WO2013091974A2 - Use of a combination of 2-methylene-1,4,5,6-tetrahydro-4-pyrimidincarboxylic acid or the derivate thereof and a blue-green algae extract for increasing the skin barrier function - Google Patents

Use of a combination of 2-methylene-1,4,5,6-tetrahydro-4-pyrimidincarboxylic acid or the derivate thereof and a blue-green algae extract for increasing the skin barrier function Download PDF

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Publication number
WO2013091974A2
WO2013091974A2 PCT/EP2012/071820 EP2012071820W WO2013091974A2 WO 2013091974 A2 WO2013091974 A2 WO 2013091974A2 EP 2012071820 W EP2012071820 W EP 2012071820W WO 2013091974 A2 WO2013091974 A2 WO 2013091974A2
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WIPO (PCT)
Prior art keywords
blue
green algae
acid
skin
formula
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PCT/EP2012/071820
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German (de)
French (fr)
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WO2013091974A3 (en
Inventor
Ira Hartmann
Soraya Heinen
Marianne DR. WALDMANN-LAUE
Claudia Jassoy
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Henkel Ag & Co. Kgaa
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Publication of WO2013091974A2 publication Critical patent/WO2013091974A2/en
Publication of WO2013091974A3 publication Critical patent/WO2013091974A3/en

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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/494Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
    • A61K8/4953Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom containing pyrimidine ring derivatives, e.g. minoxidil
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73Polysaccharides
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/96Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
    • A61K8/97Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
    • A61K8/9783Angiosperms [Magnoliophyta]
    • A61K8/9789Magnoliopsida [dicotyledons]
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00Preparations for care of the skin
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00Preparations for care of the skin
    • A61Q19/007Preparations for dry skin

Definitions

  • the barrier function of the skin protects the skin from drying out.
  • This barrier function is caused by the epidermis, which, as the outermost layer, forms the actual protective cover against the environment.
  • the epidermis is a stratified tissue in which the outer layer, the horny layer (stratum corneum) represents the barrier function function important part. It is worn down in contact with the environment and is therefore in a constant process of renewal. In this renewal process, fine dandruff is continuously released to the outside and the celluloid and lipid material, which has hardened from the inside, is subsequently reproduced.
  • Elias Skin Model (PM Elias, Structure and Function of the Stratum Corneum Permeability Barrier, Drug Dev. Res. 13, 1988, 97-105), which is now recognized in the art, describes the horny layer as a two-component system, similar to a brick wall (US Pat. Brick-mortar model).
  • the horny cells (corneocytes) correspond to the bricks
  • the complex lipid membrane in the intercellular spaces corresponds to the mortar.
  • This system essentially represents a physical barrier against hydrophilic substances, but due to its narrow and multi-layered structure, it can also be passed through by lipophilic substances just as easily.
  • the special structure of the horny layer protects the skin and stabilizes its own flexibility by binding a defined amount of water.
  • Various skincare products are known in the art which are capable of improving the epidermal barrier function.
  • these skin care products are usually occlusive in nature, eg. As Vaseline and Vaseline-containing creams, and often have a sticky skin sensation and / or uncomfortable wearing comfort.
  • the ointment or cream is, so to speak, a (second) artificial barrier that is supposed to prevent the loss of water from the skin. Accordingly, this physical barrier - for example, with cleaning agents - can be removed again, whereby the original, impaired state is reached again.
  • the skin care effect may decrease with regular treatment. After discontinuation of the product application, the skin returns to its pre-treatment state very quickly.
  • a sustainable product effect is usually not achieved or only to a limited extent.
  • lipid mixtures such as ceramides or ceramide analogues, which are to be used by the skin to rebuild the natural barrier, are increasingly being added to the topical preparations.
  • these lipids are usually very expensive raw materials, which are also difficult to formulate because of their high melting point.
  • their effect is limited because the topically applied lipids penetrate only to a small extent in the barrier-relevant lipid membranes in the middle stratum corneum and are integrated only to a small extent in these structures.
  • the prior art lacks preparations which have a positive influence on the barrier function and the hydration of the horny layer and strengthen or even restore the physicochemical properties of the horny layer and in particular the lamellae of intercellular lipids.
  • the object of the present invention was to develop topical compositions which strengthen the barrier function of the skin, for example against transepidermal water loss and simultaneously reduce further adverse skin reactions to environmental stress. Another object of the present invention was to develop topical compositions that strengthen the barrier function of the skin. Another object of the present invention was to develop topical compositions that strengthen the barrier function of the skin with a longer lasting effect than the prior art compositions. A further object of the present invention was to develop cost-effective and production-optimized topical compositions which strengthen the barrier function of the skin.
  • the present invention is the non-therapeutic cosmetic use of the active ingredient combination of at least one compound of 2-methyl-1, 4,5,6-tetrahydro-4-pyrimidinecarboxylic acid or its derivative, at least one blue-green algae extract and optionally at least one fucose-containing polysaccharide for stimulation the epidermal synthesis of epidermal synthesis of filaggrin and / or transglutaminicase and / or involucrin.
  • Another object of the present invention is the non-therapeutic cosmetic use of the active ingredient combination of at least one compound of 2-methyl-1, 4,5,6-tetrahydro-4-pyrimidinecarboxylic acid or its derivative, at least one blue-green algae extract and optionally at least one fucose-containing polysaccharide for the regeneration of the skin barrier function.
  • Another object of the present invention is the non-therapeutic cosmetic use of the active ingredient combination of at least one compound of 2-methyl-1, 4,5,6-tetrahydro-4-pyrimidinecarboxylic acid or its derivative, at least one blue-green algae extract and optionally at least one fucose-containing polysaccharide to accelerate the regeneration of the skin barrier function.
  • Another object of the present invention is the non-therapeutic cosmetic use of the active ingredient combination of at least one compound of 2-methyl-1, 4,5,6-tetrahydro-4-pyrimidinecarboxylic acid or its derivative, at least one blue-green algae extract and optionally at least one fucose-containing polysaccharide to improve the appearance of dry skin.
  • Another object of the present invention is the non-therapeutic cosmetic use of the active ingredient combination of at least one compound of 2-methyl-1, 4,5,6-tetrahydro-4-pyrimidinecarboxylic acid or its derivative, at least one blue-green algae extract and optionally at least one fucose-containing polysaccharide to reduce skin dryness.
  • Another object of the present invention is the non-therapeutic cosmetic use of the active ingredient combination of at least one compound of 2-methyl-1, 4,5,6-tetrahydro-4- pyrimidinecarboxylic acid or its derivative, at least one blue-green algae extract and optionally at least one fucose-containing polysaccharide for stimulating the epidermal synthesis of barrier lipids, for regeneration of the skin barrier function, for accelerating the regeneration of the skin barrier function and / or for improving the appearance of dry skin and at the same time for reducing reddening of the skin.
  • a second subject of the invention is a cosmetic agent containing a combination of active ingredients in a cosmetic carrier
  • the active ingredient combination according to the invention necessarily comprises at least one 2-methyl-1, 4,5,6-tetrahydro-4-pyrimidinecarboxylic acid or its derivative.
  • a derivative erfindun accordingly be compounds with the structural unit
  • Preferred 2-methyl-1, 4,5,6-tetrahydro-4-pyrimidinecarboxylic acid or derivatives thereof are preferably from at least one compound of general formula (I) and / or a physiologically acceptable salt and / or an isomeric or stereoisomeric form thereof Selected compounds in which
  • R is a hydrogen atom or a hydroxy group and R 'is a moiety
  • Suitable physiologically acceptable salts of the general compounds of the formula (I) are, for example, the alkali metal, alkaline earth metal, ammonium, triethylamine or tris (2-hydroxyethyl) amine salts and those which are obtained from the reaction of compounds of the formula (I ) with inorganic and organic acids such as hydrochloric acid, phosphoric acid, sulfuric acid, branched or unbranched, substituted or unsubstituted (for example by one or more hydroxy groups) Ci-C4 mono- or dicarboxylic acids, aromatic carboxylic acids and sulfonic acids such as acetic acid, citric acid, benzoic acid, maleic acid , Fumaric, tartaric and p-toluenesulfonic acid.
  • physiologically acceptable salts are the Na, K, Mg, Ca and ammonium salts of the compounds according to the formula (I), and the salts which are obtained by the reaction of compounds of the formula (I) with hydrochloric acid , Acetic acid, citric acid and benzoic acid.
  • amino acid is understood to mean the stereoisomeric forms, for example D and L forms, of the following compounds: asparagine, arginine, aspartic acid, glutamine, glutamic acid, ⁇ -alanine, ⁇ -aminobutyrate, N 8 -acetyllysine, N 8 -acetylornitin, N y -acetyldiaminobutyrate, N a -acetyldiaminobutyrate, histidine, isoleucine, leucine, methionine, phenylalanine, serine, threonine and tyrosine.
  • L-amino acids are preferred.
  • Amino acid residues are derived from the corresponding amino acids. The following amino acids are preferred:
  • the short notation of the amino acids was carried out according to the usual notation.
  • the Dioder tripeptide radicals are acid amides in their chemical nature and decompose on hydrolysis in 2 or 3 amino acids.
  • the amino acids in the di- or tripeptide moiety are linked together by amide bonds.
  • C 1 -C 4 -alkyl groups in the compounds according to the invention are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl and tert-butyl.
  • Preferred alkyl groups are methyl and ethyl, methyl is a particularly preferred alkyl group.
  • Preferred C 2 -C 4 hydroxyalkyl groups are Groups 2-hydroxyethyl, 3-hydroxypropyl or 4-hydroxybutyl; 2-hydroxyethyl is a particularly preferred hydroxyalkyl group.
  • R represented by the general formula (I) is preferably a hydrogen atom.
  • Cosmetic skin treatment agents which can be used according to the invention preferably comprise the 2-methyl-1, 4,5,6-tetrahydro-4-pyrimidinecarboxylic acid and / or derivatives thereof, in particular the compounds of the formula (I) (preferably ectoine) in a total amount of 0.0005 to 10.0% wt .-%, particularly preferably 0.001 to 3.0 wt .-% and most preferably 0.01 to 1, 0 wt .-%, each based on the weight of the total composition.
  • At least one blue-green algae extract must be present in the composition according to the invention.
  • Blue algae - also called cyanobacteria - are bacteria that lack the nucleus, mitochondria, and chloroplasts.
  • the cell envelope of the blue-green algae consists of a cytoplasmic mambrane surrounded by a murein layer and an outer cell wall of lipopolysaccharides and proteins. Blue-green algae also contain pigments for photosynthesis.
  • a blue-green extract of blue-green algae of the order Oscillatoriales (according to the taxonomy database of the National Center for Biotechnology Information of the USA) in the compositions according to the invention. It is particularly preferred to use an extract of the blue-green algae of the genus Spirulina.
  • a blue-green algae extract from Spirulina Platensis can be used very particularly preferably within the scope of the invention.
  • the blue-green extract used according to the invention preferably contains
  • the extracts of a blue-green algae according to the invention can be obtained by conventional extraction methods.
  • Cosmetic skin treatment agents which can be used according to the invention preferably contain the blue-green algae extract in an amount of 0.0001 to 5.0% by weight, preferably 0.001 to 3.0% by weight, particularly preferably 0.005 to 1.0% by weight, based in each case on the weight of the entire composition.
  • the agent according to the invention contains as optional component of the combination of active substances according to the invention at least one fucose-containing polysaccharide.
  • the fucose-containing polysaccharides according to the invention therefore necessarily comprise at least one structural unit of the formula (F1)
  • a bond denoted by * within a general formula of this application is - unless otherwise defined - a free valency of the structure shown.
  • the bonds marked with * according to formula (F1) represent a glycosidic bond to another saccharide residue of the fucose-containing polysaccharide.
  • the structural units of the formula (F1) are derived from L-fucose and / or from D-fucose.
  • the structural units of the formula (F1) are preferably derived from the L-fucose with formation of the preferred structural units of the formula (F1-1)
  • bonds marked with * according to formula (F1-1) represent a glycosidic bond to another saccharide residue of the fucose-containing polysaccharide.
  • the fucose-containing polysaccharide is preferably anionic. It therefore preferably contains in addition to said fucose structural unit additionally at least one structural unit derived from a uronic acid, in particular of galacturonic acid, glucuronic acid or iduronic acid. Particularly preferably, the additional structural unit is derived from the formula (F2)
  • bonds indicated by * according to formula (F2) represent a glycosidic bond to another saccharide residue of the fucose-containing polysaccharide.
  • the fucose-containing polysaccharides according to the invention in addition to the structural unit derived from fucose, additionally contain at least one structural unit which is derived from galactose.
  • the additional galactose structural unit is derived from the formula (F3)
  • bonds indicated by * according to formula (F3) represent a glycosidic bond to another saccharide residue of the fucose-containing polysaccharide.
  • An inventively particularly preferred fucose-containing polysaccharide contains at least one previously defined structural unit of the formula (F1-1) and at least one previously defined structural unit of the formula (F2) at least one previously defined structural unit of the formula (F3).
  • a still preferred fucose Anlagens polysaccharide of this embodiment carries the INCI nomenclature Biosaccharide Gum-1 and is marketed, for example, by the company Solabia under the trade name Fucogel 1000 ® or Fucocert ®.
  • Cosmetic skin treatment agents which can be used according to the invention preferably contain the fucose-containing polysaccharide in an amount of 0.0001 to 2.0% by weight, preferably 0.001 to 1.5% by weight, particularly preferably 0.005 to 0.5% by weight, in each case on the weight of the entire composition.
  • Particularly preferred cosmetic skin treatment agents are those of the embodiments (A) to (F)
  • composition comprising, in a cosmetic carrier, an active ingredient combination of at least one compound of the formula (I) and / or a physiologically tolerable salt and / or an isomeric or stereoisomeric form of these compounds,
  • R is a hydrogen atom or a hydroxy group and R 'is a grouping -COOR or a grouping -CO (NH) R 1 , wherein R is a hydrogen atom, a C- ⁇ - C 4 alkyl radical, an amino acid residue, a dipeptide or a tripeptide radical, and
  • At least one blue-green algae extract of blue-green algae of the genus Spirulina in particular Spirulina platensis, and
  • At least one fucose-containing polysaccharide comprising at least one structural unit of the formula (F1-1) and at least one structural unit of the formula (F2) at least one structural unit of the formula (F3)
  • composition comprising, in a cosmetic carrier, a combination of active ingredients, each based on the total weight of the agent
  • R is a hydrogen atom or a hydroxy group and R 'is a grouping -COOR 1 or a grouping -CO (NH) R 1 , where R is a hydrogen atom, a C 1 -C 4 -alkyl radical, an amino acid radical, a dipeptide radical or a tripeptide radical, and From 0.0001 to 5.0% by weight, preferably from 0.001 to 3.0% by weight, more preferably from 0.005 to 1.0% by weight, of at least one blue-green algae extract of the genus Spirulina, in particular Spirulina platensis, and
  • At least one blue-green algae extract of blue-green algae of the genus Spirulina in particular Spirulina platensis, and
  • At least one fucose-containing polysaccharide comprising at least one structural unit of the formula (F1-1) and at least one structural unit of the formula (F2) at least one structural unit of the formula (F3)
  • At least one blue-green algae extract of blue-green algae of the genus Spirulina in particular Spirulina platensis, and
  • biosaccharides Gum-1 as fucose-containing polysaccharide.
