EP2654687A1 - Dihydroxyacétonemonoéther - Google Patents

Dihydroxyacétonemonoéther

Info

Publication number
EP2654687A1
EP2654687A1 EP11790562.0A EP11790562A EP2654687A1 EP 2654687 A1 EP2654687 A1 EP 2654687A1 EP 11790562 A EP11790562 A EP 11790562A EP 2654687 A1 EP2654687 A1 EP 2654687A1
Authority
EP
European Patent Office
Prior art keywords
atoms
branched
formula
radicals
groups
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Withdrawn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
EP11790562.0A
Other languages
German (de)
English (en)
Inventor
Philipp Buehle
Thomas Rudolph
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 EP2654687A1 publication Critical patent/EP2654687A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/04—Saturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/175—Saturated compounds containing keto groups bound to acyclic carbon atoms containing ether groups, groups, groups, or groups
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
    • C07C45/57—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom
    • C07C45/60—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom in six-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/255—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing ether groups, groups, groups, or groups

Definitions

  • the present invention relates to the use of
  • 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.
  • the observed skin tone is determined by the ratio of these two types of melanin.
  • this pigmentation is primarily initiated by UVB radiation and is termed "indirect pigmentation.” Its development proceeds over several days, resulting in a few weeks of suntan is used, predominantly colorless melanin precursors are oxidized by UVA radiation to dark colored melanin. Since this oxidation is reversible, it leads to a short-lasting tanning of the skin.
  • An artificial tanning of the skin can be produced externally with the help of make-up and orally by taking carotenoids.
  • the artificial tanning of the skin which can be achieved by applying so-called self-tanner.
  • 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 24 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. These Instability is also associated with the development of cosmetically undesirable off-odors.
  • the object underlying the present invention was therefore to provide self-tanning substances having improved properties, in particular a more natural skin color.
  • X is O, S (O) m or NR 1 ;
  • Y is H, -SiR 2 R 3 R 4 or - [Si (R 2 ) 2 ] q SiR 3 R 4 R 5 or -Sp-R;
  • R 1 is H, C 1-24 alkyl or R;
  • R 2 , R 3 , R 4 and R 5 are 1-30-alkyl;
  • m is 0, 1 or 2;
  • n, o, p stand for 0 to 24;
  • R is a substituent of UV radiation absorbed.
  • WO 2006/024361 A1 describes the use of dimeric dihydroxyacetone monoester derivatives as precursors for self-tanning compounds.
  • EP 0709081 A1 and EP 0796838 A1 disclose preparations containing dihydroxyacetone ester derivatives which are precursors for dihydroxyacetone. None of these documents discloses the use of dihydroxyacetone monoether derivatives as a self-tanning substance.
  • a first object of the present invention is therefore the
  • R 1 is a branched or unbranched alkyl radical having 1 to 20 C atoms, a branched or unbranched alkenyl radical having 2 to 20 C atoms or a branched or unbranched alkynyl radical having 2 to 20 C atoms,
  • radicals can be substituted by one or more OH groups, by one or more cyclic alkyl radicals having from 3 to 8 carbon atoms and / or by one or more aromatic ring systems having from 5 to 6 carbon atoms, where the one or more aromatic radicals Ring systems with one or more groups selected from -OH, -OR, -NR2, -CN, -COOR and -COOR 'may be substituted; where R stands independently for each occurrence
  • R ' is an aromatic ring system having 5 or 6 C atoms.
  • R 2 is H or a branched or unbranched alkyl radical having 1 to 20 C atoms and R 1 is as defined for formula (I).
  • R2 is methyl or ethyl.
  • the compounds of the formula (II) may be obtained, for example, by hydrolysis in the formulation, even after addition of an activating reagent (eg an acid), or by
  • Skin hydrolysis can be converted to the corresponding monomeric DHA ethers of formula (I) due to the natural acidic pH of the skin.
  • R 1 is preferably a branched or unbranched alkyl radical having 1 to 20 C atoms
  • radicals can be substituted by one or more OH groups, by one or more cyclic alkyl radicals having from 3 to 8 carbon atoms and / or by one or more aromatic ring systems having from 5 to 6 carbon atoms, where the one or more aromatic radicals Ring systems with one or more groups selected from -OH and -OR may be substituted,
  • R1 particularly preferably represents a branched or unbranched alkyl radical having 1 to 20 C atoms
  • radicals can be substituted by one or more OH groups, by one or more cyclic alkyl radicals having from 5 to 6 carbon atoms and / or by one or more aromatic ring systems having from 5 to 6 carbon atoms, where the one or more aromatic radicals are substituted by one or more OH radicals Ring systems with one or more groups -OR may be substituted,
  • the branched or unbranched alkyl group preferably has 1 to 17 carbon atoms.
  • the cyclic alkyl radical having 5 to 6 C atoms is preferably one
  • the aromatic ring system having 5 to 6 C atoms is preferably a phenyl radical.
  • R is preferably a branched or unbranched alkyl radical having 1 to 8 C atoms, particularly preferably methyl or ethyl.
  • R1 is selected from the following radicals: benzyl, 2-ethylhexyl, unbranched or branched hexyl,
