EP1572146A1 - Preparation cosmetique et/ou dermatologique contenant un acide dicarbonique octadecene et un agent eclaircissant - Google Patents

Preparation cosmetique et/ou dermatologique contenant un acide dicarbonique octadecene et un agent eclaircissant

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Publication number
EP1572146A1
EP1572146A1 EP03792423A EP03792423A EP1572146A1 EP 1572146 A1 EP1572146 A1 EP 1572146A1 EP 03792423 A EP03792423 A EP 03792423A EP 03792423 A EP03792423 A EP 03792423A EP 1572146 A1 EP1572146 A1 EP 1572146A1
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EP
European Patent Office
Prior art keywords
acid
weight
preparations
derivatives
cosmetic
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Withdrawn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
EP03792423A
Other languages
German (de)
English (en)
Inventor
Rainer Wolber
Christoph Smuda
Jan Batzer
Helga Biergiesser
Thomas Raschke
Heiner Max
Sven Beiersdorf Inc. FEY
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.)
Beiersdorf AG
Original Assignee
Beiersdorf AG
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Filing date
Publication date
Application filed by Beiersdorf AG filed Critical Beiersdorf AG
Publication of EP1572146A1 publication Critical patent/EP1572146A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • 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
    • A61Q19/02—Preparations for care of the skin for chemically bleaching or whitening the skin
    • 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
    • A61K8/34—Alcohols
    • A61K8/347—Phenols
    • 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
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A61K8/362—Polycarboxylic acids
    • 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
    • A61K8/602—Glycosides, e.g. rutin
    • 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
    • A61K8/63—Steroids; Derivatives thereof
    • 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
    • A61K8/64—Proteins; Peptides; Derivatives or degradation products thereof
    • 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
    • A61K8/67—Vitamins
    • 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
    • A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
    • A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
    • A61K8/9783—Angiosperms [Magnoliophyta]
    • A61K8/9789—Magnoliopsida [dicotyledons]
    • 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
    • A61Q5/08—Preparations for bleaching the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/02—Preparations containing skin colorants, e.g. pigments
    • 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

Definitions

  • the present invention relates to the use of active ingredients known per se for cosmetic and topical dermatological skin lightening or for preventing skin tanning, in particular skin tanning caused by UV radiation, and for lightening the natural hair color.
  • the present invention relates to cosmetic and dermatological preparations for the prophylaxis and treatment of cosmetic or dermatological skin changes such as e.g. unwanted pigmentation, e.g. local hyper- and deficient pigmentation (e.g. liver spots, freckles), inhibition of natural pigmentation, but also for purely cosmetic lightening of larger areas of the skin, which are pigmented appropriately for the individual skin type.
  • unwanted pigmentation e.g. local hyper- and deficient pigmentation (e.g. liver spots, freckles)
  • inhibition of natural pigmentation e.g. e.g. liver spots, freckles
  • purely cosmetic lightening of larger areas of the skin which are pigmented appropriately for the individual skin type.
  • Melanocytes are responsible for the pigmentation of the skin, which can be found in the lowest layer of the epidermis, the stratum basale, next to the basal cells as - depending on the skin type, either isolated or more or less frequently occurring pigment-forming cells.
  • melanocytes contain melanosomes, in which the melanin is formed. When stimulated by UV radiation, among other things, melanin is increasingly formed. This is ultimately transported via the living layers of the epidermis (keratinocytes) into the horny layer (corneocytes) and causes a more or less pronounced brown to brown-black skin color.
  • DHICA and DHI melanin are produced via the common intermediate stages dopaquinone and dopachrome. The latter is implemented, partly with the participation of further enzymes, either in indole-5,6-quinone carboxylic acid or in indole-5,6-quinone, from which the two eumelanins mentioned arise.
  • the formation of phaeomelanin occurs among other things via the intermediates dopaquinone and cysteinyldopa.
  • melanin-producing melanocytes are also responsible for the hair color (pigmentation of the hair).
  • the amount and composition of melanin in the hair determines the natural hair color, which is genetically determined.
  • UV radiation e.g. freckles, ephelides
  • genetic disposition e.g. incorrect pigmentation of the skin during wound healing or scarring or skin aging (e.g. Lentigines seniles).
  • the melanin-synthesizing enzymes are usually in an inhibited state; this inhibition is eliminated by solar, alpha or X-ray radiation, so that more melanin is formed. Conversely, the formation of melanin e.g. are artificially inhibited by hydroquinone benzyl ether so that such compounds counteract pigmentation.
  • melanotropin in the melanocytes stimulates the production of eumelanins.
  • the agouti signal protein restricts the synthesis of the entire melanins and rather stimulates that of the pheomelanins by acting as an antagonist on the MSH receptor (melanocortin receptor 1).
  • 8-Hexadecen-1, 16-dicarboxylic acid (dioic acid, CAS number 20701-68-2; provisional INCI name Octadecendioic acid) is a metabolite of yeast cells of the Candida strain. It is characterized by the following structure:
  • a fatty acid of purely vegetable origin serves as the starting substance. This is converted into the hydroxy fatty acid, which is then oxidized to the fatty acid aldehyde and ultimately to the dicarboxy acid.
  • the yeast cells come from selected mutant strains.
