EP1960342A1 - Ester d`erythrulose en tant que filtre uv - Google Patents

Ester d`erythrulose en tant que filtre uv

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Publication number
EP1960342A1
EP1960342A1 EP06828978A EP06828978A EP1960342A1 EP 1960342 A1 EP1960342 A1 EP 1960342A1 EP 06828978 A EP06828978 A EP 06828978A EP 06828978 A EP06828978 A EP 06828978A EP 1960342 A1 EP1960342 A1 EP 1960342A1
Authority
EP
European Patent Office
Prior art keywords
formula
preparation
skin
sub
polyethylene glycol
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Withdrawn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
EP06828978A
Other languages
German (de)
English (en)
Inventor
Thomas Rudolph
Herwig Buchholz
Frank Pfluecker
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 EP1960342A1 publication Critical patent/EP1960342A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
    • C07C255/41—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by carboxyl groups, other than cyano 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
    • A61K8/37—Esters of carboxylic acids
    • A61K8/375—Esters of carboxylic acids the alcohol moiety containing more than one hydroxy group
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
    • C07C69/734—Ethers
    • 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
    • A61Q19/007—Preparations for dry skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/08—Anti-ageing preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair

Definitions

  • the invention relates to UV filters, preparations containing such UV filters, corresponding processes for the production of the UV filters or the preparations containing them and their use.
  • the invention relates to the use of erythrulose esters as light protection filters for cosmetic or pharmaceutical products as well as new erythrulose esters, processes for their preparation and their
  • Human skin is subject to certain aging processes, which are partly due to intrinsic processes (chronoaging) and partly to exogenous factors (environmental, e.g. photoaging).
  • temporary or permanent changes in the skin appearance can occur, such as acne, oily or dry skin, keratoses, rosaceae, photosensitive, inflammatory, erythematous, allergic or autoimmune-reactive reactions such as dermatoses and photodermatoses.
  • the exogenous factors include in particular sunlight or artificial radiation sources with a comparable spectrum as well
  • undefined reactive photo products which can also be radical or ionic. These factors also include cigarette smoke and the reactive compounds it contains, such as ozone, free radicals, for example that
  • MMPs matrix metalloproteinases
  • X represents O, NH or N-alkyl
  • Y stands for O, NH or N-alkyl
  • Z stands for O, NH or N-alkyl
  • A, A ' and A " are omitted at the positions at which Sp, Sp ' or Sp " are equal to H.
  • Erythrulose is present in monomeric, dimeric or isomeric form (for example as D- or L-isomer or as tetrose (as threose or erythrose) or as a mixture of these forms.
  • D- or L-isomer or as tetrose (as threose or erythrose) or as a mixture of these forms.
  • tetrose as threose or erythrose
  • human hair in particular for prophylaxis against dry skin, wrinkling and / or pigment disorders, and / or for reducing or preventing damaging effects of UV rays on the skin and for prophylaxis against or reducing skin imperfections, such as wrinkles, fine lines, rough skin or Large-pored skin are further objects of the present invention in accordance with the advantageous properties of the compounds according to the invention.
  • the conventional light protection filters usually have little or insufficient skin adhesion, which leads to a shorter duration of the protective effect of the filter and in particular to the almost complete removal of the filter when bathing.