  • the compounds of the formula (I) are preferably selected from the compounds of the formulas (Ia) to (Ik)
  • R 1 preferably represents a branched or unbranched alkyl radical having 1 to 20 C atoms, the radicals having one or more OH groups, having one or more cyclic alkyl radicals having 5 to 6 C atoms and / or substituted with one or more aromatic ring systems having 5 to 6 carbon atoms wherein the one or more aromatic ring systems may be substituted with one or more groups selected from -OH and -OR,
  • R.sup.1 particularly preferably represents a branched or unbranched alkyl radical having 1 to 20 C atoms, the radicals having one or more cyclic alkyl radicals having 5 to 6 C atoms and / or having one or more aromatic ring systems having 5 to 6 C atoms may be substituted, wherein the one or more aromatic ring systems having one or more groups selected from
  • aromatic ring system as well as the radical R are here defined as described above.
  • Very particularly preferred compounds of the formula (I) are in this case the compounds of the formula (Ia), (Ib), (Ic), (Id), (Ie) and (If).
  • a branched or unbranched (straight-chain) alkyl radical having 1 to 8 C atoms is, for example, methyl, ethyl, isopropyl, propyl, butyl, sec-butyl or tert-butyl, pentyl, isopentyl , 1-, 2- or 3-methylbutyl, 1, 1-, 1, 2- or 2,2-dimethylpropyl, 1-ethylpropyl, 1-ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl, 1, 1 , 2- or 1,2,2-trimethylpropyl, 1, 1-, 1, 2-, 1, 3-, 2,2-, 2,3- or 3,3-dimethylbutyl, 1- or 2-ethylbutyl, 1-, 2-, 3- or 4-methylpentyl, hexyl, heptyl, 1-ethyl-pentyl, octyl or 1-ethyl-hexyl.
  • the above-listed C1 to C8-alkyl radicals may, for example, also be nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl or heptadecyl.
  • An alkyl radical having 1 to 20 C atoms is understood in addition to the above listed radicals also octadecyl, nonadecyl or eicosyl.
  • an alkenyl radical may contain one or more double bonds.
  • a branched or unbranched Aikyl group having 2 to 20 C atoms is, for example, allyl, vinyl, propenyl, 2- or 3-butenyl, isobutenyl, sec-butenyl, 2-methyl-1 - or 2-butenyl, 3-methyl- 1 -butenyl, 1, 3-butadienyl, 2-methyl-1,3-butadienyl, 2,3-dimethyl-1,3-butadienyl, 1-, 2-, 3- or 4-pentenyl, iso-pentenyl, hexenyl , Heptenyl or Octenyl, -C 9 Hi 7 , -C 10 H 19 to -C20H39.
  • An alkynyl radical may contain one or more triple bonds.
  • Examples of a branched or unbranched alkynyl group having 2 to 20 C atoms are ethynyl, 1- or 2-propynyl, 2- or 3-butynyl, furthermore 4-pentynyl, 3-pentynyl, hexynyl, heptynyl, octynyl, -C9H15, -C10H17 to -C20H37.
  • alkyl, alkenyl or alkynyl radical of the formula (I) can be via any ring member of the cycloalkyl group.
  • suitable cycloalkyl radicals are cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclopentenyl, cyclopentadienyl, cyclohexenyl and cyclooctadienyl.
  • a cyclic alkyl radical having 6 C atoms is preferably cyclohexyl.
  • aromatic ring system having 5 to 6 carbon atoms in the context of the present invention may be substituted or unsubstituted. Binding to the alkyl, alkenyl or alkynyl moiety of formula (I) can be via any ring member of the aromatic ring system. Examples of such aromatic ring systems having 5 to 6 C atoms are phenyl, Methoxyphenyl, 2,6-dimethoxyphenyl, 3,5-dimethoxyphenyl, 2,4-dimethoxyphenyl, 2,4,6-trimethoxyphenyl or 2,3,4-trimethoxyphenyl. Preferred are aromatic ring systems which may be substituted with one or more -OR groups. Particularly preferred are phenyl and methoxyphenyl.
  • the compounds of the formulas (Ia), (Ie) and (If) may have the advantage that they can release odors by cleavage of the ether radical as the corresponding alcohol during the browning reaction.
  • Phenethyl alcohol (obtainable by cleavage of Etherrestes of
  • Compound of formula (le)) is perceived, for example, as a rose hyacinth-like fragrance. These released odors are advantageous because the perceived in the tanning reaction odor is usually perceived as negative.
  • the compounds of formula (I) can be derived from dimeric
  • Veretherungsre force be modified with an alkyl halide or an alkyl tosylate or mesylate.
  • the monomer compounds of formula (I) can then be obtained by acid hydrolysis, for example with 95% sulfuric acid.
  • Dimer dihydroxyacetone as well as the other reactants in the synthesis are commercially available or accessible by syntheses known to those skilled in the literature.
  • the preparation can also be carried out biotechnologically starting from the corresponding glycerol ether derivatives.
  • the compounds of the formula (I) can be used in self-tanning products, for example as an alternative to DHA and / or erythrulose.
  • An advantage of using the compounds of formula (I) over DHA as a self-tanning substance is, for example, that they allow the achievement of a more natural or other skin hue.
  • compounds of formula (Ic) promote a darker coloration of the skin.
  • the shift to a redder hue allows a more natural skin tone
  • Another advantage is the accelerated by the compounds of formula (I) tanning reaction.
  • the compounds of the formula (I) can also be used in combination with DHA and / or erythrulose.
  • Another object of the present invention is therefore also the use of a compound of formula (I) as a self-tanning substance, characterized in that the use takes place together with DHA and / or erythrulose.
  • the combination preferably takes place with DHA.
  • such a combination can have a positive influence on the shade of shade achieved in the browning reaction.
  • the resulting skin tone by the specific selection of one or more particular compounds of formula (I) and by setting a certain ratio of the compounds of formula (I) to DHA and / or erythrulose to the specific needs of
