WO2012168049A2 - Utilisation de ε-polylysine (epsilon-polylysine) pour améliorer l'hydrorésistance de formulations cosmétiques ou dermatologiques - Google Patents

Utilisation de ε-polylysine (epsilon-polylysine) pour améliorer l'hydrorésistance de formulations cosmétiques ou dermatologiques Download PDF

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Publication number
WO2012168049A2
WO2012168049A2 PCT/EP2012/059233 EP2012059233W WO2012168049A2 WO 2012168049 A2 WO2012168049 A2 WO 2012168049A2 EP 2012059233 W EP2012059233 W EP 2012059233W WO 2012168049 A2 WO2012168049 A2 WO 2012168049A2
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WO
WIPO (PCT)
Prior art keywords
polylysine
cosmetic
dermatological
epsilon
water
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PCT/EP2012/059233
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German (de)
English (en)
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WO2012168049A3 (fr
Inventor
Manuela Köhler
Stefanie Von Thaden
Hülya GÖKSEL
Original Assignee
Beiersdorf Ag
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Application filed by Beiersdorf Ag filed Critical Beiersdorf Ag
Publication of WO2012168049A2 publication Critical patent/WO2012168049A2/fr
Publication of WO2012168049A3 publication Critical patent/WO2012168049A3/fr

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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
    • A61K8/64—Proteins; Peptides; Derivatives or degradation products thereof
    • 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

