WO2004022019A1 - Emulsions contenant de la microcellulose - Google Patents

Emulsions contenant de la microcellulose Download PDF

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Publication number
WO2004022019A1
WO2004022019A1 PCT/EP2003/009684 EP0309684W WO2004022019A1 WO 2004022019 A1 WO2004022019 A1 WO 2004022019A1 EP 0309684 W EP0309684 W EP 0309684W WO 2004022019 A1 WO2004022019 A1 WO 2004022019A1
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WIPO (PCT)
Prior art keywords
emulsion
cosmetic
branched
unsaturated
saturated
Prior art date
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PCT/EP2003/009684
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German (de)
English (en)
Inventor
Rainer Kröpke
Andreas Bleckmann
Astrid Heptner
Silke FÜLLER
Celina Konz
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Beiersdorf AG
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Beiersdorf AG
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Publication of WO2004022019A1 publication Critical patent/WO2004022019A1/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
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04—Dispersions; Emulsions
    • A61K8/06—Emulsions
    • A61K8/064—Water-in-oil emulsions, e.g. Water-in-silicone emulsions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73—Polysaccharides
    • A61K8/731—Cellulose; Quaternized cellulose derivatives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/08—Anti-ageing preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/41—Particular ingredients further characterized by their size
    • A61K2800/412—Microsized, i.e. having sizes between 0.1 and 100 microns

Definitions

  • Emulsions with microcellulose Emulsions with microcellulose
  • the present invention relates to microcrystalline cellulose-containing emulsions with a lipophilic outer phase and their use.
  • the skin is the largest organ in humans. Among its many functions (e.g. for heat regulation and an internal organ), the barrier function, which prevents the skin (and ultimately the entire organism) from drying out, is probably the most important. At the same time, the skin acts as a protective device against the penetration and absorption of external substances and UV radiation. This barrier function is brought about by the epidermis, which as the outermost layer forms the actual protective cover against the environment. At around a tenth of the total thickness, it is also the thinnest layer of the skin.
  • Emulsions are generally understood to mean heterogeneous systems which consist of two or not at all there are miscible liquids which are usually referred to as phases and in which one of the two liquids is dispersed in the form of very fine droplets in the other liquid. When viewed externally and with the naked eye, emulsions appear homogeneous.
  • O / W emulsion e.g. milk
  • the basic character of an O / W emulsion is characterized by the water.
  • a water-in-oil emulsion (W / O emulsion, e.g. butter) is the opposite principle, whereby the basic character is determined by the oil.
  • Emulsifiers are added to the emulsions in order to keep emulsions stable over a longer period of time and to prevent separation of the phases.
  • Emulsifiers are generally molecules with a polar, hydrophilic structural element and an apolar, lipophilic structural element.
  • HLB value a dimensionless number between 0 and 20
  • Numbers below 9 indicate oil-soluble, hydrophobic emulsifiers, numbers above 11 water-soluble, hydrophilic.
  • the HLB value says something about the balance between the size and strength of the hydrophilic and lipophilic groups of an emulsifier. It can be derived from these considerations that the effectiveness of an emulsifier can also be characterized by its HLB value. The following list shows the relationship between the HLB value and the possible area of application:
  • the HLB value of an emulsifier can also be calculated from increments, the HLB increments for the various hydrophilic and hydrophobic groups that make up a molecule. As a rule, it can be found in tables (e.g. HPFiedler, encyclopedia of auxiliary substances for pharmacy, cosmetics and related areas, Editio Cantor Verlag, Aulendorf, 4th ed. 1996) or in the manufacturer's information.
  • the solubility of the emulsifier in the two phases practically determines the type of emulsion. If the emulsifier is more soluble in water, an O / W emulsion is obtained. On the other hand, if the emulsifier has better solubility in the oil phase, a W / O emulsion is produced under otherwise identical production conditions.
  • the oil phase of emulsions can have different compositions.
  • silicone oils the person skilled in the art differentiates between water-in-oil and water-in silicone oil emulsions, the latter being characterized by a silicone oil content of more than 50% by weight.
  • Special emulsifiers are required for silicone oil emulsions, which distinguish them from ordinary W / O emulsifiers.
  • silicone oils are particularly good on the skin.
  • Water-in-oil and water-in-silicone oil emulsions can be summarized under the term emulsion with an external lipophilic phase.
  • Microcrystalline cellulose has long been known as a cosmetic-pharmaceutical additive. It is generally used as a filler and binder in tablets and as a suspending and / or thickening agent in cosmetic and / or pharmaceutical preparations (HPFiedler, encyclopedia of auxiliaries for pharmacy, cosmetics and related areas, Editio Cantor Verlag, Aulendorf, 5 Ed. 2002).
  • a disadvantage of the prior art is the fact that cosmetic and / or dermatological emulsions with an external lipophilic phase leave a greasy, greasy skin feeling after application to the skin, which feeling is retained over a longer period of time.
  • skin moisturizers usually glycerin
  • glycerin can only be used to a very limited extent (approx. 5% by weight). work in, as the preparations leave a sticky skin feeling that is no longer acceptable to the user at higher concentrations of skin humidifiers.
  • Emulsions with an external lipophilic phase of the prior art usually have the disadvantage of not being particularly temperature and storage stable. At temperatures above 30 ° C, irreversible oil deposits and a gradual destruction of the emulsion occur within a very short time.
  • cosmetic and / or dermatological emulsions with an external lipophilic phase have a high care effect on the skin. Furthermore, they can be manufactured without any preservatives. However, their greasy, uncomfortable skin feel and the long-lasting greasy shine they leave on the skin has so far led to their acceptance by consumers being rather low compared to the O / W emulsions. Because skin gloss and greasy skin feeling is generally perceived as unpleasant and unattractive.
  • W / O and W / S emulsifiers are also increasingly affected by this development, since they partially penetrate into the skin and remain there for a relatively long time. Therefore, the concentration of W / O or W / S emulsifiers in cosmetic and / or dermatological preparations should be kept as low as possible.