  • Self tanning substance or self tanning substance synonymous
  • melanoids are yellow-brown to almost black-colored, organic compounds, which are mainly due to the
  • Another object of the present invention is a preparation containing at least one compound of formula (I)
  • R 1 is a branched or unbranched alkyl radical having 1 to 20 C atoms, a branched or unbranched alkenyl radical having 2 to 20 C atoms or a branched or unbranched alkynyl radical having 2 to 20 C atoms,
  • radicals can be substituted by one or more OH groups, one or more cyclic alkyl radicals having 3 to 8 C atoms and / or by one or more aromatic ring systems having 5 to 6 C atoms, wherein the one or more aromatic ring systems may be substituted with one or more groups selected from -OH, -OR, -NR 2 , -CN, -COOR and -COOR '; where R stands independently for each occurrence
  • R ' is an aromatic ring system having 5 or 6 C atoms.
  • R2 is H or a branched or non-branched alkyl having 1 to 20 carbon atoms and R1 is as defined for formula (I).
  • R2 is methyl or ethyl.
  • the preparations may continue to have a certain percentage of
  • 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. Is it pharmaceutical
  • the 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 at least one compound of the formula (I) is used in the preparations according to the invention in amounts of from 0.01 to 20% by weight, preferably in amounts of from 0.05 to 10% by weight, more preferably in amounts of 0.1% by weight .-% to 5 wt .-% and most preferably in amounts of 0.5 to 2 wt .-%, based on the total amount of
  • the preparations according to the invention may contain at least one further self-tanning substance as further ingredient.
  • the further self-tanning substance is selected from DHA and erythrulose.
  • the at least one further self-tanning substance in the preparation 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 5 Wt .-%, based on the total amount of the preparation.
  • the preparation according to the invention can also be used as formaldehyde scavengers and / or flavonoids. Therefore, the preparation according to the invention can also be used as formaldehyde scavengers and / or flavonoids. Therefore, the preparation according to the invention can also be used as formaldehyde scavengers and / or flavonoids. Therefore, the preparation according to the invention can also be used as formaldehyde scavengers and / or flavonoids. Therefore, the preparation according to the invention can also be used as formaldehyde scavengers and / or flavonoids. Therefore, the preparation according to the invention can also be used as formaldehyde scavengers and / or flavonoids. Therefore, the preparation according to the invention can also be used as formaldehyde scavengers and / or flavonoids. Therefore, the preparation according to the invention can also be used as formaldehyde scavengers and / or flavonoids.
  • the compounds of the formula (I) which are claimed for preparations according to the invention can also in their turn contribute to improving the odor.
  • the formaldehyde scavenger is selected from the group alkali metal, alkaline earth metal or ammonium disulfite.
  • the preparations according to the invention may particularly preferably contain flavonoids for improving odor and for
  • Tanning scrubber included.
  • 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.
  • it is a flavonoid in which one or more phenolic hydroxy groups are blocked by etherification or esterification.
  • phenolic hydroxy groups are blocked by etherification or esterification.
  • esterification For example, have hydroxyethyl-substituted
  • Flavonoids such as preferably troxerutin, troxequercetin,
  • Flavonoid phosphates such as preferably rutin sulfates, proved to be particularly suitable flavonoids.
  • 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. It is believed that by these flavonoids
  • Metal ions such as Fe 2+ / Cu 2+ be complexed and so autooxidation processes in fragrances or compounds whose degradation to
  • preferred preparations additionally contain at least one UV filter.
  • Organic UV filters called hydrophilic or lipophilic
  • Sunscreen filters are effective in the UVA range and / or UVB range and / or IR and / or VI S range (absorbers). These substances can be obtained, in particular, from cinnamic acid derivatives, salicylic acid derivatives,
  • UV filters are given in patent application EP-A 0 487 404.
  • the named UV filters are usually named according to the INCI nomenclature.
  • 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. sold under the name "Uvinul P25” from the company.
  • BASF 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. sold under the name "Uvinul P25” from the company.
  • BASF BASF.
  • Salicylates Homosalates sold under the name "Eusolex HMS” by Merck; Ethyl hexyl salicylates, e.g. B. sold 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. marketed under the name “Neo Heliopan TS" of the Fa. Symrise. ⁇ , ⁇ -diphenylacrylate derivatives: octocrylenes, e.g. B. under the name “Eusolex® OCR” from Merck "," Uvinul N539 "from BASF, Etocrylene, z. B. sold under the name "Uvinul N35” from BASF.
  • Benzophenone Derivatives Benzophenone-1, e.g. Sold under the name "Uvinul 400"; Benzophenone-2, e.g. Sold under the name “Uvinul D50”; Benzophenone-3 or oxybenzone, e.g. B. sold under the name “Uvinul M40” Benzophenone-4, z. Sold under the name "Uvinul MS40”; Benzophenone-9, e.g. B. sold under the
  • Benzophenone-6 e.g. B. marketed under the name "Helisorb 11" by the company Norquay
