EP3723712A1 - Neue alkylpolyrhamnoside, verfahren zur herstellung davon und kosmetische und/oder pharmazeutische zusammensetzungen damit - Google Patents

Neue alkylpolyrhamnoside, verfahren zur herstellung davon und kosmetische und/oder pharmazeutische zusammensetzungen damit

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Publication number
EP3723712A1
EP3723712A1 EP18830908.2A EP18830908A EP3723712A1 EP 3723712 A1 EP3723712 A1 EP 3723712A1 EP 18830908 A EP18830908 A EP 18830908A EP 3723712 A1 EP3723712 A1 EP 3723712A1
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EP
European Patent Office
Prior art keywords
weight
composition
equal
formula
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Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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Application number
EP18830908.2A
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English (en)
French (fr)
Inventor
Georges DACOSTA
Stéphane Dessilla
Jérôme GUILBOT
Virginie POMMERY
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 EP3723712A1 publication Critical patent/EP3723712A1/de
Pending legal-status Critical Current

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Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/60Sugars; Derivatives thereof
    • A61K8/604Alkylpolyglycosides; Derivatives thereof, e.g. esters
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/60Sugars; Derivatives thereof
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/19Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34Alcohols
    • A61K8/342Alcohols having more than seven atoms in an unbroken chain
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34Alcohols
    • A61K8/347Phenols
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36Carboxylic acids; Salts or anhydrides thereof
    • A61K8/365Hydroxycarboxylic acids; Ketocarboxylic acids
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37Esters of carboxylic acids
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41Amines
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/494Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
    • A61K8/4946Imidazoles or their condensed derivatives, e.g. benzimidazoles
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4973Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
    • A61K8/498Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom having 6-membered rings or their condensed derivatives, e.g. coumarin
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/60Sugars; Derivatives thereof
    • A61K8/602Glycosides, e.g. rutin
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/89Polysiloxanes
    • A61K8/891Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/14Preparations for removing make-up
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00Preparations for care of the skin
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00Preparations for care of the skin
    • A61Q19/10Washing or bathing preparations
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/02Preparations for cleaning the hair

Definitions

  • New alkyl polyramnosides process for their preparation and cosmetic and / or pharmaceutical composition
  • the present invention relates to a novel composition based on sugar derivatives, the process for its preparation and its use as an emulsifier.
  • the invention is mainly used in cosmetics and pharmacy.
  • compositions generally do not comprise more than 40% by weight of alkyl polyglycosides since obtaining compositions with a higher concentration of alkyl polyglycosides requires a subsequent step of either distilling fatty alcohols or a step of extraction with a fluid. the super-critical state, both energy-intensive.
  • the subject of the invention is a composition (Ci) comprising, for 100% of its mass:
  • R-OH An amount greater than 0% by weight and less than or equal to 60% by weight of an alcohol of formula (I): R-OH, in which R represents a radical saturated or unsaturated, linear or branched hydrocarbon-based hydrocarbon, which may comprise at least one hydroxyl function, and comprising from fourteen to twenty-two carbon atoms or from a mixture of alcohols of formula (I);
  • compositions (b) - An amount greater than or equal to 40% and less than 100% by weight of a composition (CR) represented by the formula (II): R-O- (Rham) x -H, in which the Rham residue represents the rest of the rhamnose, R is as defined previously in formula (I) and x, which indicates the average degree of polymerization of said Rham remainder, represents a decimal number greater than 1, 0 and less than or equal to 5; or a mixture of compositions (CR), and
  • aliphatic radical, saturated or unsaturated, linear hydrocarbon which may comprise at least one hydroxyl function, and comprising from fourteen to twenty-two carbon atoms, is denoted more particularly for R, in the formula (I) as defined above,
  • a radical derived from saturated or unsaturated linear primary alcohols such as the myristyl (or tetradecyl), pentadecyl, cetyl (or hexadecyl), heptadecyl, stearyl (or octadecyl), palmitoleyl (or 9-hexadecenyl), oleyl ( or 9-octadecenyl), linoleyl (9,12-octadecadienyl), linolenyl (or 6,9,12-octadecatrienyl) nonadecyl, arachidyl (or eicosyl), behenyl (or docosyl), erucyl (13-docosenyl), or 12- hydroxy stearyl.