  • the commercial product has a purity of 95%. 8-Hexadecen-1, 16-dicarboxylic acid is present as a mixture of the ice and trans isomers, the cis isomer predominating in terms of quantity. Oleic acid can be contained in the product at a concentration of approximately 3%.
  • Ursolic acid is a triterpene carboxylic acid that is found in numerous plants such as bearberry leaves, in the wax coating of apples, pears, in the fruit peel of rice or blueberries, in spice or medicinal plants such as rosemary, sage, thyme, marjoram, hawthorn, lemon balm and also in different types of vegetables. It is believed to have anticarcinogenic effects.
  • the Agouti signal protein was first isolated from Central American rodents (Agoutis from the Dasyproctidae family, occurs in approximately 20 species in the forests of Central America) in its murine and human form.
  • WO-97/00892 discloses a skin-lightening effect of these forms.
  • Licorice is a woody perennial that grows to a height of around 1 to 1.5 meters. The plant takes its name from the sweet taste of its roots.
  • the licorice root extract is also called liquorice.
  • Licorice was used in ancient Egypt as a medicinal plant for diseases of the upper respiratory tract. In India and China, liquorice is traditionally used and cultivated as a medicinal herb with an antispasmodic effect. Licorice has a beneficial effect on the ejection, anti-inflammatory and antispasmodic and is therefore mainly used for coughing and stomach irritation. Studies have also identified a component of licorice root that is considered effective in hepatitis C.
  • the liquorice root extract contains 3-8% glycyrrhizin (ammonium and calcium salts of glycyrrhizic acid (20 ß-carboxy-11-oxo-30-norolean-12-en-3ß-yl-2-0-ß-D-glucopyranuronoxyl- ⁇ -D -glucopyranosiduronic acid)), which causes the sweet taste.
  • Glycyrrhizin (C 42 H 62 0 16 ) is about 150 times sweeter than cane sugar and hydrolyzes to the aglycone glycyrrhetic acid (C 3 oH 6 0 4 ) and two molecules of glucuronic acid.
  • Other ingredients are coumarins, flavonoids, various sugars, resins and sterols
  • Hydroquinone is used as an antioxidant, as a photo developer and as a polymerization inhibitor. In nature it occurs in leaf buds of the pear and in blackberry leaves.
  • Green tea has a tradition of almost two thousand years. He is attributed a positive effect on health. Due to the gentle processing, the ingredients carotenoids, caffeine, vitamins A, B2, B12, C and E, secondary plant substances such as polyphenols, flavonoids, saponins are preserved in this tea variant. Drunk regularly, green tea is said to strengthen the immune system and even protect against cancer. Green tea extract can be used for topical application.
  • Arbutin occurs naturally in bearberry, cranberry and blueberry and acts as an antioxidant. Chemically, it is hydroquinone-ß-D-glucopyranoside. It prevents the development of the skin pigment melanin by blocking the enzyme tyrosinase.
  • Biotin (D-cis-hexahydro-2-oxothieno [3,4-d] imidazole-4-valeric acid) is also known as coenzyme R and is involved in carboxylation reactions in the organism. It is synthesized by the human intestinal flora. It is used to treat seborrheic dermatitis in young children.
  • Bearberry Arctostaphylos uva-ursi (whitebeam, cranberry, sandberry, Wider boxwood, wolf grape) belongs to the heather family. and is widespread in Europe and America.
  • the dried, whole or cut leaves had a high content of hydroquinone derivatives: up to 12, occasionally up to 15% phenol glycosides, including in particular arbutin and methylarbutin as well as other hydroquinone derivatives (gallic acid esters of arbutin, free hydroquinone). They have antibacterial activity against various microorganisms and are used to prepare tea for inflammatory diseases.
  • Placenta extracts are used in the manufacture of cosmetic products. These are lipoid or water soluble extracts from animal placents. These extracts (usage concentration 2-5%) have a regenerating influence on aging skin or skin damaged by strong solar radiation and are said to stimulate hair growth.
  • Ascorbyl glucoside is a synthetic ascorbic acid derivative and can be described as a precursor of ascorbic acid.
  • the active ascorbic acid is released e.g. enzymatically in the cells or biological tissues. Chemically, this is ascorbic acid-2- ß-D-glucopyranoside.
  • the glycosylation in the 2-position of the enol function of the ascorbic acid leads, just like the introduction of the phosphate protective group at this position (ascorbyl phosphate), to an increase in stability against degradation reactions in aqueous solution.
  • the corresponding ascorbic acid 3-ß-D-glucopyranoside is also known and increases the stability of the ascorbic acid before chemical degradation.
  • Chamomile extract contains substances that act as endothelin antagonists. Endothelin indirectly activates skin pigmentation via the endothelin receptor by enhancing UV-B-induced skin tanning. Pigment Cell Res. 10: 218-228, 1997 describes the depigmenting effect of various endothelin antagonists (e.g. chamomile extract). However, this publication could not point the way to the present invention.
  • Water-soluble flavonoids such as alpha glucosyl rutin are described as whitening active ingredients in JP 08099859, JP 6321759, but these publications could not point the way to the present invention.
  • MSH antagonists inhibit the melanogenesis-promoting effect of the ⁇ -melanocyte stimulating hormone (-MSH).
  • -MSH ⁇ -melanocyte stimulating hormone
  • Competitive inhibitory peptide derivatives of the active ⁇ -MSH sequence His-Phe-Arg-Trp
  • Other physiological MSH antagonists are the products of the agouti locus (see there) or the ⁇ 3-MSH.
