WO2011063865A2 - Cosmetic or dermatological preparations containing combinations of zingerone and interface- or surface-active citric acid esters - Google Patents

Cosmetic or dermatological preparations containing combinations of zingerone and interface- or surface-active citric acid esters Download PDF

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WO2011063865A2
WO2011063865A2 PCT/EP2010/004558 EP2010004558W WO2011063865A2 WO 2011063865 A2 WO2011063865 A2 WO 2011063865A2 EP 2010004558 W EP2010004558 W EP 2010004558W WO 2011063865 A2 WO2011063865 A2 WO 2011063865A2
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preparations
cosmetic
zingerone
citric acid
acid esters
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PCT/EP2010/004558
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German (de)
French (fr)
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WO2011063865A3 (en
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Stefan Heuser
Sabrina Ahlheit
Marc Winnefeld
Michael WÖHRMANN
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Beiersdorf Ag
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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/35Ketones, e.g. benzophenone
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37Esters of carboxylic acids
    • A61K8/375Esters of carboxylic acids the alcohol moiety containing more than one hydroxy group
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00Preparations for care of the skin
    • A61Q19/08Anti-ageing preparations

Definitions

  • Cosmetic or dermatological preparations containing combinations of zingerone and borderline or surface active citric acid esters containing combinations of zingerone and borderline or surface active citric acid esters
  • the present invention relates to cosmetic or dermatological preparations containing active ingredients for the care and protection of the skin, in particular the sensitive skin as well as especially in the foreground standing of intrinsic and / or extrinsic factors aged or aging skin and the use of such agents and combinations such active ingredients in the field of cosmetic and dermatological skin care.
  • Exogenous factors such as UV light and chemical noxae can be cumulatively effective and e.g. accelerate or supplement endogenous aging processes.
  • exogenous factors occur, e.g. on the following structural damage and dysfunction in the skin that go beyond the extent and quality of the damage caused by chronological aging: d) visible vascular dilations (telangiectasias, cuperosis);
  • CONFIRMATION COPY e slackness and formation of wrinkles
  • subcutaneous adipose tissue decreases in age, especially in the periphery (e.g., in the face), so that typical aging skin manifestations may occur.
  • the present invention relates in particular to products for the care of naturally aged skin, as well as for the treatment of the consequential damages of photoageing, in particular of the phenomena listed under a) to g).
  • Products for the care of aged skin are known per se. They contain e.g. Retinoids (vitamin A acid and / or derivatives thereof) or vitamin A and / or its derivatives. Their effect on the structural damage, however, is limited in scope. In addition, there are significant difficulties in product development in stabilizing the active ingredients sufficiently against oxidative degradation. In addition, the use of vitamin A acid-containing products often causes severe erythematous skin irritation. Retinoids can therefore only be used in low concentrations.
  • the present invention relates to cosmetic preparations capable of stimulating the subcutaneous adipose tissue of aging skin for increased fat synthesis.
  • the object of the present invention was therefore to find ways that avoid the disadvantages of the prior art.
  • the effect of repairing the damage associated with endogenous, chronological and exogenous skin aging and the prophylaxis should be permanent, sustainable and without the risk of side effects.
  • zingiberone stimulates the differentiation of pre-adipocytes into adipocytes and the accumulation of triglycerides in adipocytes.
  • Zingiberone (also zingerone, vanillylacetone, 4- (4-hydroxy-3-methoxyphenyl) butan-2-one) is characterized by the following structure:
  • Zingeron is a substance that is falsely claimed to be found in ginger.
  • zingerone is a substance which is first produced by the degradation of substances found in ginger such as e.g. Gingerols is produced and their occurrence in extracts is a measure of their poor and barely usable quality (Hänsel, Stichler, Pharmacognosia Phytopharmacy, 7th edition, Springer-Verlag, p 617). In fact, economically and biologically meaningful amounts can only be obtained by chemical synthesis.
  • zingerone is completely protonated at a pH of about 5. This is about the pH of healthy skin, and cosmetic and dermatological preparations are also often buffered in the slightly acidic pH range. As a phenol derivative, zingerone is more volatile in this protonated form and therefore smells more easily than at higher pHs.
  • a further object of the present invention was therefore to provide preparations in which potentially unpleasant odor could emanate from zingerone, could be reduced or even prevented, without it becoming necessary to base the pH.
  • the solution to these objects is present in cosmetic or dermatological preparations containing combinations of zingerone and one or more surface- or interface-active citric acid esters.
  • the invention furthermore relates to the use of combinations of zingerone and surface-active or surface-active citric esters for the preparation of cosmetic or dermatological preparations for the treatment and prophylaxis of the symptoms of intrinsic and / or extrinsic skin aging.
