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WO2017129432A1 - Produit de protection solaire contenant de l'isononanoate de tricyclodécane-méthyle - Google Patents

Produit de protection solaire contenant de l'isononanoate de tricyclodécane-méthyle Download PDF

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Publication number
WO2017129432A1
WO2017129432A1 PCT/EP2017/050777 EP2017050777W WO2017129432A1 WO 2017129432 A1 WO2017129432 A1 WO 2017129432A1 EP 2017050777 W EP2017050777 W EP 2017050777W WO 2017129432 A1 WO2017129432 A1 WO 2017129432A1
Authority
WO
WIPO (PCT)
Prior art keywords
preparation
ethylhexyl
preparation according
cosmetic preparation
cosmetic
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.)
Ceased
Application number
PCT/EP2017/050777
Other languages
German (de)
English (en)
Inventor
Kathrin BORCHERS
Heike Lerg
Andreas Bleckmann
Janina ZIPPEL
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.)
Beiersdorf AG
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 WO2017129432A1 publication Critical patent/WO2017129432A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • 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
    • 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

Definitions

  • the present invention relates to a cosmetic preparation containing
  • Tricyclodecanmethyl isononanoate (INCI: tricyclodecanemethyl isononanoate) and a precursor for 4- (tert-butyl) -4'-methoxydibenzoylmethane.
  • UVB and UVA radiation (wavelength: 320-400 nm) also leads to a weakening of the elastic and collagen fibers of the connective tissue. This leads to numerous
  • UVA and UVB filters are in the form of positive lists in most industrialized countries such as Appendix 7 of the
  • UV filter 4- (tert-butyl) -4'-methoxydibenzoylmethane is usually used as UV filter.
  • this UV filter has the known disadvantage of not being particularly photostable on its own, but slowly decomposing under UV-B radiation in particular. If no further stabilizers (for example octocrylene) are added to the preparation, This decomposition process leads to a lower durability of the product as a whole and in particular to a decreasing with time UV-A protection.
  • 4- (tert-butyl) -4'-methoxydibenzoylmethane has the likewise known disadvantage of not being particularly soluble in cosmetic preparations, but of being able to extract it from the preparation relatively quickly. This also affects the durability and shelf life of the sunscreen, in particular their storage and temperature stability.
  • Precursor) of 4- (tert-butyl) -4'-methoxydibenzoylmethan use in the preparations. These then serve, since they transform under sunlight into the 4- (tert-butyl) -4'-methoxydibenzoylmethane, as starting material for a UV-protection which arises in the application.
  • Such starting materials (precursors) are disclosed, for example, in WO2006 / 100225.
  • a cosmetic preparation comprising a) tricyclodecanmethyl isononanoate (INCI: tricyclodecanemethyl isononanoate) and b)
  • 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'-methoxydiben- zoylmethane included.
  • the preparations according to the invention lead to a significantly reduced textile stain (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 Tncyclodecanmethylisononanoat in a concentration of 0.1% to 15% by weight, based on the total weight of the preparation.
  • Tncyclodecanmethylisononanoat 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 contain one or more dialkyl adipates.
  • the total concentration of dialkyl adipates in the preparation is from 0.5 to 3% by weight, based on the total weight of the preparation (that is, if the preparation contains only one dialkyl adipate, this concentration corresponds to
  • 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 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.
  • 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.
  • Embodiments which are advantageous according to the invention are characterized in that the preparation contains one or more dialkyl carbonates.
  • these dialkyl adipates are preferably selected according to the invention from the group of compounds dicaprylyicarbonate 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.
  • the total concentration of dialkyl carbonates in the preparation is advantageously from 1 to 20% by weight, based on the total weight of the preparation (that is, if the preparation contains only one dialkyl carbonate, this concentration corresponds to the individual concentration of this dialkyl carbonate).
  • preparation according to the invention may contain other lipophilic components, for example natural or synthetic oils, fats, waxes, as they are
  • Embodiments of the present invention which are advantageous according to the invention are furthermore 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,
  • Advantageous embodiments in the context of the present invention are further characterized in that the preparation contains one or more alkanediols from the group of compounds 1, 2-pentanediol, 1, 2-hexanediol, 1, 2-octanediol, 1, 2-decanediol, 2 Methyl-1, 3-propanediol contains.
  • 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. According to the invention, the total concentration of these substances in the
  • Preparation of 0.1 to 1% by weight, based on the total weight of the preparation i.e., 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-bomylidenemethyl) benzene and its salts; 4- (2-oxo-3-bomylidenemethyl) benzenesulfonic acid salts; 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
  • Dioctylbutylamidotriazone (INCI: diethylhexyl-butamidotriazone); 2,4-bis- [5-1 (dimethylpropyl) benzoxazol-2-yl- (4-phenyl) -imino] -6- (2-ethylhexyl) -imino-1,3,5-triazine with the CAS no.
  • the preparation contains no 3- (4-methylbenzylidene) - camphor and 2-hydroxy-4-methoxybenzophenone (INCI: oxybenzone), that is free of these ingredients.
  • 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.
  • Salicylates it is according to the invention advantageous to use this in a concentration of 3 to 5% by weight, based on the total weight of the preparation.
  • Embodiments of the present invention which 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 according to the invention comprises 2,4-bis - ⁇ [4- (2-ethylhexyloxy) -2-hydroxy] -phenyl ⁇ -6- (4-methoxyphenyl) -1, 3,5-triazine (INCI: bis-ethylhexyloxyphenol methoxyphenyl triazines) 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
  • Preparation contains one or more emulsifiers selected from the group of the compounds glyceryl stearate citrate, glyceryl stearate (self-emulsifying), stearic acid,
  • Stearate salts polyglyceryl-3-methylglycose distearate, sodium cetearylsulfate,
  • 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 advantageous from the group of polyacrylates, preferably a polyacrylate from the group of so-called
  • Carbopols for example Carbopols types 980, 981, 1382, 2984, 5984, each individually or in combination.
  • Further thickeners which are advantageous according to the invention are those with the INCI Description Acrylates / C 10-30 Alkyl Acrylate Crosspolymer (eg Pemulen TR 1, Pemulen TR 2, Carbopol 1328 from NOVEON) and Aristoflex AVC (INCI: Ammonium
  • Acryloyldimethyltaurate / VP copolymer it is preferred according to the invention, when 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,
  • the preparation according to the invention comprises one or more perfume substances selected from the group of the compounds limonene, citral, linalool, alpha-isomethylionone, geraniol, citronellol, 2-isobutyl-4-hydroxy-4-methyltetrahydropyran, 2-tert-pentylcyclohexylacetate, 3-methyl-5-phenyl-1-pentanol, 7-acetyl-1,1,1,4,4,6-hexamethyltetralin, adipic diester, alpha-amylcinnamaldehyde, alpha-methylionone, amyl C butylphenylmethylpropionalcinnamal, Amyl salicylate, amyl cinnamyl alcohol, aniseed alcohol, benzoin, benzyl alcohol, benzyl benzoate,
  • Tangerine oil Menthyl PCA, methylheptenone, nutmeg oil, rosemary oil, sweet orange oil, terpineol, tonka bean oil, triethyl citrate and / or vanillin.
  • 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 Essentially, it serves to fix the light filters on the skin, thus increasing 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. and / or polyisobutene, available from Rewo under the tradename Rewopal PIB1000.
  • 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
  • Compound 1 is dissolved in a concentration of 1: 10,000 in the solvent.
  • 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-Arc Lamp
  • Tricyclodecanmethylisononanoat significantly more molecules of the compound 1 are rearranged in 4- (tert-butyl) -4'-methoxydibenzoylmethan under irradiation as in Dimethicone.
  • Example 1 Example 2 Example 3 Example 4 Example 5

