EP2590619A2 - Substances renforçant le bronzage et substances à effet autobronzant - Google Patents

Substances renforçant le bronzage et substances à effet autobronzant

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Publication number
EP2590619A2
EP2590619A2 EP11730566.4A EP11730566A EP2590619A2 EP 2590619 A2 EP2590619 A2 EP 2590619A2 EP 11730566 A EP11730566 A EP 11730566A EP 2590619 A2 EP2590619 A2 EP 2590619A2
Authority
EP
European Patent Office
Prior art keywords
formula
tanning
dihydroxyacetone
preparation
self
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP11730566.4A
Other languages
German (de)
English (en)
Inventor
Valerie Bicard-Benhamou
Christophe Carola
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Merck Patent GmbH
Original Assignee
Merck Patent GmbH
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Merck Patent GmbH filed Critical Merck Patent GmbH
Publication of EP2590619A2 publication Critical patent/EP2590619A2/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/35—Ketones, e.g. benzophenone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/60—Sugars; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/04—Preparations for care of the skin for chemically tanning the skin

Definitions

  • the invention relates to the use of at least one compound of formula I and / or its salt as a self-tanning substance or as a tanning booster for dihydroxyacetone or for a mixture of self-tanning substances containing dihydroxyacetone.
  • the invention furthermore relates to the use of at least one compound of the formula I and / or salt thereof for the modulation of the color shade which is achieved in the browning with dihydroxyacetone or by the mixture or preparation comprising dihydroxyacetone.
  • the invention further relates to the use of at least one compound of the formula I and / or its salt in a mixture or preparation comprising at least one self-tanning substance as a contrast reducing agent.
  • the invention further provides a preparation comprising a compound of the formula I and / or its salt and at least dihydroxyacetone (DHA) as self-tanning substance and a preparation process for such a preparation.
  • DHA dihydroxyacetone
  • the epidermis contains in its lowest layer, the basal layer, in addition to the basal cells, individual pigment-forming cells, the melanocytes.
  • UV light in these cells stimulates the production of melanin, which is transported to the keratinocytes (horny cells) where it becomes visible as a brown skin color.
  • Melanin protects the cell nuclei from further irradiation and the resulting negative effects on the cell DNA. It covers the cell nucleus like a parasol, protecting it from damaging UV radiation.
  • An artificial tanning of the skin can be produced externally with the help of make-up and orally by taking carotenoids.
  • DHA 1,3-dihydroxyacetone
  • Self-tanning agents can be reacted with the proteins and amino acids of the horny layer of the skin in the sense of a Maillard reaction or via a Michael addition, whereby polymers which give the skin a brownish hue emerge via a not yet fully elucidated reaction pathway. This reaction is completed in about 4 to 6 hours. The tan thus obtained is not washable and is removed only with the normal Hautabschuppung.
  • DHA is a water-soluble crystalline solid that is not stable under neutral to basic conditions. This instability is also associated with the development of cosmetically undesirable off-odors.
  • the present invention is concerned with the task of improving the staining of proteinaceous matrices, in particular with regard to a more natural hue.
  • Alk is a straight or branched C 1 to C 4 alkyl group
  • Acy represents a straight-chain or branched C 1 to C 4 acyl group.
  • Ci Ci to C 4 acyl formyl, acetyl, propionyl and 2-methyl-propionyl.
  • An object of the invention is therefore the use of at least one compound of formula I. wherein R, R 2 , R 3 and R 4 are each independently H, OH, O " Kt + , OAlk, NH 2 , NHCOCH 3 or OAcy,
  • Kt + is Na ⁇ K + , NH 4 + ,
  • carbon atoms to which R 1 , R 2 , R 3 or R 4 are attached may each independently be in R or S configuration, the compounds of formula I being in an open-chain form or in a furanoid or pyranoid lactone and / or lactol form, and / or its salt as a tanning enhancer for dihydroxyacetone or for a dihydroxyacetone-containing mixture of self-tanning substances.
  • Another object of the invention is therefore the use of at least one compound of formula I. wherein R 1 , R 2 , R 3 and R 4 are each independently H, OH, O " Kt ⁇ OAlk, NH 2> NHCOCH 3 or OAcy,
  • Kt + is Na + , K + , NH 4 + ,
  • R 1 , R 2 , R 3 or R 4 may each independently be in R or S configuration, the compounds of formula I being in an open-chain form or in a furanoid or pyranoid lactone and / or lactol form,
  • Another object of the invention is the use of at least one compound of formula I. wherein R 1 , R 2 , R 3 and R 4 each independently represent H, OH, O " Kt + , OAlk, NH 2) NHCOCH 3 or OAcy,
  • Kt + is Na + , K + , NH 4 +
  • the carbon atoms to which R 1 , R 2 , R 3 or R 4 are attached may each independently be in R or S configuration, the compounds of formula I being in an open-chain form or in a furanoid or pyranoid lactone and / or lactol form,
  • the self-tanning of the skin can be carried out with a more natural looking tint without an undesirable yellow tint of the tinted skin.
  • self-tanning or self-tanning substance or self-tanner substance is used interchangeably. These terms refer to a substance which dyes the skin and reacts in the sense of a Maillard reaction or via a Michael addition with the proteins and / or amino acids of the protein-containing matrix and thus forms melanoids.
  • the melanoids are yellow-brown to almost black-colored, organic compounds that can be formed mainly by the reaction of carbonyl groups with amino or thiofunctions.
  • the principle of staining to form melanoid is the basic staining principle of self-tanning substances. In this case, the coloring ability of such self-tanning substances by use of at least one compound of formula I, as described above.
  • the dihydroxyacetone which can be used inter alia as a self-tanner, dyes the skin.
  • the dyeing process can be enhanced with dihydroxyacetone and / or the color shade obtained can be improved.
  • a tanning booster is understood to mean a compound of the formula I which is capable of producing, when coloring the skin with dihydroxyacetone, an optionally darker hue, which is more redshifted than a tint associated with dihydroxyacetone or a mixture of Dböstedssubstanzen containing dihydroxyacetone alone, is achieved.
  • tanning enhancer or a compound of formula I when used on the skin, dehydration thereof is reduced as compared to the use of dihydroxyacetone or a mixture of self-tanning substances containing dihydroxyacetone alone.
  • compounds of Formula I may have a contrast-reducing effect which, when used with dihydroxyacetone or a mixture of self-tanning substances containing dihydroxyacetone, reduces uneven skin coloration and thus lowers the contrast between more and less colored skin areas.
  • a contrast reducing agent is therefore a substance that has a reduces uneven skin coloration by reducing the contrast between stronger and less stained areas of skin.
  • Compounds according to formula I, as described above, are also self-tanning substances, in particular glucuronolactone.
  • Another object of the invention is therefore the use of at least one compound of formula I. wherein R 1 , R 2 , R 3 and R 4 each independently represent H, OH, O " Kt + , OAlk, NH 2 , NHCOCH 3 or OAcy,
  • Kt + is Na + , K + , NH 4 + ,
  • R 1 , R 2 , R 3 or R 4 may each independently be in R or S configuration, the compounds of formula I being in an open-chain form or in a furanoid or pyranoid lactone and / or lactol form,
  • the at least one compound of the formula I acts in mixtures or formulations containing at least dihydroxyacetone.
  • the at least one Binding according to formula I the compounds given as being preferred or, more preferably, glucuronolactone, in a preparation containing dihydroxyacetone as self-tanning substance.
  • a contrast reduction can therefore be achieved in particular by preparations in which combinations according to the invention of dihydroxyacetone or a mixture of self-tanning substances containing dihydroxyacetone and at least one compound of the formula I, as described above, are additionally brought together with a biochemical melanin-inhibiting substance.
  • the combination of tanning mixtures based on the Maillard reaction or Michael addition with melanogenesis inhibiting substances causes already hyperpigmented areas of skin to lose their high melanin concentrations and the hue produced by the staining agent on the surface of the skin to spread over a large area.