  • the invention furthermore relates to the use of one or more surface-active or surface-active citric acid esters for reducing or preventing unpleasant odors caused by zingerone, in particular in cosmetic or dermatological preparations, preferably those which are buffered to a slightly acidic pH.
  • the preparations according to the invention are particularly advantageously in the form of emulsions.
  • a particularly advantageous surface or surface active citric acid ester is glyceryl stearate citrate and glyceryl stearate tartrate.
  • Cosmetic or dermatological preparations according to the invention preferably contain from 0.001 to 10% by weight, particularly preferably from 0.01 to 1% by weight, of zingiberone, based on the total composition of the preparations.
  • Cosmetic or dermatological preparations according to the invention preferably contain 0.001-10% by weight of one or more surface-active or surface-active citric acid esters, based on the total weight of the preparations.
  • Emulsions are advantageous dosage forms in the sense of the present invention, e.g. in the form of a cream, a lotion, a cosmetic milk are advantageous and contain e.g. Fats, oils, waxes and / or other fatty substances, as well as water and one or more emulsifiers, as they are commonly used for such a type of formulation.
  • Medicinal topical compositions according to the present invention usually contain one or more drugs in effective concentration.
  • the simplicity For a clear distinction between cosmetic and medical use and corresponding products, reference is made to the statutory provisions of the Federal Republic of Germany (eg Cosmetics Ordinance, Food and Medicinal Products Act).
  • the cosmetic or dermatological preparation in the sense of the present invention is a solution or emulsion or dispersion, it is possible to use as solvent:
  • oils such as triglycerides of capric or caprylic acid, but preferably castor oil; Fats, waxes and other natural and synthetic fats, preferably esters of fatty acids with lower C-number alcohols, e.g. with isopropanol, propylene glycol or glycerol, or esters of fatty alcohols with alkanoic acids of low C number or with fatty acids;
  • 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 monobutyl ether, diethylene glycol monomethyl or monoethyl ether and analogous products ,
  • mixtures of the abovementioned solvents are used.
  • alcoholic solvents water can be another ingredient.
  • 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 carbon atoms and saturated and / or or unsaturated, branched and / or unbranched alcohols having a chain length of from 3 to 30 carbon atoms, from the group of esters of aromatic carboxylic acids and saturated and / or unsaturated, branched and / or unbranched alcohols having a chain length of 3 to 30 carbon atoms.
  • ester oils can then advantageously be selected from the group isopropyl myristate, isopropyl palmitate, isopropyl stearate, isopropyl oleate, n-butyl stearate, n-hexyl laurate, n-decyl oleate, isooctyl stearate, isononyl stearate, isononyl isononanoate, 2-ethylhexyl palmitate, 2-ethylhexyl laurate, 2-hexyldecyl stearate, 2 Octyldodecyl palmitate, oleyl oleate, oleyl erucate, erucyl oleate, erucyl erucate and also synthetic, semisynthetic and natural mixtures of such esters, eg jojoba oil.
  • the oil phase can be advantageously 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 the fatty acid triglycerides, namely the triglycerol esters of saturated and / or unsaturated, branched and / or unbranched alkanecarboxylic acids of a chain length of 8 to 24, in particular 12 to 18 carbon atoms.
  • the fatty acid triglycerides may be advantageously selected from the group of synthetic, semisynthetic and natural oils, e.g. Olive oil, sunflower oil, soybean oil, peanut oil, rapeseed oil, almond oil, palm oil, coconut oil, palm kernel oil, and the like.
  • the aqueous phase of the preparations according to the invention advantageously 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 monobutyl ether , Diethylenglykolmonomethyl- or -monoethylether and analogous products, furthermore low C-number alcohols, eg Ethanol, isopropanol, 1, 2-propanediol, glycerol and in particular one or more thickening agents, which or which can be advantageously selected from the group of silica, aluminum silicates, polysaccharides or their derivatives, e.g.
  • Hyaluronic acid, xanthan gum, hydroxypropylmethylcellulose particularly advantageously from the group of polyacrylates, preferably a polyacrylate from the group of the 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.
  • Gels used according to the invention usually contain alcohols of low C number, for example ethanol, isopropanol, 1,2-propanediol, glycerol and water or one mentioned above Oil in the presence of a thickener, which is preferably silica or an aluminum silicate in oily-alcoholic gels, preferably a polyacrylate in aqueous-alcoholic or alcoholic gels.
  • a thickener which is preferably silica or an aluminum silicate in oily-alcoholic gels, preferably a polyacrylate in aqueous-alcoholic or alcoholic gels.
  • Fixed pins contain e.g. natural or synthetic waxes, fatty alcohols or fatty acid esters.