  • ⁇ -polylysine epsilon-polylysine
  • the present invention relates to waterproof cosmetic and dermatological sunscreen preparations containing ⁇ -polylysine (epsilon-polylysine) and to the use of such substances for increasing the water resistance of cosmetic and dermatological sunscreen preparations.
  • ⁇ -polylysine epsilon-polylysine
  • UV-C radiation with a wavelength between 100 and 280 nm is absorbed by the ozone layer of the earth's atmosphere and is therefore not found in the solar spectrum. It is therefore physiologically meaningless when sunbathing.
  • the so-called UV-B range is between 290 nm and 320 nm. UV-B rays are essential for the long-lasting tanning of the skin, but can also cause erythema, simple sunburn or even more or less severe burns. Chronic photo damage, photodermatoses and herpes solaris can also be caused by UV-B radiation.
  • UV-A radiation having a wavelength between 320 nm and 400 nm has only a negligible biological effect and that accordingly the UV-B rays are responsible for most photodamage on the human skin.
  • UV-A radiation is far more dangerous than UV-B radiation in triggering photodynamic, especially phototoxic, and chronic skin changes.
  • the damaging effect of UV-B radiation can be enhanced by UV-A radiation.
  • UV-A radiation is sufficient to rapidly damage the collagen and elastin fibers, which are essential for the structure and firmness of the skin.
  • the appearance of light-aged skin may include wrinkles and wrinkles and an irregular, ragged relief, and the areas affected by photodamaging may be irregularly pigmented Brown spots, keratoses, and even carcinomas or malignant melanomas are possible, and premature aging of the skin due to UV exposure is also associated with lower activity of Langerhans cells and mild, chronic inflammation.
  • UV-B radiation varies widely depending on many factors (eg, time of year, day or latitude)
  • UV-A radiation remains relatively constant day and day regardless of year, daytime or geographical factors.
  • most of the UV-A radiation penetrates into the living epidermis, while about 70% of the UV-B rays are retained by the horny layer.
  • UV-B filters absorption range 280 to 320 nm
  • UV-A filters absorption range 320 to 400 nm
  • broadband filters absorption range 290 to 380 nm
  • UV-B filters Numerous compounds are known for protection against UV-B radiation, with their absorption maximum possibly being around 308 nm, since here the highest erythema activity of solar radiation is present.
  • Typical UV-B filters are z.
  • UV-A filter substances are certain water-soluble, sulfonated UV filter substances, such as.
  • phenylene-1, 4-bis (2-benzimidazyl) -3,3'-5,5'-tetrasulfonic acid and its salts In addition to the pure UV-A or UV-B filters, there are substances that cover both areas.
  • broadband filters include, for example, asymmetrically substituted s-triazine compounds, such as.
  • the 2-hydroxy-4-methoxy-benzophenone (INCI: Benzophenone 3) or the 2,2'-methylenebis (6- (2H-benzotriazol-2-yl) -4- (1, 1 , 3,3-tetramethylbutyl) -phenol) (INCI: Methylene bis-benzotriazolyl tetramethylene-butylphenol).
  • the light absorption behavior of sunscreen filter substances is very well known and documented, especially since in most industrialized countries there are positive lists for the use of such substances, which apply quite strict standards to the documentation. Since not only the position of the absorption maximum, but above all the absorption range is important for the characterization of a filter substance, absorption spectra of each substance are recorded. For the dosage of substances in However, the absorbance values can at best provide orientation guidance in the finished formulations because interactions with ingredients of the skin or the surface of the skin itself can lead to imponderabilities. Furthermore, it is usually difficult to estimate in advance how uniformly and in which layer thickness the filter substance is distributed in and on the horny layer of the skin.
  • the IPD method is usually used (IPD-immediate pigment darkening).
  • a value is determined which indicates how much longer the skin protected with the sunscreen can be irradiated with UV-A radiation until the same pigmentation occurs as with the unprotected skin.
  • sunscreen filter substances are generally expensive and since some sunscreen filter substances are also difficult to incorporate into cosmetic or dermatological preparations in higher concentrations, it was an object of the invention to arrive at preparations in a simple and inexpensive manner, which at unusually low concentrations of conventional UV filter substances nevertheless achieve an acceptable or even high UV-A and / or UV-B protection performance.
  • emulsions play the crucial role. Flowable or low-viscosity emulsions are preferred because they are easier to apply than viscous creams. Most sunscreens are used near water or during exercise (sweating), which is why the water resistance of such formulations is of particular importance.
  • a waterproof sunscreen protects the user not only after bathing, but also protects him during the bathing from sunburn. It is a common misconception that water is a good one or even sufficient protection against ultraviolet radiation. Rather, studies have shown that the permeability to UV-B rays is about 1 m below the water surface at about 50%. It is therefore advisable that also water sports, which z. As swimmers, surfers or snorkelers, and especially children who often play for hours on or in the water, protect the skin with a well-adherent, difficult to rinse off by water and sweat sun product from excessive and excessive sunlight.
  • W / O formulations are generally advantageous.
  • W / O emulsions often have unsatisfactory cosmetic properties: when applied, they can leave on the skin a greasy, shiny and sometimes sticky impression and - especially on hairy skin - difficult to distribute.
  • O / W emulsions on the other hand, have less of a greasy effect on the skin, are more mattifying and quickly penetrate the skin. They are generally perceived by consumers as lighter and more cosmetically elegant than W / O emulsions.
  • water is the outer phase
  • O / W emulsions are usually only partially waterproof.
  • copolymers of the polyvinylpyrrolidone for example the PVP hexadecene copolymer and the PVP eicosene copolymer which are present under the trade names Antaron V216 and Antaron V220 are available from the GAF Chemicals Cooperation, as well as the Tricontayl PVP and the like.