  • a radical derived from saturated branched alcohols such as 2-hexyl octyl, 2-hexyl decyl, 2-hexyl dodecyl, 2-octyl decyl, 2-octyl dodecyl, 2-hexyl dodecyl, 2-decyl tetradecyl or 2-octyl decyl isostearyl (or 16-methylheptadecyl) or isomyristyl (or 13-methyltridecyl).
  • composition (CR) consists essentially of a mixture of compounds represented by the formulas (II-i), (II 2 ), (l) ,
  • the subject of the invention is mainly the composition (C1) as defined above, for which, in the formulas (I) and (II), R represents a hydrocarbon radical, linear or branched, saturated or unsaturated having from sixteen to twenty atoms of carbon ; and more particularly from sixteen to eighteen carbon atoms, such as that comprising, for 100% of its mass:
  • C RA composition represented by the formula (M A ): R A -O- (Rham) r H, in which the Rham residue represents the rest of the rhamnose, R A is as defined previously in the formula (U) and y represents a decimal number greater than 1, 0 and less than or equal to 5; and
  • C RB a composition represented by the formula (M B ): R B -O- (Rham) z -H, in which the Rham residue represents the rest of the rhamnose, R B is as defined previously in formula (I B ) and Z represents a decimal number greater than 1, 0 and less than or equal to 5; and (c) optionally an amount greater than 0% by weight and less than or equal to 5% by weight of rhamnose,
  • the invention also more particularly relates to the composition (C1) as defined above, for which, in formulas (I) and (II), R represents a hydrocarbon radical, linear or branched saturated or unsaturated comprising from twenty to twenty two carbon atoms, such as that comprising, for 100% of its mass:
  • composition represented by the formula (IIc): Rc-O- (Rham) rH , in which the Rham residue represents the rest of the rhamnose, Rc is as defined previously in the formula (le) and t represents a decimal number greater than 1, 0 and less than or equal to 5; and
  • composition represented by the formula (II D ): R D -O- (Rham) u -H, in which the Rham residue represents the rest of the rhamnose, RD is as defined previously in the formula (ID) and u represents a decimal number greater than 1, 0 and less than or equal to 5; and
  • composition (Ci) as defined above comprises, for 100% of its mass:
  • (c) optionally an amount of greater than 0% by weight and less than or equal to 5% by weight of rhamnose; and more particularly : (a) - An amount greater than 0% by weight and less than or equal to 20% by weight of said alcohol of formula (I) or said mixture of alcohols of formulas (I);
  • composition (Ci) as defined above is characterized in that in formulas (II), (MA), (MB), (II), and (II D ), the respective numbers x, y, z, t, and u each represents a decimal number greater than zero and less than or equal to 2.
  • the subject of the invention is also a method for preparing the composition (Ci) as defined in any one of Claims 1 to 9, characterized in that it comprises the following successive stages:
  • step c) of acetalization by adding under stirring in the liquid medium from step b) a catalytic amount of strong acid, maintaining the reaction mixture while partial vacuum and distilling the water formed;
  • step d) Filtration of the reaction mixture obtained in step c), and if necessary or if desired,
  • the term “moderate agitation” means mechanical agitation constituted by an agitator equipped with an “anchor” or “propeller” type blade, operated at a speed greater than or equal to 50 towers.
  • the strong acid is chosen in particular from sulfuric acid, hydrochloric acid, phosphoric acid, nitric acid, hypophosphorous acid, methanesulfonic acid, para-toluenesulphonic acid, trifluoromethanesulfonic acid and acid ion exchange resins.
  • the catalytic system used in step c) is a mixture of 98% sulfuric acid and hypophosphorous acid or a mixture of 98% sulfuric acid supported on silica and hypophosphorous acid.
  • step c the acetalization reaction is carried out at a temperature (T 2 ) of 70 ° C to 105 ° C under a vacuum of 300 to 20 10 2 Pa (300 to 20 mbar).
  • the d) filtration step of the process as defined above is generally carried out hot to keep the mixture to be filtered in sufficiently liquid state.
  • composition (Ci) as defined above can be used as an oil-in-water emulsifier for preparing any type of cosmetic or pharmaceutical composition intended to be applied to the skin or the mucous membranes in the form of an oil-in-oil emulsion. water.
  • the subject of the invention is also a topical cosmetic-dermocosmetic oil-in-water emulsion (C), characterized in that it comprises, as emulsifier, an effective amount of the composition (Ci) as defined. previously; and a topical pharmaceutical or dermopharmaceutical oil-in-water emulsion (C '), characterized in that it comprises as emulsifier an effective amount of the composition (Ci) as defined above; and finally the use of the composition (Ci) as defined above, as an emulsifying agent for preparing oil-in-water type emulsions.