  • liquid oils for example paraffin oils, castor oil, isopropyl myristate
  • semi-solid constituents eg petrolatum, lanolin
  • solid constituents eg beeswax, ceresin and microcrystalline Waxes or ozokerite
  • high-melting waxes eg carnauba wax, candelilla wax
  • Suitable propellants for sprayable from aerosol containers cosmetic and / or dermatological preparations in the context of the present invention the usual known volatile, liquefied propellants, such as hydrocarbons (propane, butane, isobutane) are suitable, which can be used alone or in mixture with each other. Also, compressed air is advantageous to use.
  • hydrocarbons propane, butane, isobutane

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Abstract

The invention relates to cosmetic or dermatological preparations containing combinations of zingerone and surface- or interface-active citric acid esters.

Description

Beschreibung  description
Kosmetische oder dermatologische Zubereitungen enthaltend Kombinationen aus Zingeron und grenz- oder oberflächenaktiven Citronensäureestern Cosmetic or dermatological preparations containing combinations of zingerone and borderline or surface active citric acid esters
Die vorliegende Erfindung betrifft kosmetische bzw. dermatologische Zubereitungen, enthaltend Wirkstoffe zur Pflege und zum Schutze der Haut, insbesondere der empfindlichen Haut wie auch ganz besonders im Vordergrunde stehend der durch intrinsische und/oder extrinsische Faktoren gealterten oder alternden Haut sowie die Verwendung solcher Wirkstoffe und Kombinationen solcher Wirkstoffe auf dem Gebiete der kosmetischen und dermatologischen Hautpflege. The present invention relates to cosmetic or dermatological preparations containing active ingredients for the care and protection of the skin, in particular the sensitive skin as well as especially in the foreground standing of intrinsic and / or extrinsic factors aged or aging skin and the use of such agents and combinations such active ingredients in the field of cosmetic and dermatological skin care.
Die chronologische Hautalterung wird z.B. durch endogene, genetisch determinierte Faktoren verursacht. In Epidermis und Dermis kommt es alterungsbedingt z.B. zu folgenden Strukturschäden und Funktionsstörungen, die auch unter den Begriff„Senile Xerosis" fallen können: a) Trockenheit, Rauhigkeit und Ausbildung von Trockenheitsfältchen, Chronic skin aging is e.g. caused by endogenous, genetically determined factors. In epidermis and dermis, age-related e. on the following structural damage and dysfunctions, which may also fall under the term "senile xerosis": a) dryness, roughness and formation of dryness lines,
b) Juckreiz und b) itching and
c) verminderte Rückfettung durch Talgdrüsen (z.B. nach Waschen). c) Reduced fatty acid regurgitation (e.g., after washing).
Exogene Faktoren, wie UV-Licht und chemische Noxen, können kumulativ wirksam sein und z.B. die endogenen Alterungsprozesse beschleunigen bzw. sie ergänzen. In Epidermis und Dermis kommt es insbesondere durch exogene Faktoren z.B. zu folgenden Strukturschäden- und Funktionsstörungen in der Haut, die über Maß und Qualität der Schäden bei chronologischer Alterung hinausgehen: d) Sichtbare Gefäßerweiterungen (Teleangiektasien, Cuperosis); Exogenous factors such as UV light and chemical noxae can be cumulatively effective and e.g. accelerate or supplement endogenous aging processes. In epidermis and dermis, exogenous factors occur, e.g. on the following structural damage and dysfunction in the skin that go beyond the extent and quality of the damage caused by chronological aging: d) visible vascular dilations (telangiectasias, cuperosis);
1  1
BESTÄTIGUNGSKOPIE e) Schlaffheit und Ausbildung von Falten; CONFIRMATION COPY e) slackness and formation of wrinkles;
f) lokale Hyper-, Hypo- und Fehlpigmentierungen (z.B. Altersflecken) und f) local hyper, hypo and false pigmentation (e.g., age spots) and
g) vergrößerte Anfälligkeit gegenüber mechanischem Stress (z.B. Rissigkeit). g) increased susceptibility to mechanical stress (e.g., cracking).
Insbesondere nimmt im Alter das subkutane Fettgewebe, insbesondere in der Peripherie (z.B. im Gesicht) ab, sodaß es zu typischen Altershauterscheinungen kommen kann. In particular, subcutaneous adipose tissue decreases in age, especially in the periphery (e.g., in the face), so that typical aging skin manifestations may occur.
Die vorliegende Erfindung betrifft insbesondere Produkte zur Pflege der auf natürliche Weise gealterten Haut, sowie zur Behandlung der Folgeschäden der Lichtalterung, insbesondere der unter a) bis g) aufgeführten Phänomene. The present invention relates in particular to products for the care of naturally aged skin, as well as for the treatment of the consequential damages of photoageing, in particular of the phenomena listed under a) to g).