  • the present invention solves this problem with the compounds preferred according to the invention, in which X, Y and / or Z are O. These compounds according to the invention are able to chemically link to the skin. It is known that the ⁇ -hydroxyketone derivatives have excellent skin adhesion and, in some cases, a self-tanning effect, such as other hydroxyketone compounds (dihydroxyacetone). From EP 0 758 314 B1 maleimides and maleic acid derivatives are known which can react with SH groups present in the skin.
  • ⁇ -Hydroxyketoalkyl derivatives are known from EP 0 581 954 B1.
  • EP 710478 A1 and EP 709081 A1 disclose DHA fatty acid esters which can be used together with lipase as a self-tanning agent in creams.
  • A, A ' or A ' stand for structures which are known from conventional UV filters. It is particularly preferred according to the invention if A, A ' or A "stand for a radical selected from the group with the following elements:
  • CH 3 COO an alkyl radical with 1 to 8 C atoms, particularly preferably an alkoxy radical with 1 to 8 C atoms, particularly preferably -O- C (CH 3 ) 3 ⁇ -O-CH (CH 3 ) 2 ⁇ or -ethylhexyloxy, or a monoglycoside residue
  • n is 0, 1, 2 or 3, m 0 or 1, k 0, 1, 2, 3 or 4 and MH, Na or K.
  • a compound of formula I which is a 1, 3,4-tri, 1, 3-di, 1, 4-di, 3,4-di, 1-mono, 3-mono - or 4-monoester of erythrulose. Even more preferred is a 1-mono, 3-mono, or 4-monoester of erythrulose, with a 4-monoester of erythrulose being the most preferred.
  • the compounds according to the invention can, depending on the heteroatom X, Y and Z and chromophore "A, A 'and A"", according to different
  • Preparative acylation takes place in solvents that are inert to acid chlorides (such as pyridine, dimethylformamide, acetonitrile and ionic liquids). It is also preferred to implement the perform aqueous alkaline solution.
  • acid chlorides such as pyridine, dimethylformamide, acetonitrile and ionic liquids.
  • aqueous alkaline solution For this purpose, the so-called Schotten-Baumann method is preferably used, in which, for. B. the corresponding acid chlorides with erythrulose in the presence of sodium hydroxides.
  • the erythrulose molecule can also be coupled with other electrophilic reagents.
  • the Ar-CH 3 group in methylbenzylidene camphor can be converted to an alkyl bromide.
  • the camphor derivative is brominated by N-bromosuccinimide in the presence of initiators (C. Bouillon, C. Vayssie, in Ger. Offen., (Oreal SA, Fr.). Appl: DE 19780314. 78-2811041, 1978, p. 71. C. Bouillon, C. Vayssie, in Fr. Demande, (Oreal SA, Fr.), Fr, Number 2421878, 1979, p. 31. C. Bouillon, C. Vayssie, (Oreal SA, Fr.). Ca, Number 1113480, 1981, p. 61).
  • the preparation is a preparation for the protection of
  • Body cells against oxidative stress in particular for reducing skin aging, characterized in that, in addition to one or more compounds according to formula I, one or more others
  • Chlorogenic acid and its derivatives, lipoic acid and its derivatives e.g. dihydroliponic acid
  • aurothioglucose e.g. propylthiouracil and other thiols (e.g. thioredoxin, glutathione, cysteine, cystamine and their glycosyl, N-acetyl, methyl, ethyl, propyl, amyl) , Butyl and lauryl, palmitoyl, oleyl, ⁇ -linoleyl, cholesteryl and glyceryl esters) and their salts, dilauryl thiodipropionate, distearyl thiodipropionate, thiodipropionic acid and their derivatives (esters, ethers, peptides, lipids, nucleotides, nucleosides and salts) as well as sulfoximine compounds (e.g. buthioninsulfoxim
  • Homocysteine sulfoximine, buthionine sulfones, penta-, hexa-, heptathionine sulfoximine) in very low tolerable doses e.g. pmol to ⁇ mol / kg
  • also (metal) chelators e.g. ⁇ -hydroxy fatty acids, palmitic acid, phytic acid, lactoferrin
  • ⁇ -hydroxy acids e.g. citric acid
  • vitamin C and derivatives e.g. ascorbyl palmitate, magnesium ascorbyl phosphate, ascorbyl acetate
  • tocopherols and derivatives e.g. vitamin E-acetate
  • vitamin A and derivatives e.g. vitamin A palmitate
  • antioxidants are also suitable for use in the cosmetic preparations according to the invention.