  • C topical cosmetic-dermocosmetic oil-in-water emulsion
  • an effective amount is meant, in the definitions of oil-in-water emulsions (C) and (C ') mentioned above, a mass proportion generally greater than or equal to 2.0% by weight and less than or equal to 5.0%, of their total mass and more particularly of 2.5% by mass to 4.0% by mass of their total mass.
  • oil-in-water emulsions (C) and (C ') means that the latter are implemented by application to the skin, scalp or mucous membranes.
  • Said oil-in-water emulsions (C) and (C ') mentioned above may be used as cream, milk, bubble bath, shampoo, conditioner or lotion for the care or for the protection of the face, hands and the body, especially for their short-term moisturizing effect of the epidermis after prolonged exposure to low temperatures, or solar radiation; or to prevent or slow the appearance of external signs of aging of human skin, such as the appearance of wrinkles, fine lines, an alteration of microrelief, lack of elasticity and / or tone, lack of density and / or firmness of human skin; or again after shaving the face or for washing and / or treatment of the scalp.
  • said oil-in-water emulsions (C) and (C ') also comprise excipients and / or active ingredients usually used in the field of topical formulations, such as foaming and / or detergent surfactants.
  • foaming and / or detergent surfactants optionally present in said oil-in-water emulsions (C) and (C ') as defined above, include anionic, cationic and amphoteric foaming and / or detergent surfactants. or non-ionic topically acceptable usually used in this field of activity.
  • foaming and / or detergent anionic surfactants optionally present in said oil-in-water emulsions (C) and (C ') as defined previously there may be mentioned alkali metal salts, alkaline earth metal salts, ammonium salts, amine salts, salts of amino-alcohols, alkyl ether sulfates, alkyl sulphates, alkyl amido ether sulphates alkylaryl polyethersulfates, monoglyceridesulfates, alpha-olefinesulfonates, paraffinsulfonates, alkylphosphates, alkyletherphosphates, alkylsulfonates, alkylamidesulfonates, alkylarylsulfonates, alkylcarboxylates, alkylsulfosuccinates, alkylethersulfosuccinates, alkylamidesulfosuccinates, alkylsulfoacetates, alkyls
  • foaming and / or detergent amphoteric surfactants optionally present in said oil-in-water type (C) and (C ') emulsions as defined above, there are alkyl betaines, alkyl amidobetaines, sultaines, alkylamidoalkylsulfobetaines, imidazoline derivatives, phosphobetaines, amphopolyacetates and amphopropionates.
  • foaming and / or detergent cationic surfactants optionally present in said oil-in-water emulsions (C) and (C ') as defined above, there are particularly the quaternary ammonium derivatives.
  • foaming and / or detergent nonionic surfactants optionally present in said oil-in-water emulsions (C) and (C ') as defined above, there are more particularly the alkyl polyglycosides, the oil derivatives. castor oil, polysorbates, coconut amides, N-alkylamines.
  • composition (C3) consisting essentially of a mixture of compounds represented by the formulas (IV1), (IV 2 ), (IV 3 ), (IV 4 ) and (IV 5 ): R 2 -O- (G 2 ) rH (IV I ),
  • Examples of emulsifying anionic surfactants optionally present in said oil-in-water emulsions (C) and (C) as defined above include decyl phosphate, cetyl phosphate sold under the name AMPFIISOL TM, glyceryl stearate citrate; cetearyl sulphate; arachidyl / behenyl phosphates and arachidyl / behenyl alcohols sold under the name SENSANOV TM WR; soaps, for example sodium stearate or triethanolammonium stearate, N-acyl derivatives of salified amino acids, for example stearoyl glutamate.
  • decyl phosphate cetyl phosphate sold under the name AMPFIISOL TM, glyceryl stearate citrate
  • cetearyl sulphate arachidyl / behenyl phosphates and arachidyl / behenyl alcohols sold under the name SEN
  • Examples of emulsifying cationic surfactants optionally present in said oil-in-water emulsions (C) and (C ') as defined above include aminoxides, QUATERNIUM TM 82 and the surfactants described in the published international application. under the number WO 96/00719 and mainly those whose fatty chain comprises at least 16 carbon atoms.