Produkte zur Pflege gealterter Haut sind an sich bekannt. Sie enthalten z.B. Retinoide (Vitamin A-Säure und/oder deren Derivate) bzw. Vitamin A und/oder dessen Derivate. Ihre Wirkung auf die Strukturschäden ist allerdings umfangsmäßig begrenzt. Daüber hinaus gibt es bei der Produktentwicklung erhebliche Schwierigkeiten, die Wirkstoffe in ausreichendem Maße gegen oxidativen Zerfall zu stabilisieren. Die Verwendung Vitamin A-Säure-haltiger Produkte bedingt darüber hinaus oft starke erythematode Hautreizungen. Retinoide sind daher nur in geringen Konzentrationen einsetzbar. Products for the care of aged skin are known per se. They contain e.g. Retinoids (vitamin A acid and / or derivatives thereof) or vitamin A and / or its derivatives. Their effect on the structural damage, however, is limited in scope. In addition, there are significant difficulties in product development in stabilizing the active ingredients sufficiently against oxidative degradation. In addition, the use of vitamin A acid-containing products often causes severe erythematous skin irritation. Retinoids can therefore only be used in low concentrations.
Insbesondere betrifft die vorliegende Erfindung kosmetische Zubereitungen, die imstande sind, das subkutane Fettgewebe der Altershaut zur gesteigerten Fettsynthese zu stimulieren. In particular, the present invention relates to cosmetic preparations capable of stimulating the subcutaneous adipose tissue of aging skin for increased fat synthesis.
Aufgabe der vorliegenden Erfindung war es somit, Wege zu finden, die die Nachteile des Standes der Technik vermeiden. Insbesondere soll die Wirkung der Behebung der mit der endogenen, chronologischen und exogenen Hautalterung verbundenen Schäden und die Prophylaxe dauerhaft, nachhaltig und ohne das Risiko von Nebenwirkungen sein. The object of the present invention was therefore to find ways that avoid the disadvantages of the prior art. In particular, the effect of repairing the damage associated with endogenous, chronological and exogenous skin aging and the prophylaxis should be permanent, sustainable and without the risk of side effects.
Es hat sich überraschenderweise herausgestellt, daß Zingiberon die Differenzierung von Prä-Adipozyten zu Adipozyten und die Akkumulation von Triglyceriden in Adipozyten anregt. It has surprisingly been found that zingiberone stimulates the differentiation of pre-adipocytes into adipocytes and the accumulation of triglycerides in adipocytes.
Zingiberon (auch Zingeron, Vanillylaceton, 4-(4-Hydroxy-3-methoxyphenyl)butan-2-on ) ist durch die folgende Struktur gekennzeichnet:
Figure imgf000004_0001
Zingiberone (also zingerone, vanillylacetone, 4- (4-hydroxy-3-methoxyphenyl) butan-2-one) is characterized by the following structure:
Figure imgf000004_0001
Zingeron ist ein Stoff, von dem fälschlicherweise häufig behauptet wird, daß er in Ingwer zu finden sei. Tatsächlich jedoch ist Zingeron eine Substanz, die erst durch den Abbau von in Ingwer vorkommenden Substanzen wie z.B. Gingerolen entsteht und deren Vorkommen in Extrakten ein Maß für deren mangelhafte und kaum nutzbare Qualität ist (Hänsel, Stichler; Pharmakognosie Phytopharmazie, 7. Auflage, Springer-Verlag, S. 617). In der Tat ist es so, daß wirtschaftlich und biologisch sinnvolle Mengen nur durch chemische Synthese gewonnen werden können. Zingeron is a substance that is falsely claimed to be found in ginger. In fact, however, zingerone is a substance which is first produced by the degradation of substances found in ginger such as e.g. Gingerols is produced and their occurrence in extracts is a measure of their poor and barely usable quality (Hänsel, Stichler, Pharmacognosia Phytopharmacy, 7th edition, Springer-Verlag, p 617). In fact, economically and biologically meaningful amounts can only be obtained by chemical synthesis.
Nachteilig an Zingeron ist, daß es bei einem pH-Wert von etwa 5 vollständig protoniert ist. Das ist ungefähr der pH-Wert der gesunden Haut, und kosmetische und dermatologische Zubereitungen werden zudem häufig im leicht sauren pH-Bereich gepuffert. Als Phenolderivat ist Zingeron in dieser protonierten Form flüchtiger und damit leichter riechbar als bei höheren pH-Werten. A disadvantage of zingerone is that it is completely protonated at a pH of about 5. This is about the pH of healthy skin, and cosmetic and dermatological preparations are also often buffered in the slightly acidic pH range. As a phenol derivative, zingerone is more volatile in this protonated form and therefore smells more easily than at higher pHs.