  • Known and commercially available mixtures are, for example, mixtures containing lecithin, L - (+) - ascorbyl palmitate and citric acid (for example (e.g. Oxynex ® AP), 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- ⁇ -tocopherol
  • L - (+) - Ascorbyl palmitate citric acid and lecithin
  • BHT butylated hydroxytoluene
  • L - (+) - ascorbyl palmitate citric acid
  • Such antioxidants are used with compounds of formula I or formula II in such compositions are usually used in ratios in the range from 1000: 1 to 1: 1000, preferably in amounts of 100: 1 to 1: 100.
  • the preparations according to the invention can contain vitamins as further ingredients.
  • Vitamins and vitamin derivatives are preferred. selected from vitamin A, vitamin A propionate, vitamin A palmitate, vitamin A acetate, retinol, vitamin B, thiamine chloride hydrochloride (vitamin Bi), riboflavin (vitamin B 2 ), nicotinic acid amide, vitamin C (ascorbic acid), vitamin D, ergocalciferol (vitamin D 2 ), vitamin E, DL- ⁇ -tocopherol, tocopherol E acetate, tocopherol hydrogen succinate, vitamin Ki, esculin (vitamin P active ingredient), thiamine (vitamin Bi), nicotinic acid (niacin), pyri- doxin, pyridoxal, pyridoxamine, (vitamin B 6 ), pantothenic acid, biotin, folic acid and cobalamin (vitamin B 12 ) in the invention
  • Sophoretin, Ericin, 3,3 ', 4', 5,7-Pentahydroxyflavon mentioned as a particularly effective antioxidant (e.g. CA.Rice-Evans, NJ Miller, G. Paganga, Trends in Plant Science 1997, 2 (4), 152 -159).
  • Organic UV filters are generally incorporated into cosmetic formulations in an amount of 0.5 to 20 percent by weight, preferably 1-15%.
  • Conceivable inorganic UV filters are those from the group of titanium dioxides, such as coated titanium dioxide (for example Eusolex® T-2000, Eusolex ® T-AQUA, Eusolex® T-AVO), zinc oxides (eg Sachtotec.RTM), iron oxides and also
  • Cerium oxides conceivable. These inorganic UV filters are generally incorporated into cosmetic preparations in an amount of 0.5 to 20 percent by weight, preferably 2 to 10%. Preferred compounds with UV filtering properties are 3- (4 ' -
  • Suitable capsules can have walls made of inorganic or organic polymers.
  • walls made of inorganic or organic polymers.
  • the preparations according to the invention can also contain other customary skin-protecting or skin-care active ingredients. In principle, these can be all active substances known to the person skilled in the art.
  • Sprays form the main part of the commercially available products.
  • the basis for these two product forms are mostly alcoholic or aqueous alcoholic solutions with the addition of greasy substances and light perfuming.
  • compatible solutes are substances that are involved in the osmoregulation of plants or microorganisms and can be isolated from these organisms.
  • the generic term compatible solutes also includes the osmolytes described in German patent application DE-A-10133202. Suitable osmolytes are, for example, the polyols, methylamine compounds and amino acids and their respective precursors. In the sense of German patent application DE-A-10133202, osmolytes are understood in particular to be 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:
  • Precursors of these substances are, for example, glucose, glucose polymers, phosphatidylcholine, phosphatidylinositol, inorganic phosphates, proteins, peptides and polyamic acids.
  • Precursors are e.g. B. Compounds that are converted to osmolytes by metabolic steps.
  • compatible solutes are preferably selected from the group consisting of pyrimidinecarboxylic acids (such as ectoin and hydroxyectoin), 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), ß-mannosylglycerate (Firoin), ß-mannosylglyceramide (Firoin-A) or / and di-mannosyl-di-inositol phosphate (DMIP) or an optical isomer, derivative, e.g. an acid, a salt or ester of these compounds or combinations thereof.
  • pyrimidinecarboxylic acids such as ectoin and hydroxyectoin
  • proline such as ecto
  • hydroxyectoin and other ectoin derivatives are typically in areas in which e.g. Trehalose is used as an additive.