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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) de l'isononanoate de tricyclodécane-méthyle et b) le composé 1.
PCT/EP2017/050777 2016-01-27 2017-01-16 Produit de protection solaire contenant de l'isononanoate de tricyclodécane-méthyle Ceased WO2017129432A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102016000800.8A DE102016000800A1 (de) 2016-01-27 2016-01-27 Sonnenschutzmittel mit Tricyclodecanmethylisononanoat
DE102016000800.8 2016-01-27

Publications (1)

Publication Number Publication Date
WO2017129432A1 true WO2017129432A1 (fr) 2017-08-03

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PCT/EP2017/050777 Ceased WO2017129432A1 (fr) 2016-01-27 2017-01-16 Produit de protection solaire contenant de l'isononanoate de tricyclodécane-méthyle

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DE (1) DE102016000800A1 (fr)
WO (1) WO2017129432A1 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3574888A1 (fr) * 2018-05-30 2019-12-04 The Boots Company PLC Système de conservateur cosmétique

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1707558A1 (fr) * 2005-03-21 2006-10-04 Ferrer Internacional, S.A. Esters de l'acide benzoique, compositions, utilisations et procedes associes
WO2013045016A2 (fr) * 2011-09-29 2013-04-04 Merck Patent Gmbh Oxydes de phosphane en tant qu'accélérateurs de réaction

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2857663B1 (fr) 2003-07-17 2007-12-21 Bioderma Lab Nouveau composes derives de dibenzoylmethane, utilisation en tant que filtres solaires photoactivables et compositions cosmetiques les contenant
EP1709994A1 (fr) 2005-04-04 2006-10-11 Ion Beam Applications S.A. Dispositif et méthode d'imagerie pour le positionnement d'un patient
EP2311844A1 (fr) 2009-10-15 2011-04-20 Interquim, S.A. Composés d'ester d'acide benzoïque polymérique en silyl, utilisations, et compositions associées
WO2011141111A2 (fr) * 2010-05-12 2011-11-17 Merck Patent Gmbh Triazines utilisées comme accélérateurs de réaction

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1707558A1 (fr) * 2005-03-21 2006-10-04 Ferrer Internacional, S.A. Esters de l'acide benzoique, compositions, utilisations et procedes associes
WO2013045016A2 (fr) * 2011-09-29 2013-04-04 Merck Patent Gmbh Oxydes de phosphane en tant qu'accélérateurs de réaction

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
ADAYA GALLARDO ET AL: "An international journal Themed issue: Topical and systemic photoprotection", PHOTOCHEMICAL AND PHOTOBIOLOGICAL SCIENCES, vol. 9, no. 4, 1 April 2010 (2010-04-01), GB, pages 530 - 534, XP055346908, 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 *
HAI: "KAK TCIN - Ester with high refractive index suitable for suncare products", 1 July 2015 (2015-07-01), pages 1, XP055346910, Retrieved from the Internet <URL:http://www.hai-global.com/wp/wp-content/uploads/2015/09/HAI_PF2_KAK-TCIN_en_2015_fin_x1a.jpg> [retrieved on 20170216] *

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Publication number Publication date
DE102016000800A1 (de) 2017-07-27

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