  • a cosmetic and / or dermatological emulsion with an outer lipophilic phase comprising a) an aqueous phase, b) a lipophilic phase, c) one or more W / O and / or W / S emulsifiers, d) one or more microcrystalline celluloses, d) one or more skin moisturizers, in addition to any further cosmetic and / or dermatological active ingredients, auxiliaries and additives.
  • the preparations according to the invention are distinguished by a pleasantly dry, dull skin feel.
  • the oily sheen on the skin so typical of emulsions with an external lipophilic phase is significantly reduced.
  • the preparations according to the invention are particularly skin-friendly, since on the one hand they reduce the emulsifier concentration by up to 50% and on the other hand the concentration of skin moisturizers (in particular glycerol) can be roughly doubled compared to products without microcrystalline celluloses, without this being the case when the preparation is applied a sticky skin feeling arises.
  • Emulsions containing microcrystalline cellulose are known per se.
  • Japanese patent JP 55162710 describes emulsions containing microcrystalline cellulose.
  • this document could not point the way to the present invention.
  • the emulsion according to the invention advantageously contains one or more emulsifiers with an active content of 0.01 to 12% by weight, preferably with an active content of from 1.5 to 8% by weight, and particularly preferably with one Active content of 2.5 to 5.5% by weight, based in each case on the total weight of the emulsion and the total amount of emulsifiers according to the invention.
  • the minimum amount (active content) of one or more emulsifiers is 0.01% by weight, preferably 1.5% by weight and particularly preferably 2.5% by weight, in each case based on the total weight of the emulsion and the total amount of emulsifiers according to the invention.
  • the maximum amount (active content) one or more emulsifiers advantageously 12% by weight, preferably 8% by weight and particularly preferably 5.5% by weight, in each case based on the total weight of the emulsion and the total amount of emulsifiers according to the invention.
  • the active content means that amount of an emulsifier substance that is or is effective as an emulsifier. It can usually be found in the manufacturer's instructions.
  • the emulsion according to the invention advantageously contains one or more microcrystalline celluloses in an amount of 0.01 to 2% by weight, preferably in an amount of 0.1 to 1% by weight and particularly preferably in an amount of 0.15 to 0, 75% by weight, based in each case on the total weight of the emulsion.
  • the minimum amount of one or more microcrystalline celluloses is 0.01% by weight, preferably 0.1% by weight and particularly preferably 0.15% by weight, and the maximum amount of one or more microcrystalline celluloses is advantageously 2% by weight, preferably 1 % By weight and particularly preferably 0.75% by weight, in each case based on the total weight of the emulsion and the total amount of microcrystalline celluloses according to the invention.
  • the cellulose used according to the invention consists of a mixture of microcrystalline cellulose and sodium carboxymethyl cellulose in a mixing ratio of 100: 0 to 80:20 and preferably in a mixing ratio of 91.7: 8.3 to 81.2: 18.8.
  • the particle size of the cellulose particles is preferably selected such that 0.1% of the particles have a size of> 250 ⁇ m and 40-50% of the particles have a size of> 44 ⁇ m.
  • the emulsion according to the invention contains more or more skin moisturizers in a concentration of 3 to 25% by weight, preferably in a concentration of 5 to 12% by weight and particularly preferably in a concentration of 7.5 up to 10% by weight, based in each case on the total weight of the emulsion.
  • the minimum amount of one or more skin moisturizers is 3% by weight, preferably 5% by weight and particularly preferably 7.5% by weight, and the maximum amount of one or more skin moisturizers is advantageously 25% by weight, preferably 12% by weight and particularly preferably 10% by weight, based in each case on the total weight of the emulsion and the total amount of skin moisturizers according to the invention.
  • one or more skin wetting agents can advantageously be selected from the group consisting of glycerol, lactic acid and / or lactates, butylene glycol, propylene glycol, sorbitol, biosaccaride Gum-1, glycine soya, ethylhexyloxyglycerol, pyrrolidonecarboxylic acid urea and polysaccharides such as hyalanuronic acid and / or a fucose-rich polysaccharide, which is filed in the Chemical Abstracts under the registration number 178463-23-5.
  • Glycerol, sorbitol, urea and butylene glycol are preferred according to the invention.
  • the cosmetic and / or dermatological emulsion according to the invention can advantageously be present according to the invention in the form of a water-in-oil emulsion (W / O emulsion).
  • W / O emulsion water-in-oil emulsion
  • one or more W / O emulsifiers are advantageously selected according to the invention from the group of substances of the general formula
  • a and A ' represent identical or different hydrophobic organic radicals, - a represents a number from 1 to 100, preferably 2 to 60, in particular 5 to 40,
  • X is a single bond or the group - CH— I
  • OIR 3 represents, R 1 and R 2 are selected independently of one another H, methyl, but not both radicals simultaneously represent methyl, R 3 is selected from the group H, and the branched and unbranched, saturated and unsaturated alkyl and acyl radicals with 1 - 20 carbon atoms, or that the W / O emulsifier (s) are selected from the group of fatty alcohols with 8 - 30 carbon atoms, monoglycerol esters of saturated and / or unsaturated, branched and / or unbranched alkane carboxylic acids with a chain length of 8 - 24, in particular 12-18 C atoms, diglycerol esters of saturated and / or unsaturated, branched and / or unbranched alkane carboxylic acids with a chain length of 8-24, in particular 12-18 C atoms, triglycerol esters of saturated and / or unsaturated, branched and / or unbranched alkane carboxylic acids with a chain length of
  • the W / O emulsifier or the W / O emulsifiers are chosen such that the residues A and A 'are advantageously chosen from the group of the branched and unbranched, saturated and unsaturated alkyl and acyl residues and hydroxyacyl residues with 10 - 30 carbon atoms and also from the group of the hydroxyacyl groups connected to one another via ester functions, according to the scheme.
  • R ' is selected from the group of branched and unbranched alkyl groups with 1 to 20 carbon atoms and R "is selected from the group of branched and unbranched alkylene groups with 1 to 20 carbon atoms and b can assume numbers from 0 to 200.
  • emulsifiers can be used according to the invention:
  • the W / O emulsifier (s) are selected from the group PEG-30 dipolyhydroxystearate, decaglyceryl heptaoleate, polyglyceryl 3-diisostearate, PEG-8 distearate, diglycerol dipolyhydroxystearate.