  • opacifying agents and / or nacrants optionally present in said oil-in-water emulsions (C) and (C ') as defined above, mention may be made of sodium palmitate, sodium stearate, sodium hydroxystearate, magnesium palmitate, magnesium stearate, magnesium hydroxystearate, ethylene glycol monostearate, ethylene glycol distearate, polyethylene glycol monostearate, polyethylene glycol distearate, and fatty alcohols comprising from 12 to 22 carbon atoms.
  • Examples of texturizing agents optionally present in said oil-in-water emulsions (C) and (C ') as defined above, include N-acyl derivatives of amino acids, for example lauroyl lysine. sold 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.
  • solvents and cosolvents optionally present in said oil-in-water emulsions (C) and (C ') as defined above, mention may be made of water, ethylene glycol, propylene glycol and butylene. glycol, hexylene glycol, diethylene glycol, water-soluble alcohols such as ethanol, isopropanol or butanol, water mixtures and said solvents.
  • oils optionally present in said oil-in-water emulsions (C) and (C ') as defined above, mention may be made of mineral oils such as liquid paraffin, liquid petroleum jelly, 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,nadooulier oil, passionflower oil , hazelnut oil, palm oil, shea butter, apricot kernel oil, calophyllum oil, sysymbrium oil, avocado oil, calendula, oils derived from flowers or vegetables; ethoxylated vegetable oils; synthetic oils such as fatty acid
  • waxes optionally present in said oil-in-water emulsions (C) and (C) as defined above include beeswax, carnauba wax, candelilla wax, uricury, Japanese wax, cork fiber wax, sugar cane wax, paraffin waxes, lignite waxes, microcrystalline waxes, lanolin wax; 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 fats optionally present in said oil-in-water emulsions (C) and (C) as defined above include saturated or unsaturated fatty alcohols, linear or branched, comprising from eight to thirty-six carbon atoms, or saturated or unsaturated fatty acids, linear or branched, having from eight to thirty-six carbon atoms.
  • thickening and / or gelling agents optionally present in said oil-in-water emulsions (C) and (C) as defined above are polyelectrolytes, linear or branched polymers or crosslinked, such as homopolymer of partially or totally salified acrylic acid, homopolymer of partially or totally salified methacrylic acid, homopolymer of racide-2-methyl - [(1-oxo-2-propenyl) amino) ] 1-propane sulfonic acid (AMPS) partially or completely salified, copolymers of acrylic acid and AMPS, copolymers of acrylamide and AMPS, copolymers of vinylpyrrolidone and AMPS, copolymers of AMPS and (2-hydroxyethyl) acrylate, copolymers of AMPS and (2-hydroxyethyl) methacrylate, copolymers of AMPS and hydroxyethylacrylamide, copolymers of AMPS and N, N-di
  • R represents a hydrogen atom or a methyl radical
  • R 8 represents a linear or branched alkyl radical containing from eight to thirty carbon atoms
  • z represents a number greater than or equal to one and less than or equal to fifty.
  • the polyelectrolytic polymers, linear or branched or crosslinked optionally present at said oil-in-water emulsions (C) and (C '), as defined above, can be in the form of a solution, a aqueous suspension, a water-in-oil emulsion, an oil-in-water emulsion, a powder.
  • the polyelectrolytic polymers, linear or branched or crosslinked optionally present at said oil-in-water emulsions (C) and (C '), as defined above, may be selected from the products sold under the names SIMULGEL TM EG, SIMULGEL TM EPG, SEPIGEL TM 305, SIMULGEL TM 600, SIMULGEL TM NS, SIMULGEL TM INS 100, SIMULGEL TM FL, SIMULGEL TM A, SIMULGEL TM SMS 88, SEPINOV TM EMT 10, SEPIPLUS TM 400, SEPIPLUS TM 265, SEPIPLUS TM S , SEPIMAX TM Zen, ARISTOFLEX TM AVC, ARISTOFLEX TM AVS, NOVEMER TM EC-1, NOVEMER TM EC 2, ARISTOFLEX TM HMB, COSMEDIA TM SP, FLOCARE TM AND 25, FLOCARE TM AND 75, FLOCARE
  • thickening and / or gelling agents optionally present in said oil-in-water emulsions (C) and (C ') as defined above, mention may be made of polysaccharides consisting of derivatives of monosaccharides, such as galactans. sulphates and more particularly carrageenans and agar, uronans and more particularly algin, alginates and pectins, heteropolymers of monosaccharides and uronic acids and more particularly xanthan gum, gellan gum, exudates of gum of arabic and karaya gum, glucosaminoglycans.
