WO2017102302A1 - Produit de protection solaire contenant un précurseur d'avobenzone - Google Patents

Produit de protection solaire contenant un précurseur d'avobenzone Download PDF

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Publication number
WO2017102302A1
WO2017102302A1 PCT/EP2016/079088 EP2016079088W WO2017102302A1 WO 2017102302 A1 WO2017102302 A1 WO 2017102302A1 EP 2016079088 W EP2016079088 W EP 2016079088W WO 2017102302 A1 WO2017102302 A1 WO 2017102302A1
Authority
WO
WIPO (PCT)
Prior art keywords
preparation
ethylhexyl
cosmetic preparation
preparation according
cosmetic
Prior art date
Application number
PCT/EP2016/079088
Other languages
German (de)
English (en)
Inventor
Kathrin BORCHERS
Heike Lerg
Andreas Bleckmann
Janina ZIPPEL
Original Assignee
Beiersdorf Ag
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Beiersdorf Ag filed Critical Beiersdorf Ag
Publication of WO2017102302A1 publication Critical patent/WO2017102302A1/fr

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Classifications

    • 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
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37—Esters of carboxylic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37—Esters of carboxylic acids
    • A61K8/375—Esters of carboxylic acids the alcohol moiety containing more than one hydroxy group

Definitions

  • the present invention relates to a cosmetic preparation containing isosorbide dicaprylate (INCI: isosorbide dicaprylate) and a precursor for 4- (tert-butyl) -4'-methoxydibenzoylmethane.
  • ICI isosorbide dicaprylate
  • 4- (tert-butyl) -4'-methoxydibenzoylmethane 4- (tert-butyl) -4'-methoxydibenzoylmethane
  • UV-A filter 4- (tert-butyl) -4'-methoxydibenzoylmethane is usually used as the UV-A filter.
  • this UV filter has the known disadvantage, not alone To be photostable, but slowly decompose especially under UV-B radiation.
  • 4- (tert-butyl) -4'-methoxydibenzoylmethane has the likewise known disadvantage of not being particularly soluble in cosmetic preparations, but rather of crystallizing out of the preparation relatively quickly. This also affects the durability and shelf life of the sunscreen, in particular their storage and temperature stability.
  • a relatively new approach to solving these problems of 4- (tert-butyl) -4'-methoxydibenzoylmethane in cosmetic preparations is to use precursors of 4- (tert-butyl) -4'-methoxydibenzoylmethane to be used in the preparations. These are then used, since they transform under sunlight into the 4- (tert-butyl) -4'-methoxydibenzoylmethane, as the starting material for a resulting in the application of UV-A protection.
  • the object is achieved by containing a cosmetic preparation
  • compositions according to the invention are distinguished by a significantly faster and more complete conversion of the precursor under UV light into 4- (tert-butyl) -4'-methoxydibenzoylmethane than is the case in the preparations of the prior art ,
  • the preparations according to the invention have the surprising advantage that they have a significantly lower yellowing before application (ie before the skin creamed with the preparation is exposed to sunlight) than is the case with preparations which contain an equivalent amount of (tert-butyl) -4'-methoxydibenzoylmethane included.
  • the preparations according to the invention lead to a significantly reduced textile staining (yellowing), as is the case with preparations which contain an equivalent amount of 4- (tert-butyl) -4'-methoxydibenzoylmethane, if the preparations before, during or advised to come into contact with textiles after use on the skin.
  • the cosmetic preparation contains compound 1 in a concentration of 0.1 to 6% by weight, based on the total weight of the preparation.
  • the cosmetic preparation contains compound 1 in a concentration of 1 to 4.75% by weight, based on the total weight of the preparation. It is advantageous for the purposes of the present invention if the preparation contains isosorbide dicaprylate in a concentration of 0.1 to 15% by weight, based on the total weight of the preparation.
  • the preparation contains isosorbide dicaprylate in a concentration of 1 to 10% by weight, based on the total weight of the preparation.
  • the preparation according to the invention can advantageously one or more
  • Embodiments of the present invention which are advantageous according to the invention are characterized in that one or more dialkyl adipates are selected from the group of the compounds dimethyl adipate, diethyl adipate, dipropyl adipate, diisopropyl adipate, diisobutyl adipate, di-n-butyl adipate, di-2-ethylhexyl adipate and dicyclohexyl adipate.
  • di-n-butyl adipate it is particularly preferable to use di-n-butyl adipate as the dialkyl adipate.
  • the dialkyl adipate used is exclusively di-n-butyl adipate. In this case it is