  • Ectoin derivatives such as hydroxyectoin can be used as a protective substance in dried yeast and bacterial cells.
  • pharmaceutical products such as non-glycosylated, pharmaceutically active peptides and proteins e.g. t-PA can be protected with ectoin or its derivatives.
  • the preparations according to the invention preferably contain pyrimidinecarboxylic acids of this type in amounts of up to 15% by weight.
  • the pyrimidinecarboxylic acids are preferably used in ratios of 100: 1 to 1: 100 to the compounds of the formula I, ratios in the range 1:10 to 10: 1 being particularly preferred.
  • the compatible solutes are selected from di-myo-inositol phosphate (DIP), cyclic 2,3-diphosphoglycerate (cDPG), 1,1-diglycerol phosphate (DGP), ⁇ -mannosylglycerate ( Firoin), ⁇ -mannosylglyceramide (Firoin-A) and / or di-mannosyl-di-inositol phosphate (DMIP), ectoin, hydroxyectoin or mixtures thereof.
  • DIP di-myo-inositol phosphate
  • cDPG cyclic 2,3-diphosphoglycerate
  • DGP 1,1-diglycerol phosphate
  • Firoin ⁇ -mannosylglycerate
  • Firoin-A ⁇ -mannosylglyceramide
  • DMIP di-mannosyl-di-inositol phosphate
  • cosmetic products is, for example, from the German
  • Compound of formula I additionally contain an aryl oxime, preferably 2-hydroxy-5-methyllaurophenone oxime, show surprising anti-inflammatory suitability.
  • the preparations contain
  • the preparation according to the invention contains at least one self-tanner.
  • the preparations according to the invention can also contain dyes and color pigments.
  • the dyes and pigments can be selected from the corresponding positive list of the Cosmetics Regulation or the EC list of cosmetic colorants. In most cases, they are identical to the colorants approved for food.
  • Advantageous color pigments are, for example, titanium dioxide, mica, iron oxides (for example Fe 2 O 3 , Fe 3 O 4 , FeO (OH)) and / or tin oxide.
  • Advantageous dyes are, for example, carmine, Berlin blue, chrome oxide green, ultramarine blue and / or manganese violet. It is particularly advantageous to choose the dyes and / or color pigments from the list below.
  • the Color Index Numbers (CIN) are taken from the Rowe Color Index, 3rd edition, Society of Dyers and Colorists, Bradford, England, 1971.
  • Natural pearlescent pigments such as. B.
  • Monocrystalline pearlescent pigments such as B. bismuth oxychloride
  • (BiOCI) 3rd layer substrate pigments e.g. B. mica / metal oxide
  • pearlescent pigment types based on mica / metal oxide are also advantageous:
  • Pearlescent pigments are available in numerous ways known per se.
  • other substrates besides mica can be coated with other metal oxides, such as. B. silica and the like.
  • metal oxides such as. B. silica and the like.
  • TiO 2 and Fe 2 O 3 coated SiO 2 particles (“Ronaspheren"), which are sold by Merck and are particularly suitable for the optical reduction of fine wrinkles.
  • Pearlescent pigments which are produced using SiO 2 are particularly preferred. Such pigments, which can also have gonichromatic effects, are z. B. available under the trade name Sicopearl Fantastico from BASF.
  • Pigments from Engelhard / Mearl based on calcium sodium borosilicate, which are coated with titanium dioxide, can also be used advantageously. These are available under the name Reflecks.
  • Dyes such as dyes with the Color Index (Cl)
  • One or more compounds of the formula I can be incorporated into cosmetic or dermatological preparations in the customary manner. Preparations are suitable for external use, for example as a cream, lotion, gel, or as a solution which can be sprayed onto the skin. For internal use Dosage formulas such as capsules, coated tablets, powders, tablets or solutions are suitable.
  • preparations according to the invention e.g. called: solutions, suspensions, emulsions, PIT emulsions, pastes, ointments, gels, creams, lotions, powders, soaps, surfactant-containing cleaning preparations, oils, aerosols and sprays.
  • Other forms of application are e.g. Sticks, shampoos and shower baths. Any customary carrier substances, auxiliary substances and optionally further active substances can be added to the preparation.
