WO2007096088A1 - Preparations effective against blemished skin and mild forms of acne with a content of hydroxymatairesinol as active principle - Google Patents

Preparations effective against blemished skin and mild forms of acne with a content of hydroxymatairesinol as active principle Download PDF

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Publication number
WO2007096088A1
WO2007096088A1 PCT/EP2007/001352 EP2007001352W WO2007096088A1 WO 2007096088 A1 WO2007096088 A1 WO 2007096088A1 EP 2007001352 W EP2007001352 W EP 2007001352W WO 2007096088 A1 WO2007096088 A1 WO 2007096088A1
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Prior art keywords
acne
hydroxymatairesinol
oil
preparations
mild forms
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PCT/EP2007/001352
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German (de)
French (fr)
Inventor
Anette Bürger
Svena Cerv
Julia Eckert
Ludger Kolbe
Christopher Mummert
Gitta Neufang
Michael WÖHRMANN
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Beiersdorf Ag
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    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/34—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
    • A61K31/341—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide not condensed with another ring, e.g. ranitidine, furosemide, bufetolol, muscarine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/557—Eicosanoids, e.g. leukotrienes or prostaglandins
    • A61K31/558—Eicosanoids, e.g. leukotrienes or prostaglandins having heterocyclic rings containing oxygen as the only ring hetero atom, e.g. thromboxanes
    • A61K31/5585—Eicosanoids, e.g. leukotrienes or prostaglandins having heterocyclic rings containing oxygen as the only ring hetero atom, e.g. thromboxanes having five-membered rings containing oxygen as the only ring hetero atom, e.g. prostacyclin
    • 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
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/10—Anti-acne agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A61P7/08—Plasma substitutes; Perfusion solutions; Dialytics or haemodialytics; Drugs for electrolytic or acid-base disorders, e.g. hypovolemic shock
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A61P7/10—Antioedematous agents; Diuretics
    • 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
    • A61Q19/10—Washing or bathing preparations

Definitions

  • the present invention relates to active ingredients and preparations containing such active ingredients which are effective against blemished skin and mild forms of acne.
  • Impure skin and / or comedones affect the well-being of those affected but even in mild cases. Since virtually every adolescent or person is affected by blemished skin of some kind, many people need to remedy this condition.
  • Object of the present invention was therefore to find against blemished skin, mild forms of acne or Propionibacterium acnes active substance.
  • Hydroxymatairesinol is a so-called lignan.
  • Lignans are dimers of phenylpropane derivatives which are linked to one another via the C-2 atom of the propane chain (2,2'-linkage). These are mostly colorless, crystalline, hardly volatile compounds without odor and striking taste. They are formed as compounds of plant secondary metabolism probably by radical-oxidative coupling of two phenylpropane derivatives.
  • Hydroxymatairesinol as such occurs in the spruce (Picea abies) and is obtainable, for example, by methods as described by Eklund, Lindholm, Mikkola, Smeda, Lehtilä and Söholm in the essay "Synthesis of (-) - matairesinol, (-) - enterolactone, and (-) - enterodiol from the natural lignan hydroxymatairesinol "in Org. Lett.2003, 5, pp. 491-493.
  • the cosmetic preparations according to the invention against blemished skin or against mild forms of acne are particularly advantageously characterized in that the hydroxymatairesinol is present in concentrations of 0.05-10.00% by weight, preferably 0.1-5.0% by weight. , in each case based on the total weight of the preparations.
  • the preparations according to the invention which are active against blemished skin or mild forms of acne may be in the form of liquid compositions which can be applied by means of paint brushes or wipers or roll-on devices, as pens and in the form of W / O or O can be applied from normal bottles and containers.
  • W emulsions eg Creams or lotions.
  • the preparations according to the invention which are active against impure skin can advantageously be in the form of face lotions, tinctures or cleansing formulations.
  • emulsifiers for the preparation of the present invention against blemished skin or mild forms of acne effective preparations which are advantageously applied as liquid preparations to the desired areas of the skin, preferably by means of a cotton swab, and in the preparations in a small amount, e.g. 2 to 5 weight. % based on the total composition
  • nonionic types such as polyoxyethylene fatty alcohol ethers, e.g.
  • pH preferably e.g. is adjusted to 4.0 to 9.0, in particular 5.0 to 6.5
  • perfume dyes
  • BHT 2,6-di-tert.
  • the pH of the preparations according to the invention which are active against blemished skin or against mild forms of acne is advantageously adjusted in the weakly acidic to neutral range, preferably from 4.0 to 7.0, particularly preferably from 5.0 to 6.5.
  • the cosmetic and / or dermatological formulations according to the invention may be composed as usual and used for the treatment of the skin and / or the hair in the sense of a dermatological treatment or a treatment in the sense of nourishing cosmetics. NEN. But they can also be used in make-up products in decorative cosmetics or in the cosmetic and dermatological cleaning products.
  • Cosmetic and dermatological preparations according to the invention also e.g. to protect the skin from UV rays may be in various forms, such as e.g. Usually used for this type of preparations. So they can e.g. a solution, a water-in-oil (W / O) or oil-in-water (O / W) type emulsion, or a multiple emulsions, such as water-in-oil-in-water (W / O / W), oil-in-water-in-oil (O / W / O), a gel, a hydrodispersion, a lamellar phase, a liquid isotropic solution phase, a micellar phase, a solid or dispersed one or more times hexagonal phase, a solid or dispersed single or multi-cubic phase, a lyotropic phase, a crystalline phase, a solid stick or even an aerosol.
  • W / O water-in-oil
  • O / W oil-in-water
  • the active compounds according to the invention can also be used with particular advantage in microemulsions, for example as described in German Offenlegungsschrift DE-195 9 079.
  • the oil phase of the preparations according to the invention is advantageously selected from the group of esters of saturated and / or unsaturated, branched and / or unbranched alkanecarboxylic acids having a chain length of 3 to 30 carbon atoms and saturated and / or unsaturated, branched and / or unbranched alcohols a chain length of 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 consisting of 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, as well as synthetic, semi-synthetic and natural mixtures of such esters, eg 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 the fatty acid triglycerides, namely the triglycerol esters of saturated and / or unsaturated, branched and / or unbranched alkanecarboxylic acids having a chain length of 8 to 24, in particular 12 - 18 C atoms.
  • the fatty acid triglycerides can be selected, for example, advantageously from the group of synthetic, semi-synthetic and natural oils, such as olive oil, sunflower oil, soybean oil, peanut oil, rapeseed oil, almond oil, palm oil, coconut oil, palm kernel oil and the like.
  • the oil phase selected from the group 2-ethylhexyl isostearate, octyldodecanol, isotridecyl isononanoate, isoeicosane, 2-ethylhexyl cocoate, C 12 -i 5 alkyl benzoate, caprylic-capric acid triglyceride, dicaprylyl ether.
  • Particularly advantageous are mixtures of C 12-15 -alkyl benzoate and 2-ethylhexyl isostearate, mixtures of C 12-15 -alkyl benzoate and isotridecyl isononanoate and mixtures of C 12 - I5 - benzoate, 2-ethylhexyl isostearate and isotridecyl isononanoate.
  • hydrocarbons paraffin oil, squalane and squalene are to be used advantageously in the context of the present invention.
  • the oil phase may further comprise 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 silicone oils.
  • cyclomethicone octamethylcyclotetrasiloxane
  • silicone oils are also advantageous 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 particularly advantageous.
  • the content of the oil phase is between 1 and 50 wt .-%, based on the total weight of the preparations, preferably 2.5 to 30 wt .-%, particularly preferably 5 to 15 wt .-%.
  • the cosmetic and / or dermatological formulations according to the invention are applied to the skin and / or the hair in a sufficient amount in the manner customary for cosmetics and dermatological agents.