  • the cosmetic and / or dermatological emulsion according to the invention can be in the form of a water-in-silicone oil emulsion (W / S emulsion).
  • silicone emulsifiers can advantageously be selected from the group of alkyl methicone copolyols and / or alkyl dimethicone copolyols, in particular from the group of compounds which are characterized by the following chemical structure:
  • X and Y are selected independently of one another from the group H (hydrogen) and the branched and unbranched alkyl groups, acyl groups and alkoxy groups having 1 to 24 carbon atoms, p represents a number from 0 to 200, q represents a number from 1 to 40, and r represents a number from 1 to 100.
  • silicone emulsifiers to be used particularly advantageously for the purposes of the present invention are dimethicone copolyols, which are available from Th. Goldschmidt AG under the trade names ABIL® B 8842, ABIL® B 8843, ABIL® B 8847, ABIL® B 8851, ABIL® B 8852, ABIL® B 8863, ABIL® B 8873 and ABIL® B 88183.
  • cetyl PEG / PPG-10/1 dimethicone (Cetyl dimethicone copolyol), which is sold by the company Th.Goldschmidt AG under the trade name ABIL® EM 90.
  • cyclomethicone dimethicone copolyol which is sold by the company Th.Goldschmidt AG under the trade name ABIL® EM 97 and ABIL® WE 09.
  • the emulsifier Lauryl PEG / PPG-18/18 Methicone (Laurylmethiconcopolyol) has proven to be particularly advantageous, which under the
  • Another advantageous silicone emulsifier is "Octyl Dimethicone Ethoxy Glucoside" from Wacker.
  • emulsifiers used for this type of emulsion can be used for a water-in-silicone oil emulsion according to the invention.
  • Water-in-silicone emulsifiers which are particularly preferred according to the invention are cetyl PEG / PPG-10/1 dimethicone and lauryl PEG / PPG-18/18 methicone [e.g. ABIL EM 90 (Goldschmidt), DC5200 Formulation Aid (Dow Coming)] and any mixture of both emulsifiers.
  • Emulsions according to the invention which are in the form of a low viscosity (with a viscosity of 3000 to 8000 mPas, measured at 25 ° C. with the Haake Viscotester VT-02) and / or sprayable W / O or W / S emulsion or W / OW / S-mixed emulsions with a viscosity of ⁇ 1500 mPas (measured at 25 ° C with the Haake Viscotester VT-02) are particularly preferred to contain emulsifiers such as polyglyceryl-2 dipolyhydroxystearate and polyglyceryl-3 diisostearate in combination with polysorbate.
  • emulsifiers such as polyglyceryl-2 dipolyhydroxystearate and polyglyceryl-3 diisostearate in combination with polysorbate.
  • W / O emulsions, W / S emulsions or W / OW / S mixed emulsions according to the invention which are in the form of a soft to firm cream with a viscosity above 9000 mPas (measured at 25 ° C. with the Haake Viscotester VT-02) are present According to the invention, a ratio of emulsifier to lipid phase of 1: 5 to 1:10 is particularly advantageous.
  • W / O emulsions, W / S emulsions or W / OW / S mixed emulsions according to the invention which are in the form of a flowable and / or liquid lotion with a viscosity of 3000 to 9000 mPas, according to the invention particularly advantageously assign a ratio of emulsifier Lipid phase from 1:10 to 1:20.
  • the total amount (active content) of silicone emulsifiers used according to the invention in the cosmic or dermatological preparations according to the invention is advantageously in the range from 0.1-10.0% by weight, preferably 0.5-5%. 0% by weight and very particularly preferably 1- 2.5% by weight, in each case based on the total weight of the preparations.
  • the preparation according to the invention is advantageously in the form of an ointment, cream, lotion or an emulsion foam (French mousse).
  • the emulsion according to the invention can also contain other ingredients according to the invention, for example alcohols, diols or polyols of low C number, and their ethers, preferably ethanol, isopropanol, propylene glycol, glycerol, ethylene glycol, ethylene glycol monoethyl or monobutyl ether, propylene glycol monomethyl, monoethyl or monobutyl ether, diethylene glycol monomethyl or monoethyl ether and analog products, furthermore alcohols of low C number, for example Ethanol, isopropanol, 1, 2-propanediol and glycerin.
  • alcohols, diols or polyols of low C number, and their ethers preferably ethanol, isopropanol, propylene glycol, glycerol, ethylene glycol, ethylene glycol monoethyl or monobutyl ether, propylene glycol monomethyl, monoethyl or monobut
  • the lipid phase of the emulsion according to the invention is advantageously chosen from the group of polar oils, for example from the group of lecithins and fatty acid triglycerides, especially the triglycerol esters of saturated and / or unsaturated, branched and / or unbranched alkane carboxylic acids with a chain length of 8 to 24, in particular 12 to 18 carbon atoms.
  • the fatty acid triglycerides can for example be advantageously selected from the group of synthetic, semi-synthetic and natural oils, such as. B.
  • cocoglyceride olive oil, sunflower oil, soybean oil, peanut oil, rapeseed oil, almond oil, palm oil, coconut oil, castor oil, wheat germ oil, grape seed oil, safflower oil, evening primrose oil, macadamia nut oil and the like.
  • natural waxes of animal and vegetable origin are advantageous, such as beeswax and other insect waxes, and berry wax, steam butter, lanolin (wool wax alcohol, trade name E ucerit der er company Beiersdorf), candella wax, carnauba wax.
  • waxes which are advantageous according to the invention can be synthetic in nature, such as, for example, myristyl myristate, fatty alcohols (C16-C24), paraffin wax, cetyl palmitate, tripalmitin, ceresin, hydrogenated cocosglycerides, C15-C40 alkyl stearyl stearate (for example trade names Kesterwachs K40P, K48P, K70P, the company, Keunen), polyvinyl stearyl ether.
