant compounds such as DISSOLVINED GL 47S marketed by Akzo Nobel under the name INCI: Tetrasodium Glutamate Diacetate.
  • sunscreens that can be associated with the water-in-oil emulsion (E) in said compositions (F) and (G) as defined above, mention may be made of all those appearing in the cosmetic directive 76/768 / EEC as amended Annex VII.
  • the family of the derivatives of the benzoic acid such as para-aminobenzoic acids (PABA), in particular the monoglycerol esters of PABA, the ethyl esters of N, N-propoxy PABA, the ethyl esters of N, N-diethoxy PABA, the ethyl esters of N, N- dimethyl PABA, N, N-dimethyl PABA methyl esters, butyl N, N-dimethyl PABA esters; the family of anthranilic acid derivatives such as homomenthyl-N-acetyl anthranilate; the family of salicylic acid derivatives such as amyl salicylate, homomenthyl salicylate, ethylhexyl salicylate, phenyl salicylate, benzyl salicy
  • inorganic screens which can be associated with the water-in-oil emulsion (E) in said compositions (F) and (G) as defined above, it is possible to mention titanium oxides, zinc oxides, cerium oxide, zirconium oxide, iron oxides yellow, red or black, chromium oxides.
  • These inorganic screens may or may not be micronized, have undergone or not surface treatments and may be presented in the form of aqueous or oily pre-dispersions.
  • the mixture (Mi) is homogenized at 90 ° C for thirty minutes, then added 8.7 kilograms (one molar equivalent) of glucose, then 80 grams of 98% sulfuric acid.
  • the reaction medium is then placed under a partial vacuum of 90x10 2 Pa (90mbar) at 45x10 2 Pa (45mbar), and maintained at a temperature of 100 ° C to 105 ° C for five hours with evacuation of the water formed.
  • the reaction medium is then cooled to 80 ° C. and neutralized by adding 76 grams of 40% sodium hydroxide.
  • the product is filtered to remove unreacted glucose.
  • 36.6 kilograms of the reaction medium thus neutralized are then introduced into a thin film film evaporator, under a reduced pressure of 3 ⁇ 10 2 Pa (3mbar) at 5 ⁇ 10 Pa (5mbar) with a wall temperature of 240 ° C., to distil most of the residual alcohols and obtain 4.5 kilograms of a concentrate, to which 4.5 kilograms of glycerol are added gradually with stirring, so as to obtain 9.0 kilograms of the composition (C e 2a) expected.
  • Example 1 The procedure of Example 1 described above is reproduced by replacing the glycerol with diglycerol, in mass proportions such that they make it possible to obtain the composition (C e 2B), comprising for 100% of its mass, 50% by weight of diglycerol.
  • C e 2c Preparation of a composition (C e 2c) based on alkylpolyglucosides and polyglycerol-6
  • Example 1 The procedure of Example 1 described above is reproduced by replacing the glycerol with polyglycerol-6 (marketed under the brand name Polyglycerol TM TM from the company SPIGA), in mass proportions such that they make it possible to obtain the composition (C e 2c), comprising for 100% of its mass, 50% by mass of polyglycerol-6.
  • polyglycerol-6 marketed under the brand name Polyglycerol TM TM from the company SPIGA
  • Example 1 The procedure of Example 1 described above is reproduced by replacing glycerol with 1,3-propanediol (sold under the trade name Zemea TM propanediol Dupont-Tate & Lyle), in mass proportions such that they make it possible to obtain the composition (C e 2 T ) comprising for 100% of its mass, 22% by weight of 1,3-propanediol.