  • PH blockers are substances that block the ATP-dependent proton pump in melanosomes and thus prevent the pH value required for melanogenesis to be reduced to 3-5 (JID 105: 3-7, 1995) Publication does not point the way to the present invention.
  • pH blockers are, for example, the compounds 2,4-dinitrophenol and carbonylcyanide-p-trifluoromethoxyphenylhydrazone.
  • depigmenting agents used in depigmenting preparations can therefore be reduced.
  • a combination of these substances can achieve a more uniform, lighter skin tone.
  • 8Hexadecen-1, 16-dicarboxylic acid in a total concentration of 0.001-10% by weight, preferably 0.005-8% by weight, in particular 0.05-5% by weight, based on the total weight of the preparations , is present.
  • the further active ingredient in a total concentration of 0.001-3% by weight, preferably 0.005-1% by weight, in particular 0.01-0.2% by weight, based on the total weight of the preparations , is present.
  • preparations according to the invention against undesired pigmentation of the skin and / or for the treatment of pigmentation disorders or against undesired pigmentation of the hair and / or for lightening the hair.
  • active ingredient according to the invention 8-Hexadecen-1, 16-dicarboxylic acid and at least one further active ingredient specified above, hereinafter referred to as “active ingredient according to the invention”, has proven to be outstandingly effective against unwanted pigmentation, in particular local hyperpigmentation, as well as against skin tanning caused by UV radiation, both preventively and in the sense of treatment.
  • active ingredient or cosmetic or topical dermatological preparations used according to the invention with an effective content of active ingredient used according to the invention for cosmetic or dermatological treatment of undesired skin pigmentation, that is to say for example inhomogeneous pigmentation of the aging skin, lentigines senile or post-inflammatory hyperpigmentation.
  • the depigmenting activity of short oligopeptides (length 4-9 amino acids) from the active sequences pos. 42-48 (SMNSLDFSS) and in particular pos. 83-89 (WRPRTP) of the human agouti signal protein was also described.
  • the peptides and also effective derivatives of these peptides can easily be produced synthetically or biotechnologically.
  • Advantageous agouti peptides in the sense of the invention are one or more monomeric or homo- or heterodimeric or homo- or heterotrimeric or homo- or heterotetrameric oligopeptides,
  • Terminus is supplemented by up to 5 amino acids, according to the structure
  • ⁇ and ⁇ can independently represent amino acid sequences of up to 5 amino acids
  • R represents a branched or unbranched, saturated or unsaturated hydrocarbon radical, in particular an alkyl radical having 1 to 30 carbon atoms,
  • ⁇ and ⁇ can independently represent amino acid sequences of up to 5 amino acids, and wherein R 'and R "can be selected independently of one another from the group consisting of hydrogen and the branched or unbranched, saturated or unsaturated hydrocarbon radicals, in particular the alkyl radical with 1 to 30 carbon atoms.
  • R is a branched or unbranched, saturated or unsaturated hydrocarbon radical, in particular an alkyl radical with 4 to 30 carbon atoms
  • R 'and R can be selected independently of one another from the group consisting of hydrogen and the branched or unbranched, saturated or unsaturated hydrocarbon radicals, in particular the alkyl radical with 1 to 30 carbon atoms.
  • amino acid sequences which supplement the peptide sequence at the C or N terminus are preferably composed of proteinogenic amino acids.
  • the L-selenocysteine can replace the L-cysteine and the L-selenomethionine the L-methionine.
  • individual, several or even all positions can also be replaced by the appropriately D-configured stereoisomers.
  • R represents the stearoyl or the palmitoyl radical.
  • Amino acid sequences or oligopeptides to be used according to the invention are advantageously obtainable by customary, for example also automated, methods (for example via so-called peptide synthesizers).
  • Individual peptides can, for example, advantageously with the aid of an automatic MilliGen 9050 peptide synthesizer, overlapping peptides with the aid of a multiple peptide synthesizer SMPS 350 (ZINSSER analytics) by solid phase synthesis (RBMerrifield (1966) J.Am.Chem.Soc. 85, 2149) according to Fmoc / But strategy (E. Atherton, RCSheppard; "Solid Phase Peptide Synthesis: A Practical Approach", IRL Press, Oxford, England (1989).
  • Coupling and splitting steps can be controlled using on-line UV monitoring.
  • a p-alkoxybenzyl alcohol-modified polystyrene resin (S.-S. Wang; J. Am. Chem. Soc. 95 (1973), p. 1328), for peptide amides, can advantageously be used as the solid phase matrix for free peptides, for example the Rink amide resin ( H.Rink; Tetrahedron Lett. 28 (1987), p.3787) can be used.
  • TBTU (2- (1 H-benzotriatol-1-yl) -1, 1,3,3-tetramethyluronium tetrafluoroborate) (R. Knorr, A. Trzeciak, W.Bannwarth, D.
  • the peptides can be cleaved from the resin, for example with the help of trifluoroacetic acid and, if desired, additional substances (e.g. phenol, thioanisole, but also water) and at the same time freed from all protective groups.
  • additional substances e.g. phenol, thioanisole, but also water
  • the reaction solution can e.g. by dropping in ice-cold diethyl ether to give a crude product which, if desired while washing with a suitable washing liquid, e.g. cold diethyl ether, can be cleaned and then lyophilized.