  • biosaccharides Gum-1 as a fucose-containing polysaccharide optionally 0.0001 to 2.0 wt .-%, preferably 0.001 to 1, 5 wt .-%, particularly preferably 0.005 to 0.5 wt .-%, biosaccharides Gum-1 as a fucose-containing polysaccharide.
  • the cosmetic skin treatment agents used according to the invention are in the form of a liquid, flowable or solid oil-in-water emulsion, water-in-oil emulsion, multiple emulsion, in particular an oil-in-water-in-oil or water In-oil-in-water emulsion, macroemulsion, miniemulsion, microemulsion, PIT emulsion, nanoemulsion, Pickering emulsion, hydrodispersion, a hydrogel, a lipogel, a single- or multiphase solution, a foam, a powder or a Mixture with at least one suitable as a medical adhesive polymer.
  • the skin treatment agents are present as microemulsions.
  • microemulsions are understood as meaning not only the thermodynamically stable microemulsions but also the so-called "PIT" emulsions.
  • PIT phase inversion temperature
  • these emulsions are systems with the 3 Components water, oil and emulsifier, which are present at room temperature as an oil-in-water emulsion. When these systems are heated, microemulsions are formed in a certain temperature range (referred to as the phase inversion temperature or "PIT”) and, on further heating, convert to water-in-oil emulsions.
  • PIT phase inversion temperature
  • O / W emulsions are again formed, but they are also present at room temperature as microemulsions or as very finely divided emulsions having an average particle diameter of less than 400 nm and in particular of about 100-300 nm. According to the invention, those micro- or "PIT" emulsions may be preferred which have an average particle diameter of about 200 nm.
  • the compositions according to the invention contain at least one surface-active substance as emulsifier or dispersant.
  • Suitable emulsifiers are for example adducts of from 4 to 30 mol ethylene oxide and / or 0 to 5 mol propylene oxide onto linear C 8 -C 2 2-fatty alcohols, on C 2 -C 2 2 fatty acids and C 8 -C-
  • the commercially available products Montanov ® 68, Montanov ® 202 or Montanov ® L addition products of 5 to 60 moles of ethylene oxide with castor oil and hydrogenated castor oil, partial esters of polyols having 3-6 carbon atoms with saturated C 8 -C 2 2 fatty acids
  • Sterols in particular cholesterol, lanosterol, beta-sitosterol, stigmasterol, campesterol and ergosterol, and also mycosterols, phospholipids, especially glucose phospholipids, fatty acid esters of sugars and sugar alcohols such as sorbitol, polyglycerols and polyglycerol derivatives, preferably polyglyceryl-2 dipolyhydroxystearate (Dehymuls ® PGPH commercial product) and polyglyceryl-3 diisostearate (Lameform ® TGI commercial product) as well as linear and branched C 8 -C 30 fatty acids and their Na, K, ammonium, Ca, Mg
  • the skin treatment agents used according to the invention preferably contain the emulsifiers in amounts of from 0.1 to 25% by weight, in particular from 0.5 to 15% by weight, based on the total composition.
  • at least one nonionic emulsifier having an HLB value of 8 and below is included.
  • Further preferred emulsifiers with an HLB value of 8 and below are the adducts of 1 or 2 moles of ethylene oxide or propylene oxide with behenyl alcohol, erucyl alcohol, arachidyl alcohol or behenic acid or erucic acid.
  • the monoesters of C 16 -C 3 o fatty acids with polyols such.
  • polyols such as pentaerythritol, trimethylolpropane, diglycerol, sorbitol, glucose or methyl glucose. Examples of such products are z.
  • an emulsifier system is particularly preferably suitable as a mixture
  • o-mono- or diacylglycerides preferably at least one Ci6-i8-mono- or diacylglyceride, particularly preferably selected from hardened palm oil glycerides, can be formulated and stored particularly stable in storage.
  • the at least one salt of a C 2 -2O-alkyl phosphate is present in the inventive compositions used in a total amount from 0.2 to 2.0 wt .-%, preferably 0.3 - 1. 8 wt .-%, particularly preferably 1, 0 - 1, 5 wt .-%, each based on the total weight of the composition.
  • Preferred compositions used according to the invention comprise at least one salt of cetyl phosphate in a total amount of 0.2-2.0% by weight, preferably 0.3-1.8% by weight, more preferably 1.0-0.5% by weight. -%, in each case based on the total weight of the composition.
  • compositions used according to the invention comprise a mixture of dipotassium monocetyl phosphate and potassium dicetyl phosphate in a total amount of 0.2-2.0% by weight, preferably 0.3-1.8% by weight, more preferably 1.0-0.1 , 5 wt .-%, each based on the total weight of the composition.
  • Other suitable additives are thickeners, for.
  • Example natural and synthetic clays and sheet silicates such as bentonite, hectorite, montmorillonite or Laponite ® , or anionic polymers of acrylic acid, methacrylic acid, crotonic acid, maleic anhydride and 2-acrylamido-2-methylpropanesulfonic acid, where the acidic groups wholly or partly as sodium , Potassium, ammonium, mono- or triethanolammonium salt, and wherein at least one nonionic monomer may be contained.
  • Preferred nonionic monomers are acrylamide, methacrylamide, acrylates, methacrylates, vinylpyrrolidone, vinyl ethers and vinyl esters.
  • Preferred anionic copolymers are acrylic acid-acrylamide copolymers and in particular polyacrylamide copolymers with sulfonic acid-containing monomers. These copolymers can also be present in crosslinked form. Suitable commercial products are NS Sepigel ® 305 Simulgel® ® 600, Simulgel® ®, Simulgel® ® EC and Simulgel® ® EPG SEPPIC. Further particularly preferred anionic homopolymers and copolymers are uncrosslinked and crosslinked polyacrylic acids. Such compounds are for example the commercial products Carbopol ®. A particularly preferred anionic copolymer contains as monomer 80-98% of an unsaturated, optionally substituted C 3 .
  • Suitable nonionic polymers include polyvinyl alcohols, which may be partially saponified, for. B. the commercial products Mowiol ® and vinylpyrrolidone / vinyl ester copolymers and polyvinylpyrrolidones z. B. under the trademark Luviskol ® (BASF) are sold.
  • the skin treatment agents used in the invention preferably contain fatty substances selected from oils, in particular vegetable oils, such as sunflower oil, olive oil, soybean oil, rapeseed oil, almond oil, jojoba oil, orange oil, wheat germ oil, peach kernel oil and the liquid portions of coconut oil, lanolin and its derivatives, liquid paraffin oils , Isoparaffin oils and synthetic hydrocarbons, di-n-alkyl ethers having a total of 12 to 36 carbon atoms, eg. B.
  • vegetable oils such as sunflower oil, olive oil, soybean oil, rapeseed oil, almond oil, jojoba oil, orange oil, wheat germ oil, peach kernel oil and the liquid portions of coconut oil, lanolin and its derivatives
  • liquid paraffin oils Isoparaffin oils and synthetic hydrocarbons
  • di-n-alkyl ethers having a total of 12 to 36 carbon atoms, eg. B.
  • fatty acids especially linear and / or branched, saturated and / or unsaturated C 8 -3o fatty acids, fatty alcohols, particularly saturated, mono- or polyunsaturated, branched or unbranched fatty alcohols having 4-30 carbon atoms which may be ethoxylated with 1-75, preferably 5-20 ethylene oxide units and / or propoxylated with 3-30, preferably 9-14 propylene oxide units, ester oils, ie esters of C 6 - 30- fatty acids with C 2 -3o fatty alcohols, hydroxycarboxylic acid alkyl esters, dicarboxylic acid esters such as di-n-butyl adipate and diol esters such as ethylene glycol diol or propylene glycol di (2-ethylhexanoate), symmetrical, asymmetrical or cyclic esters of carbonic acid with
  • Hardened triglyceride fats for example soybean lecithin, egg lecithin and cephalins, silicone compounds selected from decamethylcyclopentasiloxane, dodecamethylcyclohexasiloxane and silicone polymers which may, if desired, be cross-linked, e.g.
  • polydialkylsiloxanes polyalkylarylsiloxanes, ethoxylated and / or propoxylated polydialkylsiloxanes with the earlier INCI name dimethicone copolyol, and polydialkylsiloxanes containing amine and / or hydroxyl groups, preferably substances with the INCI names Dimethiconol, Amodimethicone or Trimethylsilylamodimethicone.
  • the amount used of the fatty substances is 0, 1-50 wt.%, Preferably 0.1-20 wt.% And particularly preferably 0, 1-15 wt.%, Each based on the total skin treatment agent.
  • antioxidants are antioxidants, preservatives, solvents such as ethanol, isopropanol, ethylene glycol, propylene glycol, propylene glycol, glycerol and diethylene glycol, adsorbents and fillers such as talc and Veegum ®, perfume oils, pigments and dyes for coloring the composition, substances for adjusting the pH Value, complexing agents such as EDTA, NTA, ß-Alanindiessigklare and phosphonic acids, propellants such as propane-butane mixtures, pentane, isopentane, isobutane, N 2 0, dimethyl ether, C0 2 and air.
  • solvents such as ethanol, isopropanol, ethylene glycol, propylene glycol, propylene glycol, glycerol and diethylene glycol
  • adsorbents and fillers such as talc and Veegum ®
  • perfume oils pigments and dyes for coloring the composition

Abstract

The invention relates to a combination of at least one compound of 2-methylene-1,4,5,6-tetrahydro-4-pyrimidine carboxylic acid or the derivates thereof and at least one blue-green algae extract and if necessary at least one fucose-containing polysaccharide (in particular in the embodiment of one of the cosmetic products of claims 1 to 6) stimulates the epidermal syntheses of filaggrin and/or transglutaminase and/or involucrin. The skin barrier is strengthened.

Description

„Verwendung von einer Kombination von 2-Methyl-1 ,4,5,6-tetrahydro-4-pyrimidincarbonsäure oder deren Derivat und einem Blaualgenextrakt zur Steigerung der Hautbarrierefunktion" "Use of a combination of 2-methyl-1, 4,5,6-tetrahydro-4-pyrimidinecarboxylic acid or its derivative and a blue-green algae extract to increase the skin barrier function"
Die Barrierefunktion der Haut schützt die Haut vor dem Austrocknen. Bewirkt wird diese Barrierefunktion durch die Epidermis, welche als äußerste Schicht die eigentliche Schutzhülle gegenüber der Umwelt bildet. Die Epidermis ist ein stratifiziertes Gewebe, in dem die äußere Schicht, die Hornschicht (Stratum corneum) den für die Barrierefunktion bedeutenden Teil darstellt. Sie wird im Kontakt mit der Umwelt abgenutzt und befindet sich deshalb in einem ständigen Erneuerungsprozess. In diesem Erneuerungsprozess werden nach außen kontinuierlich feine Schuppen abgegeben und von innen verhorntes Zell- und Lipidmaterial nachproduziert. The barrier function of the skin protects the skin from drying out. This barrier function is caused by the epidermis, which, as the outermost layer, forms the actual protective cover against the environment. The epidermis is a stratified tissue in which the outer layer, the horny layer (stratum corneum) represents the barrier function function important part. It is worn down in contact with the environment and is therefore in a constant process of renewal. In this renewal process, fine dandruff is continuously released to the outside and the celluloid and lipid material, which has hardened from the inside, is subsequently reproduced.
Das heute in der Fachwelt anerkannte Hautmodell von Elias (P. M. Elias, Structure and Function of the Stratum Corneum Permeability Barrier, Drug Dev. Res. 13, 1988, 97 - 105) beschreibt die Hornschicht als Zwei-Komponenten-System, ähnlich einer Ziegelsteinmauer (Ziegelstein-Mörtel- Modell). In diesem Modell entsprechen die Hornzellen (Corneozyten) den Ziegelsteinen, die komplex zusammengesetzte Lipidmembran in den Interzellularräumen entspricht dem Mörtel. Dieses System stellt im wesentlichen eine physikalische Barriere gegen hydrophile Substanzen dar, kann aber aufgrund seiner engen und mehrschichtigen Struktur gleichermaßen auch von lipo- philen Substanzen nur schwer passiert werden. Die besondere Struktur der Hornschicht schützt einerseits die Haut und stabilisiert andererseits ihre eigene Flexibilität durch Bindung einer definierten Wassermenge. Elias Skin Model (PM Elias, Structure and Function of the Stratum Corneum Permeability Barrier, Drug Dev. Res. 13, 1988, 97-105), which is now recognized in the art, describes the horny layer as a two-component system, similar to a brick wall (US Pat. Brick-mortar model). In this model, the horny cells (corneocytes) correspond to the bricks, the complex lipid membrane in the intercellular spaces corresponds to the mortar. This system essentially represents a physical barrier against hydrophilic substances, but due to its narrow and multi-layered structure, it can also be passed through by lipophilic substances just as easily. The special structure of the horny layer protects the skin and stabilizes its own flexibility by binding a defined amount of water.
Auch mechanische Belastungen, wie beispielsweise Druck-, Stoß- oder Scherkräfte, können in erstaunlichem Maße durch die Hornschicht allein oder im Verbund mit den tieferen Hautschichten abgefangen werden. Größere Druck-, Dreh- oder Scherkräfte werden über die Verzahnung der Epidermis mit dem Corium an tiefere Hautschichten weitergegeben. Die Regulation des Wasser- und Feuchtigkeitsgehaltes ist eine der wichtigsten Funktionen der epidermalen Lipidmembran. Allerdings hat sie nicht nur eine Barrierewirkung gegen externe chemische und physikalische Einflüsse, sondern trägt auch zum Zusammenhalt der Hornschicht bei.  Even mechanical stress, such as pressure, shock or shear forces, can be intercepted to an amazing extent by the horny layer alone or in combination with the deeper skin layers. Greater pressure, turning or shearing forces are passed on to the deeper skin layers via the interlocking of the epidermis with the corium. The regulation of water and moisture content is one of the most important functions of the epidermal lipid membrane. However, it not only has a barrier effect against external chemical and physical influences, but also contributes to the cohesion of the horny layer.