  • the use concentration of di-n-butyl adipate is from 0.5 to 3% by weight, based on the total weight of the preparation.
  • Embodiments of the present invention that are advantageous according to the invention are further characterized in that the preparation contains ethanol.
  • inventively advantageous embodiments of the present invention are characterized in that the preparation contains ethanol in a concentration of 0, 1 to 99% by weight, based on the total weight of the preparation.
  • the cosmetic preparation contains ethanol in a concentration of 2 to 60% by weight, based on the total weight of the preparation. It is also advantageous for the purposes of the present invention if the preparation contains C 12 -C 15 -alkyl benzoate.
  • the embodiments according to the invention are characterized in that the preparation contains C12-C15 alkyl benzoate in a concentration of 1 to 20% by weight, based on the total weight of the preparation.
  • Preparation contains one or more dialkyl carbonates.
  • these dialkyl adipates are preferably selected according to the invention from the group of compounds dicaprylyl carbonate dimethyl carbonate. Diethyl carbonate. Diisopropyl. Di-n-butyl carbonate. Particularly preferred according to the invention are the dialkyl carbonates diisopropyl carbonate and di-n-butyl carbonate.
  • preparation of the invention may contain other lipophilic components, for example natural or synthetic oils, fats, waxes, as are commonly used in cosmetics.
  • Embodiments of the present invention that are advantageous according to the invention are further characterized in that the preparation comprises one or more compounds selected from the group of the compounds alpha-lipoic acid, folic acid, phytoene, D-biotin, coenzyme Q10, alpha-glucosylrutin, carnitine, carnosine, natural and / or or synthetic isoflavonoids, flavonoids, creatine, creatinine, taurine, ⁇ -alanine, panthenol, magnolol, honokiol, tocopheryl acetate,
  • the total concentration of these alkanediols in the preparation is from 0.1 to 5% by weight, based on the total weight of the preparation (that is, if the preparation contains only one alkanediol, this concentration corresponds to
  • the preparation contains phenoxyethanol and / or ethylhexylglycerol.
  • the total concentration of these substances in the preparation is from 0.1 to 1% by weight, based on the total weight of the preparation (ie if the preparation contains only phenoxyethanol or ethylhexylglycerol, this concentration corresponds to the individual concentration of this substance).
  • the preparation contains one or more UV filters which are selected from the group of the compounds 2-phenylbenzimidazole-5-sulfonic acid and / or salts thereof; Phenylene-1,4-bis (2-benzimidazyl) -3,3'-5,5'-tetrasulfonic acid salts; 1,4-di (2-oxo-10-sulfo-3-bornylidenemethyl) benzene and its salts; 4- (2-oxo-3-bornylidenemethyl) benzenesulfonic acid; 2-methyl-5- (2-oxo-3-bornylidenemethyl) sulfonic acid salts; 2,2'-methylenebis (6- (2H-benzotriazol-2-yl) -4- (1,1,3,3-tetramethylbutyl) -phenol); 2- (2H-Benzotriazol-2-yl) -4-methyl-6- [2-methyl-3- [1,3,
  • the preparation contains no 3- (4-methylbenzylidene) - camphor and 2-hydroxy-4-methoxybenzophenone (INCI: oxybenzone), that is free of these ingredients. It is preferred according to the invention if the preparation according to the invention contains 2-phenylbenzimidazole-5-sulfonic acid salts.
  • the preparation contains 2-phenylbenzimidazole-5-sulfonic acid salts in a concentration of 1 to 4% by weight, based on the total weight of the preparation.
  • the preparation contains both salicylates, it is advantageous according to the invention 2-ethylhexyl 2-hydroxybenzoate (INCI: ethylhexyl salicylates) in a concentration of 2 to 5% by weight and 3,3,5-trimethylcyclohexyl 2-hydroxybenzoate (INCI: Homosalate) in a concentration of 2 to 10% by weight, based in each case on the total weight of the preparation.
  • Embodiments of the present invention that are advantageous according to the invention are characterized in that the preparation according to the invention comprises 2,4,6-tris [anilino (p-carbo-2'-ethyl-1'-hexyloxy)] - 1, 3,5-triazine ( INCI: ethylhexyl triazone).
  • the preparation according to the invention comprises 2,4,6-tris [anilino- (p-carbo-2'-ethyl-1'-hexyloxy)] - 1, 3,5-triazine (INCI: ethylhexyl triazone ) in an amount of 2 to 5% by weight, based on the total weight of the preparation.
  • the preparation is in the form of an emulsion. It is preferred according to the invention if the preparation is in the form of an O / W emulsion.
  • the preparation according to the invention is in the form of an emulsion
  • the embodiments which are advantageous according to the invention are characterized in that the preparation contains one or more emulsifiers selected from the group of compounds