  • a suitable washing liquid e.g. cold diethyl ether
  • the crude peptide is then advantageously obtained by preparative reversed-phase high-performance liquid chromatography (RP-HPLC) on a C18 column (250 ⁇ 10 mm) using an acetonitrile / 0.05% trifluoroacetic acid / water system to a purity of> 98 % highly cleaned.
  • peptides acylated at the N-terminus can be obtained in high yields.
  • acid chlorides or acid anhydrides e.g. palmitoyl chloride or lauryl chloride
  • a suitable solvent e.g. dimethylformamide / N-methylmorpholine
  • peptides acylated at the N-terminus can be obtained in high yields.
  • the cosmetically or pharmaceutically acceptable oligopeptides used according to the invention hereinafter, regardless of whether a single substance or an isomer mixture or a mixture of different individual substances is present, collectively also called “active substance used according to the invention”, have proven to be excellent active substances against undesired pigmentation, in particular local hyperpigmentation, and both preventively and in the sense of treatment.
  • Emulsions according to the invention in the sense of the present invention are advantageous and contain e.g. Fats, oils, waxes and / or other fat bodies, as well as water and one or more emulsifiers, as are usually used for such a type of formulation.
  • the active ingredient used according to the invention in aqueous systems or surfactant preparations Insert cleaning and care of the skin and hair.
  • This includes shower gels, shampoos but also conditioners, hair care treatments, hair rinses, hair tonics, sprays etc.
  • the active ingredient 8-hexadecene-1,16-dicarboxylic acid in the form of molecular adducts with cyclodextrins. It is believed that the cyclodextrin skeletons act as the host molecule and 8-hexadecen-1, 16-dicarboxylic acid as the guest molecule.
  • cyclodextrins are dissolved in water and 8-hexadecen-1, 16-dicarboxylic acid is added.
  • the molecular adduct then precipitates as a solid and can be subjected to the usual cleaning and preparation steps.
  • cyclodextrin-guest complexes in an appropriate solvent e.g. water
  • Such balance systems are also advantageous in the sense of the present invention.
  • Medical topical compositions in the sense of the present invention generally contain one or more medicaments in an effective concentration.
  • medicaments in an effective concentration.
  • compositions within the meaning of the present invention, depending on their structure, can be used, for example, as skin protection cream, cleansing milk, sunscreen lotion, nutritional cream, day or night cream, etc. It is possibly possible and advantageous to add the compositions according to the invention as the basis for pharmaceutical formulations use.
  • the preparations in the sense of the present invention preferably contain at least one further UV-A, UV-B and / or broadband filter substance.
  • the formulations may, although not necessary, optionally also contain one or more organic and / or inorganic pigments as UV filter substances, which may be present in the water and / or the oil phase.
  • Organic surface coatings in the sense of the present invention can consist of vegetable or animal aluminum stearate, vegetable or animal stearic acid, lauric acid, dimethylpolysiloxane (also: dimethicone), methylpolysiloxane (methicone), simethicone (a mixture of dimethylpolysiloxane with an average chain length of 200 to 350 Dimethylsiloxane units and silica gel) or alginic acid.
  • dimethylpolysiloxane also: dimethicone
  • methicone methylpolysiloxane
  • simethicone a mixture of dimethylpolysiloxane with an average chain length of 200 to 350 Dimethylsiloxane units and silica gel
  • alginic acid can consist of vegetable or animal aluminum stearate, vegetable or animal stearic acid, lauric acid, dimethylpolysiloxane (also: dimethicone), methylpolysiloxane (
  • Suitable titanium dioxide particles and predispersions of titanium dioxide particles are available under the following trade names from the companies listed:
  • Phenylene-1,4-bis (2-benzimidazyl) -3,3'-5,5'-tetrasulfonic acid and its salts especially the corresponding sodium, potassium or triethanolammonium salts, in particular phenylene-1,4- bis- (2-benzimidazyI) -3,3'-5,5'-tetrasulfonic acid bis-sodium salt with the INCI name bisimidazylate (CAS No .: 180898-37-7), which, for example, under the trade name Neo Heliopan AP is available from Haarmann &Reimer; Salts of 2-phenylbenzimidazole-5-sulfonic acid, such as its sodium, potassium or triethanammonium salt, and sulfonic acid itself with the INCI name phenylbenzimidazole sulfonic acid (CAS No. 27503-81-7), which, for example, under the
  • Sulfonic acid derivatives of 3-benzylidene camphor such as. B. 4- (2-oxo-3-bornylidene methyl) benzenesulfonic acid, 2-methyl-5- (2-oxo-3-bornylidene methyl) sulfonic acid and salts thereof.
  • Advantageous broadband filters or UV-B filter substances are, for example, triazine derivatives, such as, for. B.
  • Diethylhexylbutylamidotriazon (INCI: Diethylhexylbutamidotriazone), which is available under the trade name UVASORB HEB from Sigma 3V;
  • An advantageous broadband filter in the sense of the present invention is also the 2,2'-methylene-bis- (6- (2H-benzotriazol-2-yl) -4- (1,1,3,3-tetramethylbutyl) phenol), which is available under the trade name Tinosorb® M from CIBA-Chemicals GmbH.