  • melanogenesis inhibitors e.g. Ascorbic acid and its derivatives, niacinamide, emblica, ellagic acid, mulberry extract, kojic acid, liquorice root extract, rucinol, hydroquinone, azelaic acid, arbutin or magnesium ascorbyl phosphate.
  • An object of the invention is therefore likewise a preparation containing at least one compound of the formula I as described above and a melanogenesis inhibitor.
  • Uneven pigmentation is by no means uncommon in the population and is based on a different degree of melanin production of the melanocytes or an irregular distribution of the melanocytes in the skin.
  • the melanin production is triggered by the enzyme tyrosinase, which ultimately sets the color of the skin, the eyes and the hair.
  • tyrosinase which ultimately sets the color of the skin, the eyes and the hair.
  • dihydroxyacetone it is possible to achieve a coloring of the skin with more natural, especially in the red color range shifted, skin colorations, in addition, a favorable contrast reduction unevenly colored skin is possible.
  • skin dehydration is also advantageously reduced by compounds of formula I.
  • the substituents R, R 2 , R 3 and R 4 are each independently H, OH; O " Kt + , OAlk or OAcy, where Kt + , Alk or Acy has one of the meanings mentioned above or later or mentioned as preferred.
  • a compound according to formula I preferably comprises derivatives derivable from aldoses, but not the aldoses themselves.
  • aldoses are monosaccharides having an aldehyde group and a total of six carbon atoms.
  • the term aldoses includes hexoses.
  • the substituents R 1 , R 2 , R 3 and R 4 have a corresponding meaning, selected from the meanings H, OH, NH 2 or NHCOCH 3 , of which then derive the compounds of formula I, as described above.
  • the substituents R 1 , R 2 , R 3 and R 4 are identical and denote OH.
  • R 1 is NHCOCH 3 and R 2 , R 3 and R 4 are the same and are OH.
  • the compounds according to formula I preferably comprise the alduronic acids and the dialdehydes of the aldoses, as well as their derivatives.
  • alduronic acid In an alduronic acid, the original aldehyde group of the parent aldose is unchanged and the CHaOH group is oxidized to the carboxylic acid.
  • the alduronic acids are named with the word stem of the basic aldose and the ending -uron.
  • the alduronic acid of D-glucose is D-glucuronic acid.
  • the compounds according to formula I therefore preferably also include dialdehydes, the CH 2 OH group being oxidized starting from the aldose to form the aldehyde group.
  • dialdehyde of the respective aldose These compounds are to be referred to in the following as dialdehyde of the respective aldose.
  • At least one of the OH groups of the respective aldose derivative can be substituted by OAlk, O " Kt + or OAcy.
  • Alk is preferably methyl, ethyl, propyl, / 'so-propyl or te / t-butyl, particularly preferably methyl, ethyl, or terf.-butyl and most preferably methyl.
  • Acy is preferably formyl, acetyl, propionyl and butyryl, particularly preferably formyl, acetyl and most preferably acetyl.
  • At least one of the OH groups is substituted by OAlk or OAcy and most preferably all OH groups are unsubstituted.
  • R 1 , R 2 , R 3 and R 4 OH are particularly preferred.
  • Cyclic forms of the aldonic acids and the dialdehydes of the aldoses and their derivatives are, for example, intramolecular monocyclic esters, so-called lactones, monocyclic hemiacetals, so-called lactols, and their bicyclic Mixed forms, such as glucoronolactone, in which a ⁇ -lactone may be combined with a cyclic ⁇ -lactol.
  • the compound of the formula I preferably has an aldehyde group which is in the form of an intramolecular hemiacetal, the so-called lactol.
  • a lactol is understood to mean a cyclic hemiacetal, as commonly occurs with monosaccharides.
  • compounds of formula I also explicitly include their ⁇ -anomeric and ⁇ -anomeric forms and mixtures thereof, the particular shape being determined by the position of the OH group on the anomeric carbon atom.
  • the anomeric C atom is the C atom of the original aldehyde group, which becomes the anomeric C atom by formation of the lactol.
  • X is COOH.
  • Preferred compounds of the formula I in which X denotes CHO are the dialdehydes of the following aldoses:
  • x-allose D, L
  • x-glucose D, L
  • x-gulose D, L
  • x-galactose D, L
  • x-mannose D, L
  • x-isose D, L
  • x-talose D, L
  • those compounds of the formula I which have at least one ring can occur in a furanoid or pyranoid ring form, analogously to the furanoses or the pyranoses.
  • a furanoid ring form is to be understood as a ring having five carbon atoms in which a carbon atom is replaced by an oxygen
  • a pyranoid ring form is to be understood as meaning a ring of six carbons in which a carbon atom is replaced by an oxygen atom.
  • Lactones can be named according to the Lacton notation.
  • the ⁇ -C atom designates the C atom following the original Caboxyl group, the ⁇ -C atom the C atom next to the C atom after the original Caboxyl group, the ⁇ -C atom the ⁇ -C atom following and the ⁇ -C atom following the ⁇ -C atom.
  • a ⁇ -lactone has a furanoidal form while a ⁇ -lactone has a pyranoidal form.
  • Lactols may be named according to the Lactol notation and similar to the Lacton notation.
  • the ⁇ -C atom designates the C atom following the original aldehyde group, the ⁇ -C atom the next-but-one C atom after the original aldehyde group, the ⁇ -C atom the ⁇ -C atom following and the ⁇ -C atom following the ⁇ -C atom.
  • a ⁇ -lactol thus has a furanoid form, while a ⁇ -lactol has a pyranoid form.
  • the compounds of the formula I Preference is given to the compounds of the formula I, the compounds of the formula I described as being preferred or the dialdehydes of the aldoses or alduronic acids mentioned being at least monocyclic, particularly preferably monocyclic lactones or bicyclic compounds.
  • Preferred monocyclic lactones or lactones are ⁇ -lactols and ⁇ -lactones or ⁇ -lactols and ⁇ -lactones; ⁇ -lactols and ⁇ -lactones are particularly preferred and most preferred is a ⁇ -lactol of a ⁇ -lactone.
  • a ⁇ -lactol of the respective ⁇ -lactone there is an O-bridged ring closure between the aldehyde group and the OH group of the ⁇ -carbon atom according to the Lacton notation.
  • Very particular preference is given to using glucuronolactone in the bicyclic form.
  • Advantageous self-tanning agents in a mixture or preparation containing dihydroxyacetone may include, but are not limited to:
  • Glycerol aldehyde hydroxymethylglyoxal, ⁇ -dialdehyde, erythrulose, 6-aldo-D-fructose, ninhydrin, 5-hydroxy-1,4-naphthoquinone (juglone) or 2-hydroxy-1,4-naphthoquinone (Lawson), or a mixture thereof Links.
  • Erythrulose is particularly preferably used in the mixture containing dihydroxyacetone.
  • the at least one compound of the formula I as described above or described as preferred may also be used according to the invention together with a mixture of self-tanning substances containing at least dihydroxyacetone and another self-tanner selected from the aforementioned group.
  • a mixture of self-tanning substances containing at least dihydroxyacetone and another self-tanner selected from the aforementioned group.
  • the mixture of dihydroxyacetone and at least one other self-tanning substance as described above.
  • This mixture can then be combined according to the invention with at least one compound of formula I and used in cosmetic, dermatological or pharmaceutical preparations, as described below.
  • the invention furthermore relates to preparations containing at least one carrier suitable for cosmetic, pharmaceutical, dermatological preparations and at least dihydroxyacetone and at least one compound of the formula I as described above or described as being preferred.
  • the preparation contains at least dihydroxyacetone in an amount of 0.01 to 20 wt .-%, particularly preferably in an amount of 0.5 to 15 wt .-% and most preferably in an amount of 1 to 8 wt .-% , based on the total amount of the preparation.
  • the preparation contains the at least one compound of the formula I, as described above or described as preferred, in an amount of 0.01 to 20 wt .-%, particularly preferably in an amount of 0.5 to 15 wt .-% and most preferably in an amount of 1 to 8 wt .-%, based on the total amount of the preparation.