  • Benzophenone-8 z. B. sold under the name
  • Benzylidene camphor derivatives 3-benzylidenecamphor, e.g. B. sold under the name "Mexoryl SD” from the company. Chimex, 4-
  • benzalkonium methosulfates e.g. Sold under the name "Mexoryl SO” from the company. Chimex, Terephthalylidenedicamphorsulfonklare, z. Sold under the name "Mexoryl SX” by Chimex,
  • Phenylbenzimidazole derivatives phenylbenzimidazolesulfonic acid, e.g. B.
  • Phenylbenzotriazole derivatives Drometrizole trisiloxanes, e.g. B. marketed under the name “Silatrizole” by the company. Rhodia Chimie,
  • Methylenebis (benzotriazolyl) tetramethylbutylphenol in solid form e.g. B. sold under the name "MIXXIM BB / 00" from the company. Fairmount Chemical, or in micronized form as an aqueous dispersion, eg. B.
  • Triazine derivatives ethylhexyltriazone, e.g. B. sold under the name "Uvinul T150" from the company. BASF, Diethylhexylbutamidotriazone, z. B.
  • menthyl anthranilate e.g. B. sold under the
  • Imidazole derivatives Ethylhexyldimethoxybenzylidenedioxoimidazoline propionate.
  • Benzalmalonate Derivatives Polyorganosiloxanes containing functional benzalmalonate groups, e.g. Polysilicone-15, e.g. 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 containing this.
  • UV filters are specific. Of course, other UV filters can be used.
  • 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, disodium phenyldibenzimidazoletetrasulfonate,
  • 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) and the optionally organic UV filters, as described above, further inorganic UV filters, so-called particulate UV filters.
  • coated titanium dioxide e.g., Eusolex® T-2000, Eusolex® T-AQUA,
  • Eusolex® T-AVO Eusolex® T-OLEO
  • zinc oxides e.g., Sachtotec®
  • Iron oxides or else cerium oxides and / or zirconium oxides are preferred.
  • Zinc oxide is 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 may further be preferred if the preparations contain inorganic UV filters which are prepared by customary methods, such as, for example, in US Pat
  • one or more of the following aftertreatment components may be selected: amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids, amino acids,
  • 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 glycerin.
  • 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 glycerin.
  • untreated titanium dioxides e.g. the products Microtitanium Dioxide MT 500 B from Tayca; Titanium Dioxide P25 from Degussa,
  • Silica post-treatment such as e.g. the product "Microtitanium Dioxide MT 100 SA of Tayca; or the product “Tioveil Fin” from Uniqema,
  • micronised titanium dioxides with alumina and / or aluminum stearates / laurate aftertreatment such as e.g. Micro Titanium
  • micronised titanium dioxides with iron oxide and / or iron stearates aftertreatment such as e.g. the product "Microtitanium Dioxide MT 100 F" from Tayca,
  • Alumina and silicone aftertreatment such as e.g. the product "Microtitanium Dioxide MT 100 SAS", the company Tayca,
  • Natrumhexameta- phosphates such as e.g. the product "Microtitanium Dioxide MT 150 W” from Tayca.
  • the treated micronised titanium dioxides used for combination may also be post-treated with: octyltrimethoxysilanes; such as. the product Tego Sun T 805 of the Fa.
  • Alumina and stearic acid such as. the product UV-Titan M160 of the company Sachtleben,
  • Sachtleben Aluminum and silicone oils such as, for example, the product UV titanium M262 from Sachtleben,
  • Polydimethylsiloxanes e.g. the product 70250 Cardre UF TiO2SI3 "from the company Cardre,
  • Escalol Z100 from ISP (alumina aftertreated ZnO dispersed in an ethylhexyl methoxycinnamate / PVP-hexadecenes / methicone copolymer blend)
  • Fuji ZNO-SMS-10 from Fuji Pigment (ZnO aftertreated with silica and polymethylsilsquioxane);
  • mixtures of different metal oxides such as, for example, titanium dioxide and cerium oxide with and without secondary treatment be such as the product Sunveil A Fa. Ikeda.
  • 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.
  • organic UV filters it is beneficial to use organic UV filters in
  • the capsules in preparations to be used according to the invention are preferably present in amounts which ensure that the encapsulated UV filters in the abovementioned
  • Weight percent ratios are present in the preparation.
  • Color pigments may be included, wherein the layer structure of the pigments is not limited.
  • the color pigment when used from 0.5 to 5 wt .-% should be skin-colored or brownish.
  • the selection of a corresponding pigment is familiar to the person skilled in the art.
  • Preferred preparations may also contain at least one further cosmetic active ingredient, for example selected from
  • Antioxidants anti-aging, anti-wrinkle, anti-dandruff, anti-acne, anti-cellulite, deodorants, skin lighteners 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.
  • imidazoles eg urocaninic acid
  • peptides such as D, L-carnosine, D-carnosine, L-carnosine and their derivatives (eg anserine)
  • carotenoids eg a-carotene, ⁇ -carotene, lycopene
  • carotenes eg a-carotene, ⁇ -carotene,
  • Aurothioglucose, propylthiouracil and other thiols eg thioredoxin, glutathione, cysteine, cystine, cystamine and their glycosyl, N-acetyl, methyl, ethyl, propyl, amyl, butyl and lauryl, palmitoyl, oleyl , ⁇ -linoleyl, cholesteryl and glyceryl esters
  • thiols eg thioredoxin, glutathione, cysteine, cystine, cystamine and their glycosyl, N-acetyl, methyl, ethyl, propyl, amyl, butyl and lauryl, palmitoyl, oleyl , ⁇ -linoleyl, cholesteryl and glyceryl esters