  • Another advantageous broadband filter for the purposes of the present invention is 2- (2H-benzotriazol-2-yl) -4-methyl-6- [2-methyl-3- [1, 3,3,3-tetramethyl-1- [(trimethylsilyl) oxy] disiloxanyl] propyl] - phenol (CAS no .: 155633-54-8) with the INCI name Drometrizole Trisiloxane, which is available under the trade name Mexoryl® XL from Chimex.
  • Advantageous oil-soluble UV-B and / or broadband filter substances in the sense of the present invention are e.g. B .:
  • 4-aminobenzoic acid derivatives preferably 4- (dimethylamino) benzoic acid (2-ethylhexyl) ester, 4- (dimethylamino) benzoic acid amyl ester;
  • benzophenone preferably 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-methoxy-4'-methylbenzophenone, 2,2'-dihydroxy-4-methoxybenzophenone
  • Advantageous water-soluble filter substances are e.g. B .:
  • Sulfonic acid derivatives of 3-benzylidene camphor such as. B. 4- (2-oxo-3-bornylidene methyl) benzenesulfonic acid, 2-methyl-5- (2-oxo-3-bornylidene methyl) sulfonic acid and their salts.
  • a further light protection filter substance according to the invention to be used advantageously is ethylhexyl-2-cyano-3,3-diphenyIacrylat (octocrylene), which is available from BASF under the name Uvinul N 539 ®.
  • Particularly advantageous preparations within the meaning of the present invention which are distinguished by a high or very high UV-A and / or UV-B protection, preferably contain further UV-A and in addition to the filter substance (s) according to the invention / or broadband filters, especially dibenzoylmethane derivatives [for example the 4- (tert-butyl) -4'-meth-oxydibenzoylmethane], phenylene-1,4, bis (2-benzimidazyl) -3,3'-5,5'- tetrasulfonic acid and / or its salts, the 1,4-di (2-oxo-10-sulfo-3-bornylidenemethyl) benzene and / or its salts and / or the 2,4-bis - ⁇ [4- (2- Ethyl-hexyloxy) -2-hydroxy] phenyl ⁇ -6- (4-methoxyphenyl) -1, 3,5-triazine, in each case individually or in any combination with
  • the preparations according to the invention advantageously contain the substances which absorb UV radiation in the UV-A and / or UV-B range in a total amount of, for. B. 0.1 wt .-% to 30 wt .-%, preferably 0.5 to 20 wt .-%, in particular 1, 0 to 15.0 wt .-%, each based on the total weight of the preparations to cosmetic To provide preparations that protect the hair or skin from the entire range of ultraviolet radiation.
  • the cosmetic and dermatological preparations according to the invention can contain cosmetic active ingredients, auxiliaries and / or additives as are usually used in such preparations, e.g. Antioxidants, preservatives, bactericides, perfumes, substances to prevent foaming, dyes, pigments that have a coloring effect, thickeners, surface-active substances, emulsifiers, softening, moisturizing and / or moisturizing substances, fats, oils, waxes or other usual constituents a cosmetic or dermatological formulation such as alcohols, polyols, polymers, foam stabilizers, electrolytes, organic solvents or silicone derivatives.
  • cosmetic active ingredients e.g. Antioxidants, preservatives, bactericides, perfumes, substances to prevent foaming, dyes, pigments that have a coloring effect, thickeners, surface-active substances, emulsifiers, softening, moisturizing and / or moisturizing substances, fats, oils, waxes or other usual constituents a cosmetic or dermatological formulation
  • antioxidants it is also advantageous to add customary antioxidants to the preparations for the purposes of the present invention. According to the invention, all the antioxidants suitable or customary for cosmetic and / or dermatological applications can be used as favorable antioxidants.
  • the antioxidants are advantageously selected from the group consisting of amino acids (eg glycine, histidine, tyrosine, tryptophan) and their derivatives, imidazoles (eg uro- canic acid) and their derivatives, peptides such as D, L-carnosine, D-camosine, L-carnosine and their derivatives (e.g. anserine), carotenoids, carotenes (e.g.
  • amino acids eg glycine, histidine, tyrosine, tryptophan
  • imidazoles eg uro- canic acid
  • peptides such as D, L-carnosine, D-camosine, L-carnosine and their derivatives (e.g. anserine)
  • carotenoids e.g.
  • buthioninsulfoximines homocysteine sulfoximine, buthioninsulfones, penta-, hexa-, heptathioninsulfoximine
  • very low tolerable dosages e.g. pmol to ⁇ mol / kg
  • 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, biliary extracts, bilirubin, biliverdin, EDTA, EGTA and their derivatives, unsaturated fatty acids and their derivatives (e.g.
  • the amount of the antioxidants (one or more compounds) in the preparations is preferably 0.001 to 30% by weight, particularly preferably 0.05-20% by weight, in particular 0.1-10% by weight, based on the total weight the preparation.
  • vitamin E and / or its derivatives represent the antioxidant (s)
  • the cosmetic or dermatological preparation in the sense of the present invention is a solution or emulsion or dispersion, the following can be used as solvents:
  • Oils such as triglycerides of capric or caprylic acid, but preferably
  • Fats, waxes and other natural and synthetic fat bodies preferably esters of fatty acids with low C alcohols, e.g. with isopropanol, propylene glycol or glycerin, or esters of fatty alcohols with low C number alkanoic acids or with fatty acids;
  • Alcohols, diols or polyols of low C number, and 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 ,
  • Water can also be a component of alcoholic solvents.