  • the weight percent ratio of the at least one compound of the formula I to dihydroxyacetone, when used as a browning enhancer and / or self-tanning substance and / or color modulator, is from 1:20 to 20: 1, preferably 1:10 or 10: 1, more preferably from 1: 3 to 3: 1 and most preferably 1: 1.
  • Self-tanning preparations, especially those containing dihydroxyacetone, are prone to malodour when applied to human skin, presumably caused by degradation products of the dihydroxyacetone itself or by products of side reactions, and which are sometimes found to be unpleasant by users. It has been found that these off-odors are avoided when using formaldehyde scavengers and / or flavonoids.
  • the preparation according to the invention containing at least one compound of formula I, as described above with the specified and preferably mentioned substituents and the individual compounds and at least one self-tanner preferably also contain formaldehyde scavengers and optionally flavonoids to improve the odor.
  • the compounds of the formula I claimed for preparations according to the invention, as well as the corresponding preferred compounds can in turn also contribute to improving the odor.
  • the formaldehyde scavenger is selected from the group alkali metal, alkaline earth metal or ammonium disulfite.
  • Particularly preferred is a formulation containing in combination DHA Plus, a mixture of DHA, sodium disulfite and magnesium stearate.
  • DHA Plus is a product blend containing sodium metabisulfite, equivalent to Na 2 S 2 O 5 or INCI: sodium disulfite, for masking, elimination or neutralization of formaldehyde.
  • sodium metabisulfite equivalent to Na 2 S 2 O 5 or INCI: sodium disulfite, for masking, elimination or neutralization of formaldehyde.
  • the addition of sodium metabisulfite in finished formulations leads to a significant reduction or elimination of the unpleasant odor.
  • DHA Plus is distributed by Merck, Darmstadt.
  • the preparation according to the invention comprising at least one compound of the formula I as described above with the specified and also preferably mentioned substituents and the compounds mentioned gen, and at least dihydroxyacetone as a self-tanner, may more preferably contain flavonoids to improve the odor and, optionally, for tanning.
  • the flavonoid additionally acts as a stabilizer for the self-tanner or the self-tanning substances and / or reduces or avoids or improves storage-dependent off-odors, which can also be caused by additives or auxiliaries contained.
  • flavonoid in which one or more phenolic hydroxy groups are blocked by etherification or esterification.
  • hydroxyethyl-substituted flavonoids such as preferably troxerutin, troxequercetin, troxeisoquercetin or troxeluteolin
  • flavonoid sulfates or flavonoid phosphates such as preferably rutosulfates
  • Particularly preferred in the context of the use according to the invention are rutin sulfate and troxerutin. Very particularly preferred is the use of troxerutin.
  • the preferred flavonoids have a non-positively charged FlavangrundMech. These flavonoids are thought to complex metal ions such as Fe 2+ / Cu 2+ , thus preventing or reducing auto-oxidation processes in fragrances or compounds whose degradation leads to off-odors.
  • DHA Rapid is a product mixture containing dihydroxyacetone and troxerutin, Merck, Darmstadt.
  • this particularly preferred preparation may also contain a formaldehyde scavenger, for example sodium disulfite.
  • formaldehyde scavengers and preparations which contain formaldehyde scavengers and, if appropriate, flavonoids for improving the odor on the skin are described in German Patent Application DE 10 2007 013 368 A1, the content of which relates expressly to the disclosure content of the present application.
  • the preparations are usually topically applicable preparations, for example cosmetic or cosmetic preparations
  • compositions or medical devices contain a cosmetically or dermatologically suitable carrier and, depending on the desired property profile, optionally further suitable ingredients.
  • preparations in this case contain a pharmaceutically acceptable carrier and optionally further pharmaceutical active ingredients.
  • agent or formulation is used synonymously in addition to the term preparation.
  • compositions may comprise or contain, consist essentially of or consist of said necessary or optional ingredients. Any compounds or components which may be used in the compositions are either known and commercially available or may be synthesized by known methods.
  • the invention also provides a process for the preparation of a preparation as described above, wherein at least one compound of the formula I, as described above or described as preferred, is mixed with a carrier and optionally with other active or auxiliary substances. Then, if appropriate, at least one further self-tanning substance is added and mixed and added and mixed as the last dihydroxyacetone. Suitable carriers and active or auxiliary substances are described in detail in the following part.
  • color pigments may furthermore also be present, the layer structure of the pigments not being limited.
  • the color pigment should be skin colored or brownish at a level of from 0.5 to 5% by weight.
  • the selection of a corresponding pigment is familiar to the person skilled in the art.
  • preferred preparations may comprise further organic UV filters, so-called hydrophilic or lipophilic sunscreen filters which are in the UVA range and / or UVB range and / or IR and / or These substances can be described in particular in the application WO-93/04665, among cinnamic acid derivatives, salicylic acid derivatives, camphor derivatives, triazine derivatives, ⁇ , ⁇ -diphenylacrylate derivatives, p-aminobenzoic acid derivatives and polymeric filters and silicone filters Further examples of organic filters are given in patent application EP-A 0 487 404. The following the named UV filters are usually named according to the INCI nomenclature.
  • PABA para-aminobenzoic acid and its derivatives: PABA, ethyl PABA, ethyl dihydroxypropyl PABA, ethylhexyl dimethyl PABA, e.g. B. under the name "Escalol 507" from the company.
  • ISP glyceryl PABA, PEG-25 PABA, z. B. under the name "Uvinul P25” from BASF.
  • Salicylates Homosalates are sold under the name "Eusolex HMS” by Merck; Ethyl hexyl salicylates, e.g. B. under the name “Neo Heliopan OS” from the Fa. Symrise, Dipropylene glycol salicylate, z. B. under the name “Dipsal” from the company. Scher, TEA salicylate, z. B. under the name “Neo Heliopan TS” of the Fa. Symrise. ⁇ , ⁇ -diphenylacrylate derivatives: octocrylenes, e.g. For example, sold under the name "Eusolex® OCR” by Merck, "Uvinul N539” by BASF, Etocrylene, for example, marketed under the name "Uvinul N35” by BASF.
  • Benzophenone Derivatives Benzophenone-1, e.g. B. operated under the name "Uvinul 400"; Benzophenone-2, e.g. B. operated under the name “Uvinul D50”; Benzophenone-3 or oxybenzone, e.g. B. sold under the name “Uvinul M40” Benzophenone-4, z. B. operated under the name "Uvinul MS40"; Benzophenone-9, e.g. B. under the name "Uvinul DS-49" from the company. BASF, Benzophenone-5, Benzophenone- 6, z. B. under the name "Helisorb 11" from the company.
  • Phenylbenzimidazole derivatives phenylbenzimidazolesulfonic acid, e.g. B. under the name “Eusolex 232" from the company Merck, disodium phenyl dibenzimidazole tetrasulfonate, z. B. operated under the name "Neo Heliopan AP" of the Fa. Symrise.
  • Phenylbenzotriazole derivatives Drometrizole trisiloxanes, e.g. B. under the name "Silatrizole” from the Fa. Rhodia Chimie, Methylenebis (benzotriazolyl) tetramethylbutylphenol in solid form, eg. B. under the name "MIXXIM BB / 100" from the company Fairmount Chemical, or in a micronized form as an aqueous dispersion, eg. B. under the name "Tinosorb M” from BASF.
  • Triazine derivatives ethylhexyltriazone, e.g. B. under the name "Uvinul T150" from the Fa. BASF, Diethylhexylbutamidotriazone, z. From the company Sigma 3V, 2,4,6-tris (diisobutyl 4'-aminobenzalmalonate) -s-triazines or 2,4,6-tris (biphenyl) -1, 3,5-triazines.
  • Tinosorb A2B sold as Tinosorb A2B by BASF, 2,2 '- [6- (4-methoxyphenyl) -1, 3,5-triazine-2,4-diyl] bis [5- (2-ethylhexyl) oxy] phenol as Tinosorb S from BASF, N2, N4-bis [4- [5- (1, 1-dimethylpropyl) -2-benzoxazolyl] phenyl] -N6- (2-ethylhexyl) -1, 3,5-triazine-2, 4,6-triamine sold as Uvasorb K 2A from Sigma 3V.