  • polysaccharides consisting of derivatives of monosaccharides, such as galactans. sulphates and more particularly carrageenans and agar, uronans and more particularly algin, alginates and pectins, heteropolymers of monosaccharides and uronic acids and more particularly xanthan gum, gellan gum, exudates of
  • thickening and / or gelling agents optionally present in said oil-in-water emulsions (C) and (C ') as defined above are cellulose, cellulose derivatives such as methylcellulose , ethyl cellulose, hydroxypropyl cellulose, silicates, starch, hydrophilic derivatives of starch, polyurethanes.
  • stabilizing agents optionally present in said oil-in-water emulsions (C) and (C ') as defined above are microcrystalline waxes, and more particularly ozokerite, mineral salts such as sodium chloride or magnesium chloride, silicone polymers such as polysiloxane polyalkyl polyether copolymers.
  • thermal or mineral waters optionally present in said oil-in-water emulsions (C) and (C ') as defined above, are thermal or mineral waters having a mineralization of at least 300 mg / l, in particular Avene water, Vittel water, Vichy basin water, Uriage water, Roche Posay water, Bourboule water, water of Enghien-les-Bains, the water of Saint-Gervais-les Bains, the water of Neris-les-Bains, the water of Allevard-les-Bains, the water of Digne, the water of Maizieres, the water of Neyrac-les-bains, the water of Lons le Saunier, the water of Rochefort, the water of Saint Christau, the water of the Fumades and the water of Tercis-les-bains.
  • hydrotropic agents optionally present in said oil-in-water emulsions (C) and (C ') as defined above are xylenesulfonates, cumenesulfonates, hexyl polyglucoside, (2) ethyl hexyl) polyglucoside, n-heptyl polyglucoside.
  • deodorant agents optionally present in said oil-in-water emulsions (C) and (C ') as defined above are alkali silicates, zinc salts such as zinc sulphate, gluconate zinc, zinc chloride, zinc lactate; quaternary ammonium salts such as cetyltrimethylammonium salts, cetylpyridinium salts; glycerol derivatives such as glycerol caprate, glycerol caprylate, polyglycerol caprate; 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 chlorohydrates, aluminum trichlorohydrate and zirconium, aluminum and zirconium tetrachlorohydrate, aluminum and zirconium pentach
  • sunscreens optionally present in said oil-in-water type emulsions (C) and (C ') as defined above, there are all those appearing in the cosmetic directive 76/768 / EEC modified Annex VII.
  • the solar organic filters optionally present in said oil-in-water emulsions (C) and (C ') as defined above, there is the family of benzoic acid derivatives such as para-amino benzoic 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, the methyl esters of N, N-dimethyl PABA, butyl esters of N, N-dimethyl PABA; the family of anthranilic acid derivatives such as homomenthyl-N-acetyl anthranilate; the family of salicylic acid derivatives such as amyl salicylate, homomenthyl salicylate, ethyl hexyl salicylate, phenyl salicylate, benzyl salicylate, p-iso
  • inorganic screens optionally present in said oil-in-water emulsions (C) and (C) as defined above, there are 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, may or may not have undergone surface treatments and may optionally be presented in the form of aqueous or oily pre-dispersions.
  • Examples of active principles optionally present in said oil-in-water emulsions (C) and (C) as defined above are 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 ( 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-undecelynoyl phenylalanine;
  • compositions Ci according to the invention and comparative compositions C'i.
  • compositions Ci A1 - Preparation of compositions Ci according to the invention.
  • the general procedure of the glycosylation reaction used to prepare the compositions according to the invention is as follows:
  • Cetearyl alcohol is an equimolar mixture of hexadecyl alcohol (or cetyl alcohol) and octadecyl alcohol (or stearyl alcohol).
  • Oil-in-water type emulsions ((Ei) to (E 4 )) are prepared by mixing at 80 ° C. with stirring 20% by weight of oil, effective amount of emulsifier composition according to the invention and the results are compared to that of an oil-in-water emulsion (E T ) prepared under the same conditions with MONTANOV TM 68 (composition (Cu) comprising 80% by weight). mass of the mixture of cetyl and stearyl alcohols (50/50 by weight) and 20% by weight of cetearyl polyglucoside).