  • the binding ability of the UV filter in or on the skin is of great importance for the water resistance of the formulation. It is understood that oil-soluble UV filters are better bound to the (lipophilic) surface of the skin or are more difficult to wash off this than water-soluble UV filters.
  • a further object of the invention was therefore to arrive at preparations (in particular O / W formulations) in a simple and inexpensive manner, which are distinguished by good water resistance.
  • preparations should be found which have a high content of water-soluble UV filters and nevertheless show a very good water resistance.
  • the preparations according to the present invention represent in all respects extremely satisfactory preparations, which are not limited to a limited choice of raw materials. Accordingly, they are particularly suitable for serving as a basis for multi-purpose preparation forms.
  • the preparations according to the present invention show very good sensory and cosmetic properties, such as, for example, the spreadability to the skin or the ability to penetrate into the skin, and are also distinguished by a very good light-protection effectiveness extremely high UV-A and / or UV-B protection performance as well as excellent water resistance combined with excellent skincare data. It was particularly surprising that can be completely dispensed with conventional film formers, which are used according to the prior art to increase the water resistance.
  • ⁇ -Polylysine represents a polymer in which the ⁇ -terminal amino group of a lysine molecule is linked to the acid function of another lysine molecule
  • the index "n" (more precisely, the value n / 2) defines the degree of polymerization of the polylysine.
  • the INCI name is poly [imino [(2S) -2-amino-1-oxo-1,6-hexanediyl]], it has CAS no. 2821 1-04-3
  • the homopolymer ⁇ -polylysine is known to be described and used as an antimicrobial agent against yeasts, fungi and gram-positive and gram-negative bacteria. Currently it is used as a preservative, especially in Japan, Korea and the US. The production of the ⁇ -polylysine takes place via a natural fermentative process. References:
  • ⁇ -polylysines which have a degree of polymerization n / 2 of from 2 to 200, preferably from 10 to 100, particularly preferably from 25 to 35.
  • ⁇ -polylysine is preferably used in cosmetic or dermatological compositions in a content of 0.0005-50.0% by weight, in particular 0.01-20.0% by weight, based on the total weight of the composition.
  • the compositions advantageously contain 0.02-10.0% by weight, more preferably 0.02-5.0% by weight, of ⁇ -polylysine, very particularly preferably 0.5-3.0% by weight, in each case based on the total weight of the composition.
  • the prior art knows a number of possible methods of investigation: The preparation to be examined is applied to the skin and the sun protection factor is determined. Then water is allowed to act on the skin for a certain amount of time and then determines the sun protection factor again.
  • the other organic UV filters are selected from the group of compounds of anthralinates, cinnamates, salicylates, derivatives of camphor, derivatives of benzophenone, derivatives of ß, ß-diphenylacrylates, derivatives of benzotriazole, derivatives of Benzalmalonaten , Derivatives of benzimidazoles, imidazolines, derivatives of bis-benzoazolyl, derivatives of p-aminobenzoic acid, derivatives of methylenebis (hydroxyphenylbenzotriazole), polymeric filters, silicone filters, dimer derivatives of ⁇ -alkylstyrene, 4,4-diarylbutadiene.
  • UV filters include, for example, the following UV filters whose names are given in the INCI usual for cosmetics:
  • Filters are selected from the group of the following compounds:
  • the preparation contains one or more UV filters selected from the group of 1- (4'-tert-butylphenyl) -3- (4'-methoxyphenyl) propane
  • the preparation according to the invention contains pigments and / or nanopigments (also called micropigments, i.e. pigments with an average diameter of 5 to 100 nm and preferably between 10 and 50 nm) of coated and / or uncoated metal oxides.
  • pigments and / or nanopigments also called micropigments, i.e. pigments with an average diameter of 5 to 100 nm and preferably between 10 and 50 nm
  • Such pigments and / or nanopigments are advantageously selected according to the invention from the oxides of titanium, zinc, iron, zirconium, cerium, and mixtures thereof.
  • the pigments can advantageously also be used in the form of commercially available oily or aqueous predispersions for the purposes of the present invention.
  • dispersants and / or solubilizers can be added to these predispersions.
  • the pigments can advantageously be surface-treated ("coated"), whereby, for example, a hydrophilic, amphiphilic or hydrophobic character is to be formed or retained.
  • This surface treatment can consist in that the pigments are present per se
  • the various surface coatings may also comprise water, It is advantageous according to the invention if the preparation according to the invention contains one or more of these further UV filters in which the total amount of the filter substances is 0.1% by weight to 30% by weight, preferably 0.5 to 10% by weight, based on the total weight of the preparations, in order to provide cosmetic preparations containing the hair or hair the skin in front of the entire area of the ultraviolet n Protect radiation.
  • the preparation according to the invention contains as further constituent at least one compound for tanning the skin, for example dihydroxyacetone (DHA).
  • DHA dihydroxyacetone
  • the preparation according to the invention contains as further components at least one compound chosen from the group of lipid compounds, organic solvents, ionic or nonionic thickeners, skin soothing substances, antioxidants, radical scavengers, opacifiers, fragrances, dyes, stabilizers , Emulsifiers, skin softeners, silicones, ⁇ -hydroxy acids, defoamers, humectants, vitamins, fillers, polymers, blowing agents, acids or bases for pH adjustment, dyes.
  • the lipids may include oils, waxes and mixtures thereof.
  • the oil is understood to be a lipophilic component which is liquid at room temperature.
  • waxes are lipophilic components which are solid at room temperature and have a melting point above 35 ° C.
  • the lipids include, for example, fatty acids, fatty alcohols or esters.