Eine weitere Aufgabe der vorliegenden Erfindung war es daher, Zubereitungen zur Verfügung zu stellen, in welcher potentiell unangenehmer Geruch der von Zingeron ausgehen könnte, vermindert oder gar verhindert werden könnte, ohne, daß es notwendig würde, den pH-Wert basisch zu stellen. A further object of the present invention was therefore to provide preparations in which potentially unpleasant odor could emanate from zingerone, could be reduced or even prevented, without it becoming necessary to base the pH.
Die Lösung dieser Aufgaben besteht erfindungegsgemäß in kosmetischen oder dermatologischen Zubereitungen, enthaltend Kombinationen aus Zingeron und einem oder mehreren ober- oder grenzflächenaktiven Citronensäureestern. Erfindungsgemäß ist ferner die Verwendung von Kombinationen aus Zingeron und ober- oder grenzflächenaktiven Citronensäureestern zur Herstellung kosmetischer oder dermatologischer Zubereitungen zur Behandlung und Prophylaxe der Symptome der intrinsischen und/oder extrinsischen Hautalterung. According to the invention, the solution to these objects is present in cosmetic or dermatological preparations containing combinations of zingerone and one or more surface- or interface-active citric acid esters. The invention furthermore relates to the use of combinations of zingerone and surface-active or surface-active citric esters for the preparation of cosmetic or dermatological preparations for the treatment and prophylaxis of the symptoms of intrinsic and / or extrinsic skin aging.
Erfindungsgemäß ist weiterhin die Verwendung einer oder mehrerer ober- oder grenzflächenaktiven Citronensäureestern zur Verminderung oder Verhinderung unangenehmer Gerüche, hervorgerufen durch Zingeron, insbesondere in kosmetischen oder dermatologischen Zubereitungen, bevorzugt solchen, die auf einen leicht sauren pH-Wert gepuffert sind. The invention furthermore relates to the use of one or more surface-active or surface-active citric acid esters for reducing or preventing unpleasant odors caused by zingerone, in particular in cosmetic or dermatological preparations, preferably those which are buffered to a slightly acidic pH.
Besonders vorteilhaft liegen die erfindungsgemäßen Zubereitungen in Form von Emulsionen vor. The preparations according to the invention are particularly advantageously in the form of emulsions.
Ein besonders vorteilhafter ober- oder grenzflächenaktiver Citronensäureester sind Glycerylstearatcitrat und Glycerylstearattartrat, . A particularly advantageous surface or surface active citric acid ester is glyceryl stearate citrate and glyceryl stearate tartrate.
Bevorzugt enthalten kosmetische oder dermatologische Zubereitungen gemäß der Erfindung 0,001 - 10 Gew.-%, besonders bevorzugt 0,01 - 1 Gew.-% Zingiberon, bezogen auf die Gesamtzusammensetzung der Zubereitungen. Cosmetic or dermatological preparations according to the invention preferably contain from 0.001 to 10% by weight, particularly preferably from 0.01 to 1% by weight, of zingiberone, based on the total composition of the preparations.
Bevorzugt enthalten kosmetische oder dermatologische Zubereitungen gemäß der Erfindung 0,001 - 10 Gew.-% an einem oder mehreren ober- oder grenzflächenaktiven Citronensäureestern, bezogen auf das Gesamtgewicht der Zubereitungen. Cosmetic or dermatological preparations according to the invention preferably contain 0.001-10% by weight of one or more surface-active or surface-active citric acid esters, based on the total weight of the preparations.
Emulsionen sind vorteilhafte Darreichungsformen im Sinne der vorliegenden Erfindung, z.B. in Form einer Creme, einer Lotion, einer kosmetischen Milch sind vorteilhaft und enthalten z.B. Fette, öle, Wachse und/oder andere Fettkörper, sowie Wasser und einen oder mehrere Emulgatoren, wie sie üblicherweise für einen solchen Typ der Formulierung verwendet werden. Emulsions are advantageous dosage forms in the sense of the present invention, e.g. in the form of a cream, a lotion, a cosmetic milk are advantageous and contain e.g. Fats, oils, waxes and / or other fatty substances, as well as water and one or more emulsifiers, as they are commonly used for such a type of formulation.
Medizinische topische Zusammensetzungen im Sinne der vorliegenden Erfindung enthalten in der Regel ein oder mehrere Medikamente in wirksamer Konzentration. Der Einfachheit halber wird zur sauberen Unterscheidung zwischen kosmetischer und medizinischer Anwendung und entsprechenden Produkten auf die gesetzlichen Bestimmungen der Bundesrepublik Deutschland verwiesen (z.B. Kosmetikverordnung, Lebensmittel- und Arzneimittelgesetz). Medicinal topical compositions according to the present invention usually contain one or more drugs in effective concentration. The simplicity For a clear distinction between cosmetic and medical use and corresponding products, reference is made to the statutory provisions of the Federal Republic of Germany (eg Cosmetics Ordinance, Food and Medicinal Products Act).