  • myristyl myristate C16-C24
  • paraffin wax cetyl palmitate
  • tripalmitin ceresin
  • ceresin hydrogenated cocosglycerides
  • C15-C40 alkyl stearyl stearate for example trade names Kesterwachs K40P, K48P, K70P, the company, Keunen
  • polyvinyl stearyl ether for example trade names Kesterwachs K40P, K48P, K70P, the company, Ke
  • further advantageous polar oil components can also be selected from the group of esters from saturated and / or unsaturated, branched and / or unbranched alkane carboxylic acids with a chain length of 3 to 30 carbon atoms and saturated and / or unsaturated, branched and / or unbranched alcohols with a chain length of 3 to 30 C atoms and from the group of esters from aromatic carboxylic acids and saturated and / or unsaturated, branched and / or unbranched alcohols with a chain length of 3 to 30 C atoms.
  • ester oils can then advantageously be selected from the group octyl palmitate, octyl co-coat, octyl isostearate, octyl dodeceyl myristate, octyl dodecanol, cetearyl isononanoate, isopropyl myristate, isopropyl palmitate, isopropyl stearate, isopropyl oleate, n-butyl stearate, n-stonolate, n-stonolate, n-stonyl-n-stonate, 2-ethylhexyl palmitate, 2-ethylhexyl laurate, 2-hexyldecyl stearate, 2-octyldodecyl palmitate, stearyl heptanoate, oleyl oleate, olerlerucate, erucyl oleate, erucylerucate
  • an oil phase can advantageously be selected from the group of dialkyl ethers and dialkyl carbonates.
  • Myritol® 331 by Henkel C ⁇ 2 , 13 alkyl lactate, di-C 12 . 13- alkyl tartrate, triisostearin, dipentaerythrityl hexaprylate / hexacaprate, propylene glycol monoisostearate, tricaprylin, dimethyl isosorbide. It is particularly advantageous if the oil phase of the formulations according to the invention has a content of Ci ⁇ .is alkyl benzoate or consists entirely of this.
  • Advantageous oil components are also z.
  • the ratio of the oils which are liquid at room temperature to the proportion of the waxes which are solid or semisolid at room temperature in the lipid particles according to the invention is from 0: 100 to 1: 4.
  • an oil phase can also advantageously also contain non-polar oils, for example those which are selected from the group of branched and unbranched hydrocarbons and waxes, in particular mineral oil, petroleum jelly (petrolatum), paraffin oil, squalane and squalene, polyolefins, hydrogenated polyisobutenes and Isohexadecane.
  • non-polar oils for example those which are selected from the group of branched and unbranched hydrocarbons and waxes, in particular mineral oil, petroleum jelly (petrolatum), paraffin oil, squalane and squalene, polyolefins, hydrogenated polyisobutenes and Isohexadecane.
  • Polydecenes are the preferred substances among the polyofins.
  • An oil phase can advantageously also have a content of cyclic or linear silicone oils or consist entirely of such oils, although it is preferred to use an additional content of other oil phase components in addition to the silicone oil or the silicone oils.
  • Silicone oils are high-molecular synthetic polymeric compounds in which silicon atoms are linked in a chain and / or network-like manner via oxygen atoms and the remaining valences of silicon by hydrocarbon residues (mostly methyl, more rarely ethyl, propyl, phenyl groups, etc.) are saturated.
  • the silicone oils are systematically referred to as polyorganosiloxanes.
  • the methyl-substituted polyorganosiloxanes are also known as polydimethylsiloxane or dimethicone (INCI). Dimethicone is available in different chain lengths or with different molecular weights.
  • Particularly advantageous polyorganosiloxanes for the purposes of the present invention are, for example, dimethylpolysiloxanes [poly (dimethylsiloxane)], which are available, for example, under the trade names Abil 10 to 10,000 from Th. Goldschmidt.
  • phenylmethylpolysiloxanes (INCI: phenyl dimethicone, phenyltrimethicone), cyclic silicones (octamethylcyclotetrasiloxane or decamethylcyclopentasiloxane), which are also referred to as NCyls as cyclomethicones, and are arnino-modified (INCI: siliconized) Amodimethicone) and silicone waxes, e.g. B.
  • polysiloxane-polyalkylene copolymers (INCI: stearyl dimethicone and cetyl dimethicone) and dialkoxydimethyl polysiloxanes (stearoxy dimethicone and behenoxy stearyl dimethicone), which as different A bil wax types b ei T h. G oldschmidt is available.
  • Other silicone oils are also to be used advantageously for the purposes of the present invention, for example cetyldimethicone, hexamethylcyclotrisiloxane, polydimethylsiloxane, poly (methylphenylsiloxane).
  • compositions are also obtained if antioxidants are used as additives or active ingredients.
  • the preparations advantageously contain one or more antioxidants. All of the antioxidants suitable or customary for cosmetic and / or dermatological applications can be used as inexpensive, but nevertheless optional, antioxidants.
  • the antioxidants are advantageously selected from the group consisting of amino acids (eg glycine, histidine, tyrosine, tryptophan) and their derivatives, imidazoles (eg urocanic acid) and their derivatives, peptides such as D, L- Camosin, D-camosin, L-carnosine and their derivatives (e.g. anserine), carotenoids, carotenes (e.g. ⁇ -carotene, ß-carotene, lycopene) and their derivatives, lipoic acid and their derivatives (e.g. Dihydrolipoic acid), aurothioglucose, propylthiouracil and other thiols (e.g.
  • amino acids eg glycine, histidine, tyrosine, tryptophan
  • imidazoles eg urocanic acid
  • peptides such as D, L- Camosin, D-camosin,
  • thioredoxin glutathione, cysteine, cystine, cystamine and their glycosyl, N-acetyl, methyl, ethyl, propyl, amyl, Butyl and lauryl, palmitoyl, oleyl, ⁇ -linoleyl, cholesteryl and glyceryl esters) and their salts, dilauryl thiodipropionate, distearyl thiodipropionate, thiodipropionic acid and their derivatives (esters, ethers, peptides, lipids, nucleotides, nucleosides and salts) and Sulfoximine compounds (e.g.
  • buthionine sulfoximines in very low tolerable dosages (e.g. B. pmol to ⁇ mol / kg), also (metal) chelators (e.g. ⁇ -hydroxy fatty acids, palmitic acid, phytic acid, lactoferrin), ⁇ -hydroxy acids (e.g.