  • Preferred additives come from the group of preservatives, antioxidants, stabilizers, solubilizers, vitamins, colorants, odor improvers.
  • Ointments, pastes, creams and gels can contain the usual carriers, e.g. animal and vegetable fats, waxes, paraffins, starch, tragacanth, cellulose derivatives, polyethylene glycols, silicones, bentonites, silica, talc and zinc oxide or mixtures of these substances.
  • Powders and sprays can contain the usual carriers, e.g. Milk sugar, talc, silica, aluminum hydroxide, calcium silicate and polyamide powder or mixtures of these substances. Sprays can also contain the usual propellants, e.g. Chlorofluorocarbons, propane / butane or dimethyl ether.
  • Solutions and emulsions can contain 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-butyl glycol, oils, especially cottonseed oil, peanut oil, corn oil, olive oil, castor oil and sesame oil, glycerol fatty acid esters, polyethylene glycols and fatty acid esters of sorbitol contain these substances.
  • solvents e.g. Water, ethanol, isopropanol, ethyl carbonate, ethyl acetate, benzyl alcohol, benzyl benzoate, propylene glycol, 1, 3-butyl glycol, oils, especially cottonseed oil, peanut oil, corn oil, olive oil, castor oil and sesame oil, glycerol fatty acid esters, poly
  • Soaps Contain polyoxyethylene sorbitan esters, microcrystalline cellulose, aluminum meta-hydroxide, bentonite, agar-agar and tragacanth or mixtures of these substances. Soaps can contain the usual carriers such as alkali salts of fatty acids,
  • Surfactant-containing cleaning products can contain the usual carriers such as salts of fatty alcohol sulfates, fatty alcohol ether sulfates, sulfoberstein acid half-esters, fatty acid protein hydrolysates, isothionates, imidazolinium derivatives, methyl thaiates, sarcosinates, fatty acid amide ether sulfates, alkyl amidobetaine, fatty alcohol ethoxylates, fatty alcohol ethoxylates Contain glycerin fatty acid esters or mixtures of these substances.
  • Face and body oils can use the usual carriers such as
  • oils such as fatty acid esters, fatty alcohols, silicone oils, natural oils such as vegetable oils and oily plant extracts, paraffin oils, lanolin oils or mixtures of these substances.
  • the preferred preparation forms according to the invention include, in particular, emulsions.
  • Emulsions according to the invention are advantageous and contain z.
  • the lipid phase can advantageously be selected from the following group of substances:
  • oils such as triglycerides of capric or caprylic acid, as well as natural oils such.
  • Fats, waxes and other natural and synthetic fat bodies preferably esters of fatty acids with alcohols of low C number, e.g. with isopropanol, propylene glycol or glycerin, or esters of fatty alcohols with low C number alkanoic acids or with fatty acids;
  • Silicone oils such as dimethylpolysiloxanes, diethylpolysiloxanes, and
  • the oil phase of the emulsions, oleogels or hydrodispersions or lipodispersions in the sense of the present invention is advantageously selected from the group of esters from saturated and / or unsaturated, branched and / or unbranched alkane carboxylic acids with a chain length of 3 to 30 carbon atoms and saturated and / or unsaturated, branched and / or unbranched alcohols with a chain length of 3 to 30 carbon atoms, from the group of the esters of aromatic carboxylic acids and saturated and / or unsaturated, branched and / or unbranched alcohols with a chain length of 3 to 30 carbon atoms Atoms.
  • ester oils can then advantageously be selected from the group of isopropyl myristate, isopropyl palmitate, isopropyl stearate, isopropyl oleate, n-butyl stearate, n-hexyl laurate, n-decyl oleate, isooctyl stearate, isononyl stearate, isononylisononanoate, 2-ethyl-2-ethylhexyl palate 2-octyldodecyl palmitate, oleyl oleate, olerlerucate, erucyl oleate, erucylerucate as well as synthetic, semi-synthetic and natural mixtures of such esters, e.g. B. Jojoba oil.