Es ist dabei ebenfalls von Vorteil, den erfindungsgemäß verwendeten Wirkstoff als Zusatzstoff zu Zubereitungen zu geben, die bereits andere Wirkstoffe für andere Zwecke enthalten. It is also advantageous to add the active ingredient used according to the invention as an additive to preparations which already contain other active ingredients for other purposes.
Sofern die kosmetische oder dermatologische Zubereitung im Sinne der vorliegenden Erfindung eine Lösung oder Emulsion oder Dispersion darstellt, können als Lösungsmittel verwendet werden: If the cosmetic or dermatological preparation in the sense of the present invention is a solution or emulsion or dispersion, it is possible to use as solvent:
Wasser oder wäßrige Lösungen  Water or aqueous solutions
öle, wie Triglyceride der Caprin- oder der Caprylsäure, vorzugsweise aber Rizinusöl; Fette, Wachse und andere natürliche und synthetische Fettkörper, vorzugsweise Ester von Fettsäuren mit Alkoholen niedriger C-Zahl, z.B. mit Isopropanol, Propylenglykol oder Glycerin, oder Ester von Fettalkoholen mit Alkansäuren niedriger C-Zahl oder mit Fettsäuren;  oils, such as triglycerides of capric or caprylic acid, but preferably castor oil; Fats, waxes and other natural and synthetic fats, preferably esters of fatty acids with lower C-number alcohols, e.g. with isopropanol, propylene glycol or glycerol, or esters of fatty alcohols with alkanoic acids of low C number or with fatty acids;
Alkohole, Diole oder Polyole niedriger C-Zahl, sowie deren Ether, vorzugsweise Ethanol, Isopropanol, Propylenglykol, Glycerin, Ethylenglykol, Ethylenglykol- monoethyl- oder -monobutylether, Propylenglykolmonomethyl, -monoethyl- oder - monobutylether, Diethylenglykolmonomethyl- oder -monoethylether und analoge Produkte.  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 monobutyl ether, diethylene glycol monomethyl or monoethyl ether and analogous products ,
Insbesondere werden Gemische der vorstehend genannten Lösungsmittel verwendet. Bei alkoholischen Lösungsmitteln kann Wasser ein weiterer Bestandteil sein. In particular, mixtures of the abovementioned solvents are used. For alcoholic solvents, water can be another ingredient.
Die ölphase der Emulsionen, Oleogele bzw. Hydrodispersionen oder Lipodispersionen im Sinne der vorliegenden Erfindung wird vorteilhaft gewählt aus der Gruppe der Ester aus gesättigten und/oder ungesättigten, verzweigten und/oder unverzweigten Alkancarbonsäuren einer Kettenlänge von 3 bis 30 C-Atomen und gesättigten und/oder ungesättigten, verzweigten und/oder unverzweigten Alkoholen einer Kettenlänge von 3 bis 30 C-Atomen, aus der Gruppe der Ester aus aromatischen Carbonsäuren und gesättigten und/oder ungesättigten, verzweigten und/oder unverzweigten Alkoholen einer Kettenlänge von 3 bis 30 C-Atomen. Solche Esteröle können dann vorteilhaft gewählt werden aus der Gruppe Isopropylmyristat, Isopropylpalmitat, Isopropylstearat, Isopropyloleat, n-Butylstearat, n-Hexyllaurat, n- Decyloleat, Isooctylstearat, Isononylstearat, Isononylisononanoat, 2-Ethylhexylpalmitat, 2- Ethylhexyllaurat, 2-Hexyldecylstearat, 2-Octyldodecylpalmitat, Oleyloleat, Oleylerucat, Eru- cyloleat, Erucylerucat sowie synthetische, halbsynthetische und natürliche Gemische solcher Ester, z.B. Jojobaöl. 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 carbon atoms and saturated and / or or unsaturated, branched and / or unbranched alcohols having a chain length of from 3 to 30 carbon atoms, from the group of esters of aromatic carboxylic acids and saturated and / or unsaturated, branched and / or unbranched alcohols having a chain length of 3 to 30 carbon atoms. Such ester oils can then advantageously be selected from the group isopropyl myristate, isopropyl palmitate, isopropyl stearate, isopropyl oleate, n-butyl stearate, n-hexyl laurate, n-decyl oleate, isooctyl stearate, isononyl stearate, isononyl isononanoate, 2-ethylhexyl palmitate, 2-ethylhexyl laurate, 2-hexyldecyl stearate, 2 Octyldodecyl palmitate, oleyl oleate, oleyl erucate, erucyl oleate, erucyl erucate and also synthetic, semisynthetic and natural mixtures of such esters, eg jojoba oil.