  • citric acid citric acid, lactic acid, malic acid
  • humic acid bile acid, bile extracts , Bilirubin, biliverdin, EDTA, EGTA and their derivatives
  • unsaturated fatty acids and their derivatives e.g. ⁇ -linolenic acid, linoleic acid, oleic acid
  • folic acid and their derivatives ubiquinone and ubiquinol and their derivatives
  • vitamin C. and derivatives e.g. ascorbyl palmitate, Mg ascorbyl phosphate, ascorbyl acetate
  • tocopherols and derivatives e.g.
  • vitamin E acetate
  • vitamin A and derivatives vitamin A palmitate
  • water-soluble antioxidants such as vitamins, e.g. B. ascorbic acid and its derivatives.
  • Preferred antioxidants are also vitamin E and its derivatives and vitamin A and its derivatives.
  • the amount of the antioxidants (one or more compounds) in the preparations is preferably 0.001 to 30% by weight, particularly preferably 0.05 to 20% by weight, in particular 0.1 to 10% by weight , based on the total weight of the preparation.
  • vitamin E and / or its derivatives represent the antioxidant (s)
  • vitamin A or vitamin A derivatives or carotenes or their derivatives represent the antioxidant or antioxidants, it is advantageous to add their respective concentrations in the range from 0.001 to 10% by weight, based on the total weight of the formulation choose. It is particularly advantageous if the cosmetic preparations according to the present invention contain cosmetic or dermatological active ingredients, preferred active ingredients being antioxidants which can protect the skin from oxidative stress.
  • active ingredients in the sense of the present invention are natural active ingredients and / or their derivatives, such as.
  • z. B known anti-wrinkle active ingredients such as flavone glycosides (especially ⁇ -glycosylrutin), coenzyme Q10, vitamin E and / or derivatives and the like are particularly suitable for the prophylaxis and treatment of cosmetic or dermatological skin changes, such as z. B. occur with skin aging (such as dryness, roughness and formation of dry lines, itching, reduced regreasing (e.g. after washing), visible vasodilation (telangiectasias, cuperosis), flaccidity and formation of wrinkles and fine lines, local hyper- , Hypo and incorrect pigmentation (eg age spots), increased susceptibility to mechanical stress (eg cracking) and the like). They are also advantageous against the appearance of dry or rough skin.
  • compositions according to the invention include, for example, panthenol, allantoin, tannin, antihistamines, antiphlogistics, glucocorticoids (e.g. hydrocortisone) as well as plant substances such as azulene and bisabolol, glycyrrhizin, hamamelin and plant extracts such as chamomile, aloe vera, hamazelis, licorice root.
  • glucocorticoids e.g. hydrocortisone
  • plant substances such as azulene and bisabolol, glycyrrhizin, hamamelin and plant extracts such as chamomile, aloe vera, hamazelis, licorice root.
  • Vitamin D 3 - analogous tacalcitol, calcipotriol, tacalcitol, colecalciferol and calcitrol (vitamin D 3 ) and / or fumaric acid esters can also be successfully incorporated into the preparations.
  • the cosmetic or dermatological preparations according to the invention can furthermore advantageously, although not necessarily, contain fillers which, for. B. the senso- Further improve the cosmetic and cosmetic properties of the formulations and, for example, create or intensify a velvety or silky feeling on the skin.
  • Advantageous fillers for the purposes of the present invention are starch and starch derivatives (such as tapioca starch, distarch phosphate, aluminum or sodium starch, octenyl succinate and the like), pigments which have neither mainly UV filter nor coloring effects (such as e.g. B. boron nitride etc.) and / or Aerosile ® (CAS No. 7631-86-9).
  • the emulsion according to the invention can advantageously be used as a sunscreen.
  • the preparation according to the present invention advantageously contains at least one UV-A, UV-B and / or broadband filter substance and / or at least one inorganic pigment reflecting and / or absorbing UV light.
  • the formulation may, although not necessary, optionally also contain one or more organic and / or inorganic pigments as UV filter substances, which may be present in the water and / or the oil phase
  • UV protective substances are exclusively in one of the two phases or in both phases of the preparation according to the invention.
  • Preferred inorganic pigments are metal oxides and / or other metal compounds which are sparingly soluble or insoluble in water, in particular oxides of titanium (Ti0 2 ), zinc (ZnO), iron (e.g. Fe 2 0 3 ), zirconium (Zr0 2 ), silicon ( Si0 2 ), manganese (e.g. MnO), aluminum (Al 2 0 3 ), cerium (e.g. Ce 2 0 3 ), mixed oxides of the corresponding metals as well as mixtures of such oxides and the sulfate of barium (BaS0 ).
  • the pigments can also advantageously be used in the form of commercially available oily or aqueous predispersions. Dispersing aids and / or solubilizing agents can advantageously be added to these predispersions.
  • the pigments can advantageously be surface-treated (“coated”), with a hydrophilic, amphiphilic or hydrophobic character, for example, being formed or retained.
  • This surface treatment can consist in that the pigments are coated with a thin film using methods known per se hydrophilic and / or hydrophobic inorganic and / or organic layer
  • the various surface coatings can also contain water in the sense of the present invention.
  • Inorganic surface coatings in the sense of the present invention can consist of aluminum oxide (Al 2 0 3 ), aluminum hydroxide Al (OH) 3 , or aluminum oxide hydrate (also: alumina, CAS no .: 1333-84-2), sodium hexametaphosphate (NaP0 3 ) 6 , sodium metaphosphate (NaP0 3 ) n , silicon dioxide (Si0 2 ) (also: silica, CAS No .: 7631-86-9), barium sulfate (BaS0 4 ) or iron oxide (Fe 2 0 3 ).
  • These inorganic surface coatings can occur alone, in combination and / or in combination with organic coating materials.
  • Organic surface coatings in the sense of the present invention can consist of vegetable or animal aluminum stearate, vegetable or animal stearic acid, lauric acid, dimethylpolysiloxane (also: dimethicone), methylpolysiloxane (methicone), simethicone (a mixture of dimethylpolysiloxane with an average chain length of 200 to 350 dimethylsiloxane Units and silica gel) or Alginic acid.