  • the oil phase of the emulsions, oleogels or hydrodispersions or lipodispersions for the purposes 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 esters from 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-ethylhexyluryl, 2-ethylhexyl palylate, Octyldodecyl palmitate, oleyl oleate, olerlerucate, erucyl oleate, erucylerucate and synthetic, semi-synthetic and natural mixtures of such esters, for example jojoba oil.
  • the oil phase can advantageously be selected from the group of branched and unbranched hydrocarbons and waxes, the silicone oils, the dialkyl ethers, the group of saturated or unsaturated, branched or unbranched alcohols, and also the fatty acid triglycerides, in particular the triglycerol esters of saturated and / or unsaturated saturated, branched and / or unbranched alkane carboxylic acids with a chain length of 8 to 24, in particular 12-18 carbon atoms.
  • the fatty acid triglycerides can, for example, advantageously be selected from the group of synthetic, semisynthetic and natural oils, for example 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 advantageously selected from the group consisting of 2-ethylhexyl isostearate, octyldecanol, isotridecyl isononanoate, isoeicosane, 2-ethylhexyl cocoate, C 12 . 15 alkyl benzoate, caprylic capric acid triglyceride, dicaprylyl ether.
  • Particularly advantageous are mixtures of C- ⁇ 2-15 -alkyl benzoate and 2-ethylhexyl isostearate, mixtures of C 12th 15- Alkylbenzoate and isotridecyl isononanoate and mixtures of Ci2- 5-alkylbenzoate, 2-ethylhexyl isostearate and isotridecyl isononanoate.
  • hydrocarbons paraffin oil, squalane and squalene can be used advantageously for the purposes of the present invention.
  • the oil phase can advantageously also have a content of cyclic or linear silicone oils or consist entirely of such oils, although it is preferred to use an additional content of other oil phase components in addition to the silicone oil or the silicone oils.
  • Cyclomethicone (octamethylcyclotetrasiloxane) is advantageously used as the silicone oil to be used according to the invention.
  • other silicone oils 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.
  • Gels used in the present invention usually contain low C number alcohols, e.g. Ethanol, isopropanol, 1, 2-propanediol, glycerol and water or an oil mentioned above in the presence of a thickener which is preferably silicon dioxide or an aluminum silicate in the case of oily-alcoholic gels, and is preferably a polyacrylate in the case of aqueous-alcoholic or alcoholic gels.
  • low C number alcohols e.g. Ethanol, isopropanol, 1, 2-propanediol, glycerol and water or an oil mentioned above in the presence of a thickener which is preferably silicon dioxide or an aluminum silicate in the case of oily-alcoholic gels, and is preferably a polyacrylate in the case of aqueous-alcoholic or alcoholic gels.
  • Fixed pens contain e.g. natural or synthetic waxes, fatty alcohols or fatty acid esters. Lip care sticks and stick formulations for body deodorization are preferably used.
  • liquid oils for example paraffin oils, castor oil, isopropyl myristate
  • semi-solid components for example petroleum jelly, lanolin
  • solid components for example beeswax, ceresin and microcrystallines
  • Waxes or ozokerite for example beeswax, ceresin and microcrystallines
  • high-melting waxes eg camauba wax, candelilla wax
  • Suitable blowing agents for cosmetic and / or dermatological preparations which can be sprayed from aerosol containers for the purposes of the present invention are the customarily known volatile, liquefied blowing agents, for example hydrocarbons (propane, butane, isobutane), which can be used alone or in a mixture with one another. Compressed air can also be used advantageously.
  • volatile, liquefied blowing agents for example hydrocarbons (propane, butane, isobutane)
  • Cosmetic preparations in the sense of the present invention can also be in the form of gels which, in addition to an effective content of the active ingredient according to the invention and the solvents usually used therefor, preferably water, and also organic thickeners, for example gum arabic, xanthan gum, sodium alginate, cellulose derivatives, preferably methyl cellulose, hydroxymethyl cellulose, Hydroxyethyl cellulose, hydroxypropyl cellulose, hydroxypropyl methyl cellulose or inorganic compounds thickener, e.g. B. aluminum silicates such as bentonite, or a mixture of polyethylene glycol and polyethylene glycol stearate or distearate.
  • the thickener is contained in the gel, for example, in an amount between 0.1 and 30% by weight, preferably between 0.5 and 15% by weight.
  • Preparations according to the invention which represent hair cosmetic cleaning preparations for the hair or the scalp, can be in liquid or solid form. They preferably contain at least one anionic, non-ionic or amphoteric surface-active substance or mixtures thereof, optionally an electrolyte and auxiliary agents, as are usually used therefor.
  • the surface-active substance can be present in the cleaning preparations at a concentration of between 1 and 94% by weight, based on the total weight of the preparations, but in particular between 1 and 50% by weight.
  • aqueous cosmetic cleaning agents according to the invention or water-poor or anhydrous cleaning agent concentrates intended for aqueous cleaning may contain anionic, nonionic and / or amphoteric surfactants, for example conventional soaps, e.g.
  • Anionic surfactants are preferably used in concentrations between 5% and 20% by weight.
  • Sodium Laureth Sulfate as it is offered under the name Texapon N 70 by the company Henkel or Disodium Laureth Sulfosuccinate as it is offered under the name Rewopol SBFA 30 by the company Witco.