  • Dilauryl thiodipropionate, distearyl thiodipropionate, thiodipropionic acid and its derivatives esters, ethers, peptides, lipids, nucleotides, nucleosides and salts
  • sulfoximine compounds for example buthionine sulfoximines
  • Heptathionine sulfoximine in very low tolerated dosages (e.g., pmol to pmol / kg), further (metal) chelators (e.g., ⁇ -hydroxy fatty acids, palmitic acid, phytic acid, lactoferrin), ⁇ -hydroxy acids (e.g.
  • Citric acid lactic acid, malic acid), humic acid, bile acid,
  • Bile extracts bilirubin, biliverdin, EDTA, EGTA, pentasodium ethylenediamin tetramethylene phosphonate and its derivatives, unsaturated fatty acids and their derivatives, vitamin C and derivatives (eg
  • Ascorbyl palmitate magnesium ascorbyl phosphate, ascorbyl acetate
  • Tocopherols and derivatives e.g., vitamin E acetate
  • vitamin A and derivatives e.g., vitamin A palmitate
  • benzoic acid coniferyl benzoate rutinic acid and derivatives thereof, ⁇ -glycosyl rutin, ferulic acid,
  • 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) 2
  • X is O or NH, 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 H or linear or branched alkyl having 1 to 8 C atoms
  • R 5 is H, linear or branched alkyl having 1 to 8 C atoms or linear or branched alkoxy having 1 to 8 C atoms
  • R 6 is 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 acid, more preferably 2- (4-hydroxy-3,5-dimethoxybenzylidene) -malonic acid bis- (2-ethylhexyl) ester (eg Oxynex® ST Liquid) and / or 2- (4-hydroxy-3,5-dimethoxybenzyl) -malonic acid bis (2-ethylhexyl) ester (eg
  • antioxidants are also suitable for use in the cosmetic preparations according to the invention.
  • Known and commercially available mixtures are, for example, mixtures containing as active ingredients lecithin, L - (+) - ascorbyl palmitate and citric acid, natural tocopherols, L - (+) - ascorbyl palmitate, L - (+) - ascorbic acid and
  • Citric acid e.g., Oxynex® K LIQUID
  • tocopherol extracts from natural sources L - (+) - ascorbyl palmitate, L - (+) - ascorbic acid and citric acid (e.g., Oxynex® L LIQUID), DL-a-tocopherol, L (+) -
  • Ascorbyl palmitate citric acid and lecithin (e.g., Oxynex® LM) or butylhydroxytoluene (BHT), L - (+) - ascorbyl palmitate and citric acid (e.g., Oxynex® 2004).
  • lecithin e.g., Oxynex® LM
  • BHT butylhydroxytoluene
  • L - (+) - ascorbyl palmitate e.g., Oxynex® 2004.
  • Such antioxidants are with the
  • Compounds of the invention in such compositions usually in weight percent ratios ranging from 1000: 1 to 1: 1000, preferably used in weight percent ratios of 100: 1 to 1: 100.
  • the polyphenols which occur in part as natural substances, are of particular interest for applications in the pharmaceutical, cosmetic or nutritional field.
  • the mainly as plant dyes Flavonoids or bioflavonoids often have an antioxidant potential.
  • Quercetin (cyanidanol, cyanidolone 1522, meietin,
  • effective antioxidant e.g., CA Rice-Evans, N.J. Miller, G.A.
  • Suitable anti-aging agents especially for skin care
  • Preparations are preferably so-called compatible solutes. These are substances that are involved in the osmoregulation of
  • osmolytes Plants or microorganisms are involved and can be isolated from these organisms. Under the generic term compatible solutes also the described in the German patent application DE-A-10133202 osmolytes are taken. Suitable osmolytes are, for example, the polyols, methylamine compounds and amino acids and in each case their precursors. As osmolytes are in the sense of the Germans
  • Patent application DE-A-10133202 in particular substances from the
  • polyols such as myo-inositol, mannitol or sorbitol and / or one or more of the following osmolytically effective substances: taurine, choline, betaine, phosphorylcholine, glycerophosphorylcholine, glutamine, glycine, ⁇ -alanine, glutamate, aspartate, proline, and taurine.
  • osmolytically effective substances are, for example, glucose, glucose polymers, phosphatidylcholine, phosphatidylinositol, inorganic phosphates, proteins, peptides and polyamic acids. Precursors are z. B.
  • compatible solute substances selected from the group consisting of Pyrimidincarbonklaren (such as ectoine and hydroxyectoine), proline, betaine, glutamine, cyclic
  • Diphosphoglycerate 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.
  • DIP di-oxide di-myo-inositol phosphate
  • cDPG cyclic 2,3-diphosphoglycerate
  • DGP 1, 1-diglycerol phosphate
  • ⁇ -mannosylglycerate Firoin
  • ⁇ -Mannosylglyceramide Firoin-A
  • ectoine ((S) - 1, 4,5,6-tetrahydro-2-methyl-4-pyrimidinecarboxylic acid) and hydroxyectoine are among the pyrimidinecarboxylic acids
  • Ronacare® tiliroside or Ronacare® cyclopeptide 5 can be used.
  • the preparations may also have one or more skin lightening
  • skin-lightening active ingredients can be all active ingredients known to the person skilled in the art.
  • Compounds with skin-lightening activity are hydroquinone, kojic acid, arbutin, aloesin, niacinamide, azelaic acid, elagic acid,
  • Licorice root extract Licorice root extract, Emblica, ascorbic acid or rucinol.
  • Preparations containing a combination of the compounds of the formula (I) with skin-lightening active ingredients can be, for example
  • compositions to be used may be further ingredients
  • vitamins and vitamin derivatives selected from vitamin A, vitamin A propionate, vitamin A palmitate, vitamin A acetate, retinol, vitamin B, thiamine hydrochloride hydrochloride (vitamin B, 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 Ki, esculin (vitamin P active ingredient), thiamine (vitamin B ⁇ , nicotinic acid (Niacin),