Ferner kann die ölphase vorteilhaft gewählt werden aus der Gruppe der verzweigten und unverzweigten Kohlenwasserstoffe und -wachse, der Silkonöle, der Dialkylether, der Gruppe der gesättigten oder ungesättigten, verzweigten oder unverzweigten Alkohole, sowie der Fettsäuretriglyceride, namentlich der Triglycerinester gesättigter und/oder ungesättigter, verzweigter und/oder unverzweigter Alkancarbonsäuren einer Kettenlänge von 8 bis 24, insbesondere 12 - 18 C-Atomen. Die Fettsäuretriglyceride können beispielsweise vorteilhaft gewählt werden aus der Gruppe der synthetischen, halbsynthetischen und natürlichen öle, z.B. Olivenöl, Sonnenblumenöl, Sojaöl, Erdnußöl, Rapsöl, Mandelöl, Palmöl, Kokosöl, Palmkernöl und dergleichen mehr. Furthermore, the oil phase can be advantageously 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 the fatty acid triglycerides, namely the triglycerol esters of saturated and / or unsaturated, branched and / or unbranched alkanecarboxylic acids of a chain length of 8 to 24, in particular 12 to 18 carbon atoms. For example, the fatty acid triglycerides may be advantageously selected from the group of synthetic, semisynthetic and natural oils, e.g. Olive oil, sunflower oil, soybean oil, peanut oil, rapeseed oil, almond oil, palm oil, coconut oil, palm kernel oil, and the like.
Die wäßrige Phase der erfindungsgemäßen Zubereitungen enthält gegebenenfalls vorteilhaft Alkohole, Diole oder Polyole niedriger C-Zahl, sowie deren Ether, vorzugsweise Ethanol, Isopropanol, Propylenglykol, Glycerin, Ethylenglykol, Ethylenglykolmonoethyl- oder -monobutylether, Propylenglykolmonomethyl, -monoethyl- oder -monobutyl- ether, Diethylenglykolmonomethyl- oder -monoethylether und analoge Produkte, ferner Alkohole niedriger C-Zahl, z.B. Ethanol, Isopropanol, 1 ,2-Propandiol, Glycerin sowie insbesondere ein oder mehrere Verdickungsmittel, welches oder welche vorteilhaft gewählt werden können aus der Gruppe Siliciumdioxid, Aluminiumsilikate, Polysaccharide bzw. deren Derivate, z.B. Hyaluronsäure, Xanthangummi, Hydroxypro- pylmethylcellulose, besonders vorteilhaft aus der Gruppe der Polyacrylate, bevorzugt ein Polyacrylat aus der Gruppe der sogenannten Carbopole, beispielsweise Carbo- pole der Typen 980, 981 , 1382, 2984, 5984, jeweils einzeln oder in Kombination. If appropriate, the aqueous phase of the preparations according to the invention advantageously 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 monobutyl ether , Diethylenglykolmonomethyl- or -monoethylether and analogous products, furthermore low C-number alcohols, eg Ethanol, isopropanol, 1, 2-propanediol, glycerol and in particular one or more thickening agents, which or which can be advantageously selected from the group of silica, aluminum silicates, polysaccharides or their derivatives, e.g. Hyaluronic acid, xanthan gum, hydroxypropylmethylcellulose, particularly advantageously from the group of polyacrylates, preferably a polyacrylate from the group of the so-called carbopols, for example carbopols of types 980, 981, 1382, 2984, 5984, in each case individually or in combination.
Erfindungsgemäß verwendete Gele enthalten üblicherweise Alkohole niedriger C-Zahl, z.B. Ethanol, Isopropanol, 1 ,2-Propandiol, Glycerin und Wasser bzw. ein vorstehend genanntes öl in Gegenwart eines Verdickungsmittels, das bei ölig-alkoholischen Gelen vorzugsweise Siliciumdioxid oder ein Aluminiumsilikat, bei wäßrig-alkoholischen oder alkoholischen Gelen vorzugweise ein Polyacrylat ist. Gels used according to the invention usually contain alcohols of low C number, for example ethanol, isopropanol, 1,2-propanediol, glycerol and water or one mentioned above Oil in the presence of a thickener, which is preferably silica or an aluminum silicate in oily-alcoholic gels, preferably a polyacrylate in aqueous-alcoholic or alcoholic gels.
Feste Stifte enthalten z.B. natürliche oder synthetische Wachse, Fettalkohole oder Fettsäureester. Fixed pins contain e.g. natural or synthetic waxes, fatty alcohols or fatty acid esters.