  • Anthraniline derivatives menthyl anthranilate, e.g. B. operated under the name "Neo Heliopan MA" by Fa. Symrise.
  • Imidazole derivatives ethylhexyldimethoxybenzylidenedioxoimidazoline propionate.
  • Benzalmalonate Derivatives Polyorganosiloxanes containing functional bengal malonate groups, e.g. Polysilicone-15, e.g. B. sold under the name "Parsol SLX” by Hoffmann LaRoche.
  • 4,4-Diarylbutadiene derivatives 1,1-dicarboxy (2,2'-dimethylpropyl) -4,4-diphenylbutadiene.
  • Benzoxazole derivatives 2,4-bis [5- (1-dimethylpropyl) benzoxazol-2-yl (4-phenyl) imino] -6- (2-ethylhexyl) imino-1,3,5-triazines, e.g. B. sold under the name Uvasorb K2A from the company. Sigma 3V and mixtures thereof containing.
  • Suitable organic UV-protective substances are preferably to be selected from the following list: ethylhexyl salicylate, phenylbenzimidazolesulfonic acid, benzophenone-3, benzophenone-4, benzophenone-5, n-hexyl 2- (4-diethylamino-2-hydroxybenzoyl) benzoate, 4-methylbenzylidenecamphor, terephthalylidenedicamphorsulfonic acid, di-sodium phenyldibenzimidazoletetrasulfonate, methylene-bis (benzotriazolyl) tetramethylbutylphenol, ethylhexyl triazone, diethylhexyl butamido triazone, drometrizole trisiloxane, polysilicone-15, 1, 1-dicarboxy (2,2'-dimethylpropyl) 4,4-dip
  • organic UV filters are usually incorporated in formulations in an amount of from 0.01% to 20% by weight, preferably 1% to 10% by weight.
  • the preparations may contain, in addition to the compounds of the formula I, at least dihydroxyacetone as self-tanning substance and optionally other organic UV filters, as described above, further inorganic UV filters, so-called particulate UV filters.
  • both those from the group of titanium dioxides such as overall coatetes titanium dioxide (for example Eusolex ® T-2000, Eusolex ® T-AQUA, Eusolex ® T-AVO, Eusolex ® T-OLEO), zinc oxides (eg Sachtotec® ®), iron oxides or else cerium oxides and / or zirconium oxides.
  • overall coatetes titanium dioxide for example Eusolex ® T-2000, Eusolex ® T-AQUA, Eusolex ® T-AVO, Eusolex ® T-OLEO
  • zinc oxides eg Sachtotec® ®
  • iron oxides or else cerium oxides and / or zirconium oxides e.g Sachtotec® ®
  • combinations with pigmentary titanium dioxide or zinc oxide are also possible, the particle size of these pigments being greater than or equal to 200 nm, for example Hombitan® FG or Hombitan® FF-Pharma.
  • the preparations contain inorganic UV filters which have been aftertreated by customary methods, as described, for example, in Cosemics & Toiletries, 1990, 105, 53-64.
  • the following aftertreatment components may be selected: amino acids, beeswax, fatty acids, fatty acid alcohols, anionic surfactants, lecithin, phospholipids, sodium, potassium, zinc, iron or aluminum salts of fatty acids, polyethylenes, silicones, proteins (especially Collagen or elastin), alkanolamines, silica, alumina, other metal oxides, phosphates, such as sodium hexametaphosphate or glycerol.
  • Preferably used particulate UV filters are:
  • untreated titanium dioxides e.g. the products Microtitanium Dioxide MT 500 B from Tayca; Titanium Dioxide P25 from Degussa,
  • micronised titanium dioxides with alumina and / or aluminum stearates / laurate aftertreatment e.g. Microtitanium Dioxide MT 100 T from Tayca, Eusolex T-2000 from Merck,
  • micronised titanium dioxides with iron oxide and / or iron stearates aftertreatment such as e.g. the product "Microtitanium Dioxide MT 100 F" from Tayca,
  • Aftertreated micronised titanium dioxides with silicas, alumina and silicon aftertreatment such as the product "Microtitanium Dioxide MT 100 SAS", the company Tayca, Aftertreated micronised titanium dioxides with sodium hexametaphosphates, for example the product "Microtitanium Dioxide MT 150 W” from Tayca.
  • the treated micronized titanium dioxides used for combination may also be post-treated with:
  • Octyltrimethoxysilane such as. the product Tego Sun T 805 from Evonik Goldschmidt GmbH,
  • silica such as. the product Parsol T-X from DSM,
  • Alumina and stearic acid such as. the product UV-Titan M160 of the company Sachtleben,
  • Aluminum and glycerin such as. the product UV-Titan from the company Sachtleben,
  • Aluminum and silicone oils e.g. the product UV-Titan M262 of the company Sachtleben,
  • Polydimethylsiloxanes e.g. the product 70250 Cardre UF Ti02SI3 "from the company Cardre,
  • Polydimethylhydrogensiloxanes e.g. Microtitanium Dioxide USP Grade Hydrophobie "from Color Techniques.
  • Untreated zinc oxides such as the product Z-Cote from BASF (Sunsmart), Nanox from the company Elementis
  • Post-treated zinc oxides such as the following products:
  • Nanogard Zinc Oxide FN from Nanophase Technologies o "SPD-Z1" from Shin-Etsu (ZnO aftertreated with a silicone-grafted acrylic polymer dispersed in cyclodimethylsiloxanes
  • Escalol Z100 of the company ISP (aluminum oxide aftertreated ZnO dispersed in an ethylhexyl methoxycinnamate / PVP-hexadecenes / methicone copolymer mixture)
  • mixtures of various metal oxides e.g. Titanium dioxide and cerium oxide with and without Nachbenmaschine be used, such. the product Sunveil A of the company Ikeda.
  • mixtures of alumina, silica, and silicon aftertreated titanium dioxide may also be used.
  • Zinc oxide mixtures such. the product UV titanium M261 Fa. Sachtleben be used in combination with the UV protection agent according to the invention.
  • inorganic UV filters are incorporated usually in an amount of 0.1 weight percent to 25 weight percent, preferably 2 wt .-% - 10 wt .-%, in the preparations.
  • UV filters can also be used in encapsulated form.
  • the capsules in preparations to be used according to the invention are preferably present in amounts which ensure that the encapsulated UV filters are present in the preparation in the above-indicated weight percentages.
  • Preferred preparations may also comprise at least one further cosmetic active ingredient, for example selected from antioxidants, anti-aging active ingredients, anti-wrinkles, anti-dandruff, anti-acne, deodorants, anti-cellulite active substances, self-tanning substances, skin-lightening active ingredients or vitamins.
  • at least one further cosmetic active ingredient for example selected from antioxidants, anti-aging active ingredients, anti-wrinkles, anti-dandruff, anti-acne, deodorants, anti-cellulite active substances, self-tanning substances, skin-lightening active ingredients or vitamins.
  • the protective effect of preparations against oxidative stress or against the action of radicals can be improved if the preparations contain one or more antioxidants, wherein the skilled person has no difficulty in selecting suitable fast or delayed-acting antioxidants.
  • antioxidants eg amino acids (eg glycine, histidine, tyrosine, tryptophan) and their derivatives, imidazoles, (eg urocaninic acid) and their derivatives, peptides such as D, L- Carnosine, D-carnosine, L-carnosine and their derivatives (eg anserine), carotenoids, carotenes (eg a-carotene, ß-carotene, lycopene) and their derivatives, chlorogenic acid and its derivatives, lipoic acid and derivatives thereof (eg Dihydroli - ponic acid), aurothioglucose, propylthiouracil and other thiols (eg thio-redoxin, glutathione, cysteine, cystine, cystamine and their Glycosyh N-acetyl, methyl, ethyl, propyl, amyl,
  • amino acids eg glycine, histidine,
  • Suitable antioxidants are also compounds of the formulas A or B.