  • dimethylpolysiloxane also: dimethicone
  • methicone methylpolysiloxane
  • simethicone a mixture of dimethylpolysiloxane with an average chain length of 200 to 350 dimethylsiloxane Units and silica gel
  • Alginic acid Alginic acid.
  • Zinc oxide particles and predispersions of zinc oxide particles suitable according to the invention are available from the companies listed under the following names:
  • Suitable titanium dioxide particles and predispersions of titanium dioxide particles are available under the following trade names from the companies listed:
  • UV-A filter substances for the purposes of the present invention are dibenzoyl methane derivatives, in particular 4- (tert-butyl) -4'-methoxydibenzoylmethane (CAS No. 70356-09-1), which is available from Givaudan under the Parsol brand ® 1789 and is sold by Merck under the trade name Eusolex® 9020.
  • dibenzoyl methane derivatives in particular 4- (tert-butyl) -4'-methoxydibenzoylmethane (CAS No. 70356-09-1), which is available from Givaudan under the Parsol brand ® 1789 and is sold by Merck under the trade name Eusolex® 9020.
  • UV filter substances in the sense of the present invention are sulfonated, water-soluble UV filters, such as. B .:
  • 1,4-di (2-oxo-10-sulfo-3-bornylidenemethyl) benzene also: 3,3 '- (1,4-phenylenedimethylene)
  • Benzene-1, 4- di (2-oxo-3-bomylidenemethyl-10-sulfonic acid) has the INCI name terephthalic dicampher sulfonic acid (CAS No. 90457-82-2) and is available, for example, under the trade name Mexoryl SX from Chimex;
  • Sulfonic acid derivatives of 3-benzylidene camphor such as. B. 4- (2-oxo-3-bornylidene-methyl) benzenesulfonic acid, 2-methyl-5- (2-oxo-3-bomylidene-methyl) sulfonic acid and salts thereof.
  • Hydroxybenzophenone derivatives such as e.g. 2- (4-Diethylamino-2-hydroxybenzoyl) - benzoic acid hexyl ester, which is available, for example, from BASF under the
  • Benzoxazole derivatives such as e.g. the 2,4-bis- [5-1 (dimethylpropyl) benzossazol-2-yl- (4-phenyl) imino] -6- (2-ethylhexyl) imino-1, 3,5-triazine (CAS no .: 288254-16-0), which is available, for example, from 3V Sigma under the trade name UVASorb® K2A.
  • Advantageous UV filter substances in the sense of the present invention are also so-called broadband filters, i.e. Filter substances that absorb both UV-A and UV-B radiation.
  • Advantageous broadband filters or UV-B filter substances are, for example, triazine derivatives, such as. B. • 2,4-bis - ⁇ [4- (2-ethylhexyloxy) -2-hydroxy] phenyl ⁇ -6- (4-methoxyphenyl) -1, 3,5-triazine (INCI: Aniso Triazine), which is available from CIBA-Chemicals GmbH under the trade name Tinosorb® S;
  • Diethylhexylbutylamidotriazon (INCI: Diethylhexylbutamidotriazone), which is available under the trade name UVASORB HEB from Sigma 3V;
  • An advantageous broadband filter in the sense of the present invention is also 2,2'-methylene-bis- (6- (2H-benzotriazol-2-yl) -4- (1, 1, 3,3-tetramethylbuty! - phenol), which is available under the trade name Tinosorb® M from CIBA-Chemicals GmbH.
  • Another advantageous broadband filter for the purposes of the present invention is 2- (2H-benzotriazol-2-yl) -4-methyl-6- [2-methyl-3- [1,3,3,3-tetramethyl-1- [(trimethylsilyl) oxy] disiloxanyl] propyl] phenol (CAS no .: 155633-54-8) with the INCI name Drometrizole Trisiloxane, which is available under the trade name Mexoryl® XL from Chimex ,
  • the other UV filter substances can be oil-soluble or water-soluble.
  • Advantageous oil-soluble UV-B and / or broadband filter substances in the sense of the present invention are e.g.
  • ⁇ 3-benzylidene camphor derivatives preferably 3- (4-methylbenzylidene) camphor, 3-benzylidene camphor;
  • 4-aminobenzoic acid derivatives preferably 4- (dimethylamino) benzoic acid (2-ethylhexyl) ester, 4- (dimethylamino) benzoic acid amyl ester;
  • benzophenone preferably 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-methoxy-4'-methylbenzophenone, 2,2'-dihydroxy-4-methoxybenzophenone
  • Particularly advantageous preparations within the meaning of the present invention which are distinguished by a high or very high UV-A and / or UV-B protection, preferably contain further UV-A and in addition to the filter substance (s) according to the invention / or broadband filter, in particular dibenzoylmethane derivatives [for example the 4- (tert-butyl) -4'-methoxydibenzoylmethane], phenylene-1, 4-bis- (2-benzimfdazyl) -3,3'-5,5'-tetrasulfonic acid and / or their salts, the 2- (4-diethylamino-2-hydroxybenzoyl) benzoic acid hexyl ester and / or the 2,4-bis - ⁇ [4- (2-ethylhexyloxy) -2-hydroxy] phenyl ⁇ -6- (4-methoxyphenyl) -1, 3,5-triazine and / or the 2- (4-diethylamino-2-hydroxybenz
  • the UV light protection filters advantageous according to the invention are preferably used in a concentration of 0.1 to 30% by weight, in particular in a concentration of 0.5 to 15% by weight, based on the total weight of the formulation.
  • Particularly preferred embodiments of the present invention contain, as the UV filter, one or more triazine derivatives, dibenzoylmethane derivatives, UV filters which are liquid at room temperature and / or the inorganic pigments, in particular titanium dioxide.
  • film formers may be advantageous to incorporate film formers into the preparation according to the invention, for example in order to improve the water resistance of the preparations or to increase the UV protection performance (UV-A and / or UV-B boosting).
  • Both water-soluble or dispersible and fat-soluble film formers are suitable, in each case individually or in combination with one another.