Bereits bei einer Reinigung der Haut mit Hilfe eines einfachen Wasserbads - ohne Zusatz von Tensiden - kommt es zunächst zu einer Quellung der Hornschicht der Haut. Der Grad dieser Quellung hängt u. a. von der Dauer des Bads und dessen Temperatur ab. Gleichzeitig werden wasserlösliche Stoffe ab- bzw. ausgewaschen, wie z. B. wasserlösliche Schmutzbestandteile, aber auch hauteigene Stoffe, die für das Wasserbindungsvermögen der Hornschicht verantwortlich sind. Durch hauteigene oberflächenaktive Stoffe werden außerdem auch Hautfette in gewissem Ausmaß gelöst und ausgewaschen. Dies bedingt nach anfänglicher Quellung eine nachfolgende Austrocknung der Haut, die durch waschaktive Zusätze noch deutlich verstärkt werden kann.  Even when the skin is cleansed with the aid of a simple water bath - without the addition of surfactants - the horny layer of the skin initially swells. The degree of this swelling depends u. a. from the duration of the bath and its temperature. At the same time water-soluble substances are washed off or washed out, such as. As water-soluble soil constituents, but also the skin's own substances that are responsible for the water-binding capacity of the horny layer. In addition, skin fats are to a certain extent dissolved and washed out by the skin's own surfactants. This causes after initial swelling a subsequent dehydration of the skin, which can be significantly enhanced by detergent additives.
Bei gesunder Haut sind diese Vorgänge im allgemeinen belanglos, da die Schutzmechanismen der Haut solche leichten Störungen der oberen Hautschichten ohne weiteres kompensieren können. Aber bereits im Fall nicht-pathologischer Abweichungen vom Normalstatus, z. B. durch umweltbedingte Abnutzungsschäden bzw. Irritationen, Lichtschäden, Altershaut usw., ist der Schutzmechanismus an der Hautoberfläche gestört. Bei alter Haut beispielsweise erfolgt die regenerative Erneuerung verlangsamt, wobei insbesondere das Wasserbindungsvermögen der Hornschicht nachlässt. Sie wird deshalb inflexibel, trocken und rissig ("physiologisch" trockene Haut). Ein Barriereschaden ist die Folge. Die Haut wird anfällig für negative Umwelteinflüsse wie die Invasion von Mikroorganismen, Toxinen und Allergenen. Als Folge kann es sogar zu toxischen oder allergischen Hautreaktionen kommen. Die verminderte Integrität und Reparaturleistung der Hautbarriere führt zu einem gesteigerten transepidermalen Wasserverlust. Die Haut wird rau, trocken, schuppig und neigt zu Spannungsgefühlen sowie Juckreiz. In healthy skin, these processes are generally irrelevant, as the protective mechanisms of the skin can readily compensate for such minor disorders of the upper layers of the skin. But even in the case of non-pathological deviations from the normal status, eg. B. by environmental wear damage or irritation, photodamage, aging skin, etc., the protective mechanism is disturbed on the skin surface. In the case of old skin, for example, the regenerative renewal slows down, whereby in particular the water-binding capacity of the horny layer subsides. It therefore becomes inflexible, dry and cracked ("physiologically" dry skin). A barrier damage is the result. The skin becomes susceptible to negative environmental influences such as the invasion of microorganisms, toxins and allergens. As a result, even toxic or allergic skin reactions may occur. The reduced integrity and repair performance of the skin barrier results in increased transepidermal water loss. The skin becomes rough, dry, flaky and prone to tense as well as itching.
Bei pathologisch trockener und empfindlicher Haut oder bei von atopischer Dermatitis betroffener Haut liegt ein Barriereschaden a priori vor.  In the case of pathologically dry and sensitive skin or skin affected by atopic dermatitis, there is a priori barrier damage.
Im Stand der Technik sind diverse Hautpflegeprodukte bekannt, die in der Lage sind, die epidermale Barrierefunktion zu verbessern. Diese Hautpflegeprodukte sind jedoch in der Regel okklusiver Natur, z. B. Vaseline und Vaseline-haltige Cremes, und weisen häufig ein klebriges Hautgefühl und/oder einen unangenehmen Tragekomfort auf. Die Salbe oder Creme stellt sozusagen eine (zweite) künstliche Barriere dar, die den Wasserverlust der Haut verhindern soll. Entsprechend leicht kann diese physikalische Barriere - beispielsweise mit Reinigungsmitteln - wieder entfernt werden, wodurch der ursprüngliche, beeinträchtigte Zustand wieder erreicht wird. Darüber hinaus kann die Hautpflegewirkung bei regelmäßiger Behandlung nachlassen. Nach dem Absetzen der Produktanwendung kehrt die Haut sehr schnell wieder in den Zustand vor Behandlungsbeginn zurück. Eine nachhaltige Produktwirkung wird in der Regel also nicht oder nur in einem eingeschränkten Maße erreicht. Um die Haut bei ihrer natürlichen Regeneration zu unterstützen und ihre physiologische Funktion zu stärken, werden den topischen Präparaten in neuerer Zeit zunehmend Interzellularlipidmischungen, wie Ceramide oder Ceramidanaloga, zugesetzt, die von der Haut zum Wiederaufbau der natürlichen Barriere verwendet werden sollen. Allerdings handelt es sich bei diesen Lipiden zumeist um sehr teure Rohstoffe, die außerdem aufgrund ihres hohen Schmelzpunktes schwierig zu formulieren sind. Zudem ist ihre Wirkung begrenzt, da die topisch applizierten Lipide nur in geringem Umfang in die barriererelevanten Lipidmembranen im mittleren Stratum corneum penetrieren und nur zu einem geringen Teil in diese Strukturen integriert werden. Various skincare products are known in the art which are capable of improving the epidermal barrier function. However, these skin care products are usually occlusive in nature, eg. As Vaseline and Vaseline-containing creams, and often have a sticky skin sensation and / or uncomfortable wearing comfort. The ointment or cream is, so to speak, a (second) artificial barrier that is supposed to prevent the loss of water from the skin. Accordingly, this physical barrier - for example, with cleaning agents - can be removed again, whereby the original, impaired state is reached again. In addition, the skin care effect may decrease with regular treatment. After discontinuation of the product application, the skin returns to its pre-treatment state very quickly. A sustainable product effect is usually not achieved or only to a limited extent. To aid the skin in its natural regeneration and to strengthen its physiological function, more and more intercellular lipid mixtures such as ceramides or ceramide analogues, which are to be used by the skin to rebuild the natural barrier, are increasingly being added to the topical preparations. However, these lipids are usually very expensive raw materials, which are also difficult to formulate because of their high melting point. In addition, their effect is limited because the topically applied lipids penetrate only to a small extent in the barrier-relevant lipid membranes in the middle stratum corneum and are integrated only to a small extent in these structures.
Dem Stand der Technik mangelt es demnach an Zubereitungen, die die Barrierefunktion und die Hydratation der Hornschicht positiv beeinflussen und die physikalisch-chemischen Eigenschaften der Hornschicht und insbesondere der Lamellen aus Interzellularlipiden stärken bzw. sogar wiederherstellen.  Accordingly, the prior art lacks preparations which have a positive influence on the barrier function and the hydration of the horny layer and strengthen or even restore the physicochemical properties of the horny layer and in particular the lamellae of intercellular lipids.
Aufgabe der vorliegenden Erfindung war es, topische Zusammensetzungen zu entwickeln, die die Barrierefunktion der Haut, beispielsweise gegenüber dem transepidermalen Wasserverlust, stärken und gleichzeitig weitere negative Reaktionen der Haut auf Umweltstress vermindern. Eine weitere Aufgabe der vorliegenden Erfindung war es, topische Zusammensetzungen zu entwickeln, die die Barrierefunktion der Haut stärken. Eine weitere Aufgabe der vorliegenden Erfindung war es, topische Zusammensetzungen zu entwickeln, die die Barrierefunktion der Haut mit länger anhaltender Wirkung stärken als die Zusammensetzungen des Standes der Technik. Eine weitere Aufgabe der vorliegenden Erfindung war es, kosten- und herstellungsoptimierte topische Zusammensetzungen zu entwickeln, die die Barrierefunktion der Haut stärken. The object of the present invention was to develop topical compositions which strengthen the barrier function of the skin, for example against transepidermal water loss and simultaneously reduce further adverse skin reactions to environmental stress. Another object of the present invention was to develop topical compositions that strengthen the barrier function of the skin. Another object of the present invention was to develop topical compositions that strengthen the barrier function of the skin with a longer lasting effect than the prior art compositions. A further object of the present invention was to develop cost-effective and production-optimized topical compositions which strengthen the barrier function of the skin.
Überraschenderweise hat sich gezeigt, dass die Regeneration der Hautbarrierefunktion bei Anwendung einer Kombination von mindestens einer Verbindung aus 2-Methyl-1 ,4,5,6-tetrahydro- 4-pyrimidincarbonsäure oder deren Derivat und mindestens einem Blaualgenextrakt signifikant beschleunigt wird. Ferner wurde experimentell festgestellt, dass durch die erfindungsgemäße Wirkstoffkombination die epidermale Synthese von Filaggrin und/oder Transglutaminiase und/oder Involucrin stimuliert wird. Surprisingly, it has been found that the regeneration of the skin barrier function is significantly accelerated using a combination of at least one compound of 2-methyl-1, 4,5,6-tetrahydro-4-pyrimidinecarboxylic acid or its derivative and at least one blue-green algae extract. Furthermore, it has been found experimentally that the epidermal synthesis of filaggrin and / or transglutaminicase and / or involucrin is stimulated by the combination of active substances according to the invention.
Gegenstand der vorliegenden Erfindung ist die nicht-therapeutische kosmetische Verwendung der Wirkstoffkombination von mindestens einer Verbindung aus 2-Methyl-1 ,4,5,6-tetrahydro-4- pyrimidincarbonsäure oder deren Derivat, mindestens einem Blaualgenextrakt und gegebenenfalls mindestens einem fucosehaltigen Polysaccharid zur Stimulierung der epidermalen Synthese von epidermalen Synthese von Filaggrin und/oder Transglutaminiase und/oder Involucrin. Ein weiterer Gegenstand der vorliegenden Erfindung ist die nicht-therapeutische kosmetische Verwendung der Wirkstoffkombination von mindestens einer Verbindung aus 2-Methyl-1 ,4,5,6-tetrahydro-4- pyrimidincarbonsäure oder deren Derivat, mindestens einem Blaualgenextrakt und gegebenenfalls mindestens einem fucosehaltigen Polysaccharid zur Regeneration der Hautbarrierefunktion. Ein weiterer Gegenstand der vorliegenden Erfindung ist die nicht-therapeutische kosmetische Verwendung der Wirkstoffkombination von mindestens einer Verbindung aus 2-Methyl-1 , 4,5,6- tetrahydro-4-pyrimidincarbonsäure oder deren Derivat, mindestens einem Blaualgenextrakt und gegebenenfalls mindestens einem fucosehaltigen Polysaccharid zur Beschleunigung der Regeneration der Hautbarrierefunktion. Ein weiterer Gegenstand der vorliegenden Erfindung ist die nicht-therapeutische kosmetische Verwendung der Wirkstoffkombination von mindestens einer Verbindung aus 2-Methyl-1 ,4,5,6-tetrahydro-4-pyrimidincarbonsäure oder deren Derivat, mindestens einem Blaualgenextrakt und gegebenenfalls mindestens einem fucosehaltigen Polysaccharid zur Verbesserung des Erscheinungsbildes trockener Haut. Ein weiterer Gegenstand der vorliegenden Erfindung ist die nicht-therapeutische kosmetische Verwendung der Wirkstoffkombination von mindestens einer Verbindung aus 2-Methyl-1 ,4,5,6-tetrahydro-4- pyrimidincarbonsäure oder deren Derivat, mindestens einem Blaualgenextrakt und gegebenenfalls mindestens einem fucosehaltigen Polysaccharid zur Reduktion von Hauttrockenheit. Ein weiterer Gegenstand der vorliegenden Erfindung ist die nicht-therapeutische kosmetische Verwendung der Wirkstoffkombination von mindestens einer Verbindung aus 2-Methyl-1 ,4,5,6-tetrahydro-4- pyrimidincarbonsäure oder deren Derivat, mindestens einem Blaualgenextrakt und gegebenenfalls mindestens einem fucosehaltigen Polysaccharid zur Stimulierung der epidermalen Synthese von Barrierelipiden, zur Regeneration der Hautbarrierefunktion, zur Beschleunigung der Regeneration der Hautbarrierefunktion und/oder zur Verbesserung des Erscheinungsbildes trockener Haut und gleichzeitig zur Reduktion von Hautrötungen. The present invention is the non-therapeutic cosmetic use of the active ingredient combination of at least one compound of 2-methyl-1, 4,5,6-tetrahydro-4-pyrimidinecarboxylic acid or its derivative, at least one blue-green algae extract and optionally at least one fucose-containing polysaccharide for stimulation the epidermal synthesis of epidermal synthesis of filaggrin and / or transglutaminicase and / or involucrin. Another object of the present invention is the non-therapeutic cosmetic use of the active ingredient combination of at least one compound of 2-methyl-1, 4,5,6-tetrahydro-4-pyrimidinecarboxylic acid or its derivative, at least one blue-green algae extract and optionally at least one fucose-containing polysaccharide for the regeneration of the skin barrier function. Another object of the present invention is the non-therapeutic cosmetic use of the active ingredient combination of at least one compound of 2-methyl-1, 4,5,6-tetrahydro-4-pyrimidinecarboxylic acid or its derivative, at least one blue-green algae extract and optionally at least one fucose-containing polysaccharide to accelerate the regeneration of the skin barrier function. Another object of the present invention is the non-therapeutic cosmetic use of the active ingredient combination of at least one compound of 2-methyl-1, 4,5,6-tetrahydro-4-pyrimidinecarboxylic acid or its derivative, at least one blue-green algae extract and optionally at least one fucose-containing polysaccharide to improve the appearance of dry skin. Another object of the present invention is the non-therapeutic cosmetic use of the active ingredient combination of at least one compound of 2-methyl-1, 4,5,6-tetrahydro-4-pyrimidinecarboxylic acid or its derivative, at least one blue-green algae extract and optionally at least one fucose-containing polysaccharide to reduce skin dryness. Another object of the present invention is the non-therapeutic cosmetic use of the active ingredient combination of at least one compound of 2-methyl-1, 4,5,6-tetrahydro-4- pyrimidinecarboxylic acid or its derivative, at least one blue-green algae extract and optionally at least one fucose-containing polysaccharide for stimulating the epidermal synthesis of barrier lipids, for regeneration of the skin barrier function, for accelerating the regeneration of the skin barrier function and / or for improving the appearance of dry skin and at the same time for reducing reddening of the skin.
Ein zweiter Gegenstand der Erfindung ist ein kosmetisches Mittel enthaltend in einem kosmetischen Träger eine Wirkstoffkombination aus A second subject of the invention is a cosmetic agent containing a combination of active ingredients in a cosmetic carrier
mindestens einer Verbindung aus 2-Methyl-1 ,4,5,6-tetrahydro-4-pyrimidincarbonsäure oder deren Derivate, und  at least one compound of 2-methyl-1, 4,5,6-tetrahydro-4-pyrimidinecarboxylic acid or its derivatives, and
mindestens einem Blaualgenextrakt, und  at least one blue-green algae extract, and
gegebenenfalls mindestens einem fucosehaltigen Polysaccharid  optionally at least one fucose-containing polysaccharide
Die erfindungsgemäße Wirkstoffkombination umfasst zwingend mindestens eine 2-Methyl-1 ,4,5,6- tetrahydro-4-pyrimidincarbonsäure oder deren Derivat. Unter einem Derivat werden erfindun sgemäß Verbindungen mit der Struktureinheit The active ingredient combination according to the invention necessarily comprises at least one 2-methyl-1, 4,5,6-tetrahydro-4-pyrimidinecarboxylic acid or its derivative. Under a derivative erfindun accordingly be compounds with the structural unit
Figure imgf000005_0001
verstanden, wobei an den mit * gekennzeichneten Bindungen ein variabler
Figure imgf000005_0001
understood, wherein at the bonds marked with * a variable
Rest bindet. Rest binds.