  • R 1 can be selected from the group -C (O) CH 3 , -CO 2 R 3 , -C (O) NH 2 and -C (O) N (R 4 ) 2 ,
  • X is O or NH
  • ' R 2 is linear or branched alkyl having 1 to 30 C atoms
  • R 3 is linear or branched alkyl having 1 to 20 C atoms
  • R 4 are each independently of one another H or linear or branched alkyl having 1 to 8 C atoms,
  • R 5 is H or linear or branched alkyl having 1 to 8 C atoms or linear or branched alkoxy having 1 to 8 C atoms and
  • R 6 denotes linear or branched alkyl having 1 to 8 C atoms, preferably derivatives of 2- (4-hydroxy-3,5-dimethoxybenzylidene) malonic acid and / or 2- (4-hydroxy-3,5-dimethoxybenzyl) - malonic> particularly preferably 2- (4-hydroxy-3,5-dimethoxybenzylidene) malonic acid bis- (2-ethylhexyl) ester (for example Oxynex ® ST Liquid) and / or 2- (4-hydroxy-3,5-dimethoxybenzyl ) malonic acid-bis (2-ethylhexyl) ester (example RonaCare ® AP).
  • antioxidants are also suitable for use in the cosmetic preparations according to the invention.
  • Known and commercial mixtures mixtures are, for example comprising, as active ingredients, lecithin, L - (+) - ascorbyl palmitate and citric acid, natural tocopherols, L - (+) - ascorbyl palmitate, L - (+) - ascorbic acid and citric acid (for example Oxynex ® K LIQUID) , Tocopherol extracts from natural sources, L - (+) - ascorbyl palmitate, L - (+) - ascorbic acid and citric acid (eg Oxynex ® L LIQUID), DL-a-tocopherol, L - (+) - ascorbyl palmitate, citric acid and lecithin (eg Oxynex ® LM) or butylhydroxytoluene (BHT), L - (+) - ascorbyl palmitate and citric acid (eg Oxynex ® 2004).
  • the polyphenols which are sometimes present as natural substances, are of particular interest for applications in the pharmaceutical, cosmetic or food sector.
  • the flavonoids or bioflavonoids which are mainly known as plant dyes, frequently have an antioxidant potential. Effects of the substitution pattern of mono- and dihydoxy flavones are dealt with by K. Lemanska, H. Szymusiak, B. Tyrakowska, R. Zielinski, I.M.C.M. Rietjens; Current Topics in Biophysics 2000, 24 (2), 101-108.
  • dihydroxyflavones having an OH group adjacent to the keto function or OH groups in the 3'4 'or 6,7 or 7,8 position have antioxidant properties, while other mono- and dihydroxyflavones have in part no antioxidant properties exhibit.
  • Quercetin (cyanidanol, cyanidolone 1522, meietin, saccharin, ericin, 3,3 ', 4', 5,7-pentahydroxyflavone) is frequently mentioned as a particularly effective antioxidant (eg CA Rice-Evans, NJ Miller, G Paganga, Trends in Plant Science 1997, 2 (4), 152-159).
  • K. Lemanska, H. Szymusiak is frequently mentioned as a particularly effective antioxidant (eg CA Rice-Evans, NJ Miller, G Paganga, Trends in Plant Science 1997, 2 (4), 152-159).
  • Suitable anti-aging active substances are preferably so-called compatible solutes. These are substances that are involved in the osmoregulation of plants or microorganisms and can be isolated from these organisms. Under the generic term compatible solutes are also described in the German patent application DE-A-10133202 Osmoly- te. Suitable osmolytes are, for example, the polyols, methylamine compounds and amino acids and in each case their precursors.
  • osmolytes are understood as meaning, in particular, substances from the group of polyols, such as, for example, myo-inositol, mannitol or sorbitol and / or one or more of the osmolytically active substances mentioned below: taurine, choline, betaine, Phosphorylcholine, glycerophosphorylcholine, glutamine, glycine, ⁇ -alanine, glutamate, aspartate, proline, and taurine.
  • polyols such as, for example, myo-inositol, mannitol or sorbitol and / or one or more of the osmolytically active substances mentioned below: taurine, choline, betaine, Phosphorylcholine, glycerophosphorylcholine, glutamine, glycine, ⁇ -alanine, glutamate, aspartate, proline, and taurine.
  • Precursors of these substances are, for example, glucose, glucose polymers, phosphatidylcholine, phosphatidylinositol, inorganic phosphates, proteins, peptides and polyamic acids. Precursors are z.
  • compatible substances selected from the group consisting of pyrimidinecarboxylic acids (such as ectoine and hydroxyectoine), proline, betaine, glutamine, cyclic diphosphoglyceate, N-acetylornithine, trimethylamine N-oxide di-myo-inositol-phosphate ( DIP), cyclic 2,3-diphosphoglycerate (cDPG), 1, 1-diglycerol phosphate (DGP), ⁇ -mannosylglycerate (Firoin), ⁇ -mannosylglyceramide (Firoin-A) or / and di-mannosyl-di-inositol phosphate (DMIP) or an optical isomer, derivative, eg an acid, a salt or ester of these compounds or combinations thereof.
  • pyrimidinecarboxylic acids such as ectoine and hydroxyectoine
  • proline betaine
  • glutamine cyclic diphosphoglyceate
  • ectoine ((S) -1,5,6-tetrahydro-2-methyl-4-pyrimidinecarboxylic acid) and hydroxyectoine ((S, S) -1,4,5,6-tetrahydro-5 are among the pyrimidinecarboxylic acids hydroxy-2-methyl-4-pyrimidinecarboxylic acid) and their derivatives.
  • Additional can be used as anti-aging agents Merck products such as 5,7-dihydroxy-2-methyl-chromone, marketed under the trade name RonaCare®Luremine, or the commercial products RonaCa- re.solquercetin, RonaCare.Tiliroside or RonCare.RTM. cyclopeptides 5.
  • the preparations may also contain one or more further skin-lightening active ingredients or synonymously depigmentation active ingredients.
  • skin-lightening active ingredients can be all active ingredients known to the person skilled in the art. Examples of compounds with skin-lightening activity are hydroquinone, kojic acid, arbutin, aloesin, niacinamide, azelaic acid, elastinic acid, mulberry extract, magnesium ascorbyl phosphate, liquorice root extract, emblica, ascorbic acid or rucinol.
  • the preparations to be used may contain vitamins as further ingredients.
  • vitamins and vitamin derivatives selected from vitamin A, vitamin A propionate, vitamin A palmitate, vitamin A acetate, retinol, vitamin B, thiamin chloride hydrochloride (vitamin Bi), riboflavin (vitamin B 2 ), nicotinamide, Vitamin C (ascorbic acid), vitamin D, ergocalciferol (vitamin D 2 ), vitamin E, DL-a-tocopherol, tocopherol-E-acetate, tocopherol hydrogen succinate, vitamin ⁇ - ⁇ , esculin (vitamin P active substance), thiamine ( Vitamin Bi), nicotinic acid (niacin), pyridoxine, pyridoxal, pyridoxamine, (vitamin ⁇ ), pantothenic acid, biotin, folic acid and cobalamin (vitamin B 2 ), particularly preferably vitamin A palmitate, vitamin C and its derivatives, DL -a-tocophe
  • the retinoids described are also effective anti-cellulite agents.
  • Another well-known anti-cellulite drug is caffeine.
  • the said constituents of the preparation can be incorporated in the usual way, by means of techniques which are well known to the person skilled in the art.
  • Suitable preparations are for external use, for example as a cream or milk (O / W, W / O, O / W / O, W / O / W), as lotion or emulsion, in the form of oily-alcoholic, oily-aqueous or aqueous-alcoholic gels or solutions can be sprayed onto the skin. They can be present as solid pens or be packaged as aerosol.