  • the composition (Cu) by its structure, is representative of the compositions (C'I A ) and (C'IB) as described above. The information is recorded in the following table:
  • Procedure mix all the ingredients of phase A and, after homogenization, add MONTALINE TM C40 and adjust the pH to about 6.0 using lactic acid.
  • Tromethamine QS pH 7.2 Procedure: Mix all the ingredients of phase A in the order indicated until a clear phase A is obtained. Separately, add CAPIGEL TM 98 in water, then add this phase B thus prepared in phase A and adjust the pH to 7.2 using tromethamine.
  • Procedure Heat separately the phases A and B formed by mixing the various constituents. Add phase C to the hot fatty phase and make the emulsion by pouring the aqueous phase; homogenize for a few minutes with vigorous stirring (via a rotor / stator turbine). Then add the phase D in the hot emulsion and cool the emulsion with moderate stirring until it returns to room temperature. Add phase E at 40 ° C.
  • Prepare phase C by adding SEPINOV TM EMT10 to the mixture of water and glycerol and homogenize using a mixer equipped with a rotor-sator system at a rotation speed of 4000 rpm for 4 minutes. minutes.
  • SEPICALM TM S Mixture of N-cocoyl amino acids, sarcosine, potassium aspartate and magnesium aspartate as described in WO 98/0961 1.
  • PROTEOL TM APL Mixture of sodium salts of N-cocoyl amino acids, obtained by acylation of the amino acids characteristic of apple juice;
  • SEPICIDE TM HB Mixture of phenoxyethanol, methylparaben, ethylparaben, propylparaben and butylparaben, is a preservative
  • CAPIGEL TM 98 Copolymer of acrylates
  • SEPICIDE TM CI Imidazoline urea, is a preservative
  • SEPICIDE TM HB Mixture of phenoxyethanol, methylparaben, ethylparaben, propylparaben, butylparaben and isobutylparaben, is a preservative;
  • SEPICALM TM VG Mixture of N-palmitoyl proline in the form of sodium salt and Alba Nymphea flower extract;
  • EUXYL TM PE9010 Mixture of phenoxyethanol and ethyl hexyl glycerine;
  • PROTEOL TM OAT Mixture of N-lauryl amino acids obtained by total hydrolysis of oat protein as described in WO 94/26694;
  • AMISOFT TM CS-1 1 Sodium salt of N-cocoyl glutamate
  • SIMULSOL TM 165 Mixture of PEG-100 Stearate and Glycerol Stearate;
  • MONTANOV TM 202 (arachydilic alcohol, behenic alcohol and arachidyl glucoside), is a self-emulsifiable composition such as those described in EP 0 977 626;
  • SEPIPLUS TM 400 Self-invertible inverse latex of polyacrylates in polyisobutene and comprising polysorbate 20, as described in WO2005 / 040230;
  • LIPACIDE TM C8G Capryloyl glycine marketed by the company SEPPIC;
  • MICROPEARL TM M310 Cross-linked polymethylmethacrylate polymer in powder form and used as a texture modifier
  • SEPIMAX TM Zen (INCI name: Polyacrylate Crosspolymer-6): Thickening polymer in the form of a powder;
  • SEPIPLUS TM S (INCI name: Hydroxyethyl Acrylate / Sodium Acryloyldimethyl Taurate Copolymer & Polyisobutene & PEG-7 Trimethylolpropane Cononut Ether): Self-Invertible Reverse Latex; AMONYL TM 265 BA (INCI name: Cocobetaine): foaming amphoteric surfactant; SEPINOV TM EMT10 (INCI name: Hydroxyethyl Acrylate / Sodium Acryloyldimethyl Taurate Copolymer): Thickening copolymer in the form of a powder;
  • EASYNOV TM (INCI name: Octyldodecanol and Octyldodecyl Xyloside and PEG-30 Dipolyhydroxystearate): Emulsifying agent with a lipophilic tendency;
  • SEPIMAT TM H10 FW (INCI name: Methyl Methacrylate Crosspolymer and Squalane): The polymer used as a texturing agent;
  • SEPITONIC TM M3 (INCI name: Aspartate and Zinc Gluconate and Copper Gluconate Magnesium): A mixture used as an antiradical and energizing agent for cells;
  • MONTANOV TM L (INCI name: C14-22 Alcohols and C12-20 Alkylglucoside): Emulsifying agent;
  • MONTANOV TM 82 (INCI name: Cetearyl Alcohol and Coco-glucoside): Emulsifying agent;