  • Glyceryl stearate citrate glyceryl stearate (self-emulsifying), stearic acid, stearate salts, polyglyceryl-3-methyl glycose distearate, sodium cetearyl sulfate, sodium staroyl glutamate, polyglyceryl stearate, cetearyl alcohol, cetearyl sulfosuccinate, potassium cetyl phosphate.
  • the total concentration of these emulsifiers in the preparation is from 0.1 to 10% by weight, based on the total weight of the preparation (ie if the preparation contains only one emulsifier, this concentration corresponds to
  • the aqueous phase of the preparations according to the invention may advantageously contain customary cosmetic auxiliaries, such as, for example, isopropanol or polyols of low C number and their ethers, preferably propylene glycol, glycerol, electrolytes, self-tanning agents and in particular one or more thickening agents which can be advantageously selected from the group Silica, aluminum silicates, polysaccharides or their derivatives, for. Hyaluronic acid, xanthan gum, hydroxypropylmethylcellulose, particularly advantageously from the group of the polyacrylates, preferably a polyacrylate from the group of the so-called carbopols,
  • customary cosmetic auxiliaries such as, for example, isopropanol or polyols of low C number and their ethers, preferably propylene glycol, glycerol, electrolytes, self-tanning agents and in particular one or more thickening agents which can be advantageously selected from the group Silica, aluminum silicates, poly
  • Further thickeners which are advantageous according to the invention are those having the INCI name Acrylates / C10-30 alkyl acrylate crosspolymer (for example Pemulen TR 1, Pemulen TR 2, Carbopol 1328 from NOVEON) and Aristoflex AVC (INCI: ammonium acryloyldimethyltaurate / VP copolymer).
  • the preparation contains xanthan gum, crosslinked acrylate / C10-C30 alkyl acrylate polymer and / or vinylpyrrolidone / hexadecene copolymer.
  • a content of glycerol of at least 5% by weight, based on the total weight of the preparation, is particularly advantageous according to the invention.
  • Embodiments of the present invention which are advantageous according to the invention are characterized in that the preparation is free of parabens, methylisothiazolinone,
  • perfume substances selected from the group of the compounds limonene, citral, linalool, alpha-isomethylionone, geraniol, citronellol, 2-isobutyl-4-hydroxy-4-methyltetrahydropyran, 2-tert-pentylcyclohexyl acetate, 3-methyl-5-phenyl 1-pentanol, 7-acetyl-1,1,1,4,4,4,6-hexamethyltetralin, adipic diester, alpha-amylcinnamaldehyde, alpha-methylionone, amyl C, butylphenylmethylpropionalcinnamal, amylsalicylate, amylcinnamylalcohol, anisalcohol, benzoin, benzylalcohol, benzylbenzoate, benzylcinnamate , Benzylsalicylate, bergamot oil, bitter orange oil, buty
  • the preparation according to the invention advantageously contains film formers.
  • Film formers for the purposes of the present invention are substances of different composition, which are characterized by the following property: If a film former is dissolved in water or other suitable solvents and the solution is then applied to the skin, it forms a film after the solvent has evaporated which essentially serves to fix the light filters on the skin and thus to increase the water resistance of the product.
  • copolymers of polyvinylpyrrolidone for example, the PVP hexadecene copolymer and the PVP eicosene copolymer, which are among the
  • polystyrene sulfonate sold under the tradename Flexan 130 at National Starch and Chemical Corp. is available, and / or polyisobutene, available from Rewo under the tradename Flexan 130 at National Starch and Chemical Corp. is available, and / or polyisobutene, available from Rewo under the tradename Flexan 130 at National Starch and Chemical Corp. is available, and / or polyisobutene, available from Rewo under the
  • Suitable polymers are e.g. Polyacrylamides (Seppigel 305), polyvinyl alcohols, PVP, PVP / VA copolymers, polyglycols, acrylate / octylacralimide copolymer (Dermacryl 79), acrylates copolymer (Epitex 66).
  • hydrogenated castor oil Dimerdilinoleat (CAS 646054-62-8, INCI Hydrogenated Castor Oil Dimer Dilinoleate), which can be purchased from Kokyu Alcohol Kogyo under the name Risocast DA-H or PPG-3 Benzylethermyristat ( CAS 403517-45-3), which can be obtained under the trade name Crodamol STS from Croda Chemicals.
  • the use of the preparation according to the invention for protection against skin aging (in particular for protection against UV-induced skin aging) and as
  • UV absorption measuring device Helias spectrophotometer (500 fiber light sphere) with
  • Double Monochromator and Photomultiplier (M.U.T. Aviation Technology, Wedel, Germany)
  • UV absorption meter lamp LOT Lamp LSH102 (LOT Oriel, Darmstadt) with 75 W Xe Are Lamp