  • a cream or milk O / W, W / O, O / W / O, W / O / W
  • lotion or emulsion in the form of oily-alcoholic, oily-aqueous or aqueous-alcoholic gels or solutions can be sprayed onto the skin. They can be present as solid pens or be packaged as aerosol.
  • preparations to be used are preferably mentioned: solutions, suspensions, emulsions, PIT emulsions, pastes, ointments, gels, creams, lotions, powders, soaps, surfactant-containing cleaning preparations, oils, aerosols patches, envelopes, dressings and sprays.
  • Preferred excipients come from the group of preservatives, stabilizers, solubilizers, colorants, odor improvers.
  • Ointments, pastes, creams and gels may contain the usual excipients suitable for topical administration, e.g. animal and vegetable fats, waxes, paraffins, starch, tragacanth, cellulose derivatives, polyethylene glycols, silicones, bentonites, silicic acid, talc and zinc oxide, or mixtures of these substances.
  • excipients suitable for topical administration e.g. animal and vegetable fats, waxes, paraffins, starch, tragacanth, cellulose derivatives, polyethylene glycols, silicones, bentonites, silicic acid, talc and zinc oxide, or mixtures of these substances.
  • Powders and sprays may contain the usual excipients, for example lactose, talc, silicic acid, aluminum hydroxide, calcium silicate and polyamide powder or mixtures of these substances.
  • Sprays may additionally contain the usual volatile, liquefied propellants, eg chlorofluorohydrocarbons, propane / butane or dimethyl ether. Also, compressed air is advantageous to use.
  • Solutions and emulsions may contain the customary carriers such as solvents, solubilizers and emulsifiers, for example water, ethanol, isopropanol, ethyl carbonate, ethyl acetate, benzyl alcohol, benzyl benzoate, propylene glycol, 1,3-butylglycol, oils, in particular cottonseed oil, peanut oil, maize germ oil, Olive oil, castor oil and sesame oil, Glycerinfettklader, polyethylene glycols and fatty acid esters of sorbitan or mixtures of these substances.
  • solvents such as solvents, solubilizers and emulsifiers, for example water, ethanol, isopropanol, ethyl carbonate, ethyl acetate, benzyl alcohol, benzyl benzoate, propylene glycol, 1,3-butylglycol, oils, in particular cottonseed oil, peanut oil, maize germ oil, Olive
  • a preferred solubilizer in general is 2-isopropyl-5-methylcyclohexanecarbonyl-D-alanine methyl ester.
  • Suspensions may include the usual carriers such as liquid diluents, e.g. Water, ethanol or propylene glycol, suspending agents, e.g. ethoxylated isostearyl alcohols, polyoxyethylene sorbitol esters and polyoxyethylene sorbitan esters, microcrystalline cellulose, aluminum metahydroxide, bentonite, agar-agar and tragacanth or mixtures of these substances.
  • liquid diluents e.g. Water, ethanol or propylene glycol
  • suspending agents e.g. ethoxylated isostearyl alcohols, polyoxyethylene sorbitol esters and polyoxyethylene sorbitan esters, microcrystalline cellulose, aluminum metahydroxide, bentonite, agar-agar and tragacanth or mixtures of these substances.
  • Soaps may contain the usual excipients such as alkali metal salts of fatty acids, salts of fatty acid monoesters, fatty acid protein hydrolysates, isothionates, lanolin, fatty alcohol, vegetable oils, plant extracts, glycerol, sugars or mixtures of these substances.
  • excipients such as alkali metal salts of fatty acids, salts of fatty acid monoesters, fatty acid protein hydrolysates, isothionates, lanolin, fatty alcohol, vegetable oils, plant extracts, glycerol, sugars or mixtures of these substances.
  • Surfactant-containing cleaning products may include the usual excipients such as salts of fatty alcohol sulfates, fatty alcohol ether sulfates, sulfosuccinic monoesters, fatty acid protein hydrolysates, isothionates, imidazolinium derivatives, methyl taurates, sarcosinates, fatty acid amide ether sulfates, alkyl amidobetaines, fatty alcohols, fatty acid glycerides, fatty acid diethanolamides, vegetable and synthetic oils, lanolin derivatives, ethoxylated glycerol fatty acid esters or mixtures of these substances.
  • excipients such as salts of fatty alcohol sulfates, fatty alcohol ether sulfates, sulfosuccinic monoesters, fatty acid protein hydrolysates, isothionates, imidazolinium derivatives, methyl taurates, sarcosinates, fatty acid
  • Facial and body oils may contain the usual carriers such as synthetic oils such as fatty acid esters, fatty alcohols, silicone oils, natural oils such as Vegetable oils and oily vegetable extracts, paraffin oils, lanolin oils or mixtures of these substances.
  • synthetic oils such as fatty acid esters, fatty alcohols, silicone oils, natural oils such as Vegetable oils and oily vegetable extracts, paraffin oils, lanolin oils or mixtures of these substances.
  • the preferred preparation forms include, in particular, emulsions.
  • Emulsions are advantageous and contain z.
  • Oils such as triglycerides of capric or caprylic, further natural oils such. Castor oil;
  • Fats, waxes and other natural and synthetic fats preferably esters of fatty acids with lower C-number alcohols, e.g. with isopropanol, propylene glycol or glycerol, or esters of fatty alcohols with alkanoic acids of low C number or with fatty acids;
  • Silicone oils such as dimethylpolysiloxanes, diethylpolysiloxanes, diphenylpoly- siloxanes and mixed forms thereof.
  • the oil phase of the emulsions, oleogels or hydrodispersions or lipid dispersions in the context of the present invention is advantageously selected from the group of esters of saturated and / or unsaturated, branched and / or unbranched alkanecarboxylic acids having a chain length of 3 to 30 carbon atoms and saturated and / or unsaturated, branched and / or unbranched alcohols having a chain length of 3 to 30 carbon atoms, from the group of esters of aromatic carboxylic acid and saturated and / or unsaturated, branched and / or unbranched alcohols having a chain length of 3 to 30 carbon atoms.
  • ester oils can then advantageously be chosen from the group isopropyl myristate, isopropyl palmitate, isopropyl stearate, isopropyl oleate, n-butyl stearate, n-hexyl laurate, n-decyl oleate, isooctyl stearate, isononyl stearate, isononyl isononanoate, 2-ethylhexyl palmitate, 2-ethylhexyl laurate, 2-hexadecyl stearate, 2-octyl dodecyl palmitate, oleyl oleate, oleyl erucate, erucyl oleate, erucyl erucate and synthetic, semi-synthetic and natural mixtures of such esters, e.g. B. jojoba oil.
  • the oil phase can advantageously be selected from the group of branched and unbranched hydrocarbons and waxes, silicone oils, dialkyl ethers, the group of saturated or unsaturated, branched or unbranched alcohols, and fatty acid triglycerides, in particular the triglycerol esters of saturated and / or unsaturated, branched and / or unbranched alkanecarboxylic acids of a chain length of 8 to 24, in particular 12-18 C-atoms.
  • the fatty acid triglycerides can be selected, for example, advantageously from the group of synthetic, semi-synthetic and natural oils, for. As olive oil, sunflower oil, soybean oil, peanut oil, rapeseed oil, almond oil, palm oil, coconut oil, palm kernel oil and the like.
  • any mixtures of such oil and wax components are also advantageous to use in the context of the present invention. It may also be advantageous, if appropriate, to use waxes, for example cetyl palmitate, as the sole lipid component of the oil phase.
  • the aqueous phase of the preparations to be used advantageously contains alcohols, diols or polyols of low C number, and also their ethers, preferably ethanol, isopropanol, propylene glycol, glycerol, ethylene glycol, ethylene glycol monoethyl or monobutyl ether, propylene glycol monomethyl, monoethyl or monobutyl ether, diethylene glycol monomethyl or monoethyl ether and analogous products, furthermore lower C number alcohols, e.g.
  • a polyacrylate from the group of so-called Carbopols for example Carbopols types 980, 981, 1382, 2984, 5984, each individually or in combination.
  • mixtures of the abovementioned solvents are used.