  • SIMULGEL TM INS100 (INCI name: Hydroxyethyl Acrylate / Sodium Acryloylimethyl Taurate Copolymer and isohexadecane and Polysorbate 60): Polymeric thickening agent;

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EP18830908.2A 2017-12-12 2018-12-04 Neue alkylpolyrhamnoside, verfahren zur herstellung davon und kosmetische und/oder pharmazeutische zusammensetzungen damit Pending EP3723712A1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR1762000A FR3074687B1 (fr) 2017-12-12 2017-12-12 Nouveaux alkyl polyrhamnosides, procede pour leur preparation et composition cosmetiques et/ou pharmaceutiques en comprenant
PCT/FR2018/053102 WO2019115911A1 (fr) 2017-12-12 2018-12-04 Nouveaux alkyl polyrhamnosides, procédé pour leur préparation et composition cosmétiques et/ou pharmaceutiques en comprenant

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US (1) US11426341B2 (de)
EP (1) EP3723712A1 (de)
JP (1) JP7402797B2 (de)
CN (1) CN111587105B (de)
FR (1) FR3074687B1 (de)
WO (1) WO2019115911A1 (de)

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FR3074686B1 (fr) * 2017-12-12 2019-11-15 Societe D'exploitation De Produits Pour Les Industries Chimiques Seppic Nouveaux glyceryl polyrhamnosides, procede pour leur preparation et composition cosmetiques et/ou pharmaceutiques en comprenant

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Publication number Priority date Publication date Assignee Title
FR2668080B1 (fr) * 1990-10-17 1993-08-13 Seppic Sa Compositions auto-emulsionnables a base d'alcools gras, leur procede de preparation et leur utilisation pour la realisation d'emulsions.
FR2705341B1 (fr) 1993-05-17 1995-06-23 Givauban Lavirotte Procédé de préparation de mélanges d'acides aminés N-acylés, mélanges d'acides alpha aminés N-acylés, et leurs utilisations.
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.
GB9500886D0 (en) * 1995-01-18 1995-03-08 Cerester Holding B V Alkylpolyglycosides with a high degree of polymerisation and a process for the preparation thereof
FR2734496B1 (fr) * 1995-05-24 1997-07-04 Seppic Sa Composition emulsionnante a base d'alkylpolyglycosides, et ses utilisations
JP2000517335A (ja) 1996-09-09 2000-12-26 ソシエテ・デクスプロワタシオン・ド・プロデュイ・プール・レ・ザンデュストリ・シミーク―セピック リポアミノ酸構造を持つ化合物の化粧用使用、及び、この化合物のいくつかを配合した緩和活性を有する化粧用組成物
FR2761595B1 (fr) 1997-04-04 1999-09-17 Oreal Compositions comprenant des santalines, santarubines pour la coloration artificielle de la peau et utilisations
FR2762317B1 (fr) 1997-04-21 1999-07-09 Seppic Sa Composition a base d'alkylpolyglycosides et d'alcools gras, et ses utilisations
FR2830774B1 (fr) * 2001-10-11 2004-01-23 Seppic Sa Compositions emulsionnantes a base d'alcool arachidylique et/ou d'alcool behenylique et emulsions les contenant
FR2861397B1 (fr) 2003-10-22 2006-01-20 Soc Dexploitation De Produits Pour Les Industries Chimiques Seppic Nouveau latex inverse concentre, procede pour sa preparation et utilisation dans l'industrie
FR2899099A1 (fr) * 2006-03-31 2007-10-05 Seppic Sa Nouveau concentre tensioactif issu d'alkyl polyglycosides, et son utilisation pour preparer sans chauffage, des formulations cosmetiques et/ou pharmaceitiques
FR2932801B1 (fr) * 2008-06-20 2012-04-20 Seppic Sa Nouveaux ethers d'alkyl polyosides, leur utilisation comme emulsionnant et compositions cosmetiques les renfermant apg sur alkyl glyceryl ethers.
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
FR2995782B1 (fr) * 2012-09-21 2014-10-31 Oreal Sucres anti-pelliculaires

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FR3074687B1 (fr) 2020-07-17
CN111587105B (zh) 2023-07-21
US20210069085A1 (en) 2021-03-11
JP7402797B2 (ja) 2023-12-21
WO2019115911A1 (fr) 2019-06-20
US11426341B2 (en) 2022-08-30
CN111587105A (zh) 2020-08-25
JP2021505623A (ja) 2021-02-18

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