Übliche Grundstoffe, welche für die Verwendung als kosmetische Stifte im Sinne der vorliegenden Erfindung geeignet sind, sind flüssige öle (z.B. Paraffinöle, Ricinusöl, Isopropyl- myristat), halbfeste Bestandteile (z.B. Vaseline, Lanolin), feste Bestandteile (z.B. Bienenwachs, Ceresin und Mikrokristalline Wachse bzw. Ozokerit) sowie hochschmelzende Wachse (z.B. Carnaubawachs, Candelillawachs) Conventional base materials which are suitable for use as cosmetic sticks in the context of the present invention are liquid oils (for example paraffin oils, castor oil, isopropyl myristate), semi-solid constituents (eg petrolatum, lanolin), solid constituents (eg beeswax, ceresin and microcrystalline Waxes or ozokerite) and high-melting waxes (eg carnauba wax, candelilla wax)
Als Treibmittel für aus Aerosolbehältern versprühbare kosmetische und/oder dermatologische Zubereitungen im Sinne der vorliegenden Erfindung sind die üblichen bekannten leichtflüchtigen, verflüssigten Treibmittel, beispielsweise Kohlenwasserstoffe (Propan, Butan, Isobutan) geeignet, die allein oder in Mischung miteinander eingesetzt werden können. Auch Druckluft ist vorteilhaft zu verwenden. Suitable propellants for sprayable from aerosol containers cosmetic and / or dermatological preparations in the context of the present invention, the usual known volatile, liquefied propellants, such as hydrocarbons (propane, butane, isobutane) are suitable, which can be used alone or in mixture with each other. Also, compressed air is advantageous to use.
Die nachfolgenden Beispiele sollen die vorliegende Erfindung verdeutlichen. The following examples are intended to illustrate the present invention.
Anti-Falten-Creme (Beispiele 1 Anti-Wrinkle Cream (Examples 1
Figure imgf000009_0001
Butylenglykol — — 4,00 —
Figure imgf000009_0001
Butylene Glycol - - 4.00 -
Natriumydroxid q.s. q.s. q.s. q.s.Sodium hydroxide q.s. q.s. q.s. q.s.
Wasser ad 100 ad 100 ad 100 ad 100 Water ad 100 ad 100 ad 100 ad 100

Claims

Patentansprüche: claims:
1. Kosmetische oder dermatologische Zubereitungen, enthaltend Kombinationen aus Zingeron und ober- oder grenzflächenaktiven Citronensäureestern. 1. Cosmetic or dermatological preparations containing combinations of zingerone and surface or surface active citric acid esters.
2. Verwendung von Kombinationen aus Zingeron und ober- oder grenzflächenaktiven Citronensäureestern zur Herstellung kosmetischer oder dermatologischer Zubereitungen zur Behandlung und Prophylaxe der Symptome der intrinsischen und/oder extrinsischen Hautalterung. 2. Use of combinations of zingerone and surfactant or surface active citric esters for the preparation of cosmetic or dermatological preparations for the treatment and prophylaxis of the symptoms of intrinsic and / or extrinsic skin aging.
3. Verwendung einer oder mehrerer ober- oder grenzflächenaktiven Citronensäureestern zur Verminderung oder Verhinderung unangenehmer Gerüche, hervorgerufen durch Zingeron, insbesondere in kosmetischen oder dermatologischen Zubereitungen, bevorzugt solchen, die auf einen leicht sauren pH-Wert gepuffert sind. 3. Use of one or more surface-active or surface-active citric acid esters for reducing or preventing unpleasant odors caused by zingerone, in particular in cosmetic or dermatological preparations, preferably those which are buffered to a slightly acidic pH.
4. Zubereitungen nach Anspruch 1 oder Verwendung nach Anspruch 2, wobei die Zubereitungen, 0,001 - 10 Gew.-% Zingeron, bezogen auf das Gesamtgewicht der Zubereitungen enthalten. 4. Preparations according to claim 1 or use according to claim 2, wherein the preparations, 0.001 - 10 wt .-% zingerone, based on the total weight of the preparations.
5. Zubereitungen oder Verwendung nach einem der vorstehenden Ansprüche, wobei die Zubereitungen, 0,001 - 10 Gew.-% an einer oder mehreren ober- oder grenzflächenaktiven Citronensäureestern, bezogen auf das Gesamtgewicht der Zubereitungen enthalten. 5. Preparations or use according to one of the preceding claims, wherein the preparations, 0.001 - 10 wt .-% of one or more surface or surface active citric acid esters, based on the total weight of the preparations.
6 . Zubereitungen oder Verwendung nach einem der vorstehenden Ansprüche, wobei als ober- oder grenzflächenaktiver Citronensäureester das Glycerylstearatcitrat und/oder das Glycerylstearattartrat gewählt wird. 6. Preparations or use according to one of the preceding claims, wherein the glyceryl stearate citrate and / or the glyceryl stearate tartrate is chosen as the surface or surface active citric acid ester.
PCT/EP2010/004558 2009-11-27 2010-07-26 Cosmetic or dermatological preparations containing combinations of zingerone and interface- or surface-active citric acid esters WO2011063865A2 (en)

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