Bevorzugte 2-Methyl-1 ,4,5,6-tetrahydro-4-pyrimidincarbonsäure bzw. deren Derivate werden bevorzugt aus mindestens einer Verbindung der allgemeinen Formel (I) und/oder eines physiologisch verträglichen Salzes und/oder einer isomeren oder stereoisomeren Form dieser Verbindungen ausgewählt, in denen Preferred 2-methyl-1, 4,5,6-tetrahydro-4-pyrimidinecarboxylic acid or derivatives thereof are preferably from at least one compound of general formula (I) and / or a physiologically acceptable salt and / or an isomeric or stereoisomeric form thereof Selected compounds in which
Figure imgf000005_0002
Figure imgf000005_0002
R für ein Wasserstoffatom oder eine Hydroxygruppe steht und R' für eine Gruppierung  R is a hydrogen atom or a hydroxy group and R 'is a moiety
-COOR oder eine Gruppierung -CO(NH)R1 steht, wobei R ein Wasserstoffatom, einen C-ι - C4--COOR or a grouping -CO (NH) R 1 , where R is a hydrogen atom, a C 1 -C 4 -
Alkylrest, einen Aminosäurerest, einen Dipeptid- oder einen Tripeptidrest bedeutet. Geeignete physiologisch verträgliche Salze der allgemeinen Verbindungen gemäß der Formel (I) sind beispielsweise die Alkali-, Erdalkali-, Ammonium-, Triethylamin- oder Tris-(2- hydroxyethyl)aminsalze sowie solche, die sich aus der Umsetzung von Verbindungen der Formel (I) mit anorganischen und organischen Säuren wie Salzsäure, Phosphorsäure, Schwefelsäure, verzweigten oder unverzwe igten, substituierten oder unsubstituierten (beispielsweise durch eine oder mehrere Hydroxygruppen) Ci-C4-Mono- oder Dicarbonsäuren, aromatische Carbonsäuren und Sulfonsäuren wie Essigsäure, Citronensäure, Benzoesäure, Maleinsäure, Fumarsäure, Weinsäure und p-Toluolsulfonsäure ergeben. Beispiele für besonders bevorzugte physiologisch verträgliche Salze sind die Na-, K-, Mg-, Ca- und Ammoniumsalze der Verbindungen gemäß der Formel (I), sowie die Salze, die sich durch die Umsetzung von Verbindungen gemäß der Formel (I) mit Salzsäure, Essigsäure, Citronensäure und Benzoesäure ergeben. Alkyl radical, an amino acid residue, a dipeptide or a tripeptide radical means. Suitable physiologically acceptable salts of the general compounds of the formula (I) are, for example, the alkali metal, alkaline earth metal, ammonium, triethylamine or tris (2-hydroxyethyl) amine salts and those which are obtained from the reaction of compounds of the formula (I ) with inorganic and organic acids such as hydrochloric acid, phosphoric acid, sulfuric acid, branched or unbranched, substituted or unsubstituted (for example by one or more hydroxy groups) Ci-C4 mono- or dicarboxylic acids, aromatic carboxylic acids and sulfonic acids such as acetic acid, citric acid, benzoic acid, maleic acid , Fumaric, tartaric and p-toluenesulfonic acid. Examples of particularly preferred physiologically acceptable salts are the Na, K, Mg, Ca and ammonium salts of the compounds according to the formula (I), and the salts which are obtained by the reaction of compounds of the formula (I) with hydrochloric acid , Acetic acid, citric acid and benzoic acid.
Unter isomeren und stereoisomeren Formen der Verbindungen gemäß Formel (I) werden erfindungsgemäß alle auftretenden optischen Isomere, Diastereomere, Racemate oder Gemische davon verstanden. Isomeric and stereoisomeric forms of the compounds according to formula (I) are understood according to the invention to mean all occurring optical isomers, diastereomers, racemates or mixtures thereof.
Unter dem Begriff Aminosäure werden die stereoisomeren Formen, z.B. D- und L-Formen, folgender Verbindungen verstanden: Asparagin, Arginin, Asparaginsäure, Glutamin, Glutaminsäure, ß-Alanin, γ-Aminobutyrat, N8-Acetyllysin, N8-Acetylornitin, Ny-Acetyldiaminobutyrat, Na-Acetyldiaminobutyrat, Histidin, Isoleucin, Leucin, Methionin, Phenylalanin, Serin, Threonin und Tyrosin. The term amino acid is understood to mean the stereoisomeric forms, for example D and L forms, of the following compounds: asparagine, arginine, aspartic acid, glutamine, glutamic acid, β-alanine, γ-aminobutyrate, N 8 -acetyllysine, N 8 -acetylornitin, N y -acetyldiaminobutyrate, N a -acetyldiaminobutyrate, histidine, isoleucine, leucine, methionine, phenylalanine, serine, threonine and tyrosine.
L-Aminosäuren sind bevorzugt. Aminosäurereste leiten sich von den entsprechenden Aminosäuren ab. Die folgenden Aminosäuren sind bevorzugt: L-amino acids are preferred. Amino acid residues are derived from the corresponding amino acids. The following amino acids are preferred:
Gly, Ala, Thr, Val, ß-Ala, γ-Aminobutyrat, Asp, Glu, Asn, N8-Acetyllysin, N8-Acetylornitin, Ny- Acetyldiaminobutyrat und Na-Acetyldiaminobutyrat. Gly, Ala, Thr, Val, β-Ala, γ-aminobutyrate, Asp, Glu, Asn, N 8 -acetyllysine, N 8 -acetylornitine, N y -acetyldiaminobutyrate and N a -acetyldiaminobutyrate.
Die Kurzschreibweise der Aminosäuren erfolgte nach der allgemein üblichen Schreibweise. Die Dioder Tripeptidreste sind ihrer chemischen Natur nach Säureamide und zerfallen bei der Hydrolyse in 2 oder 3 Aminosäuren. Die Aminosäuren in dem Di- oder Tripeptidrest sind durch Amidbindungen miteinander verbunden. The short notation of the amino acids was carried out according to the usual notation. The Dioder tripeptide radicals are acid amides in their chemical nature and decompose on hydrolysis in 2 or 3 amino acids. The amino acids in the di- or tripeptide moiety are linked together by amide bonds.
Bezüglich der Herstellung der Di- und Tripeptidreste wird ausdrücklich auf die EP 671 161 A1 der Firma Marbert verwiesen. Auch Beispiele für Di- und Tripeptidreste sind der Offenbarung der EP 0 671 161 A1 zu entnehmen. With regard to the preparation of the di- and tripeptide radicals, reference is expressly made to EP 671 161 A1 of Marbert. Examples of di- and tripeptide radicals can also be found in the disclosure of EP 0 671 161 A1.
Beispiele für Ci-C4-Alkylgruppen in den erfindungsgemäßen Verbindungen sind Methyl, Ethyl, n- Propyl, Isopropyl, n-Butyl, Isobutyl und tert.-Butyl. Bevorzugte Alkylgruppen sind Methyl und Ethyl, Methyl ist eine besonders bevorzugte Alkylgruppe. Bevorzugte C2-C4-Hydroxyalkylgruppen sind die Gruppen 2-Hydroxyethyl, 3-Hydroxypropyl oder 4-Hydroxybutyl; 2-Hydroxyethyl ist eine besonders bevorzugte Hydroxylalkylgruppe. Examples of C 1 -C 4 -alkyl groups in the compounds according to the invention are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl and tert-butyl. Preferred alkyl groups are methyl and ethyl, methyl is a particularly preferred alkyl group. Preferred C 2 -C 4 hydroxyalkyl groups are Groups 2-hydroxyethyl, 3-hydroxypropyl or 4-hydroxybutyl; 2-hydroxyethyl is a particularly preferred hydroxyalkyl group.
Weiterhin ist die Verwendung derjenigen Verbindungen gemäß Formel (I) erfindungsgemäß begünstigt, bei denen der Rest R für die Gruppierung -COOH steht. Furthermore, the use of those compounds of formula (I) is favored according to the invention, in which the radical R is the grouping -COOH.
Ferner steht R gemäß allgemeiner Formel (I) bevorzugt für ein Wasserstoffatom. Further, R represented by the general formula (I) is preferably a hydrogen atom.
Die Verwendung von (S)-2-Methyl-1 ,4,5,6-tetrahydro-4-pyrimidincarbonsäure (Ectoin) als Verbindung der allgemeinen Formel (I) sowie die physikalisch verträglichen Salze dieser Verbindung, ist ganz besonders bevorzugt. The use of (S) -2-methyl-1, 4,5,6-tetrahydro-4-pyrimidinecarboxylic acid (ectoine) as the compound of the general formula (I) and the physically acceptable salts of this compound is very particularly preferred.
Erfindungsgemäß verwendbare kosmetische Hautbehandlungsmittel enthalten bevorzugt die 2- Methyl-1 ,4,5,6-tetrahydro-4-pyrimidincarbonsäure und/oder deren Derivate, insbesondere die Verbindungen der Formel (I) (bevorzugt Ectoin) in einer Gesamtmenge von 0,0005 bis 10,0% Gew.-%, besonders bevorzugt 0,001 bis 3,0 Gew.-% und ganz besonders bevorzugt 0,01 bis 1 ,0 Gew.-%, jeweils bezogen auf das Gewicht der gesamten Zusammensetzung. Cosmetic skin treatment agents which can be used according to the invention preferably comprise the 2-methyl-1, 4,5,6-tetrahydro-4-pyrimidinecarboxylic acid and / or derivatives thereof, in particular the compounds of the formula (I) (preferably ectoine) in a total amount of 0.0005 to 10.0% wt .-%, particularly preferably 0.001 to 3.0 wt .-% and most preferably 0.01 to 1, 0 wt .-%, each based on the weight of the total composition.
Als weitere zwingende Komponente der erfindungsgemäßen Wirkstoffkombination muss mindestens ein Blaualgenextrakt in dem erfindungsgemäßen Mittel enthalten sein. As a further obligatory component of the combination of active substances according to the invention, at least one blue-green algae extract must be present in the composition according to the invention.
Blaualgen - auch Cyanobakterien genannt - sind Bakterien, denen Zellkern, Mitochondrien und Chloroplasten fehlen. Die Zellhülle der Blaualgen besteht aus einer Cytoplasma-Mambran, die von einer Murein-Schicht und einer äußeren Zellwand aus Lipopolysacchariden und Proteinen umgeben ist. Ferner enthalten Blaualgen Pigmente zur Photosynthese. Blue algae - also called cyanobacteria - are bacteria that lack the nucleus, mitochondria, and chloroplasts. The cell envelope of the blue-green algae consists of a cytoplasmic mambrane surrounded by a murein layer and an outer cell wall of lipopolysaccharides and proteins. Blue-green algae also contain pigments for photosynthesis.
Es ist erfindungsgemäß bevorzugt, in den erfindungsgemäßen Mitteln ein Blaualgenextrakt aus Blaualgen der Ordnung Oscillatoriales (gemäß Taxonomiedatenbank des National Center for Biotechnology Information der USA) einzusetzen. Besonders bevorzugt wird ein Extrakt der Blaualge der Gattung Spirulina verwendet. Ein Blaualgenextrakt aus Spirulina Platensis ist im Rahmen der Erfindung ganz besonders bevorzugt einsetzbar. It is preferred according to the invention to use a blue-green extract of blue-green algae of the order Oscillatoriales (according to the taxonomy database of the National Center for Biotechnology Information of the USA) in the compositions according to the invention. It is particularly preferred to use an extract of the blue-green algae of the genus Spirulina. A blue-green algae extract from Spirulina Platensis can be used very particularly preferably within the scope of the invention.
Der erfindungsgemäß verwendete Blaualgenextrakt enthält bevorzugt The blue-green extract used according to the invention preferably contains
50 bis 70 g Rohprotein,  50 to 70 g of crude protein,
2 bis 15 g Lipide,  2 to 15 g lipids,
10 bis 19 g Kohlehydrate,  10 to 19 g of carbohydrates,
1 bis 9 g Mineralstoffe (wie beispielsweise Magnesiumsalze)  1 to 9 g minerals (such as magnesium salts)
sowie weitere Inhaltsstoffe der Blaualge oder deren Spaltprodukte  and other ingredients of blue-green algae or their cleavage products
jeweils bezogen auf 100 g Trockenmasse des Extrakts. Die erfindungsgemäßen Extrakte einer Blaualge können durch herkömmliche Extraktionsmethoden gewonnen werden. in each case based on 100 g dry matter of the extract. The extracts of a blue-green algae according to the invention can be obtained by conventional extraction methods.
Erfindungsgemäß verwendbare kosmetische Hautbehandlungsmittel enthalten den Blaualgenextrakt bevorzugt in einer Menge von 0,0001 bis 5,0 Gew.-%, bevorzugt 0,001 bis 3,0 Gew.-%, besonders bevorzugt 0,005 bis 1 ,0 Gew.-%, jeweils bezogen auf das Gewicht der gesamten Zusammensetzung. Cosmetic skin treatment agents which can be used according to the invention preferably contain the blue-green algae extract in an amount of 0.0001 to 5.0% by weight, preferably 0.001 to 3.0% by weight, particularly preferably 0.005 to 1.0% by weight, based in each case on the weight of the entire composition.
Das erfindungsgemäße Mittel enthält als optionale Komponente der erfindungsgemäßen Wirkstoffkombination mindestens ein fucosehaltiges Polysaccharid. The agent according to the invention contains as optional component of the combination of active substances according to the invention at least one fucose-containing polysaccharide.
Die erfindungsgemäßen fucosehaltigen Polysaccharide umfassen folglich zwingend mindestens eine Struktureinheit der Formel (F1 )  The fucose-containing polysaccharides according to the invention therefore necessarily comprise at least one structural unit of the formula (F1)
Figure imgf000008_0001
Figure imgf000008_0001
(F1 )  (F1)
Eine innerhalb einer allgemeinen Formel dieser Anmeldung mit * gekennzeichnete Bindung steht - falls nicht anders definiert - für eine freie Valenz der dargestellten Struktur. Die mit * gekennzeichneten Bindungen gemäß Formel (F1 ) stehen für eine glykosidische Bindung zu einem weiteren Saccharidrest des fucosehaltigen Polysaccharids. A bond denoted by * within a general formula of this application is - unless otherwise defined - a free valency of the structure shown. The bonds marked with * according to formula (F1) represent a glycosidic bond to another saccharide residue of the fucose-containing polysaccharide.