  • 1,3-propanediol sold under the trade name Zemea TM propanediol Dupont-Tate & Lyle
  • An aqueous phase is prepared by successively pouring into a beaker and with stirring, 277 grams of deionized water, 73.1 grams of glacial acrylic acid, 308 grams of 2-methyl - [(1-oxo-2-propenyl) acid. ) amino] 1-propanesulfonic acid, 141 grams of a 48% by weight aqueous solution of sodium hydroxide, 0.45 grams of a 40% by weight aqueous solution of diethylenetriamine penta-sodium acetate and 0.128 grams methylene bis (acrylamide). The pH of this aqueous phase is then adjusted to 5.4 and the solution supplemented with deionized water to a weight of 682 grams.
  • An organic phase is independently prepared by mixing 220 grams of isohexadecane, 15 grams of Montané TM 80, 10 grams of Montané TM 70 and 0.2 grams of azobis (isobutyronitrile) (AIBN).
  • the aqueous phase prepared is then gradually added to the oily phase and then dispersed using an Ultra Turrax type rotor rotor marketed by Ika.
  • the resulting emulsion is transferred to a reactor to be sparged with nitrogen to remove oxygen and cooled to about 5-6 ° C.
  • 5 cm 3 of a 0.42% by weight solution of cumene hydroperoxide in isohexadecane are added to the emulsion while stirring, and then a 2.5% by weight aqueous solution of sodium metabisulphite is introduced. progressively at a rate of 0.5 cm 3 per minute for sixty minutes to initiate the polymerization reaction. The temperature of the medium increases until reaching a plateau.
  • the reaction medium is then heated at 85 ° C for one hour and then the whole is cooled to about 35 ° C to obtain the mixture noted (M 2 ).
  • the mixture (M 2 ) obtained previously is fractionated into different portions to which are added the various surfactant compositions ((C e 2A)), (C e 2B), (C e 2c) and (C e 2 T ), as described above, as well as Polysorbate 80 (78% by weight of active material) sold under the brand name Montanox TM 80 (S2), and an aqueous solution of capryl / caprylyl polyglucosides (60% by weight of active ingredient) marketed under the brand name Simulsol TM SL8 (denoted Composition S'2), in mass proportions as indicated in Table 1 below.
  • the inverse self-reversible latexes resulting from these mixtures are respectively denoted (Ei), (E 2 ), (E 3 ), (Eci), (Ec 2 ) and (E ⁇ ) and are evaluated by observation of their appearance.
  • Ei The inverse self-reversible latexes resulting from these mixtures are respectively denoted (Ei), (E 2 ), (E 3 ), (Eci), (Ec 2 ) and (E ⁇ ) and are evaluated by observation of their appearance.
  • at 25 ° C by their viscosity at 25 ° C, by the rate of inversion during the preparation of an aqueous gel with 2% by mass of self-invertible inverse latex, by the viscos
  • the method for evaluating the inversion time of the self-invertible inverse latex is to pour into a one-liter beaker the amount of water needed to prepare an aqueous gel of 800 grams.
  • a Turbotest TM mechanical agitator propeller connected to a motor is placed toward the bottom of the beaker.
  • the stirring is started at a speed of 200 rpm and the necessary amount of self-invertible inverse latex to be evaluated is introduced into the beaker with stirring.
  • the stirring is gradually increased in order to maintain the same vortex height in the beaker throughout the thickening phase, until a homogeneous and smooth gel is obtained.
  • the inversion time of the inverse self-reversing latexes corresponds to the time elapsed between the beginning of the addition of the tested self-invertible inverse latex and the production of a smooth gel, free of lumps.
  • the results obtained are shown in Table 1 below.
  • the inverse self-reversing (Ei), (E 2 ) and (E 3 ) latexes according to the invention which are free of alkoxylated derivatives, make it possible to obtain smooth gels with an inversion time of less than 10 minutes, possessing excellent thickening properties. Moreover they are characterized a lower drop in the viscosity of a gel at 3% by mass in the presence of salt compared in particular with the self-invertible inverse latex (Es'2).