  • Nonionic surfactants are preferably used in concentrations of 1% by weight to 10% by weight. Examples are decyl glucoside as it is offered by the company Seppic under the name Oramix NS 10 or polysorbate 80 as it is offered by the company ICI under the name Tween 80.
  • Amphoteric surfactants are preferably used in concentrations of 1% by weight to 10% by weight.
  • Examples are cocamidopropyl betaine as it is offered as Tego betaine by the company Goldschmidt or sodium cocoamphoacetate as it is offered under the name Miranol Ultra by the company Rhone Poulenc.
  • Conditioning aids may also be present in the hair cosmetic cleaning agents, for example in amounts of 0.001 to 10% by weight, based on the total weight of the preparations.
  • the preferred conditioning aids include polymeric quaternary compounds (quats). Polymer quats are often used in shampoos, for example with a concentration of 0.01 to 2% by weight. These include polyquaternium-10 as it is offered under the name Polymer JR 400 by the company Amerchol or hydroxypropyl guar hydroxypropyltrimonium chloride as it is offered with the name Jaguar C 162 by the company Rhone-Poulenc.
  • the preparations according to the invention can contain cosmetic auxiliaries as are usually used in such preparations, e.g. Preservatives, perfumes,
  • Anti-foaming substances foam stabilizers, dyes, pigments that have a coloring effect, thickeners, surface-active substances, emulsifiers, softening, moisturizing and / or moisturizing substances, lipid-replenishing agents,
  • Components such as of perfume preparations can be included.
  • the total amount of auxiliaries is, for example, 0.001 to 15% by weight, preferably 0.01 to 10% by weight, in each case based on the total weight of the preparation.
  • the water content of the preparations is, for example, 50 to 95% by weight, preferably 55 to 90% by weight, in each case based on the total weight of the preparation.
  • the pH of the preparations can be adjusted in a known manner by adding acids or bases, preferably by adding buffer mixtures, for example based on citric acid / citrate or phosphoric acid / phosphate buffer mixtures.
  • the pH is preferably below 10, for example in the range 4-8, in particular in the range 5-7.
  • Particularly advantageous preparations are also obtained if antioxidants are used as additives or active ingredients.
  • the preparations advantageously contain one or more antioxidants. All of the antioxidants suitable or customary for cosmetic and / or dermatological applications can be used as inexpensive, but nevertheless optional, antioxidants.
  • antioxidants are advantageously selected from the group consisting of amino acids (eg glycine, histidine, tyrosine, tryptophan) and their derivatives, imidazoles (eg urocanic acid) and their derivatives, peptides such as D, L-carnosine, D-carnosine, L- Carnosine and its derivatives (eg anserine), carotenoids, carotenes (eg carotene, ⁇ -carotene, lycopene) and their derivatives, chlorogenic acid and their derivatives, lipoic acid and their derivatives (eg dihydrolipoic acid), aurothioglucose, propylthiouracil and others Thiols (e.g.
  • amino acids eg glycine, histidine, tyrosine, tryptophan
  • imidazoles eg urocanic acid
  • peptides such as D, L-carnosine, D-carnosine, L- Car
  • thioredoxin glutathione, cysteine, cystine, cystamine and their glycosyl, N-acetyl, methyl, ethyl, propyl, amyl, butyl and lauryl, palmitoyl, oleyl, ⁇ - Linoleyl, cholesteryl and glyceryl esters) and their salts, dilauryl thiodipropionate, distearyl thiodipropionate, thiodipropionic acid and their derivatives (esters, ethers, peptides, lipids, nucleotides, nucleosides and salts) as well as sulfoximine compounds (e.g.
  • buthioninsulfoximine homocysteine sulfone, homocysteine sulfone - , Hexa-, Heptathioninsulfoximin
  • very low tolerable doses eg pmol to ⁇ mol / kg
  • metal chelators eg ⁇ -hydroxy fatty acids, palmitic acid, phytic acid, lactoferrin), -hydroxy acids (eg citric acid, lactic acid, malic acid)
  • Humic acid bile acid, bile extracts, bilirubin, biliverdin, EDTA, EGTA and their derivatives, unsaturated fatty acids and their derivatives (eg ⁇ -linolenic acid, linoleic acid, oleic acid), folic acid and their derivatives, ubiquinone and ubiquinol and their derivatives, vitamin C and derivatives (e.g.
  • preparations according to the invention are very good vehicles for cosmetic or dermatological active ingredients in the skin, preferred active ingredients being antioxidants which can protect the skin against oxidative stress.
  • preferred active ingredients being antioxidants which can protect the skin against oxidative stress.
  • Preferred antioxidants are vitamin E and its derivatives and vitamin A and its derivatives.
  • the amount of the antioxidants (one or more compounds) in the preparations is preferably 0.001 to 30% by weight, particularly preferably 0.05-20% by weight, in particular 1-10% by weight, based on the total weight the preparation.
  • vitamin E and / or its derivatives represent the antioxidant (s)
  • vitamin A or vitamin A derivatives or carotenes or their derivatives represent the antioxidant or antioxidants, it is advantageous to use their respective concentrations in the range from 0.001-10% by weight, based on the total weight of the formulation, to choose.