  • the oil phase can advantageously be chosen 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 also fatty acid triglycerides, especially the triglycerol esters of saturated and / or unsaturated, branched and / or unbranched alkane carboxylic acids with a chain length of 8 to 24, in particular 12-18 C atoms.
  • the fatty acid triglycerides can for example be advantageously selected from the group of synthetic, semi-synthetic and natural oils, e.g. 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 can also be used advantageously for the purposes of the present invention. It may also be advantageous to use waxes, for example cetyl palmitate, as the sole lipid component of the oil phase.
  • the oil phase is selected from the group 2-Ethylhexylisostea- advantageous rat, octyldodecanol, isotridecyl isononanoate, isoeicosane, 2-ethylhexyl cocoate, C 2 -, caprylic-capric acid triglyceride 15 -alkyl, dicapryl ether.
  • 2-ethylhexyl isostearate mixtures of C 12 -i 5 alkyl benzoate and isotridecyl isononanoate and mixtures of Ci 2 -i 5 alkyl benzoate, 2-ethylhexyl isostearate and isotridecyl isononanoate.
  • hydrocarbons paraffin oil, squalane and squalene can be used advantageously for the purposes of the present invention.
  • Silicone oil to be used according to the invention can also be used advantageously for the purposes of the present invention, for example hexamethylcyclotrisiloxane, polydimethylsiloxane, poly (methylphenylsiloxane). Mixtures of cyclomethicone and isotridecyl isononanoate, cyclomethicone and 2-ethylhexyl isostearate are also particularly advantageous.
  • aqueous phase of the preparations according to the invention advantageously advantageously contains alcohols, diols or polyols of low C number, and also their ethers, preferably ethanol, isopropanol, propylene glycol,
  • Glycerin ethylene glycol, ethylene glycol monoethyl or monobutyl ether, propylene glycol monomethyl, monoethyl or monobutyl ether, diethylene glycol monomethyl or monoethyl ether and similar products, furthermore alcohols of low C number, e.g. As ethanol, isopropanol, 1, 2-propanediol, glycerol and in particular one or more thickeners, which one or which can advantageously be selected from the group
  • the preparations according to the invention contain hydrophilic surfactants.
  • the hydrophilic surfactants are preferably selected from the group consisting of alkyl glucosides, acyl lactylates, betaines and cocoamphoacetate.
  • the preparation according to the invention can also be in the form of an alcoholic gel which contains one or more lower alcohols or polyols, such as ethanol, propylene glycol or glycerol, and one Thickeners such as silica.
  • the oily-alcoholic gels also contain natural or synthetic oil or wax.
  • Example 2 2-cyano-3,3-diphenyl-acrylic acid 2,4-dihydroxy-3-oxobutyl ester is obtained from 2-cyano-3,3-diphenylacryl chloride in accordance with the procedure according to Example 1.
  • Preparation Phase A is heated to 75 ° C and phase B to 80 0 C.
  • Phase B is slowly added to phase A with stirring. After homogenization, the mixture is cooled with stirring. Be at a temperature of 40 0 C.
  • Phase A is heated to 75 0 C and phase B to 8O 0 C.
  • Phase B is slowly added to phase A with stirring. After homogenization, the mixture is cooled with stirring. Be at a temperature of 40 0 C.
  • Phase A is heated to 75 ° C and phase B to 8O 0 C.
  • Phase B is slowly added to phase A with stirring. After homogenization, the mixture is cooled with stirring. Be at a temperature of 40 0 C.
  • Example 6 Cream (O / W) containing Ectoin wt.%
  • phases A and B are heated separately to 75 ° C. Then phase A is slowly added to phase B with stirring and stirred until a homogeneous mixture is formed. After homogenization of the emulsion, the mixture is cooled to 30 ° C. with stirring. Then will heated to 35 ° C, phase C added and stirred until homogeneous.
  • UV pearls listed in the tables are each composed analogously, with OMC being replaced by the specified UV filters.