  • Advantageous fat-soluble film formers are e.g. B., the film formers from the group of polymers based on polyvinylpyrrolidone (PVP)
  • copolymers of polyvinylpyrrolidone for example the PVP hexadecene copolymer and the PVP eicosen copolymer, which are available under the trade names Antaron V216 and Antaron V220 from GAF Chemicals Cooperation, as well as Tricontayl PVP and the like.
  • the emulsions according to the invention can also contain all water-soluble and / or oil-soluble UV-A, UV-B and / or broadband filter substances that are permitted under the Cosmetics Regulation.
  • the compositions contain, in addition to the above-mentioned substances, optionally the additives customary in cosmology, for example perfume, dyes, antimicrobial substances, lipid-replenishing agents, complexing and sequestering agents, pearlescent agents, plant extracts , Vitamins, active ingredients, preservatives, bactericides, repellents, self-tanners (eg DHA), depigmenting agents, pigments that have a coloring effect, softening, moisturizing and / or moisturizing substances, or other usual components of a cosmetic or dermatological formulation such as emulsifiers , Polymers, foam stabilizers and electrolytes.
  • the additives customary in cosmology for example perfume, dyes, antimicrobial substances, lipid-replenishing agents, complexing and sequestering agents, pearlescent agents, plant extracts , Vitamins, active ingredients, preservatives, bactericides, repellents, self-tanners (eg DHA), depigmenting agents, pigment
  • the emulsion according to the invention can advantageously contain one or more preservatives according to the invention.
  • Advantageous preservatives for the purposes of the present invention are, for example, formaldehyde releasers (such as, for example, DMDM hydantoin, which is available, for example, from Lonza under the trade name Glydant TM), iodopropyl butyl carbamates (for example those under the trade names Glycacil-L, Glycacil -S available from Lonza and / or Dekaben LMB from Jan Dekker), parabens (ie alkyl p-hydroxybenzoate, such as methyl, ethyl, propyl and / or butyl paraben), phenoxyethanol, ethanol, benzoic acid and the like.
  • formaldehyde releasers such as, for example, DMDM hydantoin, which is available, for example, from Lonza under the trade name Glyd
  • the preservation system according to the invention advantageously also includes preservation aids, such as, for example, octoxyglycerol, glycine soya, etc.
  • preservation aids such as, for example, octoxyglycerol, glycine soya, etc.
  • preservatives or preservation aids such as dibromodicyanobutane (2-bromo-2-bromomethylglutarodinitrile), phenoxyethanol, 3-iodo-2-propynyl butylcarbamate, 2-bromo-2-nitro-propane-1,3-diol , Imidazolidinyl urea, 5-chloro-2-methyl-4-isothiazolin-3-one, 2-chloroacetamide, benzalkonium chloride, benzyl alcohol.
  • dibromodicyanobutane (2-bromo-2-bromomethylglutarodinitrile)
  • phenoxyethanol 3-iodo-2-propynyl butylcarbamate
  • 2-bromo-2-nitro-propane-1,3-diol Imidazolidinyl urea
  • 5-chloro-2-methyl-4-isothiazolin-3-one 2-chloroacetamide
  • benzalkonium chloride
  • iodopropyl butyl carbamates parabens (methyl, ethyl, propyl and / or butyl paraben) and / or phenoxyethanol are used as preservatives.
  • one or more preservatives are advantageous in a concentration of 2% by weight or less than 2% by weight, preferably 1.5% by weight or less than 1.5% by weight and particularly preferably 1% by weight or less than 1% by weight , each based on the total weight of the preparation.
  • the emulsion according to the invention advantageously contains one or more conditioners.
  • Preferred conditioners according to the invention are, for example, all compounds which are described in Section 4 below in the International Cosmetic Ingredient Dictionary and Handbook (Volume 4, publisher: RC Pepe, JA Wenninger, GN McEwen, The Cosmetic, Toiletry, and Fragrance Association, 9th edition, 2002) the keywords Hair Conditioning Agents, Humectants, Skin-Conditioning Agents, Skin-Conditioning Agents-Emollient, Skin-Conditioning Agents-Humactant, Skin-Conditioning Agents-Miscellaneous, Skin-Conditioning Agents-Occlusive and Skin Protectans are all listed in the EP 0934956 (p.11-13) under water soluble conditioning agent and oil soluble conditioning agent.
  • the emulsion according to the invention can contain glitter substances and / or other effect substances.
  • the emulsion according to the invention has one or more hydrocolloids in a concentration of 0.01 to 10% by weight, preferably in a concentration of 0.1 to 7% by weight and very particularly preferably in a concentration from 0.3 to 5% by weight, based on the total weight of the preparation.
  • hydrocolloids advantageous according to the invention are agar agar, carrageenan, tragacanth, gum arabic, alginates, pectins, polyoses, guar flour, locust bean gum, starch, dextrins, gelatin, casein, cellulose ethers, hydroxyethyl and propyl cellulose derivatives, polysaccharides, polyacrylic and polymethacrylic compounds, ammonium acryloyldimethyltaurates / vinyl pyrrolidone copolymers and ammonium polyacryl dimethyl tauramides, vinyl polymers, polycarboxylic acids, polyethers, polyimines, polyamides, polysilicic acids, clay minerals, zeolites, silicas.
  • Hydrocolloids preferred according to the invention are, for example, methyl celluloses, as the methyl ethers of cellulose are referred to. They are characterized by the following structural formula
  • R can represent a hydrogen or a methyl group.
  • cellulose mixed ethers which are generally also referred to as methyl celluloses and which, in addition to a dominant content of methyl, also contain 2-hydroxyethyl, 2-hydroxypropyl or 2-hydroxybutyl groups.
  • Particularly preferred are (hydroxypropyl) methyl celluloses, for example those sold under the trade name Methocel E4M by Dow Chemical Comp. available.
  • sodium carboxymethyl cellulose the sodium salt of the glycolic acid ether of cellulose, for which R in structural formula I can be a hydrogen and / or CH2-COONa.
  • R in structural formula I can be a hydrogen and / or CH2-COONa.
  • Particularly preferred is the sodium carboxymethyl cellulose available under the trade name Natrosol Plus 330 CS from Aqualon, also referred to as cellulose gum.