  • Example 12 Hydrodispersion / Gel Cream

Abstract

L'invention concerne des préparations topiques contenant du 8-hexadecene-1, de l'acide dicarbonique 16 et au moins un autre agent actif sélectionné dans le groupe constitué par l'acide ursolique, le peptide appelé Agouti, un extrait de réglisse, l'hydrochinone, un extrait de thé vert, l'arbutine, la biotine, un extrait de mûrier (Uvae Ursii), la glycyrrhizine, un extrait de placenta, un glucoside d'ascorbyle, des antagonistes de l'endothéline issus d'un extrait de camomille.
EP03792423A 2002-08-22 2003-06-20 Preparation cosmetique et/ou dermatologique contenant un acide dicarbonique octadecene et un agent eclaircissant Withdrawn EP1572146A1 (fr)

Applications Claiming Priority (3)

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DE10238449A DE10238449A1 (de) 2002-08-22 2002-08-22 Kosmetische und/oder dermatologische Zubereitung
DE10238449 2002-08-22
PCT/EP2003/050249 WO2004017935A1 (fr) 2002-08-22 2003-06-20 Preparation cosmetique et/ou dermatologique contenant un acide dicarbonique octadecene et un agent eclaircissant

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EP1572146A1 true EP1572146A1 (fr) 2005-09-14

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DE102005023636A1 (de) * 2005-05-19 2006-11-23 Beiersdorf Ag Wirkstoffkombinationen aus Glucosylglyceriden und Kreatin und / oder Kreatinin
FR2889808B1 (fr) * 2005-08-17 2011-07-22 Oreal Utilisation de l'acide 8-hexadecene-1,16-dicarboxylique comme agent de soin destine a favoriser la cohesion de la couche cornee
DE102006009850A1 (de) * 2006-03-01 2007-09-06 Beiersdorf Ag Verwendung von Glycyrrhetinsäure und/oder Glycyrrhizin zur Herstellung kosmetischer Zubereitungen zur Bräunung der Haut
DE102006055043A1 (de) * 2006-11-17 2008-05-21 Beiersdorf Ag Kosmetische Formulierung mit Glucosylglyceriden und Hautaufhellern
US20090317341A1 (en) 2008-06-18 2009-12-24 Conopco, Inc., D/B/A Unilever Compositions for Lightening Skin Color
DE102008048328A1 (de) * 2008-09-16 2010-04-15 Beiersdorf Ag UV-Filter haltige O/W-Wirkstoffemulsion
WO2012024395A2 (fr) * 2010-08-19 2012-02-23 Johnson & Johnson Consumer Companies Inc. Compositions comprenant de la paulownine et/ou des extraits de paulownia et utilisations de celles-ci
US9173913B2 (en) 2010-08-19 2015-11-03 Johnson & Johnson Consumer Inc. Compositions comprising Paulownia tomentosa wood extracts and uses thereof
US9168279B2 (en) 2010-08-19 2015-10-27 Johnson & Johnson Consumer Inc. Compositions comprising paulownin and/or Paulownia extracts and uses thereof
US9168207B2 (en) 2010-08-19 2015-10-27 Johnson & Johnson Consumer Inc. Compositions comprising Paulownia tomentosa wood extracts and uses thereof
US9962326B2 (en) 2010-08-19 2018-05-08 Johnson & Johnson Consumer Inc. Compositions comprising paulownia tomentosa wood extracts and uses thereof
US9387349B2 (en) 2010-08-19 2016-07-12 Johnson & Johnson Consumer Inc. Compositions comprising Paulownia tomentosa wood extracts and uses thereof
US9161958B2 (en) 2010-08-19 2015-10-20 Johnson & Johnson Consumer Inc. Methods of treating cellulite
US9168219B2 (en) 2010-08-19 2015-10-27 Johnson & Johnson Consumer Inc. Compositions comprising Paulownia tomentosa wood extracts and uses thereof
EP2522335A1 (fr) 2011-05-09 2012-11-14 DSM IP Assets B.V. Utilisation de resvératrol et phosphate à ascorbyl de sodium
EP2522332A1 (fr) 2011-05-09 2012-11-14 DSM IP Assets B.V. Utilisation de resvératrol et phosphate à ascorbyl de magnésium
EP2522331A1 (fr) 2011-05-09 2012-11-14 DSM IP Assets B.V. Utilisation de resvératrol et nicotinamide
EP2522328A1 (fr) 2011-05-09 2012-11-14 DSM IP Assets B.V. Utilisation de resvératrol et ascorbyl-2-glucoside
EP2522329A1 (fr) 2011-05-09 2012-11-14 DSM IP Assets B.V. Utilisation de resvératrol et arbutine
EP2522330A1 (fr) 2011-05-09 2012-11-14 DSM IP Assets B.V. Utilisation de resvératrol et extrait d'edelweiss
WO2013104526A1 (fr) 2012-01-09 2013-07-18 Dsm Ip Assets B.V. Utilisation de danielone et de ses dérivés pour le soin de la peau
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FR3024037B1 (fr) 2014-07-25 2018-03-02 Sederma Ingredient actif cosmetique ou dermatologique comprenant un melange d'acides dicarboxyliques gras insatures, compositions le comprenant et utilisations cosmetiques ou dermatologiques
BR112022012785A2 (pt) * 2020-05-29 2022-12-13 Oreal Composições cosméticas e usos da composição cosmética

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