  • Vitamins are usually added to the flavonoid-containing premixes or preparations when applied cosmetically in the range of 0.01% to 5.0% by weight, based on the total weight.
  • the described retinoids are also effective anti-cellulite agents.
  • Another well-known anti-cellulite drug is caffeine.
  • the present invention also provides a process for
  • At least one compound of the formula (I) is mixed with a carrier suitable for topical preparations and optionally with excipients and / or fillers.
  • a carrier suitable for topical preparations and optionally with excipients and / or fillers.
  • excipients and auxiliaries or fillers are described in detail in the following part.
  • the cosmetic and dermatological preparations can be in various forms. So they can z.
  • a solution, an anhydrous preparation, an emulsion or microemulsion of the water-in-oil (W / O) type or of the oil-in-water (O / W) type a multiple emulsion, for example of the water-in-water type.
  • Oil-in-water (W / OW) or O / W / O a gel, a solid stick, an ointment or even an aerosol.
  • O / W emulsins are especially preferred.
  • Emulsions, W / O emulsions and O / W emulsions are available in the usual way.
  • solutions solutions, suspensions, emulsions, PIT emulsions, pastes, Ointments, gels, creams, lotions, powders, soaps, surfactant-containing
  • 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.
  • Powders and sprays may contain the usual carriers, e.g.
  • Sprays may additionally contain the usual volatilized, liquefied propellants, e.g.
  • Chlorofluorocarbons propane / butane or dimethyl ether. Also, compressed air is advantageous to use.
  • Solutions and emulsions may be the usual carriers such as
  • Solvents, solubilizers and emulsifiers e.g. Water, ethanol, isopropanol, ethyl carbonate, ethyl acetate, benzyl alcohol, benzyl benzoate, propylene glycol, 1,3-butylglycol, oils, especially cottonseed oil, peanut oil, corn oil, olive oil, castor oil and sesame oil,
  • Glycerin fatty acid esters polyethylene glycols and fatty acid esters of
  • Sorbitans or mixtures of these substances are Sorbitans or mixtures of these substances.
  • a preferred solubilizer in general is 2-isopropyl-5-methylcyclohexanecarbonyl-D-alanine methyl ester.
  • Suspensions may be the usual carriers such as liquid
  • Diluent e.g. Water, ethanol or propylene glycol
  • Suspending agent 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 halides, 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 halides, fatty acid protein hydrolysates, isothionates, lanolin, fatty alcohol, vegetable oils, plant extracts, glycerol, sugars or mixtures of these substances.
  • Surfactant-containing cleaning products the usual carriers 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 diethanolamides vegetable and synthetic oils, lanolin derivatives, ethoxylated glycerol fatty acid esters or mixtures of these substances.
  • 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.
  • the preferred preparation forms include, in particular, emulsions.
  • Emulsions are advantageous and contain z.
  • Oils such as triglycerides of capric or caprylic acid, also 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
  • Silicone oils such as dimethylpolysiloxanes, diethylpolysiloxanes,
  • the oil phase of the emulsions, oleogels or hydrodispersions or lipodispersions 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 C atoms and saturated and / or unsaturated,
  • branched and / or unbranched alcohols of a chain length of 3 to 30 C atoms, from the group of esters of aromatic carboxylic acid and saturated and / or unsaturated, branched and / or
  • ester oils can then be advantageously selected from the group
  • oil phase can be advantageously selected from the group of branched and unbranched hydrocarbons and waxes, the
  • 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 contains
  • alcohols, diols or polyols of low C number, and their ethers preferably ethanol, isopropanol, propylene glycol, glycerol, ethylene glycol, ethylene glycol monoethyl or monobutyl ether, propylene glycol monomethyl, -monoethyl or -monobutylether,
  • Silica aluminum silicates, polysaccharides or their derivatives, for example hyaluronic acid, xanthan gum, hydroxypropylmethylcellulose, particularly advantageously from the group of polyacrylates, preferably a polyacrylate the group of so-called carbopols, for example Carbopols of types 980, 981, 1382, 2984, 5984, in each case individually or in combination.
  • carbopols for example Carbopols of types 980, 981, 1382, 2984, 5984, in each case individually or in combination.
  • mixtures of the abovementioned solvents are used.
  • alcoholic solvents water can be another organic solvent.
  • the preparations to be used contain hydrophilic surfactants.
  • the hydrophilic surfactants are preferably selected from the group of alkylglucosides, acyl lactylates, betaines and cocoamphoacetates.
  • 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 may be those of
  • Emulsifiers also lower or above. It is advantageous to include the fatty alcohol ethoxylates from the group of
  • Polyethylene glycol (12) isostearate, polyethylene glycol (13) isostearate,
  • Polyethylene glycol (14) isostearate, polyethylene glycol (15) isostearate,
  • Polyethylene glycol (24) isostearate, polyethylene glycol (25) isostearate,
  • polyethylene glycol glycerol fatty acid esters from the group consisting of polyethylene glycol (20) glyceryl laurate,
  • Polyethylene glycol (20) to choose sorbitan monooleate
  • W / O emulsifiers can be used:
  • Fatty alcohols having 8 to 30 carbon atoms monoglycerol esters of saturated and / or unsaturated, branched and / or unbranched