  • the oils which are advantageous according to the invention include, for example, paraffin oils (mineral oils), vegetable oils (eg macadamia oil, jojoba oil, grapeseed oil, wheat germ oil), squalane, alcohols, esters, acids, C 12 -C 15 -alkyl benzoates, octyl palmitate, isopropyl lanolate, caprylic / capric triglycerides, esters and ethers of oxyethylene and / or oxypropylene, silicone oils (eg, cyclomethicone, dimethicone, polydimethylsiloxanes).
  • the lipids according to the invention include petrolatum, paraffins, carnauba wax, hydrogenated castor oil, beeswax, myristyl myristate, isopropyl palmitate.
  • the aqueous phase of the preparation according to the invention may advantageously comprise customary cosmetic auxiliaries, for example alcohols, in particular those of low C number, preferably ethanol and / or isopropanol, diols or polyols of low C number and their ethers, preferably propylene glycol, glycerol, butylene glycol, ethylene glycol, Ethylene glycol monoethyl or monobutyl ether, propylene glycol monomethyl, monoethyl or monobutyl ether, diethylene glycol monomethyl or monoethyl ether and analogous products, polymers, foam stabilizers, electrolytes and, in particular, one or more thickeners, which can be advantageously selected from the group silicon dioxide, aluminum silicates, Polysaccharides or their derivatives, for.
  • customary cosmetic auxiliaries for example alcohols, in particular those of low C number, preferably ethanol and / or isopropanol, diols or polyols of low
  • Carbopole from the company. Bf. Goodrich
  • the preparations according to the invention may also advantageously contain repellents for protection against mosquitoes, ticks and spiders and the like.
  • repellents for protection against mosquitoes, ticks and spiders and the like.
  • Advantageous z. N, N-diethyl-3-methylbenzamide (trade name: Meta-delphene, "DEET"), dimethyl phthalate (trade name: Palatinol M, DMP), 1-piperidine carboxylic acid 2- (2-hydroxyethyl) -1-methylpropyl ester and in particular 3- (Nn-butyl-N-acetylamino) -propionic acid ethyl ester (available commercially from Merck under the trade name Insekt Repellent® 3535.
  • the repellents can be used both individually and in combination.
  • Moisturizers are substances or mixtures of substances which give cosmetic preparations the property, after application or spreading on the skin surface, to reduce the moisture release of the horny layer (also called trans-epidermal water loss (TEWL)) and / or hydration to positively influence the horny layer, measured by the so-called corneometry.
  • TEWL trans-epidermal water loss
  • humectants for the purposes of the present invention are, for example, glycerol, lactic acid and / or lactates, in particular sodium lactate, butylene glycol, propylene glycol, biosaccharide gum-1, glycine soya, ethylhexyloxyglycerol, pyrrolidonecarboxylic acid, quaternary compounds and urea.
  • polymeric moisturizers from the group of water-soluble and / or water-swellable and / or water-gellable polysaccharides.
  • Moisturizers can also be used advantageously as anti-wrinkle active ingredients for protection against skin changes, as described, for example, in US Pat. B. occur during skin aging, can be used. It is advantageous for the purposes of the present invention, when the inventive preparation one or more humectants in a total concentration of 0.1 to 25% by weight and preferably in a total concentration of 0.5 to 10% by weight, each based on the total weight of Preparation containing.
  • the cosmetic preparations according to the invention may also advantageously, although not necessarily, contain fillers which are e.g. B. further improve the sensory and cosmetic properties of the formulations and, for example, cause or enhance a velvety or silky feel on the skin.
  • Advantageous fillers for the purposes of the present invention are starch and starch derivatives (such as, for example, tapioca starch, distarch phosphate, aluminum or sodium starch, octenylsuccinate and the like), pigments which have neither mainly UV filter nor coloring action (such as, for example, US Pat. B. boron nitride etc.) and / or Aerosils ® (CAS no. 7631-86-9).
  • the cosmetic preparations according to the invention may furthermore advantageously, although not necessarily, contain siloxane elastomers which are e.g. B. further improve the sensory and cosmetic properties of the formulations and, for example, cause or enhance a velvety or silky feel on the skin.
  • siloxane elastomers for the purposes of the present invention are dimethicone crosspolymer or else not limiting cetearyl dimethicone / vinyl dimethicone crosspolymer.
  • the preparations advantageously contain one or more antioxidants.
  • antioxidants all suitable or common for cosmetic applications antioxidants can be used.
  • the amount of the antioxidants (one or more compounds) in the preparations is preferably 0.001 to 30 wt .-%, particularly preferably 0.05 to 20 wt .-%, in particular 0.1 to 10 wt .-%, based on the total weight the preparation.
  • tocopheryl acetate Contains tocopheryl acetate. It is inventively preferred to select the concentration of tocopheryl acetate from 0.001 to 10 wt .-%, based on the total weight of the formulation.
  • active ingredients in the context of the present invention are natural active substances and / or derivatives thereof, such as.
  • the preparation according to the invention generally contains preservatives.
  • preservatives In principle, all substances which are contained in Annex 6 of the Preservative Ordinance are suitable as preservatives. In such a case it is According to the invention advantageous if the preparation is free of phenoxyethanol and / or parabens such as methylparaben or propylparaben. Particularly preferred are Koonserv réellesstoff such as, but not limited to Methylisothiazolinone, Ethyllauroylarginate, These preservatives can be used according to the invention preferably in a concentration of 0.1 to 2.0% by weight, based on the total weight of the preparation.
  • the preparation according to the invention is an emulsion, dispersion or a gelatinous preparation.
  • the preparation according to the invention may advantageously be in the form of a cream, a milk, a gel, a gel cream, a powder.
  • Titanium dioxide 0.5 1 2
  • Vitamin E acetate 0.2 0.2 0.2 0.3 0.1
  • Methylisothoazolinone 0.05 0.1 0.05 0.1 0.6
  • Titanium dioxide 0.5 1 2
  • Vitamin E acetate 0.2 0.2 0.2 0.3 0.1