Erfindungsgemäß leiten sich die Struktureinheiten der Formel (F1 ) von der L-Fucose und/oder von der D-Fucose ab. Bevorzugt leiten sich die Struktureinheiten der Formel (F1 ) von der L-Fucose ab unter Bildung der bevorzugten Struktureinheiten der Formel (F1-1 )  According to the invention, the structural units of the formula (F1) are derived from L-fucose and / or from D-fucose. The structural units of the formula (F1) are preferably derived from the L-fucose with formation of the preferred structural units of the formula (F1-1)
Figure imgf000008_0002
Figure imgf000008_0002
(F1-1 )  (F1-1)
wobei die mit * gekennzeichneten Bindungen gemäß Formel (F1-1 ) für eine glykosidische Bindung zu einem weiteren Saccharidrest des fucosehaltigen Polysaccharids stehen. wherein the bonds marked with * according to formula (F1-1) represent a glycosidic bond to another saccharide residue of the fucose-containing polysaccharide.
Das fucosehaltige Polysaccharid ist bevorzugt anionisch. Es enthält daher bevorzugt neben der besagten Fucose-Struktureinheit zusätzlich mindestens eine Struktureinheit die sich ableitet von einer Uronsäure, insbesondere von Galacturonsäure, Glucuronsäure oder Iduronsäure. Besonders bevorzugt leitet sich die zusätzliche Struktureinheit von der Formel (F2) ab
Figure imgf000009_0001
The fucose-containing polysaccharide is preferably anionic. It therefore preferably contains in addition to said fucose structural unit additionally at least one structural unit derived from a uronic acid, in particular of galacturonic acid, glucuronic acid or iduronic acid. Particularly preferably, the additional structural unit is derived from the formula (F2)
Figure imgf000009_0001
wobei die mit * gekennzeichneten Bindungen gemäß Formel (F2) für eine glykosidische Bindung zu einem weiteren Saccharidrest des fucosehaltigen Polysaccharids stehen. wherein the bonds indicated by * according to formula (F2) represent a glycosidic bond to another saccharide residue of the fucose-containing polysaccharide.
Weiterhin enthalten die erfindungsgemäß fucosehaltigen Polysacharide neben der Struktureinheit abgeleitet von Fucose zusätzlich mindestens eine Struktureinheit, die sich von Galactose ableitet. Besonders bevorzugt leitet sich die zusätzliche Galactose-Struktureinheit von der Formel (F3) ab Furthermore, the fucose-containing polysaccharides according to the invention, in addition to the structural unit derived from fucose, additionally contain at least one structural unit which is derived from galactose. Particularly preferably, the additional galactose structural unit is derived from the formula (F3)
Figure imgf000009_0002
Figure imgf000009_0002
wobei die mit * gekennzeichneten Bindungen gemäß Formel (F3) für eine glykosidische Bindung zu einem weiteren Saccharidrest des fucosehaltigen Polysaccharids stehen. wherein the bonds indicated by * according to formula (F3) represent a glycosidic bond to another saccharide residue of the fucose-containing polysaccharide.
Ein erfindungsgemäß besonders bevorzugtes fucosehaltiges Polysaccharid enthält mindestens eine zuvor definierte Struktureinheit der Formel (F1-1 ) und mindestens eine zuvor definierte Struktureinheit der Formel (F2) mindestens eine zuvor definierte Struktureinheit der Formel (F3). Ein wiederum bevorzugtes fucosehaltiges Polysaccharid dieser Ausführungsform trägt die INCI- Nomenklatur Biosaccharide Gum-1 und wird beispielsweise von der Firma Solabia unter dem Handelsnamen Fucogel 1000® oder Fucocert® vertrieben. An inventively particularly preferred fucose-containing polysaccharide contains at least one previously defined structural unit of the formula (F1-1) and at least one previously defined structural unit of the formula (F2) at least one previously defined structural unit of the formula (F3). A still preferred fucosehaltiges polysaccharide of this embodiment carries the INCI nomenclature Biosaccharide Gum-1 and is marketed, for example, by the company Solabia under the trade name Fucogel 1000 ® or Fucocert ®.
Erfindungsgemäß verwendbare kosmetische Hautbehandlungsmittel enthalten das fucosehaltige Polysaccharid bevorzugt in einer Menge von 0,0001 bis 2,0 Gew.-%, bevorzugt 0,001 bis 1 ,5 Gew.-%, besonders bevorzugt 0,005 bis 0,5 Gew.-%, jeweils bezogen auf das Gewicht der gesamten Zusammensetzung. Cosmetic skin treatment agents which can be used according to the invention preferably contain the fucose-containing polysaccharide in an amount of 0.0001 to 2.0% by weight, preferably 0.001 to 1.5% by weight, particularly preferably 0.005 to 0.5% by weight, in each case on the weight of the entire composition.
Besonders bevorzugte kosmetische Hautbehandlungsmittel sind die der Ausführungsformen (A) bis (F) Particularly preferred cosmetic skin treatment agents are those of the embodiments (A) to (F)
(A): Kosmetisches Mittel, enthaltend in einem kosmetischen Träger eine Wirkstoffkombination aus mindestens eine Verbindung der Formel (I) und/oder eines physiologisch verträglichen Salzes und/oder einer isomeren oder stereoisomeren Form dieser Verbindungen ausgewählt,
Figure imgf000010_0001
(A): Cosmetic composition comprising, in a cosmetic carrier, an active ingredient combination of at least one compound of the formula (I) and / or a physiologically tolerable salt and / or an isomeric or stereoisomeric form of these compounds,
Figure imgf000010_0001
in denen R für ein Wasserstoffatom oder eine Hydroxygruppe steht und R' für eine Gruppierung -COOR oder eine Gruppierung -CO(NH)R1 steht, wobei R ein Wasserstoffatom, einen C-ι - C4-Alkylrest, einen Aminosäurerest, einen Dipeptid- oder einen Tripeptidrest bedeutet, und in which R is a hydrogen atom or a hydroxy group and R 'is a grouping -COOR or a grouping -CO (NH) R 1 , wherein R is a hydrogen atom, a C-ι - C 4 alkyl radical, an amino acid residue, a dipeptide or a tripeptide radical, and
mindestens ein Blaualgenextrakt aus Blaualgen der Gattung Spirulina, insbesondere aus Spirulina Platensis, und  at least one blue-green algae extract of blue-green algae of the genus Spirulina, in particular Spirulina platensis, and
gegebenenfalls mindestens ein fucosehaltiges Polysaccharid enthaltend mindestens eine Struktureinheit der Formel (F1-1 ) und mindestens eine Struktureinheit der Formel (F2) mindestens eine Struktureinheit der Formel (F3)  optionally at least one fucose-containing polysaccharide comprising at least one structural unit of the formula (F1-1) and at least one structural unit of the formula (F2) at least one structural unit of the formula (F3)
Figure imgf000010_0002
Figure imgf000010_0002
wobei die mit * gekennzeichneten Bindungen gemäß Formeln (F1-1 ), (F2) und (F3) für eine glykosidische Bindung zu einem weiteren Saccharidrest des fucosehaltigen Polysaccharids stehen.wherein the bonds marked with * according to formulas (F1-1), (F2) and (F3) for a glycosidic bond to another saccharide residue of the fucose-containing polysaccharide.
(B): Kosmetisches Mittel, enthaltend in einem kosmetischen Träger eine Wirkstoffkombination aus jeweils bezogen auf das Gesamtgewicht des Mittels (B): Cosmetic composition comprising, in a cosmetic carrier, a combination of active ingredients, each based on the total weight of the agent
- 0,0005 bis 10,0% Gew.-%, bevorzugt 0,001 bis 3,0 Gew.-%, besonders bevorzugt 0,01 bis 1 ,0 Gew.-%, mindestens einer Verbindung der Formel (I) und/oder eines physiologisch verträglichen Salzes und/oder einer isomeren oder stereoisomeren Form dieser Verbindungen ausgewählt,  From 0.0005 to 10.0% by weight, preferably from 0.001 to 3.0% by weight, particularly preferably from 0.01 to 1.0% by weight, of at least one compound of the formula (I) and / or a physiologically acceptable salt and / or an isomeric or stereoisomeric form of these compounds,
Figure imgf000010_0003
Figure imgf000010_0003
in denen R für ein Wasserstoffatom oder eine Hydroxygruppe steht und R' für eine Gruppierung -COOR1 oder eine Gruppierung -CO(NH)R1 steht, wobei R ein Wasserstoffatom, einen Ci - C4-Alkylrest, einen Aminosäurerest, einen Dipeptid- oder einen Tripeptidrest bedeutet, und - 0,0001 bis 5,0 Gew.-%, bevorzugt 0,001 bis 3,0 Gew.-%, besonders bevorzugt 0,005 bis 1 ,0 Gew.-%, mindestens eines Blaualgenextrakts aus Blaualgen der Gattung Spirulina, insbesondere aus Spirulina Platensis, und in which R is a hydrogen atom or a hydroxy group and R 'is a grouping -COOR 1 or a grouping -CO (NH) R 1 , where R is a hydrogen atom, a C 1 -C 4 -alkyl radical, an amino acid radical, a dipeptide radical or a tripeptide radical, and From 0.0001 to 5.0% by weight, preferably from 0.001 to 3.0% by weight, more preferably from 0.005 to 1.0% by weight, of at least one blue-green algae extract of the genus Spirulina, in particular Spirulina platensis, and
gegebenenfalls 0,0001 bis 2,0 Gew.-%, bevorzugt 0,001 bis 1 ,5 Gew.-%, besonders bevorzugt 0,005 bis 0,5 Gew.-%, mindestens eines fucosehaltigen Polysaccharids enthaltend mindestens eine Struktureinheit der Formel (F1-1 ) und mindestens eine Struktureinheit der Formel (F2) mindestens eine Struktureinheit der Formel (F3)  optionally 0.0001 to 2.0 wt .-%, preferably 0.001 to 1, 5 wt .-%, particularly preferably 0.005 to 0.5 wt .-%, of at least one fucose-containing polysaccharide containing at least one structural unit of the formula (F1-1 ) and at least one structural unit of the formula (F2) at least one structural unit of the formula (F3)
Figure imgf000011_0001
Figure imgf000011_0001
wobei die mit * gekennzeichneten Bindungen gemäß Formeln (F1-1 ), (F2) und (F3) für eine glykosidische Bindung zu einem weiteren Saccharidrest des fucosehaltigen Polysaccharids stehen.wherein the bonds marked with * according to formulas (F1-1), (F2) and (F3) for a glycosidic bond to another saccharide residue of the fucose-containing polysaccharide.
(C): Kosmetisches Mittel, enthaltend in einem kosmetischen Träger eine Wirkstoffkombination aus Ectoin, und (C): Cosmetic composition containing in a cosmetic carrier an active ingredient combination of ectoine, and
mindestens ein Blaualgenextrakt aus Blaualgen der Gattung Spirulina, insbesondere aus Spirulina Platensis, und  at least one blue-green algae extract of blue-green algae of the genus Spirulina, in particular Spirulina platensis, and
mindestens ein fucosehaltiges Polysaccharid enthaltend mindestens eine Struktureinheit der Formel (F1-1 ) und mindestens eine Struktureinheit der Formel (F2) mindestens eine Struktureinheit der Formel (F3)  at least one fucose-containing polysaccharide comprising at least one structural unit of the formula (F1-1) and at least one structural unit of the formula (F2) at least one structural unit of the formula (F3)
Figure imgf000011_0002
Figure imgf000011_0002
wobei die mit * gekennzeichneten Bindungen gemäß Formeln (F1-1 ), (F2) und (F3) für eine glykosidische Bindung zu einem weiteren Saccharidrest des fucosehaltigen Polysaccharids stehen.wherein the bonds marked with * according to formulas (F1-1), (F2) and (F3) for a glycosidic bond to another saccharide residue of the fucose-containing polysaccharide.
(D): Kosmetisches Mittel, enthaltend in einem kosmetischen Träger eine Wirkstoffkombination aus jeweils bezogen auf das Gesamtgewicht des Mittels (D): Cosmetic composition containing in a cosmetic carrier a combination of active ingredients, each based on the total weight of the agent
- 0,0005 bis 10,0% Gew.-%, bevorzugt 0,001 bis 3,0 Gew.-%, besonders bevorzugt 0,01 bis 1 ,0 Gew.-%, Ectoin, und  From 0.0005 to 10.0% by weight, preferably from 0.001 to 3.0% by weight, particularly preferably from 0.01 to 1.0% by weight, of ectoine, and
- 0,0001 bis 5,0 Gew.-%, bevorzugt 0,001 bis 3,0 Gew.-%, besonders bevorzugt 0,005 bis 1 ,0 Gew.-%, mindestens eines Blaualgenextrakts aus Blaualgen der Gattung Spirulina, insbesondere aus Spirulina Platensis, und gegebenenfalls 0,0001 bis 2,0 Gew.-%, bevorzugt 0,001 bis 1 ,5 Gew.-%, besonders bevorzugt 0,005 bis 0,5 Gew.-%, mindestens eines fucosehaltigen Polysaccharids enthaltend mindestens eine Struktureinheit der Formel (F1-1 ) und mindestens eine Struktureinheit der Formel (F2) mindestens eine Struktureinheit der Formel (F3) From 0.0001 to 5.0% by weight, preferably from 0.001 to 3.0% by weight, more preferably from 0.005 to 1.0% by weight, of at least one blue-green algae extract of the genus Spirulina, in particular Spirulina platensis, and optionally 0.0001 to 2.0 wt .-%, preferably 0.001 to 1, 5 wt .-%, particularly preferably 0.005 to 0.5 wt .-%, of at least one fucose-containing polysaccharide containing at least one structural unit of the formula (F1-1 ) and at least one structural unit of the formula (F2) at least one structural unit of the formula (F3)
Figure imgf000012_0001
Figure imgf000012_0001
wobei die mit * gekennzeichneten Bindungen gemäß Formeln (F1-1 ), (F2) und (F3) für eine glykosidische Bindung zu einem weiteren Saccharidrest des fucosehaltigen Polysaccharids stehen.wherein the bonds marked with * according to formulas (F1-1), (F2) and (F3) for a glycosidic bond to another saccharide residue of the fucose-containing polysaccharide.
(E) : Kosmetisches Mittel, enthaltend in einem kosmetischen Träger eine Wirkstoffkombination aus(E): Cosmetic composition containing a combination of active ingredients in a cosmetic carrier
Ectoin, und Ectoin, and
mindestens ein Blaualgenextrakt aus Blaualgen der Gattung Spirulina, insbesondere aus Spirulina Platensis, und  at least one blue-green algae extract of blue-green algae of the genus Spirulina, in particular Spirulina platensis, and
gegebenenfalls Biosaccharide Gum-1 als fucosehaltiges Polysaccharid.  optionally biosaccharides Gum-1 as fucose-containing polysaccharide.