  • W / O emulsifiers are glyceryl monostearate, glyceryl monoisostearate, glyceryl monomyristate, glyceryl monooleate,
  • Glyceryl monolaurate glyceryl monocaprinate, glyceryl monocaprylate or PEG-30 dipolyhydroxystearate.
  • the preparation may contain cosmetic adjuvants which are commonly used in this type of preparation, e.g.
  • Thickeners emollients, moisturizers,
  • surfactants such as soaps, emulsifiers, preservatives, antifoaming agents, perfumes, waxes, lanolin, propellants, dyes and / or pigments, and other ingredients commonly used in cosmetics.
  • polyol or mixtures thereof 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, fluoroalkanes and chlorofluoroalkanes, preferably alkanes.
  • Another object of the present invention are compounds of the formula (I)
  • R 1 is a branched or unbranched alkyl radical having 1 to 20 C atoms, a branched or unbranched alkenyl radical having 2 to 20 C atoms or a branched or unbranched alkynyl radical having 2 to 20 C atoms,
  • radicals may be substituted by one or more OH groups, one or more cyclic alkyl radicals having from 3 to 8 carbon atoms and / or by one or more aromatic ring systems having from 5 to 6 carbon atoms, where the. or more aromatic ring systems having one or more groups selected from -OH, -OR, -NR 2 , -CN, -COOR and -COOR 'may be substituted; where R stands independently for each occurrence
  • radicals R1 and R of the compounds according to the invention are defined here as described above.
  • Another object of the present invention is also a process for preparing a compound of formula (I) as defined above, characterized in that 2,5-diethoxy-2,5-bis (hydroxymethyl) -1, 4-dioxane with a compound of the formula R 1 -X and then acid-hydrolyzed, wherein R 1 is as defined above and X is Cl, Br, I, OSO 2 CH 3 (O-mesyl) or OSO 2 C 6 H 4 CH 3 (O-tosyl).
  • the Lab values show that MHDE (Ic) shows a darker coloration (lower L * value) compared to DHA and has more neutral color values (a * and b * values close to 0).
  • MBDE (la) shows a strong shift to a redder hue (higher a * than DHA), creating a more natural skin tone.
  • the combination of MBDE (Ia) with DHA also shows the positive effect on hue even at low levels of MBDE.
  • the expression of the red clay is linear to the amount of MBDE used, which allows a precise adaptation of the desired skin tone to the specific needs of the user.
  • MEHDE (Ib) shows lighter color (greater L * value) and more neutral color values (a * near 0 and b * smaller) compared to DHA.
  • DHA ethers show good solubility in cosmetic oils (Finsolv TN as an example):
  • Example 3a 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 is the formulation until it cools down
  • Citric acid adjusted to pH 6.5.
  • Example 3b 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 and cooling of the emulsion, the phase C is added at 40 ° C. Subsequently, the formulation is stirred until it cools to room temperature. The pH is adjusted with sodium hydroxide solution or
  • Citric acid adjusted to pH 5.5.
  • Example 4a O / W tanning cream
  • 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 35 ° C and the phase C added with stirring, and further cooled. The pH is adjusted with sodium hydroxide solution or
  • Citric acid adjusted to pH 5.5.
  • Example 4b O / W tanning cream
  • Example 5a O / W Tanning Cream
  • Probiol L 05018 (7) AQUA, ALCOHOL DENATE, 5:00 (empty liposomes) LELCITHIN, GLYCERINE,
  • phase 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.
  • Example 5b O / W Tanning Cream
  • Probiol L 05018 (7) AQUA, ALCOHOL DENATE, 5.00 (empty LELCITHIN, GLYCERINE,
  • 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.
  • Rhodicare S (7) XANTHAN GUM 0.20
  • Probiol L 050 8 (8) AQUA, ALCOHOL DENAT, 5.00
  • 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.
  • Example 6b O / W tanning lotion
  • Rhodicare S (7) XANTHAN GUM 0.20
  • Probiol L 05018 8 AQUA, ALCOHOL DENAT, 5.00
  • phase B is dissolved and then it is given to phase A.
  • Example 7b mild transparent W / O tanning lotion
  • phase B is dissolved and then it is given to phase A.
  • Example 8a W / O tanning lotion
  • Example 8b W / O tanning lotion
  • phase B the magnesium sulfate heptahydrate is dissolved in the water of phase B. Then the remaining components of phase B are added. Phase B is slowly added to Phase A with stirring. It is quickly stirred for a further 2 minutes and homogenized.
  • the MHDE is dissolved in the ethanol and the remaining ingredients are added with stirring. Then the dihydroxyacetone is added and homogenized.
  • Example 11a W / Si Tanning Gel
  • Phase B is released and added to Phase A.
  • Phases C and D are added successively with stirring. It is homogenized.
  • Phase B is released and added to Phase A.
  • Phase C is added successively with stirring. It is homogenized.
  • Example 12a O / W tanning cream with UV A / B protection
  • Example 12b 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. The mixture is then cooled with stirring and the phase C at 40 ° C was added.
  • Example 12c 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. The mixture is then cooled with stirring and the phase C at 40 ° C was added.
  • Example 12d O / W tanning cream with UV A / B protection
  • phase 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.
  • 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 phase D is added successively.
  • phase A and B are heated separately to 80 ° C. Thereafter, phase B is slowly added with stirring to phase A. It is homogenized. The mixture is then cooled with stirring and the phases C at 40 ° C was added. Phase D is added.