  • An aqueous phase is prepared by successively pouring into a beaker and stirring, 220 grams of deionized water, 343.5 grams of 2-methyl - [(1-oxo-2-propenyl) amino] 1-propanesulfonic acid, 138 1 gram of a 48% by weight aqueous solution of sodium hydroxide, 0.18 gram of a 40% by weight commercial solution of diethylenetriamine penta-sodium acetate and 0.140 gram of methylene bis (acrylamide). The pH of this aqueous phase is then adjusted to 3.5 and the solution supplemented with deionized water to weigh 707 grams.
  • An organic phase is independently prepared by mixing 220 grams of isohexadecane, 22 grams of Montane TM 80VG, and 0.2 gram of AIBN.
  • the aqueous phase prepared is then gradually added to the oily phase and then dispersed using an Ultra Turrax type rotor rotor marketed by Ika.
  • the resulting emulsion is transferred to a reactor to be sparged with nitrogen to remove oxygen and cooled to about 5-6 ° C.
  • 5 cm 3 of a 0.42% by weight solution of cumene hydroperoxide in isohexadecane are added to the emulsion while stirring, and then a 2.5% by weight aqueous solution of sodium metabisulphite is introduced. progressively at a rate of 0.5 cm 3 per minute for sixty minutes to initiate the polymerization reaction. The temperature of the medium will increase until reaching a plateau. The reaction medium is maintained at this temperature for one hour and a half then the whole is cooled to about 35 ° C to obtain the mixture noted (M3).
  • the mixture (M 3 ) previously obtained is fractionated into different portions, to which are added various surfactant compositions (C e 2A), (S 2) and (S'2), in mass proportions as indicated in Table 2 below. below, to obtain the inverse self-reversing latexes respectively referenced (E 4 ), (Ec 4 ) and (Ecs). They are valued as in the previous paragraph II. The results obtained are shown in Table 2 below.
  • the self-invertible inverse latex (E 4 ) according to the invention free of alkoxylated and more particularly ethoxylated derivatives, makes it possible to obtain a smooth gel, with an inversion time of less than 10 minutes, having excellent thickening properties.
  • An aqueous phase is prepared by successively pouring into a beaker and with stirring, 20.4 grams of (2-hydroxyethyl) acrylate, 660 grams of a commercial aqueous solution containing 55% by weight of Sodium [(1-oxo-2-propenyl) amino] -propanesulfonate, 0.45 grams of a 40% by weight aqueous solution of sodium diethylenetriamine pentaacetate and 0.123 grams of methylene bis (acrylamide). The pH of this aqueous phase is then adjusted to 4.0 by adding 0.55 grams of 2-methyl-[(1-oxo-2-propenyl) amino] 1-propanesulfonic acid.
  • An organic phase is independently prepared by mixing 265 grams of squalane, 17.76 grams of Montane TM 80 VG, 9.24 grams of Montanox TM 81 VG and 0.2 grams of azobis (isobutyronitrile) (AIBN).
  • the aqueous phase prepared is then gradually added to the oily phase and then dispersed using an Ultra Turrax type rotor rotor marketed by Ika.
  • the resulting emulsion is transferred to a reactor to be sparged with nitrogen to remove oxygen and cooled to about 5-6 ° C.
  • 10 cm 3 of a 0.28% by weight solution of cumene hydroperoxide in squalane are added to the emulsion while stirring, and then a 2.5% by weight aqueous solution of sodium metabisulphite is gradually introduced.
  • the reaction medium is then maintained for approximately 60 minutes at this temperature, at the end from which the resulting mixture is cooled to about 35.
  • the whole is cooled to a temperature of about 35 ° C (M 4 ).
  • the mixture (M 4 ) previously obtained is fractionated into different portions to which are added the various surfactant compositions (C e 2A), (S 2), and (S'2), in mass proportions as indicated in Table 3 above. -Dessous.
  • the self-invertible inverse latex (E 5 ) according to the invention free of alkoxylated and more particularly ethoxylated derivatives, makes it possible to obtain a smooth gel, with an inversion time of less than 10 minutes, having excellent thickening properties.