(F) : Kosmetisches Mittel, enthaltend in einem kosmetischen Träger eine Wirkstoffkombination aus jeweils bezogen auf das Gesamtgewicht des Mittels  (F): Cosmetic agent containing in a cosmetic carrier a combination of active ingredients, each based on the total weight of the agent
- 0,0005 bis 10,0% Gew.-%, bevorzugt 0,001 bis 3,0 Gew.-%, besonders bevorzugt 0,01 bis 1 ,0 Gew.-%, Ectoin, und  From 0.0005 to 10.0% by weight, preferably from 0.001 to 3.0% by weight, particularly preferably from 0.01 to 1.0% by weight, of ectoine, and
- 0,0001 bis 5,0 Gew.-%, bevorzugt 0,001 bis 3,0 Gew.-%, besonders bevorzugt 0,005 bis 1 ,0 Gew.-%, mindestens eines Blaualgenextrakts aus Blaualgen der Gattung Spirulina, insbesondere aus Spirulina Platensis, und  From 0.0001 to 5.0% by weight, preferably from 0.001 to 3.0% by weight, more preferably from 0.005 to 1.0% by weight, of at least one blue-green algae extract of the genus Spirulina, in particular Spirulina platensis, and
gegebenenfalls 0,0001 bis 2,0 Gew.-%, bevorzugt 0,001 bis 1 ,5 Gew.-%, besonders bevorzugt 0,005 bis 0,5 Gew.-%, Biosaccharide Gum-1 als fucosehaltiges Polysaccharid.  optionally 0.0001 to 2.0 wt .-%, preferably 0.001 to 1, 5 wt .-%, particularly preferably 0.005 to 0.5 wt .-%, biosaccharides Gum-1 as a fucose-containing polysaccharide.
Vorteilhafterweise liegen die erfindungsgemäß verwendeten kosmetischen Hautbehandlungsmittel in Form einer flüssigen, fließfähigen oder festen ÖI-in-Wasser-Emulsion, Wasser-in-ÖI-Emulsion, Mehrfach-Emulsion, insbesondere einer Öl-in-Wasser-in-ÖI- oder Wasser-in-ÖI-in-Wasser-Emul- sion, Makroemulsion, Miniemulsion, Mikroemulsion, PIT-Emulsion, Nanoemulsion, Pickering-Emulsion, Hydrodispersion, eines Hydrogels, eines Lipogels, einer ein- oder mehrphasigen Lösung, eines Schaumes, eines Puders oder einer Mischung mit mindestens einem als medizinischen Klebstoff geeigneten Polymer vor.  Advantageously, the cosmetic skin treatment agents used according to the invention are in the form of a liquid, flowable or solid oil-in-water emulsion, water-in-oil emulsion, multiple emulsion, in particular an oil-in-water-in-oil or water In-oil-in-water emulsion, macroemulsion, miniemulsion, microemulsion, PIT emulsion, nanoemulsion, Pickering emulsion, hydrodispersion, a hydrogel, a lipogel, a single- or multiphase solution, a foam, a powder or a Mixture with at least one suitable as a medical adhesive polymer.
In einer erfindungsgemäß besonders bevorzugt verwendeten Ausführungsform liegen die Hautbehandlungsmittel als Mikroemulsion vor. Unter Mikroemulsionen werden im Rahmen der Erfindung neben den thermodynamisch stabilen Mikroemulsionen auch die sogenannten "PIT"- Emulsionen verstanden. Bei diesen Emulsionen handelt es sich um Systeme mit den 3 Komponenten Wasser, Öl und Emulgator, die bei Raumtemperatur als ÖI-in-Wasser-Emulsion vorliegen. Beim Erwärmen dieser Systeme bilden sich in einem bestimmten Temperaturbereich (als Phaseninversiontemperatur oder "PIT" bezeichnet) Mikroemulsionen aus, die sich bei weiterer Erwärmung in Wasser-in-ÖI-Emulsionen umwandeln. Beim anschließenden Abkühlen werden wieder O/W-Emulsionen gebildet, die aber auch bei Raumtemperatur als Mikroemulsionen oder als sehr feinteilige Emulsionen mit einem mittleren Teilchendurchmesser unter 400 nm und insbesondere von etwa 100-300 nm, vorliegen. Erfindungsgemäß können solche Mikro- oder "PIT"- Emulsionen bevorzugt sein, die einen mittleren Teilchendurchmesser von etwa 200 nm aufweisen. In der Ausführungsform als Emulsion enthalten die erfindungsgemäßen Zusammensetzungen mindestens eine oberflächenaktive Substanz als Emulgator oder Dispergiermittel. Geeignete Emulgatoren sind beispielsweise Anlagerungsprodukte von 4 bis 30 Mol Ethylenoxid und/oder 0 bis 5 Mol Propylenoxid an lineare C8-C22-Fettalkohole, an Ci2-C22-Fettsäuren und an C8-C-|5-Alkylphe- nole, Ci2-C22-Fettsäuremono- und -diester von Anlagerungsprodukten von 1 bis 30 Mol Ethylenoxid an C3-C6-Polyole, insbesondere an Glycerin, Ethylenoxid- und Polyglycerin-Anlagerungsprodukte an Methylglucosid-Fettsäureester, Fettsäurealkanolamide und Fettsäureglucamide, C8-C22- Alkylmono- und -oligoglycoside und deren ethoxylierte Analoga, wobei Oligomerisierungsgrade von 1 ,1 bis 5, insbesondere 1 ,2 bis 2,0, und Glucose als Zuckerkomponente bevorzugt sind, Gemische aus Alkyl-(oligo)-glucosiden und Fettalkoholen, z. B. die im Handel erhältlichen Produkte Montanov® 68, Montanov® 202 oder Montanov® L, Anlagerungsprodukte von 5 bis 60 Mol Ethylenoxid an Rizinusöl und gehärtetes Rizinusöl, Partialester von Polyolen mit 3-6 Kohlenstoffatomen mit gesättigten C8-C22-Fettsäuren, Sterole (Sterine), insbesondere Cholesterol, Lanosterol, Beta-Sitosterol, Stigmasterol, Campesterol und Ergosterol sowie Mykosterole, Phospholipide, vor allem Glucose-Phospolipide, Fettsäureester von Zuckern und Zuckeralkoholen wie Sorbit, Polygly- cerine und Polyglycerinderivate, bevorzugt Polyglyceryl-2-dipolyhydroxystearat (Handelsprodukt Dehymuls® PGPH) und Polyglyceryl-3-diisostearat (Handelsprodukt Lameform® TGI) sowie lineare und verzweigte C8-C30-Fettsäuren und deren Na-, K-, Ammonium-, Ca-, Mg- und Zn - Salze. In an embodiment used particularly preferably according to the invention, the skin treatment agents are present as microemulsions. In the context of the invention, microemulsions are understood as meaning not only the thermodynamically stable microemulsions but also the so-called "PIT" emulsions. These emulsions are systems with the 3 Components water, oil and emulsifier, which are present at room temperature as an oil-in-water emulsion. When these systems are heated, microemulsions are formed in a certain temperature range (referred to as the phase inversion temperature or "PIT") and, on further heating, convert to water-in-oil emulsions. During the subsequent cooling, O / W emulsions are again formed, but they are also present at room temperature as microemulsions or as very finely divided emulsions having an average particle diameter of less than 400 nm and in particular of about 100-300 nm. According to the invention, those micro- or "PIT" emulsions may be preferred which have an average particle diameter of about 200 nm. In the embodiment as emulsion, the compositions according to the invention contain at least one surface-active substance as emulsifier or dispersant. Suitable emulsifiers are for example adducts of from 4 to 30 mol ethylene oxide and / or 0 to 5 mol propylene oxide onto linear C 8 -C 2 2-fatty alcohols, on C 2 -C 2 2 fatty acids and C 8 -C- | 5 -alkylphenyls, C 2 -C 2 2 -fatty acid mono- and diesters of addition products of 1 to 30 moles of ethylene oxide onto C 3 -C 6 -polyols, in particular to glycerol, ethylene oxide and polyglycerol addition products to methylglucoside fatty acid esters, Fatty acid alkanolamides and fatty acid glucamides, C 8 -C 22 -alkylmono- and -oligoglycosides and their ethoxylated analogues, with degrees of oligomerization of 1, 1 to 5, in particular 1, 2 to 2.0, and glucose being preferred as the sugar component, mixtures of alkyl ( oligo) glucosides and fatty alcohols, e.g. For example, the commercially available products Montanov ® 68, Montanov ® 202 or Montanov ® L, addition products of 5 to 60 moles of ethylene oxide with castor oil and hydrogenated castor oil, partial esters of polyols having 3-6 carbon atoms with saturated C 8 -C 2 2 fatty acids Sterols, in particular cholesterol, lanosterol, beta-sitosterol, stigmasterol, campesterol and ergosterol, and also mycosterols, phospholipids, especially glucose phospholipids, fatty acid esters of sugars and sugar alcohols such as sorbitol, polyglycerols and polyglycerol derivatives, preferably polyglyceryl-2 dipolyhydroxystearate (Dehymuls ® PGPH commercial product) and polyglyceryl-3 diisostearate (Lameform ® TGI commercial product) as well as linear and branched C 8 -C 30 fatty acids and their Na, K, ammonium, Ca, Mg and Zn - salts ,
Die erfindungsgemäß verwendeten Hautbehandlungsmittel enthalten die Emulgatoren bevorzugt in Mengen von 0,1 bis 25 Gew.-%, insbesondere 0,5 - 15 Gew.-%, bezogen auf das gesamte Mittel. In einer besonders bevorzugt verwendeten Ausführungsform ist mindestens ein nichtionischer Emulgator mit einem HLB-Wert von 8 und darunter enthalten. Derart geeignete Emulgatoren sind beispielsweise Verbindungen der allgemeinen Formel R - O - R2, in der R eine primäre lineare Alkyl-, Alkenyl- oder Acylgruppe mit 20 - 30 C-Atomen und R2 Wasserstoff, eine Gruppe mit der Formel -(CnH2nO)x-H mit x = 1 oder 2 und n = 2 - 4 oder eine Polyhydroxyalkylgruppe mit 4 - 6 C- Atomen und 2 - 5 Hydroxylgruppen ist. Weitere bevorzugt geeignete Emulgatoren mit einem HLB- Wert von 8 und darunter sind die Anlagerungsprodukte von 1 oder 2 Mol Ethylenoxid oder Propylenoxid an Behenylalkohol, Erucylalkohol, Arachidylalkohol oder auch an Behensäure oder Erucasäure. Bevorzugt eignen sich auch die Monoester von C16-C3o-Fettsäuren mit Polyolen wie z. B. Pentaerythrit, Trimethylolpropan, Diglycerin, Sorbit, Glucose oder Methylglucose. Beispiele für solche Produkte sind z. B. Sorbitanmonobehenat oder Pentaerythrit-monoerucat. Weiterhin eignet sich besonders bevorzugt ein Emulgatorsystem als Mischung ausThe skin treatment agents used according to the invention preferably contain the emulsifiers in amounts of from 0.1 to 25% by weight, in particular from 0.5 to 15% by weight, based on the total composition. In a particularly preferred embodiment, at least one nonionic emulsifier having an HLB value of 8 and below is included. Such emulsifiers are, for example, compounds of the general formula R - O - R 2 , in which R is a primary linear alkyl, alkenyl or acyl group having 20-30 C atoms and R 2 is hydrogen, a group having the formula - (C n H 2n O) x -H with x = 1 or 2 and n = 2-4 or a polyhydroxyalkyl group having 4-6 C atoms and 2-5 hydroxyl groups. Further preferred emulsifiers with an HLB value of 8 and below are the adducts of 1 or 2 moles of ethylene oxide or propylene oxide with behenyl alcohol, erucyl alcohol, arachidyl alcohol or behenic acid or erucic acid. Preferably, the monoesters of C 16 -C 3 o fatty acids with polyols such. As pentaerythritol, trimethylolpropane, diglycerol, sorbitol, glucose or methyl glucose. Examples of such products are z. B. sorbitan monobehenate or pentaerythritol monoerucate. Furthermore, an emulsifier system is particularly preferably suitable as a mixture
0,2 - 2,0 Gew.-% mindestens eines Salzes eines Ci2-2o-Alkylphosphats, insbesondere ein Salz von Cetylphosphat, als anionischen ÖI-in-Wasser-Emulgator, 0.2 to 2.0 wt .-% of at least one salt of a C 2 -2O-alkyl phosphate, and in particular a salt of cetyl phosphate, as anionic oil-in-water emulsifier,
0, 1 - 1 ,7 Gew.-% mindestens eines C14.2o-Mono- oder Diacylglycerids, bevorzugt mindestens eines Ci6-i8-Mono- oder Diacylglycerids, besonders bevorzugt ausgewählt aus gehärteten Palmölglyceriden, besonders lagerstabil formuliert und konserviert werden können. 0, 1 - 1, 7 wt .-% of at least one to C 14. 2 o-mono- or diacylglycerides, preferably at least one Ci6-i8-mono- or diacylglyceride, particularly preferably selected from hardened palm oil glycerides, can be formulated and stored particularly stable in storage.