Landscapes

  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Dermatology (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Emergency Medicine (AREA)
  • Cosmetics (AREA)

Abstract

La présente invention concerne l'utilisation de dihydroxyacétonemonoéthers comme substance auto-bronzante, des compositions contenant des dihydroxyacétonemonoéthers, ainsi que des dihydroxyacétonemonoéthers déterminés et un procédé pour leur préparation.
EP11790562.0A 2010-12-22 2011-11-30 Dihydroxyacétonemonoéther Withdrawn EP2654687A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102010055656A DE102010055656A1 (de) 2010-12-22 2010-12-22 Dihydroxyacetonmonoether
PCT/EP2011/006006 WO2012084121A1 (fr) 2010-12-22 2011-11-30 Dihydroxyacétonemonoéther

Publications (1)

Publication Number Publication Date
EP2654687A1 true EP2654687A1 (fr) 2013-10-30

Family

ID=45065861

Family Applications (1)

Application Number Title Priority Date Filing Date
EP11790562.0A Withdrawn EP2654687A1 (fr) 2010-12-22 2011-11-30 Dihydroxyacétonemonoéther

Country Status (4)

Country Link
US (1) US20130272978A1 (fr)
EP (1) EP2654687A1 (fr)
DE (1) DE102010055656A1 (fr)
WO (1) WO2012084121A1 (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2608454A (en) * 2021-07-02 2023-01-04 Mone Rebecca A tanning composition
FR3122089A1 (fr) * 2021-12-15 2022-10-28 Coty Inc. Dihydroxyacétone glycosylée

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2374283A (en) * 1940-12-17 1945-04-24 Firm Of J R Geigy A G 1-phenoxy-3-hydroxy-propanones-(2) and a process for their manufacture
GB986871A (en) * 1962-03-15 1965-03-24 Shell Int Research A process for the preparation of hydroxymethyl alpha-hydroxy alkyl ketones or monoethers thereof
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.
FR2725899B1 (fr) 1994-10-24 1996-12-13 Oreal Composition contenant un precurseur de la dihydroxyacetone
FR2746100B1 (fr) * 1996-03-18 1998-04-17 Composition contenant un precurseur de la dihydroxyacetone
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
DE102004039281A1 (de) * 2004-08-13 2006-02-23 Merck Patent Gmbh UV Filter
US20060045856A1 (en) 2004-09-01 2006-03-02 Teresa Mujica Composition containing a dihydroxyacetone precursor
DE102005043669A1 (de) * 2005-09-14 2007-03-22 Goldschmidt Gmbh Verfahren zur enzymatischen Synthese von Ethern

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2012084121A1 *

Also Published As

Publication number Publication date
DE102010055656A1 (de) 2012-06-28
US20130272978A1 (en) 2013-10-17
WO2012084121A1 (fr) 2012-06-28

Similar Documents

Publication Publication Date Title
EP2568953B1 (fr) Triazines utilisées comme accélérateurs de réaction
EP2569055A2 (fr) Photostabilisateurs
WO2013045016A2 (fr) Oxydes de phosphane en tant qu'accélérateurs de réaction
EP2665717B1 (fr) Dérivés de 7-acyloxy-chromène-4-one et leur utilisation en tant que substances auto-bronzantes
WO2012007095A2 (fr) Amplificateur de bronzage et substances auto-bronzantes
EP3402576B1 (fr) Dérivé de noreugénine glycoside
EP2427443B1 (fr) Ascorbate d'acide cinnamique
EP2654687A1 (fr) Dihydroxyacétonemonoéther
WO2018065358A1 (fr) Dérivés d'urée monosubstitués utilisés en tant que substance auto-bronzante
WO2012010242A2 (fr) Substances renforçant le bronzage et substances à effet autobronzant
EP2709731B1 (fr) Extraits de darlingtonia californica
EP2775996B1 (fr) Utilisation de dérivés de propanol et de propénol en tant qu'antioxydants
DE102009038206A1 (de) Glycerinaldehydderivate und deren Acetale
EP2600854B1 (fr) Dérivés de phényléthyle, de phényléthylène, de phényléthyne et d'indanone dans des préparations cosmétiques, notamment utilisées pour lutter contre des processus de vieillissement de la peau
DE102012016960A1 (de) Aminoester von Aminosäuren als Reaktionsbeschleuniger
WO2013020624A1 (fr) Extraits de tradescantia virginiana
WO2013167228A2 (fr) Dérivés de phénylcétone en tant qu'autobronzants
WO2011006566A2 (fr) Monométhoxy-hydroxy-benzylmalonates
DE102010023507A1 (de) UV-Filter

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 20130426

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR

DAX Request for extension of the european patent (deleted)
STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN

18D Application deemed to be withdrawn

Effective date: 20140211