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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)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Dermatology (AREA)
  • Cosmetics (AREA)

Abstract

L'invention concerne l'utilisation de ε-polylysine (epsilon-polylysine) pour améliorer l'hydrorésistance de formulations cosmétiques ou dermatologiques contenant au moins une substance courante filtrant les UV.
PCT/EP2012/059233 2011-06-07 2012-05-18 Utilisation de ε-polylysine (epsilon-polylysine) pour améliorer l'hydrorésistance de formulations cosmétiques ou dermatologiques WO2012168049A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE201110077082 DE102011077082A1 (de) 2011-06-07 2011-06-07 Verwendung von Epsilon-Polylysin zur Verbesserung der Wasserfestigkeitkosmetischer oder dermatologischer Formulierungen
DE102011077082.8 2011-06-07

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Publication Number Publication Date
WO2012168049A2 true WO2012168049A2 (fr) 2012-12-13
WO2012168049A3 WO2012168049A3 (fr) 2013-09-12

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DE (1) DE102011077082A1 (fr)
WO (1) WO2012168049A2 (fr)

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Publication number Priority date Publication date Assignee Title
DE102019219068A1 (de) * 2019-12-06 2021-06-10 Beiersdorf Ag Wasserfestes kosmetisches Sonnenschutzmittel

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CA2618223A1 (fr) * 2005-08-09 2007-02-22 Soane Labs, Llc Formulations destinees a la tenue des cheveux
WO2007050653A2 (fr) * 2005-10-25 2007-05-03 Avon Products, Inc. Composition insectifuge antisolaire resistante a l'eau
EP2192890A1 (fr) * 2007-09-14 2010-06-09 L'Oreal Compositions et procédés pour traiter des substrats kératineux
EP2067467A3 (fr) * 2007-09-14 2012-12-12 L'Oréal Compositions et procédés pour traiter des substrats kératiniques
US20090074700A1 (en) * 2007-09-14 2009-03-19 L'oreal Compositions and methods for imparting shine onto hair
WO2009150090A2 (fr) * 2008-06-12 2009-12-17 Basf Se Préparations cosmétiques pour éviter les odeurs corporelles
US20100255044A1 (en) * 2009-03-30 2010-10-07 Susan Daly Method of depositing particulate benefit agents on keratin-containing substrates

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Title
"Contact angle measurement-a reliable supportive method for screening water-restistance of ultraviolet-protecting products in vivo", INTERN. JOURNAL OF COSMETIC SCIENCE, vol. 29, 2007, pages 283 - 291
HIRAKI, J.: "Basic and applied studies on ?-polylysine", JOURNAL OF ANTIBACTERIAL ANTIFUNGAL AGENTS, vol. 23, 1995, pages 349 - 354
HIRAKI, J.: "Use of ADME studies to confirm the safety of E-polylysine as a preservative in food", REGULATORY TOXICOLOGY AND PHARMACOLOGY, vol. 37, no. 2, 2003, pages 328 - 340
SHIMA, S. ET AL.: "Antimicrobial action of E-poly-L-lysine", JOURNAL OF ANTIBIOTICS, vol. 37, no. 11, 1984, pages 1449 - 1455, XP009079625
SHIMA, S.; SAKAI H.: "Polylysine produced by Streptomyces", AGRICULTURAL AND BIOLOGICAL CHEMISTRY, vol. 41, 1977, pages 1807 - 1809

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WO2012168049A3 (fr) 2013-09-12

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