  • xanthan (CAS No. 11138-66-2), also called xanthan gum, which is an anionic heteropolysaccharide which is generally formed from corn sugar by fermentation and is isolated as the potassium salt.
  • An advantageous gelling agent in the sense of the present invention is also carrageenan, a gel-forming extract similar to agar from northern Atlantic, belonging to the floridae red algae (Chondrus crispus and Gigartina stellata).
  • Polyacrylates are also advantageous gelators to be used in the sense of the present invention.
  • Polyacrylates which are advantageous according to the invention are acrylate-alkyl acrylate copolymers, in particular those which are selected from the group of the so-called carbomers or carbopols (Carbopol® is actually a registered trademark of NOVEON Inc.).
  • carbomers or carbopols Carbopol® is actually a registered trademark of NOVEON Inc.
  • the or the stand out Acrylate-alkyl acrylate copolymers advantageous according to the invention having the following structure:
  • R ' represents a long-chain alkyl radical and x and y numbers which symbolize the respective stoichiometric proportion of the respective comonomers.
  • acrylate copolymers and / or acrylate-alkyl acrylate copolymers which are sold under the trade names Carbopol® 1382, Carbopol® 981 and Carbopol® 5984, Aqua SF-1 by NOVEON Inc. or as Aculyn® 33 by International Specialty Products Corp. are available.
  • the carbomers Carbopol EDT 2001, ETD 2020 and ETD 2050 are also preferred.
  • neutralized or partially neutralized polyacrylates e.g. Carbopole from Noveon.
  • microcrystalline celluloses in a cosmetic and / or dermatological emulsion with a lipophilic outer phase to reduce the gloss of the emulsion on the skin after application thereof.
  • the reduction in skin gloss according to the invention can be determined as follows:
  • the gloss of the skin surface is determined.
  • a reflection spectrometer e.g. MCS 500, Zeiss
  • white light is brought onto the skin surface at an entry angle of 60 °.
  • the light reflected or mirrored at the exit angle of likewise 60 ° is fed to the detector and quantified.
  • microcrystalline cellulose Even in the sensory test with subjects who subjectively assess the gloss behavior, the product with microcrystalline cellulose was rated statistically significantly as significantly less shiny.
  • the invention is also the use of one or more microcrystalline celluloses in a cosmetic and / or dermatological emulsion with a lipophilic outer phase to produce a dull, non-sticky feeling on the skin of the emulsion after application thereof.
  • microcrystalline celluloses in a cosmetic and / or dermatological emulsion with lipophilic outer phase to reduce the emulsifier concentration in the emulsion is also in accordance with the invention.
  • W / O emulsions have an emulsifier content of 3 to 8% by weight (active content), which according to the invention can be reduced to an active content of approximately 1.5-2% by weight.
  • Conventional W / S emulsions have an emulsifier content of 3 to 6% by weight (active content), which according to the invention can be reduced to an active content of approximately 1-1.5% by weight.
  • microcrystalline celluloses in a cosmetic and / or dermatological emulsion with a lipophilic outer phase to increase the temperature and storage stability of the emulsion.
  • a cosmetic and / or dermatological emulsion with a lipophilic outer phase according to one of the preceding claims, for the care of the skin as well as for the prophylaxis and therapy of UV-related and / or age-related changes of the skin.

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Abstract

L'invention concerne une émulsion cosmétique et/ou dermatologique présentant une phase extérieure lipophile, contenant a) une phase aqueuse, b) une phase lipophile, c) un ou plusieurs émulsifiants eau dans huile ou eau dans silicone, d) une ou plusieurs celluloses microcristallines, e) un ou plusieurs agents hydratant la peau, et éventuellement d'autres agents actifs, auxiliaires et additifs cosmétiques et/ou dermatologiques.
PCT/EP2003/009684 2002-09-05 2003-09-01 Emulsions contenant de la microcellulose Ceased WO2004022019A1 (fr)

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US9211238B2 (en) 2010-03-26 2015-12-15 Gabriele Blume Carrier system for the transport of active substances into the skin
CN110035663A (zh) * 2016-05-11 2019-07-19 拜耳医药保健有限责任公司 热稳定的打成泡沫的制剂
US11602493B2 (en) 2017-05-11 2023-03-14 Beiersdorf Ag Gel formulations
US11612551B2 (en) 2016-05-11 2023-03-28 Formulated Solutions, Llc Whipped formulations

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DE102005020583B4 (de) 2004-09-06 2016-02-18 Schwan-Stabilo Cosmetics Gmbh & Co. Kg Zubereitung, insbesondere kosmetische Zubereitung sowie ihre Verwendung
DE202004014644U1 (de) * 2004-09-20 2005-11-10 Schwan-Stabilo Cosmetics Gmbh & Co. Kg Zubereitung, insbesondere kosmetische Zubereitung

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JPS59210009A (ja) * 1983-05-13 1984-11-28 Kobayashi Kooc:Kk 皮膚手入れ用化粧料
EP0529396A1 (fr) * 1991-08-22 1993-03-03 Beiersdorf Aktiengesellschaft Matrice galenique
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Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9211238B2 (en) 2010-03-26 2015-12-15 Gabriele Blume Carrier system for the transport of active substances into the skin
CN110035663A (zh) * 2016-05-11 2019-07-19 拜耳医药保健有限责任公司 热稳定的打成泡沫的制剂
US11612551B2 (en) 2016-05-11 2023-03-28 Formulated Solutions, Llc Whipped formulations
US11622922B2 (en) 2016-05-11 2023-04-11 Formulated Solutions, Llc Whipped formulations
US11826440B2 (en) 2016-05-11 2023-11-28 Formulated Solutions, Llc Thermal-stable whipped formulations
US11964035B2 (en) 2016-05-11 2024-04-23 Beiersdorf Ag Whipped gel formulations
US12138332B2 (en) 2016-05-11 2024-11-12 Formulated Solutions, Llc Whipped formulations
US12161737B2 (en) 2016-05-11 2024-12-10 Formulated Solutions, Llc Whipped formulations
US11602493B2 (en) 2017-05-11 2023-03-14 Beiersdorf Ag Gel formulations

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