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

Abstract

Préparation cosmétique contenant a) du dicaprylate d'isosorbide et b) le composé 1.
PCT/EP2016/079088 2015-12-17 2016-11-29 Produit de protection solaire contenant un précurseur d'avobenzone WO2017102302A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102015225570.0 2015-12-17
DE102015225570.0A DE102015225570A1 (de) 2015-12-17 2015-12-17 Allerneustes Sonnenschutzmittel mit Ausgangsstoff für die Bildung von 4-(tert.-Butyl)-4'-methoxy-di-ben-zoylmethan

Publications (1)

Publication Number Publication Date
WO2017102302A1 true WO2017102302A1 (fr) 2017-06-22

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PCT/EP2016/079088 WO2017102302A1 (fr) 2015-12-17 2016-11-29 Produit de protection solaire contenant un précurseur d'avobenzone

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DE (1) DE102015225570A1 (fr)
WO (1) WO2017102302A1 (fr)

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2857663A1 (fr) 2003-07-17 2005-01-21 Bioderma Lab Nouveau composes derives de dibenzoylmethane, utilisation en tant que filtres solaires photoactivables et compositions cosmetiques les contenant
WO2006060886A1 (fr) 2004-12-10 2006-06-15 Ion Beam Applications Sa Dispositif d'imagerie de positionnement d'un patient et procede correspondant
WO2006100225A2 (fr) 2005-03-21 2006-09-28 Ferrer Internacional, S. A. Composes d'ester d'acide benzoique, compositions, utilisations et methodes associes
EP2311844A1 (fr) 2009-10-15 2011-04-20 Interquim, S.A. Composés d'ester d'acide benzoïque polymérique en silyl, utilisations, et compositions associées
WO2013017260A1 (fr) * 2011-08-04 2013-02-07 Clariant International Ltd Compositions cosmétiques, dermatologiques ou pharmaceutiques contenant un diester d'isosorbide et un filtre uv
US20130058879A1 (en) 2010-05-12 2013-03-07 Merck Patent Gesellschaft Mit Beschrankter Haftung Triazines as reaction accelerators
DE102011115285A1 (de) 2011-09-29 2013-04-04 Merck Patent Gmbh Phosphanoxide als Reaktionsbeschleuniger