Das mindestens eine Salz eines Ci2-2o-Alkylphosphats ist in den erfindungsgemäßen verwendeten Zusammensetzungen in einer Gesamtmenge von 0,2 - 2,0 Gew.-%, bevorzugt 0,3 - 1 ,8 Gew.-%, besonders bevorzugt 1 ,0 - 1 ,5 Gew.-%, jeweils bezogen auf das Gesamtgewicht der Zusammensetzung, enthalten. Bevorzugte erfindungsgemäß verwendete Zusammensetzungen enthalten mindestens ein Salz von Cetylphosphat in einer Gesamtmenge von 0,2 - 2,0 Gew.-%, bevorzugt 0,3 - 1 ,8 Gew.-%, besonders bevorzugt 1 ,0 - 1 ,5 Gew.-%, jeweils bezogen auf das Gesamtgewicht der Zusammensetzung. Weitere bevorzugte erfindungsgemäß verwendete Zusammensetzungen enthalten eine Mischung aus Dikaliummonocetylphosphat und Kaliumdicetyl- phosphat in einer Gesamtmenge von 0,2 - 2,0 Gew.-%, bevorzugt 0,3 - 1 ,8 Gew.-%, besonders bevorzugt 1 ,0 - 1 ,5 Gew.-%, jeweils bezogen auf das Gesamtgewicht der Zusammensetzung. Weitere geeignete Zusatzstoffe sind Verdickungsmittel, z. B. natürliche und synthetische Tone und Schichtsilikate wie Bentonit, Hectorit, Montmorillonit oder Laponite®, oder anionische Polymere aus Acrylsäure, Methacrylsäure, Crotonsäure, Maleinsäureanhydrid und 2-Acrylamido-2-methylpropan- sulfonsäure, wobei die sauren Gruppen ganz oder teilweise als Natrium-, Kalium-, Ammonium-, Mono- oder Triethanolammonium-Salz vorliegen können und wobei mindestens ein nichtionisches Monomer enthalten sein kann. Bevorzugte nichtionogene Monomere sind Acrylamid, Meth- acrylamid, Acrylsäureester, Methacrylsäureester, Vinylpyrrolidon, Vinylether und Vinylester. Bevorzugte anionische Copolymere sind Acrylsäure-Acrylamid-Copolymere sowie insbesondere Polyacrylamidcopolymere mit Sulfonsäuregruppen-haltigen Monomeren. Diese Copolymere können auch vernetzt vorliegen. Geeignete Handelsprodukte sind Sepigel®305, Simulgel®600, Simulgel® NS, Simulgel® EG und Simulgel® EPG der Firma SEPPIC. Weitere besonders bevorzugte anionische Homo- und Copolymere sind unvernetzte und vernetzte Polyacrylsäuren. Solche Verbindungen sind zum Beispiel die Handelsprodukte Carbopol®. Ein besonders bevorzugtes anionisches Copolymer enthält als Monomer zu 80 - 98 % eine ungesättigte, gewünschtenfalls substituierte C3.6-Carbonsäure oder ihr Anhydrid sowie zu 2 - 20 % gewünschtenfalls substituierte Acrylsäureester von gesättigten C10-3o-Carbonsäuren, wobei das Copolymer mit den vorgenannten Vernetzungsagentien vernetzt sein kann. Entsprechende Handelsprodukte sind Pemulen® und die Carbopol®-Typen 954, 980, 1342 und ETD 2020 (ex B.F. Goodrich). The at least one salt of a C 2 -2O-alkyl phosphate is present in the inventive compositions used in a total amount from 0.2 to 2.0 wt .-%, preferably 0.3 - 1. 8 wt .-%, particularly preferably 1, 0 - 1, 5 wt .-%, each based on the total weight of the composition. Preferred compositions used according to the invention comprise at least one salt of cetyl phosphate in a total amount of 0.2-2.0% by weight, preferably 0.3-1.8% by weight, more preferably 1.0-0.5% by weight. -%, in each case based on the total weight of the composition. Further preferred compositions used according to the invention comprise a mixture of dipotassium monocetyl phosphate and potassium dicetyl phosphate in a total amount of 0.2-2.0% by weight, preferably 0.3-1.8% by weight, more preferably 1.0-0.1 , 5 wt .-%, each based on the total weight of the composition. Other suitable additives are thickeners, for. Example, natural and synthetic clays and sheet silicates such as bentonite, hectorite, montmorillonite or Laponite ® , or anionic polymers of acrylic acid, methacrylic acid, crotonic acid, maleic anhydride and 2-acrylamido-2-methylpropanesulfonic acid, where the acidic groups wholly or partly as sodium , Potassium, ammonium, mono- or triethanolammonium salt, and wherein at least one nonionic monomer may be contained. Preferred nonionic monomers are acrylamide, methacrylamide, acrylates, methacrylates, vinylpyrrolidone, vinyl ethers and vinyl esters. Preferred anionic copolymers are acrylic acid-acrylamide copolymers and in particular polyacrylamide copolymers with sulfonic acid-containing monomers. These copolymers can also be present in crosslinked form. Suitable commercial products are NS Sepigel ® 305 Simulgel® ® 600, Simulgel® ®, Simulgel® ® EC and Simulgel® ® EPG SEPPIC. Further particularly preferred anionic homopolymers and copolymers are uncrosslinked and crosslinked polyacrylic acids. Such compounds are for example the commercial products Carbopol ®. A particularly preferred anionic copolymer contains as monomer 80-98% of an unsaturated, optionally substituted C 3 . 6- carboxylic acid or its anhydride and 2 to 20%, if desired, substituted acrylic acid esters of saturated C 10 -3o-carboxylic acids, wherein the copolymer can be crosslinked with the aforementioned crosslinking agents. Corresponding commercial products are Pemulen ® and Carbopol ® grades 954, 980, 1342 and ETD 2020 (ex BF Goodrich).
Geeignete nichtionische Polymere sind beispielsweise Polyvinylalkohole, die teilverseift sein können, z. B. die Handelsprodukte Mowiol® sowie Vinylpyrrolidon/Vinylester-Copolymere und Polyvinylpyrrolidone, die z. B. unter dem Warenzeichen Luviskol® (BASF) vertrieben werden. Die erfindungsgemäß verwendeten Hautbehandlungsmittel enthalten bevorzugt Fettstoffe, die ausgewählt sind aus Ölen, insbesondere pflanzlichen Ölen, wie Sonnenblumenöl, Olivenöl, Sojaöl, Rapsöl, Mandelöl, Jojobaöl, Orangenöl, Weizenkeimol, Pfirsichkernöl und den flüssigen Anteilen des Kokosöls, Lanolin und seinen Derivaten, flüssigen Paraffinölen, Isoparaffinölen und synthetischen Kohlenwasserstoffen, Di-n-alkylethern mit insgesamt 12 bis 36 C-Atomen, z. B. Di-n- octylether und n-Hexyl-n-octylether, Fettsäuren, besonders linearen und/oder verzweigten, gesättigten und/oder ungesättigten C8-3o-Fettsäuren, Fettalkoholen, besonders gesättigten, ein- oder mehrfach ungesättigten, verzweigten oder unverzweigten Fettalkoholen mit 4 - 30 Kohlenstoffatomen, die mit 1 - 75, bevorzugt 5 - 20 Ethylenoxid-Einheiten ethoxyliert und/oder mit 3 - 30, bevorzugt 9 - 14 Propylenoxid-Einheiten propoxyliert sein können, Esterölen, das heißt Estern von C6-30-Fettsäuren mit C2-3o-Fettalkoholen, Hydroxycarbonsäurealkylestern, Dicarbonsäureestern wie Di-n-butyladipat sowie Diolestern wie Ethylenglykoldioleat oder Propylenglykoldi(2-ethylhexanoat), symmetrischen, unsymmetrischen oder cyclischen Estern der Kohlensäure mit Fettalkoholen, z. B. Glycerincarbonat oder Dicaprylylcarbonat (Cetiol® CC), Mono,- Di- und Trifettsäureestern von gesättigten und/oder ungesättigten linearen und/oder verzweigten Fettsäuren mit Glycerin, die mit 1 - 10, bevorzugt 7 - 9 Ethylenoxid-Einheiten ethoxyliert sein können, z. B. PEG-7 Glyceryl Cocoate, Wachsen, insbesondere Insektenwachsen, Pflanzenwachsen, Fruchtwachsen, Ozokerit, Mikrowachsen, Ceresin, Paraffinwachsen, Triglyceriden gesättigter und gegebenenfalls hydroxy- lierter C16.3o-Fettsäuren, z. B. gehärteten Triglyceridfetten, Phospholipiden, beispielsweise Sojalecithin, Ei-Lecithin und Kephalinen, Siliconverbindungen, ausgewählt aus Decamethylcyclopentasiloxan, Dodecamethylcyclohexasiloxan und Siliconpolymeren, die gewünschtenfalls quervernetzt sein können, z. B. Polydialkylsiloxanen, Polyalkylarylsiloxanen, ethoxylierten und/oder propoxylierten Polydialkylsiloxanen mit der früheren INCI-Bezeichnung Dimethicone Copolyol, sowie Polydialkylsiloxanen, die Amin- und/oder Hydroxy-Gruppen enthalten, bevorzugt Substanzen mit den INCI-Bezeichnungen Dimethiconol, Amodimethicone oder Trimethylsilylamodimethicone. Suitable nonionic polymers include polyvinyl alcohols, which may be partially saponified, for. B. the commercial products Mowiol ® and vinylpyrrolidone / vinyl ester copolymers and polyvinylpyrrolidones z. B. under the trademark Luviskol ® (BASF) are sold. The skin treatment agents used in the invention preferably contain fatty substances selected from oils, in particular vegetable oils, such as sunflower oil, olive oil, soybean oil, rapeseed oil, almond oil, jojoba oil, orange oil, wheat germ oil, peach kernel oil and the liquid portions of coconut oil, lanolin and its derivatives, liquid paraffin oils , Isoparaffin oils and synthetic hydrocarbons, di-n-alkyl ethers having a total of 12 to 36 carbon atoms, eg. B. di-n-octyl ether and n-hexyl n-octyl ether, fatty acids, especially linear and / or branched, saturated and / or unsaturated C 8 -3o fatty acids, fatty alcohols, particularly saturated, mono- or polyunsaturated, branched or unbranched fatty alcohols having 4-30 carbon atoms which may be ethoxylated with 1-75, preferably 5-20 ethylene oxide units and / or propoxylated with 3-30, preferably 9-14 propylene oxide units, ester oils, ie esters of C 6 - 30- fatty acids with C 2 -3o fatty alcohols, hydroxycarboxylic acid alkyl esters, dicarboxylic acid esters such as di-n-butyl adipate and diol esters such as ethylene glycol diol or propylene glycol di (2-ethylhexanoate), symmetrical, asymmetrical or cyclic esters of carbonic acid with fatty alcohols, eg. B. glycerol carbonate or dicaprylyl carbonate (Cetiol ® CC), mono, - di- and tri fatty acid esters of saturated and / or unsaturated linear and / or branched fatty acids with glycerol, with 1 - 10, preferably 7-9 ethylene oxide units may be ethoxylated, z. PEG-7 glyceryl cocoate, waxes, in particular insect waxes, plant waxes, fruit waxes, ozokerite, microwaxes, ceresin, paraffin waxes, triglycerides of saturated and optionally hydroxylated C 16 . 3 o-fatty acids, eg. Hardened triglyceride fats, phospholipids, for example soybean lecithin, egg lecithin and cephalins, silicone compounds selected from decamethylcyclopentasiloxane, dodecamethylcyclohexasiloxane and silicone polymers which may, if desired, be cross-linked, e.g. As polydialkylsiloxanes, polyalkylarylsiloxanes, ethoxylated and / or propoxylated polydialkylsiloxanes with the earlier INCI name dimethicone copolyol, and polydialkylsiloxanes containing amine and / or hydroxyl groups, preferably substances with the INCI names Dimethiconol, Amodimethicone or Trimethylsilylamodimethicone.
Die Einsatzmenge der Fettstoffe beträgt 0, 1 - 50 Gew.%, bevorzugt 0,1 - 20 Gew.% und besonders bevorzugt 0, 1 - 15 Gew.%, jeweils bezogen auf das gesamte Hautbehandlungsmittel.  The amount used of the fatty substances is 0, 1-50 wt.%, Preferably 0.1-20 wt.% And particularly preferably 0, 1-15 wt.%, Each based on the total skin treatment agent.
Weitere geeignete Zusatzstoffe sind Antioxidantien, Konservierungsmittel, Lösungsmittel wie Ethanol, Isopropanol, Ethylenglykol, Propylenglykol, Propylenglykolmonoethylether, Glycerin und Diethylenglykol, Adsorbentien und Füllstoffe, wie Talkum und Veegum®, Parfümöle, Pigmente sowie Farbstoffe zum Anfärben des Mittels, Substanzen zur Einstellung des pH-Wertes, Komplexbildner wie EDTA, NTA, ß-Alanindiessigsäure und Phosphonsäuren, Treibmittel wie Propan-Butan-Gemische, Pentan, Isopentan, Isobutan, N20, Dimethylether, C02 und Luft. B e i s p i e l e Other suitable additives are antioxidants, preservatives, solvents such as ethanol, isopropanol, ethylene glycol, propylene glycol, propylene glycol, glycerol and diethylene glycol, adsorbents and fillers such as talc and Veegum ®, perfume oils, pigments and dyes for coloring the composition, substances for adjusting the pH Value, complexing agents such as EDTA, NTA, ß-Alanindiessigsäure and phosphonic acids, propellants such as propane-butane mixtures, pentane, isopentane, isobutane, N 2 0, dimethyl ether, C0 2 and air. Examples
1.0 Beispielrezepturen 1.0 example recipes
1.1 : Nachtcreme 1.1: Night cream
Ectoin 0, 10 Ectoin 0, 10
Algae Extract aus Spirulina Platensis 0,02Algae Extract from Spirulina Platensis 0.02
Biosaccharide Gum-1 0,02Biosaccharides Gum-1 0.02
Rosa Damascena Flower Water 15,00Rosa Damascena Flower Water 15,00
Caprylic/Capric Triglyceride 8,00Caprylic / Capric Triglycerides 8,00
1 ,6-Hexanediol 6,001, 6-hexanediol 6.00
Glycerin 5,00Glycerin 5.00
Laurus Nobilis Leaf/Stem Water 5,00Laurus Nobilis Leaf / Stem Water 5.00
Argania Spinosa Kernel Oil 3,00Argania Spinosa Kernel Oil 3.00
Dicaprylyl Carbonate 3,00Dicaprylyl Carbonate 3.00
Arachidyl Alcohol 2,75Arachidyl alcohol 2.75
Behenyl Alcohol 2,50Behenyl Alcohol 2.50
Betaine 2,00Betaine 2,00
Carthamus Tinctorius Seed Oil 2,00Carthamus Tinctorius Seed Oil 2.00
Cocoglycerides 1 ,00Cocoglycerides 1, 00
Glyceryl Stearate 1 ,00Glyceryl Stearate 1, 00
Butyrospermum Parkii Butter 1 ,00Butyrospermum Parkii Butter 1, 00
Panthenol 0,75Panthenol 0.75
Dimethylsilanol Hyaluronate 0,012Dimethylsilanol Hyaluronate 0.012
Echium Plantagineum Seed Oil 0,50Echium Plantagineum Seed Oil 0.50
Bisabolol 0,45Bisabolol 0.45
Allantoin 0,20Allantoin 0.20
Copernicia Cerifera Cera 0,50Copernicia Cerifera Cera 0,50