  • alcoholic solvents water can be another ingredient.
  • Emulsions are advantageous and contain z.
  • the preparations to be used contain hydrophilic surfactants.
  • the hydrophilic surfactants are preferably selected from the group of alkylglucosides, acyl lactylates, betaines and cocoamphoacetates.
  • the cosmetic and dermatological preparations can be in various forms. So they can z.
  • Ectoine in encapsulated form, e.g. In collagen matrices and other common encapsulating materials, e.g. As encapsulated cellulose, in gelatin, wax matrices or liposomally encapsulated.
  • wax matrices as described in DE-A-43 08 282 have been found to be favorable. Preference is given to emulsions. O / W emulsins are especially preferred. Emulsions, W / O emulsions and OA / V emulsions are available in the usual way.
  • emulsifiers for example, the known W / O and O / W emulsifiers can be used. It is advantageous to use other conventional co-emulsifiers in the preferred O / W emulsions.
  • O / W emulsifiers are selected as co-emulsifiers, principally from the group of substances with HLB values of 11-16, very particularly advantageously with HLB values of 14.5-15.5, provided that the O / W Emulsifiers have saturated radicals R and R '. If the O / W emulsifiers have unsaturated radicals R and / or R ', or if isoalkyl derivatives are present, the preferred HLB value of such emulsifiers may also be lower or higher.
  • fatty alcohol ethoxylates from the group of the ethoxylated stearyl alcohols, cetyl alcohols, cetylstearyl alcohols (cetearyl alcohols).
  • Polyethylene glycol (14) isostearate
  • polyethyleneglycol (15) isostearate
  • Polyethylene glycol (24) isostearate, polyethylene glycol (25) isostearate,
  • Polyethylene glycol (20) oleate Polyethylene glycol (20) oleate.
  • the sodium laureth-11-carboxylate can be advantageously used.
  • the alkyl ether sulfate sodium laureth-4 sulfate can be advantageously used.
  • Polyethylene glycol (30) cholesteryl ether can advantageously be used as ethoxylated cholesterol derivative.
  • polyethylene glycol (25) soybean oil has been proven.
  • polyethylene glycol glycerol fatty acid esters from the group consisting of polyethylene glycol (20) glyceryl laurate, polyethylene glycol (21) glyceryl laurate, polyethylene glycol (22) glyceryl laurate, polyethylene glycol (23) glyceryl laurate, polyethylene glycol (6) glyceryl caprate / citrate, polyethylene glycol (20). glyceryl oleate, polyethylene glycol (20) glyceryl isostearate, polyethylene glycol (18) glyceryl oleate (cocoate).
  • sorbitan esters from the group consisting of polyethylene glycol (20) sorbitan monolaurate, polyethylene glycol (20) sorbitan monostearate, Polyethylene glycol (20) sorbitan monoisostearate, polyethylene glycol (20) sorbitan monopalmitate, polyethylene glycol (20) sorbitan monooleate.
  • W / O emulsifiers can be used:
  • W / O emulsifiers are glyceryl monostearate, glyceryl, glyceryl monomyristate, glyceryl, Digly- cerylmonostearat, colmonolaurat Diglycerylmonoisostearat, propylene glycol, propylene glycol monoisostearate, propylene glycol monocaprylate glycol, propylene, nocaprylat sorbitan, sorbitan Sorbitanmo-, Sorbitanmonoisooleat, sucrose, cetyl alcohol, stearyl, arachidyl, Behenyl alcohol, isobehenyl alcohol, selachyl alcohol, chimyl alcohol, polyethylene glycol (2) stearyl ether (steareth-2), glyceryl monolaurate, glyceryl monocaprinate, glyceryl monocaprylate or PEG-30 dipolyhydroxystearate.
  • the preparation may contain cosmetic adjuvants commonly used in this type of preparation, such as thickeners, emollients, humectants, surfactants, emulsifiers, preservatives, antifoaming agents, perfumes, waxes, lanolin, propellants, dyes and / or pigments , and other ingredients commonly used in cosmetics.
  • cosmetic adjuvants commonly used in this type of preparation, such as thickeners, emollients, humectants, surfactants, emulsifiers, preservatives, antifoaming agents, perfumes, waxes, lanolin, propellants, dyes and / or pigments , and other ingredients commonly used in cosmetics.
  • An oil, wax or other fatty substance, a low monoalcohol or a low polyol or mixtures thereof can be used as the dispersing or solubilizing agent.
  • Particularly preferred monoalcohols or polyols include ethanol, i-propanol, propylene glycol, glycerine and sorbitol.
  • a preferred embodiment of the invention is an emulsion which is present as a protective cream or milk and contains, for example, fatty alcohols, fatty acids, fatty acid esters, in particular triglycerides of fatty acids, lanolin, natural and synthetic oils or waxes and emulsifiers in the presence of water.
  • oily lotions based on natural or synthetic oils and waxes, lanolin, fatty acid esters, in particular triglycerides of fatty acids, or oily alcoholic lotions based on a lower alcohol such as ethanol or a glycerol such as propylene glycol and / or a polyol such as Glycerol, and oils, waxes and fatty acid esters, such as triglycerides of fatty acids.
  • the preparation may also be in the form of an alcoholic gel comprising one or more lower alcohols or polyols, such as ethanol, propylene glycol or glycerin, and a thickener, such as silica.
  • the oily alcoholic gels also contain natural or synthetic oil or wax.
  • the solid sticks consist of natural or synthetic waxes and oils, fatty alcohols, fatty acids, fatty acid esters, lanolin and other fatty substances.
  • blowing agents are generally used, such as alkanes, air, nitrogen, dinitrogen monoxide, preferably alkanes.
  • test fields of 4 x 4.5 cm 2 were marked on both forearms of each participant.
  • test formulation was used with 6 weight percent dihydroxyacetone without the addition of glucuronolactone.
  • Glucuronolactone in the bicyclic form was used.
  • test field was treated with 2 ⁇ / cm 2 of the O / W formulation described above containing 6 percent by weight DHA, the other test field was treated with 2 ⁇ / cm 2 of the O / W formulation described above containing 5 percent by weight DHA and 5 percent by weight glucuronolactone (the weight percent ratio is therefore 1: 1).
  • the application of the sample was carried out in a grid, so that the test amount is evenly distributed on the test field. With a fingerstall, the sample was rubbed evenly with gentle pressure so that the entire test area was treated and the preparation was absorbed (about 30 seconds). One treatment per forearm was performed. In the test field, color measurement was performed before treatment and 24 hours after treatment.
  • the color measurements were carried out with a chroma- Meter of the company Minolta CR-300 carried out and determines the L, a and b values according to the definition of the CIE (Commission Internationale de l'Eclairage). Thereby the decrease of the brightness and the increase of the color of red and yellow wavelength compared to the color of the skin before the treatment were determined.
  • CIE Commission Internationale de l'Eclairage
  • B16V mouse melanoma cells (manufacturer: DSMZ, article number: ACC370) in RPMI medium (Invitrogen, article no .: 31870), which additionally contains 10% FBS (fetal bovine serum, Invitrogen, article no .: 10499044) 2mM L-glutamine (Invitrogen, Item No: 25030) and 1 mM sodium pyruvate (Invitrogen, Item No: 11360) (modified RPMI medium) are transferred to a culture flask and incubated at 37 ° C and 5% for 72h. C0 2 incubated. The medium is separated and the cells are washed with 10 ml of D-PBS (Invitrogen, Item No.
  • HyQtase-Cell Detachment Solution (Hyclone, article number SV30030.01) is added to the cells.
  • the bottle is swiveled several times and the HyQtase- Cell Detachment Solution is then removed by suction. Then the cells are incubated for 5 min in the incubator at 37 ° C and 5% CO 2.
  • the cells are taken up in the modified RPMI medium (Invitrogen, Item No .: 31870) and the number of cells determined.
  • the cells are stained with trypan blue and counted in a Neubauer chamber. Subsequently, the cells are neut in the modified RPMI medium in a defined cell number of 80000 cells per well (6 well Clear Plate, TCT, PS (Nunc)) sewn.