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
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  • Cosmetics (AREA)

Abstract

L'invention concerne des composés de formule (I) dans laquelle X, Y et Z représentent O, NH ou N-alkyle, Sp, Sp', Sp'' sont identiques ou différents et représentent -H, -(CH<SUB>2</SUB>)<SUB>n</SUB>-, -(CH<SUB>2</SUB>)<SUB>n</SUB>-<SUB/>C(=O)-(CH<SUB>2</SUB>)<SUB>o</SUB>- ou -(CH<SUB>2</SUB>)<SUB>n</SUB>-C(=O)-(CH<SUB>2</SUB>)<SUB>o</SUB>-X-(CH<SUB>2</SUB>)<SUB>p</SUB>-, n, o, p, q représentent des nombres entiers choisis indépendamment les uns des autres dans la gamme comprise entre 0 et 40 et A, A' et A'' représentent un substituant absorbant les rayonnements UV et présentant un système d'électrons p conjugués d'au moins 4 électrons p, A, A' et A'' étant également substitués avec un ou plusieurs groupements -Sp-X-CH<SUB>2</SUB>-C(=O)- CH<SUB>2</SUB>-OH et pouvant être identiques ou différents, et A, A' et A'' étant supprimés aux positions où Sp, Sp' ou Sp'' représentent H ; des préparations contenant de tels composés ; ainsi que leur utilisation.
EP06828978A 2005-12-08 2006-11-09 Ester d`erythrulose en tant que filtre uv Withdrawn EP1960342A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE200510058542 DE102005058542A1 (de) 2005-12-08 2005-12-08 Erythruloseester als UV Filter
PCT/EP2006/010741 WO2007065524A1 (fr) 2005-12-08 2006-11-09 Ester d’erythrulose en tant que filtre uv

Publications (1)

Publication Number Publication Date
EP1960342A1 true EP1960342A1 (fr) 2008-08-27

Family

ID=37681693

Family Applications (1)

Application Number Title Priority Date Filing Date
EP06828978A Withdrawn EP1960342A1 (fr) 2005-12-08 2006-11-09 Ester d`erythrulose en tant que filtre uv

Country Status (3)

Country Link
EP (1) EP1960342A1 (fr)
DE (1) DE102005058542A1 (fr)
WO (1) WO2007065524A1 (fr)

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1993016026A1 (fr) * 1992-02-15 1993-08-19 Merck Patent Gmbh UTILISATION DE DERIVES α-HYDROXYCETOALKYLE COMME SUBSTANCES FILTRANTES PROTECTRICES POUR L'EXPOSITION AUX RAYONS LUMINEUX
US5401645A (en) * 1992-03-16 1995-03-28 Monsanto Company Process for producing n-substituted polyhydroxy nitrogen-containing heterocycles utilizing acetobacteraceae and corynebacterium
GB9408994D0 (en) * 1994-05-06 1994-06-22 Vanguard Medica Ltd Compounds
FR2746100B1 (fr) * 1996-03-18 1998-04-17 Composition contenant un precurseur de la dihydroxyacetone
CN1536983A (zh) * 2001-05-30 2004-10-13 宝洁公司 包括取代的化妆品键合剂的局部组合物
US6875426B2 (en) * 2002-03-28 2005-04-05 L'oreal Self-tanning composition containing a tetrahydrocurcuminoid and a self-tanning agent
GB2413763A (en) * 2004-05-04 2005-11-09 Lifestyle Beauty Ltd Composition for application to skin

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2007065524A1 *

Also Published As

Publication number Publication date
WO2007065524A1 (fr) 2007-06-14
DE102005058542A1 (de) 2007-06-14

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