Magnesium Chlorid 0,04Magnesium chloride 0.04
Sorbitan Oleate 0,01Sorbitan Oleate 0.01
Aluminum Starch Octenylsuccinate 0,90Aluminum Starch Octenylsuccinate 0.90
Arachidyl Glucoside 0,75Arachidyl glucosides 0.75
Cetearyl Alcohol 0,50Cetearyl alcohol 0.50
Sodium Carbomer 0,30Sodium carbomer 0.30
Bis-Ethylhexyl Hydroxydimethoxy Benzylmalonate 0,40Bis-ethylhexyl hydroxydimethoxy benzyl malonates 0.40
Sodium Acrylate/Sodium Acryloyldimethyl TaurateSodium Acrylate / Sodium Acryloyl Dimethyl Taurate
Copolymer 0, 10Copolymer 0, 10
Polyisobutene 0, 10Polyisobutenes 0, 10
Butylene Glycol 0,08Butylene glycol 0.08
Pentylene Glycol 0,03Pentylene glycol 0.03
Caprylyl/Capryl Glucoside 0,01Caprylyl / caprylic glucoside 0.01
Pantolactone 0,01Pantolactone 0.01
2-Phenoxyethanol 0,502-phenoxyethanol 0.50
(2-Ethylhexyl)glycerin 0,20(2-ethylhexyl) glycerol 0.20
Natrium Benzoate 0,06Sodium benzoate 0.06
Kalium Sorbate 0,02Potassium sorbate 0.02
Wasser ad 100 .2 Feuchtigkeitsspendende Tagescreme Water ad 100 .2 moisturizing day cream
Ectoin 0, 10 Ectoin 0, 10
Algae Extract aus Spirulina Platensis 0,02Algae Extract from Spirulina Platensis 0.02
Biosaccharide Gum-1 0,03Biosaccharides Gum-1 0.03
Rosa Damascena Flower Water 15,00Rosa Damascena Flower Water 15,00
Caprylic/Capric Triglycerid 8,00Caprylic / Capric Triglyceride 8.00
1 ,6-Hexanediol 6,001, 6-hexanediol 6.00
Glycerin 4,95Glycerol 4.95
Laurus Nobilis Leaf/Stem Water 4,95Laurus Nobilis Leaf / Stem Water 4.95
Argania Spinosa Kernel Oil 3,00Argania Spinosa Kernel Oil 3.00
Arachidyl Alcohol 2,75Arachidyl alcohol 2.75
Behenyl Alcohol 2,50Behenyl Alcohol 2.50
Betaine 2,00Betaine 2,00
Carthamus Tinctorius Seed Oil 2,00Carthamus Tinctorius Seed Oil 2.00
Cetearyl Isononanoate 2,00Cetearyl Isononanoate 2.00
Cocoglycerides 1 ,00Cocoglycerides 1, 00
Glyceryl Stearate 1 ,00Glyceryl Stearate 1, 00
Butyrospermum Parkii Butter 1 ,00Butyrospermum Parkii Butter 1, 00
Panthenol 0,75Panthenol 0.75
Tocopheryl Acetate 0,50Tocopheryl acetate 0.50
Dimethylsilanol Hyaluronate 0,01Dimethylsilanol Hyaluronate 0.01
Echium Plantagineum Seed Oil 0,45Echium Plantagineum Seed Oil 0.45
Bisabolol 0,45Bisabolol 0.45
Allantoin 0,20Allantoin 0.20
Magnesium Chlorid 0,04Magnesium chloride 0.04
Sorbitan Oleate 0,01Sorbitan Oleate 0.01
Aluminum Starch Octenylsuccinate 0,90Aluminum Starch Octenylsuccinate 0.90
Arachidyl Glucoside 0,75Arachidyl glucosides 0.75
Cetearyl Alcohol 0,50Cetearyl alcohol 0.50
Sodium Carbomer 0,30Sodium carbomer 0.30
Bis-Ethylhexyl Hydroxydimethoxy Benzylmalonate 0,40Bis-ethylhexyl hydroxydimethoxy benzyl malonates 0.40
Sodium Acrylate/Sodium Acryloyldimethyl TaurateSodium Acrylate / Sodium Acryloyl Dimethyl Taurate
Copolymer 0, 10Copolymer 0, 10
Polyisobutene 0, 15Polyisobutenes 0, 15
Butylene Glycol 0,08Butylene glycol 0.08
Pentylene Glycol 0,05Pentylene glycol 0.05
Caprylyl/Capryl Glucoside 0,01Caprylyl / caprylic glucoside 0.01
Pantolactone 0,01Pantolactone 0.01
Phenoxyethanol 0,50Phenoxyethanol 0.50
(2-Ethylhexyl)glycerin 0,20(2-ethylhexyl) glycerol 0.20
Natrium Benzoat 0,06Sodium benzoate 0.06
Kalium Sorbat 0,02Potassium sorbate 0.02
Wasser ad 100 .3 Creme Water ad 100 .3 cream
Ectoin 0, 10 Ectoin 0, 10
Algae Extract aus Spirulina Platensis 0,02Algae Extract from Spirulina Platensis 0.02
Biosaccharide Gum-1 0,03Biosaccharides Gum-1 0.03
Rosa Damascena Flower Water 15,00Rosa Damascena Flower Water 15,00
Caprylic/Capric Triglyceride 8,00Caprylic / Capric Triglycerides 8,00
Glycerin 6,65Glycerol 6,65
1 ,6-Hexanediol 6,001, 6-hexanediol 6.00
Laurus Nobilis Leaf/Stem Water 4,90Laurus Nobilis Leaf / Stem Water 4,90
Argania Spinosa Kernel Oil 3,00Argania Spinosa Kernel Oil 3.00
Dicaprylyl Carbonate 2,95Dicaprylyl Carbonate 2.95
Arachidyl Alcohol 2,75Arachidyl alcohol 2.75
Behenyl Alcohol 2,50Behenyl Alcohol 2.50
Betaine 2,00Betaine 2,00
Carthamus Tinctorius (Safflower) Seed Oil 2,00Carthamus Tinctorius (Safflower) Seed Oil 2.00
Cocoglycerides 1 ,00Cocoglycerides 1, 00
Glyceryl Stearate 1 ,00Glyceryl Stearate 1, 00
Butyrospermum Parkii (Shea) Butter 0,95Butyrospermum Parkii (Shea) Butter 0.95
Panthenol 0,75Panthenol 0.75
Tocopheryl Acetate 0,50Tocopheryl acetate 0.50
Dimethylsilanol Hyaluronate 0,012Dimethylsilanol Hyaluronate 0.012
Echium Plantagineum Seed Oil 0,45Echium Plantagineum Seed Oil 0.45
Bisabolol 0,45Bisabolol 0.45
Allantoin 0,20Allantoin 0.20
Copernicia Cerifera (Carnauba) Wax 0,50Copernicia Cerifera (Carnauba) Wax 0.50
Magnesium Chlorid 0,045Magnesium chloride 0.045
Natrium Lactate 0,015Sodium lactate 0.015
Sorbitan Oleate 0,015Sorbitan Oleate 0.015
Aluminum Starch Octenylsuccinate 0,90Aluminum Starch Octenylsuccinate 0.90
Arachidyl Glucoside 0,75Arachidyl glucosides 0.75
Cetearyl Alcohol 0,50Cetearyl alcohol 0.50
Sodium Carbomer 0,40Sodium carbomer 0.40
Bis-Ethylhexyl Hydroxydimethoxy Benzylmalonate 0,40Bis-ethylhexyl hydroxydimethoxy benzyl malonates 0.40
Sodium Acrylate/Sodium Acryloyldimethyl Taurate Copolymer 0, 18Sodium Acrylate / Sodium Acryloyl Dimethyl Taurate Copolymer 0, 18
Polyisobutene 0, 15Polyisobutenes 0, 15
Butylene Glycol 0,65Butylene Glycol 0.65
Pentylene Glycol 0,035Pentylene Glycol 0.035
Coco-Glucoside 0,015Coco-glucoside 0,015
Caprylyl/Capryl Glucoside 0,012Caprylyl / caprylic glucoside 0.012
Pantolactone 0,01Pantolactone 0.01
2-Phenoxyethanol 0,552-phenoxyethanol 0.55
(2-Ethylhexyl)glycerin 0,20(2-ethylhexyl) glycerol 0.20
Natrium Benzoat 0,06Sodium benzoate 0.06
Kalium Sorbat 0,02Potassium sorbate 0.02
Wasser ad 100 Water ad 100

Claims

a t e n t a n s p r ü c h e  a t e n t a n s p r e c h e
Kosmetisches Mittel enthaltend in einem kosmetischen Träger eine Wirkstoffkombination aus mindestens einer Verbindung aus 2-Methyl-1 ,4,5,6-tetrahydro-4-pyrimidincarbonsäure oder deren Derivate, und Cosmetic agent containing in a cosmetic carrier an active ingredient combination of at least one compound of 2-methyl-1, 4,5,6-tetrahydro-4-pyrimidinecarboxylic acid or derivatives thereof, and
mindestens einem Blaualgenextrakt, und  at least one blue-green algae extract, and
gegebenenfalls mindestens einem fucosehaltigen Polysaccharid.  optionally at least one fucose-containing polysaccharide.
Kosmetisches Mittel nach Anspruch 1 , dadurch gekennzeichnet, dass als Verbindung aus 2- Methyl-1 ,4,5,6-tetrahydro-4-pyrimidincarbonsäure oder deren Derivate mindestens eine Verbindung der der allgemeinen Formel (I) (bevorzugt Ectoin) enthalten ist und/oder eines physiologisch verträglichen Salzes und/oder einer isomeren oder stereoisomeren Form dieser Verbindungen ausgewählt, in denen Cosmetic composition according to claim 1, characterized in that as the compound of 2-methyl-1, 4,5,6-tetrahydro-4-pyrimidinecarboxylic acid or derivatives thereof at least one compound of the general formula (I) (preferably ectoine) is contained, and or a physiologically acceptable salt and / or an isomeric or stereoisomeric form of these compounds, in which
Figure imgf000019_0001
Figure imgf000019_0001
R für ein Wasserstoffatom oder eine Hydroxygruppe steht und R' für eine Gruppierung  R is a hydrogen atom or a hydroxy group and R 'is a moiety
-COOR oder eine Gruppierung -CO(NH)R1 steht, wobei R ein Wasserstoffatom, einen Ci - C4-Alkylrest, einen Aminosäurerest, einen Dipeptid- oder einen Tripeptidrest bedeutet. -COOR or a grouping -CO (NH) R 1 , where R is a hydrogen atom, a C 1 -C 4 -alkyl radical, an amino acid radical, a dipeptide or a tripeptide radical.
3. Kosmetisches Mittel nach einem der Ansprüche 1 oder 2, dadurch gekennzeichnet, dass die 2- Methyl-1 ,4,5,6-tetrahydro-4-pyrimidincarbonsäure und/oder deren Derivate, insbesondere die Verbindungen der Formel (I) (bevorzugt Ectoin) in einer Gesamtmenge von 0,0005 bis 10,0% Gew.-%, besonders bevorzugt 0,001 bis 3,0 Gew.-% und ganz besonders bevorzugt 0,01 bis 1 ,0 Gew.-%, jeweils bezogen auf das Gewicht der gesamten Zusammensetzung 3. Cosmetic composition according to one of claims 1 or 2, characterized in that the 2-methyl-1, 4,5,6-tetrahydro-4-pyrimidinecarboxylic acid and / or derivatives thereof, in particular the compounds of formula (I) (preferred Ectoin) in a total amount of 0.0005 to 10.0% by weight, more preferably 0.001 to 3.0 wt .-% and most preferably 0.01 to 1, 0 wt .-%, each based on the Weight of the entire composition
4. Kosmetisches Mittel nach einem der Ansprüche 1 bis 3, dadurch gekennzeichnet, dass der Blaualgenextrakt aus Blaualgen der Ordnung Oscillatoriales (gemäß Taxonomiedatenbank des National Center for Biotechnology Information der USA), bevorzugt aus der Blaualge der Gattung Spirulina, besonders bevorzugt ein Blaualgenextrakt aus Spirulina Platensis stammt. 4. Cosmetic composition according to one of claims 1 to 3, characterized in that the blue-green extract of blue algae of the order Oscillatoriales (according to taxonomy database of the National Center for Biotechnology Information of the USA), preferably from the blue-green algae of the genus Spirulina, particularly preferably a blue-green algae extract from Spirulina Platensis is from.
5. Kosmetisches Mittel nach einem der Ansprüche 1 bis 4, dadurch gekennzeichnet, dass der Blaualgenextrakt in einer Menge von 0,0001 bis 5,0 Gew.-%, bevorzugt 0,001 bis 3,0 Gew.-%, besonders bevorzugt 0,005 bis 1 ,0 Gew.-%, jeweils bezogen auf das Gewicht der gesamten Zusammensetzung, enthalten ist. 5. Cosmetic composition according to one of claims 1 to 4, characterized in that the blue-green algae extract in an amount of 0.0001 to 5.0 wt .-%, preferably 0.001 to 3.0 wt .-%, particularly preferably 0.005 to 1 , 0 wt .-%, each based on the weight of the total composition is included.
6. Kosmetisches Mittel nach einem der Ansprüche 1 bis 5, dadurch gekennzeichnet, dass das fucosehaltige Polysaccharid mindestens eine Struktureinheit der Formel (F1-1 ) und mindestens eine Struktureinheit der Formel (F2) mindestens eine Struktureinheit der Formel (F3) enthält 6. Cosmetic composition according to one of claims 1 to 5, characterized in that the fucose-containing polysaccharide contains at least one structural unit of the formula (F1-1) and at least one structural unit of the formula (F2) at least one structural unit of the formula (F3)
Figure imgf000020_0001
Figure imgf000020_0001
wobei die mit * gekennzeichneten Bindungen gemäß Formeln (F1-1 ), (F2) und (F3) für eine glykosidische Bindung zu einem weiteren Saccharidrest des fucosehaltigen Polysaccharids stehen. wherein the bonds marked with * according to formulas (F1-1), (F2) and (F3) for a glycosidic bond to another saccharide residue of the fucose-containing polysaccharide.
7. Nicht-therapeutische kosmetische Verwendung einer Kombination aus 7. Non-therapeutic cosmetic use of a combination of
mindestens einer Verbindung aus 2-Methyl-1 ,4,5,6-tetrahydro-4-pyrimidincarbonsäure oder deren Derivate, und  at least one compound of 2-methyl-1, 4,5,6-tetrahydro-4-pyrimidinecarboxylic acid or its derivatives, and
mindestens einem Blaualgenextrakt, und  at least one blue-green algae extract, and
gegebenenfalls mindestens einem fucosehaltigen Polysaccharid  optionally at least one fucose-containing polysaccharide
(insbesondere in der Ausführung eines der kosmetischen Mittel der Ansprüche 1 bis 6) zur Stimulierung der epidermalen Synthese von Filaggrin und/oder Transglutaminiase und/oder Involucrin.  (especially in the embodiment of any of the cosmetic agents of claims 1 to 6) for stimulating the epidermal synthesis of filaggrin and / or transglutaminicase and / or involucrin.
8. Nicht-therapeutische kosmetische Verwendung nach Anspruch 7 zur Reduktion von Hauttrockenheit. 8. Non-therapeutic cosmetic use according to claim 7 for the reduction of skin dryness.
9. Nicht-therapeutische kosmetische Verwendung nach Anspruch 7 zur Reduktion von Hautrötungen. 9. Non-therapeutic cosmetic use according to claim 7 for the reduction of skin redness.
10. Nicht-therapeutische kosmetische Verwendung nach Anspruch 7 zur Reduktion des Juckreizes der Haut. 10. Non-therapeutic cosmetic use according to claim 7 for reducing the itching of the skin.
PCT/EP2012/071820 2011-12-22 2012-11-05 Use of a combination of 2-methylene-1,4,5,6-tetrahydro-4-pyrimidincarboxylic acid or the derivate thereof and a blue-green algae extract for increasing the skin barrier function WO2013091974A2 (en)

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CN107184410A (en) * 2017-04-28 2017-09-22 广州瑞誉化工科技有限公司 A kind of skin cream with steroid dependent dermatitis repair function

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CN106265477A (en) * 2016-09-28 2017-01-04 珠海姗拉娜化妆品有限公司 A kind of compositions for Skin whitening care cosmetics
CN107184410A (en) * 2017-04-28 2017-09-22 广州瑞誉化工科技有限公司 A kind of skin cream with steroid dependent dermatitis repair function

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