  • glucuronolactone dilution of the substance glucuronolactone is dissolved in DMSO and then filtered through a sterile filter (0.2 pm, Millipore, article no. SLLG013SL). Then the solution with the modified RPMI medium (in this case the FBS content in the RPMI medium is only 5%) is diluted so that the glucuronolactone concentration is 10 mM.
  • alpha-MSH alpha-MSH
  • DMSO alpha melanocyte stimulating hormone
  • Sigma article Nr.:D2650
  • the medium is aspirated and the cells are washed with 1000 ⁇ l D-PBS (Invitrogen, Item No. 14190). It is aspirated again 250pL HyQtase-Cell Detachment Solution (Hyclone, Item No. SV30030.01) is added to the cells. The 6-well plate is pivoted several times and the HyQtase-Cell Detachment Solution is then removed by suction. Then the cells are incubated for 5 min in the incubator at 37 ° C and 5% CO 2 . The cells are then taken up in 1.5mL DPBS (Invitrogen, Item No. 14190) and transferred to a cup (SARSTEDT ref.
  • D-PBS Invitrogen, Item No. 14190
  • the cell number is determined.
  • the cells are stained with trypan blue and counted in a Neubauer chamber. Then the cells are centrifuged at 3500g for 1min. The resulting pellets are photographed and then the supernatant is suctioned off. The pellets are dissolved in 1 ml of 1 N NaOH for 1 h at 80 ° C. and then cooled to RT. Then 200pL as Quadruple determination (per cup) in a 96 well plate (VWR, article no. 4100636981) pipetted and the absorption at 405nm wavelength determined. (Safire, Tecan). By means of a Calibrationsgeraden so the content of melanin can be determined.
  • the explants are maintained in a BEM medium (BIO-EC's Explants Medium) at 37 ° C in a humidified atmosphere containing 5% CO 2 .
  • BEM medium BIO-EC's Explants Medium
  • Glucuronolactone is used in the bicyclic form.
  • the color of the explants is determined by chromametry. The measurements are carried out at the task (DO), on day 1 (D1), on day 5 (D5) and on day 1 1 (D1 1).
  • the color measurements are carried out with a Chroma Meter from the company Minolta CR-300 and the L, a and b values are read off the device accordingly.
  • the sample is placed with the epidermis down on the support rail. Irradiation is from the underside through the indicated area (3 mm).
  • glucuronolactone darkens the skin (falling L values) and produces a more natural hue of the skin, evidenced by the increasing a values of a red-brown shift.
  • Glucuronolactone is a self-tanning substance.
  • Aa after a day is calculated as follows:
  • Aa (Aa P1 1 D1 + Aa P1 2 D1 + Aa P1 3 D1) / 3) - (Aa R1 D1 + Aa R2 D1 + Aa R3 D1) / 3).
  • Formulation example 1 O / W tanning cream
  • phase A is heated to 75 ° C and phase B to 80 ° C. Thereafter, phase B is slowly added with stirring to phase A and stirred until a homogeneous mixture is formed. After homogenization, phase C is added to the formulation at 40 ° C.
  • phases A and B are heated separately to 75 ° C. Thereafter, phase A is slowly added to phase B with gentle stirring. It is homogenized at 65 ° C for one minute. The mixture is then cooled with stirring to 40 ° C and the phase C added with stirring, cooled to 35 ° C and the phase D was added, and further cooled.
  • Probiol L 05018 (Empty lipo-AQUA, ALCOHOL
  • phases A and B are heated to 80 ° C. Thereafter, phase B is slowly added with stirring to phase A and homogenized. It is then cooled and the phase C at 40 ° C was added.
  • Probiol L 05018 (Empty lipo-AQUA, ALCOHOL 5 somes) DENAT, LECITHIN,
  • phases A and B are mixed separately and heated to 75 ° C. Thereafter, phase C is added to phase B and added to phase A with stirring. It is homogenized. It is then cooled with stirring and the phases D and E at 40 ° C was added.
  • phase B is dissolved and then it is given to phase A.
  • Formulation example 6 O / W tanning cream with UV A / B protection
  • phases A and B are mixed separately and heated to 80 ° C. Thereafter, phase B is slowly added with stirring to phase A. It is homogenized and cooled to 40 ° C and added phase C, then cooled to room temperature.
  • phases A and B are heated separately to 75 ° C. Thereafter, Phase A is slowly added to Phase B with stirring. At 60 ° C, Phase C is added to A / B and it is homogenized. It is then cooled to 40 ° C and the phases D and E are added successively.

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Abstract

L'invention concerne l'utilisation d'acides aldoniques et de dialdéhydes des aldoses et de leurs dérivés comme substances renforçant le bronzage pour de la dihydroxyacétone ou pour un mélange de substances à effet autobronzant contenant de la dihydroxyacétone ou en tant que substance à effet autobronzant. L'invention porte également sur leur utilisation pour moduler la tonalité que l'on veut obtenir avec un bronzage à la dihydroxyacétone ou au moyen du mélange ou de la composition contenant de la dihydroxyacétone. L'invention concerne en outre leur utilisation dans un mélange ou une composition contenant au moins de la dihydroxyacétone en tant que substance à effet autobronzant pour un agent de réduction de contraste. L'utilisation de tels composés permet d'obtenir un résultat de coloration de la peau nettement amélioré.
EP11730566.4A 2010-07-10 2011-06-24 Substances renforçant le bronzage et substances à effet autobronzant Withdrawn EP2590619A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102010026775A DE102010026775A1 (de) 2010-07-10 2010-07-10 Bräunungsverstärker
PCT/EP2011/003128 WO2012010242A2 (fr) 2010-07-10 2011-06-24 Substances renforçant le bronzage et substances à effet autobronzant

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EP2590619A2 true EP2590619A2 (fr) 2013-05-15

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EP (1) EP2590619A2 (fr)
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WO (1) WO2012010242A2 (fr)

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KR20140102386A (ko) * 2013-02-13 2014-08-22 삼성전자주식회사 디스플레이장치 및 그 제어방법
EP2958925B1 (fr) * 2013-02-25 2017-10-25 Merck Patent GmbH Dérivés glucuronolactones en tant que substances auto-bronzantes
GB2569560A (en) * 2017-12-19 2019-06-26 Pz Cussons Beauty Llp Tanning Composition

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TW197375B (fr) 1990-11-19 1993-01-01 Hayashibara Biochem Lab
FR2680683B1 (fr) 1991-08-29 1993-11-12 Oreal Composition cosmetique filtrante contenant un polymere filtre a structure hydrocarbonee et une silicone filtre.
DE4308282C2 (de) 1993-03-16 1994-12-22 Beiersdorf Ag Vorzugsweise in Form von Mikrosphärulen vorliegende galenische Matrices
DE10133202A1 (de) 2001-07-07 2003-01-16 Beiersdorf Ag Osmolyte enthaltende kosmetische und dermatologische Zubereitungen zur Behandlung und aktiven Prävention trockener Haut und anderer negativer Veränderungen der physiologischen Homöostase der gesunden Haut
EP1807039A1 (fr) * 2004-10-25 2007-07-18 Symrise GmbH & Co. KG Utilisation de flavanones glycosylees pour brunir la peau ou les cheveux
DE102005026164A1 (de) * 2005-06-06 2006-12-14 Henkel Kgaa Selbstbräunungszusammensetzungen mit UV-Schutzwirkung
DE102007013368A1 (de) 2007-03-16 2008-09-18 Merck Patent Gmbh Verwendung einer Mischung eines Selbstbräuners mit einem Formaldehydfänger
US20100158826A1 (en) * 2008-12-19 2010-06-24 Rudy Clemente Compositions comprising self-tanning agents and sugar amines

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Title
See references of WO2012010242A2 *

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WO2012010242A3 (fr) 2013-01-31
US20130115178A1 (en) 2013-05-09
WO2012010242A2 (fr) 2012-01-26

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