  • An aqueous phase is prepared by successively pouring into a beaker and with stirring, 80 grams of deionized water, 253.8 grams of a commercial aqueous solution. to 50% by weight of acrylamide, 246.7 grams of 2-methyl - [(1-oxo-2-propenyl) amino] 1-propanesulfonic acid, 95.96 grams of a 48% aqueous solution by weight sodium hydroxide, 0.45 grams of a 40% by weight commercial solution of diethylenetriamine penta-sodium acetate and 0.115 grams of methylene bis (acrylamide). The pH of this aqueous phase is then adjusted to 5.5 and the solution supplemented with deionized water to a weight of 682 grams.
  • An organic phase is independently prepared by mixing 220 grams of isohexadecane, 21 grams of Montané TM 80 VG and 0.2 grams of azobis (isobutyronitrile) (AIBN).
  • the aqueous phase prepared is then gradually added to the oily phase and then dispersed using an Ultra Turrax type rotor rotor marketed by Ika.
  • the resulting emulsion is transferred to a reactor to be sparged with nitrogen to remove oxygen and cooled to about 5-6 ° C.
  • 5 cm 3 of a 0.28% by weight solution of cumene hydroperoxide in hexadecane are added to the emulsion while stirring, and then a 2.5% by weight aqueous solution of sodium metabisulphite is introduced. gradually at a rate of 0.5 cm 3 per minute for sixty minutes to initiate the polymerization reaction and allowing the temperature to rise to 75 ° C.
  • the reaction medium is then maintained for approximately 60 minutes at this temperature, at room temperature. from which the resulting mixture is cooled to about 35 ° C.
  • the whole is cooled to a temperature of about 35 ° C (M 5 ).
  • the mixture (M 5 ) previously obtained is fractionated into different portions to which are added different mass proportions of the surfactant composition (Ce2A), as indicated in Table 4 below.
  • Carrageenan l 0.10%
  • Titanium oxide 8%
  • MICROPEARL TM M 100 is an ultra-fine powder with a very soft feel and mattifying action
  • SEPICIDE TM Cl imidazolidine urea
  • SIMULSOL TM 165 is self-emulsifiable glycerol stearate
  • SEPICIDE TM HB a mixture of phenoxyethanol, methylparaben, ethylparaben, propylparaben and butylparaben, is a preservative
  • PARSOL TM MCX is octyl para-methoxy cinnamate
  • LANOL TM 37T is glycerol triheptanoate
  • SOLAGUM TM L is a carrageenan
  • EUSOLEX TM 4360 is a sunscreen
  • DEEPALINE TM PVB is an acylated wheat protein hydrolyzate
  • PRIMOL TM 352 is a mineral oil
  • PECOSIL TM PS 100 is Dimethicone PEG-7
  • Montanov TM 68 (INCI name Cetearyl Aicohol (and) Cetearyi Giucoside) is an emulsifying agent
  • Montanov TM L (INCI name C14-22 Alcohols (and) C12-2Q Aikyi Giucoside) is an emulsifying agent
  • Montanov TM 202 (INCI name Arachidyl Aicohol & Behenyl Aicohol & Arachidyl) is an emulsifying agent

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EP18826410.5A 2017-11-21 2018-11-16 Selbstinvertierender inverser latex mit alkylpolyglycosiden als invertierungsmittel, verwendung davon als verdickungsmittel und diese enthaltende kosmetische zusammensetzungen Withdrawn EP3713539A1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR1760987A FR3073854B1 (fr) 2017-11-21 2017-11-21 Latex inverse auto-inversible, comprenant comme agent inverseur des alkylpolyglycosides, son utilisation comme agent epaississant, et compositions cosmetiques en comprenant