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20130183257A1 (en) * 2009-11-13 2013-07-18 Sytheon Ltd. Compositions and methods for improving skin appearance
US20140178314A1 (en) * 2012-12-19 2014-06-26 The Procter & Gamble Company Compositions and/or articles with improved solubility of a solid active
JP6037899B2 (ja) * 2013-03-08 2016-12-07 花王株式会社 水中油型乳化化粧料

Patent Citations (15)

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Publication number Priority date Publication date Assignee Title
FR2857663A1 (fr) 2003-07-17 2005-01-21 Bioderma Lab Nouveau composes derives de dibenzoylmethane, utilisation en tant que filtres solaires photoactivables et compositions cosmetiques les contenant
EP1648849A2 (fr) 2003-07-17 2006-04-26 Laboratoire Bioderma Composes derives de dibenzoylmethane, utilisation en tant que filtres solaires photoactivables et compositions cosmetiques les contenant
WO2006060886A1 (fr) 2004-12-10 2006-06-15 Ion Beam Applications Sa Dispositif d'imagerie de positionnement d'un patient et procede correspondant
WO2006100225A2 (fr) 2005-03-21 2006-09-28 Ferrer Internacional, S. A. Composes d'ester d'acide benzoique, compositions, utilisations et methodes associes
EP1707558A1 (fr) * 2005-03-21 2006-10-04 Ferrer Internacional, S.A. Esters de l'acide benzoique, compositions, utilisations et procedes associes
WO2011045389A1 (fr) 2009-10-15 2011-04-21 Interquim, S.A. Composés d'esters de l'acide benzoïque polymères silyliques, leurs utilisations et leurs compositions
EP2311844A1 (fr) 2009-10-15 2011-04-20 Interquim, S.A. Composés d'ester d'acide benzoïque polymérique en silyl, utilisations, et compositions associées
EP2488537A1 (fr) 2009-10-15 2012-08-22 Interquim, S.A. Composés d'esters de l'acide benzoïque polymères silyliques, leurs utilisations et leurs compositions
US20120230932A1 (en) 2009-10-15 2012-09-13 Interquim, S.A. Silyl polymeric benzoic acid ester compouonds, uses, and compositions thereof
US8945522B2 (en) 2009-10-15 2015-02-03 Interquim, S.A. Silyl polymeric benzoic acid ester compounds, uses, and compositions thereof
US20130058879A1 (en) 2010-05-12 2013-03-07 Merck Patent Gesellschaft Mit Beschrankter Haftung Triazines as reaction accelerators
EP2568953A2 (fr) 2010-05-12 2013-03-20 Merck Patent GmbH Triazines utilisées comme accélérateurs de réaction
WO2013017260A1 (fr) * 2011-08-04 2013-02-07 Clariant International Ltd Compositions cosmétiques, dermatologiques ou pharmaceutiques contenant un diester d'isosorbide et un filtre uv
DE102011115285A1 (de) 2011-09-29 2013-04-04 Merck Patent Gmbh Phosphanoxide als Reaktionsbeschleuniger
WO2013045016A2 (fr) 2011-09-29 2013-04-04 Merck Patent Gmbh Oxydes de phosphane en tant qu'accélérateurs de réaction

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Title
ADAYA GALLARDO ET AL: "Dose-dependent progressive sunscreens. A new strategy for photoprotection?", PHOTOCHEMICAL AND PHOTOBIOLOGICAL SCIENCES, vol. 9, no. 4, 1 January 2010 (2010-01-01), GB, pages 530, XP055284132, ISSN: 1474-905X, DOI: 10.1039/b9pp00188c *
ADAYA GALLARDO ET AL: "Dose-dependent progressive sunscreens. A new strategy for photoprotection?", PHOTOCHEMICAL AND PHOTOBIOLOGICAL SCIENCES, vol. 9, no. 4, 1 January 2010 (2010-01-01), GB, pages 530, XP055330327, ISSN: 1474-905X, DOI: 10.1039/b9pp00188c *

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