PCT/FR2018/052887 WO2019102116A1 (fr) 2017-11-21 2018-11-16 Latex inverse auto-inversible, comprenant comme agent inverseur des alkylpolyglycosides, son utilisation comme agent épaississant, et compositions cosmétiques en comprenant

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EP3713539A1 true EP3713539A1 (de) 2020-09-30

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EP (1) EP3713539A1 (de)
JP (1) JP2021504322A (de)
CN (1) CN111356431A (de)
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WO (1) WO2019102116A1 (de)

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EP3795134B1 (de) * 2019-09-19 2023-05-10 Société d'Exploitation de Produits pour les Industries Chimiques SEPPIC Stabile duftzusammensetzungen, die gute sprüheigenschaften besitzen
FR3104165B1 (fr) * 2019-12-09 2021-12-17 Soc Dexploitation De Produits Pour Les Industries Chimiques Seppic Latex inverse pour composition cosmétique comprenant un agent séquestrant particulier et un polyélectrolyte combinant fonction acide forte et fonction neutre
CN112169713A (zh) * 2020-09-09 2021-01-05 江南大学 一种n-烷基乳糖胺表面活性剂小分子醇凝胶及其制备方法
KR102453976B1 (ko) * 2021-03-30 2022-10-14 주식회사 비제이바이오켐 다당류 유도체 및 이의 제조 방법

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FR2721607B1 (fr) 1994-06-28 1996-10-31 Seppic Sa Nouveaux dérivés d'ammoniums quaternaires, leur procédé de préparation et leur utilisation comme agents de surface.
FR2761595B1 (fr) 1997-04-04 1999-09-17 Oreal Compositions comprenant des santalines, santarubines pour la coloration artificielle de la peau et utilisations
FR2794124B1 (fr) * 1999-05-28 2003-03-21 Seppic Sa Nouveau latex inverse auto inversible, procede de preparation et utilisation en cosmetique
FR2794034B1 (fr) 1999-05-28 2001-08-03 Seppic Sa Utilisation d'alkylpolyglycosides comme inverseur d'emulsions de polymeres, procede d'inversion d'emulsions, latex inverse auto inversible et leurs utilisations industrielles
FR2808447B1 (fr) 2000-05-05 2004-12-03 Seppic Sa Latex inverses sur huiles blanches minerales, squalane ou polyisobutene hydrogene, compositions cosmetiques, dermocosmetiques, dermopharmaceutiques ou pharmaceutiques en comportant
FR2808446B1 (fr) 2000-05-05 2004-12-03 Seppic Sa Latex inverses sur huiles blanches minerales, squalane, polyisobutene hydrogene, isohexadecane ou isododecane, compositions cosmetiques ou pharmaceutiques en comportant
FR2810883B1 (fr) 2000-06-28 2006-07-28 Seppic Sa Nouveaux latex inverses autoinversibles sur des esters d'acides gras, compositions cosmetiques, dermocosmetiques, dermopharmaceutiques ou pharmaceutiques en comportant
EP1515688B1 (de) 2002-06-11 2013-07-24 L'Oréal Verwendung vom Salen-Mangan-Komplexen als Schutzmittel für Melanocyten in Haarfollikeln und kosmetische Verwendungen
FR2933097B1 (fr) * 2008-06-27 2010-08-20 Seppic Sa Nouveaux latex inverses exempts de derives oxyethyleniques, compositions cosmetiques, dermocosmetiques, dermopharmaceutiques ou pharmaceutiques en comportant
FR2942146B1 (fr) * 2009-02-19 2011-03-11 Seppic Sa Nouvelle composition emulsionnante pulverulente d'alkyl polyglycosides, leur utilisation pour preparer des emulsions cosmetiques et procedes pour leurs preparations

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FR3073854A1 (fr) 2019-05-24
FR3073854B1 (fr) 2019-11-01
WO2019102116A1 (fr) 2019-05-31
JP2021504322A (ja) 2021-02-15

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