Abstract

Use of hydroxymatairesinol as active principle to combat blemished skin, mild forms of acne and/or to combat Propionibacterium acnes.

Description

Gegen unreine Haut und milde Formen der Akne wirksame Zubereitungen mit einem Gehalt anAgainst blemished skin and mild forms of acne effective preparations containing
Hydroxymatairesinol als wirksames PrinzipHydroxymatairesinol as an effective principle
Die vorliegende Erfindung betrifft Wirkstoffe und Zubereitungen, solche Wirkstoffe enthaltend, welche gegen unreine Haut und milde Formen der Akne wirksam sind.The present invention relates to active ingredients and preparations containing such active ingredients which are effective against blemished skin and mild forms of acne.
Bei der unreinen Haut sowie bei milden Formen der Akne sind neben anderen Einflüssen bakterielle Sekundärinfektionen von ätiologischer Bedeutung. Einer der wichtigsten Mikroorganismen, der in Zusammenhang mit unreiner Haut steht, ist Propionibacterium acnes.In the case of impure skin as well as mild forms of acne, bacterial secondary infections are of etiological significance, among other influences. One of the most important microorganisms associated with impure skin is Propionibacterium acnes.
Unreine Haut und/oder Komedonen beeinträchtigen das Wohlbefinden der Betroffenen aber selbst in leichten Fällen. Da praktisch jeder oder jede Jugendliche von unreiner Haut irgendeiner Ausprägung betroffen ist, besteht bei vielen Personen Bedarf, diesem Zustande abzuhelfen.Impure skin and / or comedones affect the well-being of those affected but even in mild cases. Since virtually every adolescent or person is affected by blemished skin of some kind, many people need to remedy this condition.
Aufgabe der vorliegenden Erfindung war es also, gegen unreine Haut, milde Formen der Akne bzw. Propionibacterium acnes wirksamen Stoff zu finden.Object of the present invention was therefore to find against blemished skin, mild forms of acne or Propionibacterium acnes active substance.
Es wurde überraschend gefunden, und darin liegt die Lösung der Aufgabe, daß die Verwendung von Hydroxymatairesinol als wirksames Prinzip gegen unreine Haut, milde Formen der Akne sowie gegen Propionibacterium acnes diese Aufgabe erfüllt.It has surprisingly been found, and therein is the solution of the problem that the use of hydroxymatairesinol as an effective principle against blemished skin, mild forms of acne and against Propionibacterium acnes accomplishes this task.
Hydroxymatairesinol zeichnet sich durch folgende chemische Struktur aus:
Figure imgf000003_0001
Hydroxymatairesinol is characterized by the following chemical structure:
Figure imgf000003_0001
Hydroxymatairesinol ist ein sogenanntes Lignan. Als Lignane bezeichnet man Dimere von Phenylpropanderivaten, die über das C-2-Atom der Propankette miteinander verbunden sind (2,2'-Verknüpfung). Es handelt sich dabei um meist farblose, kristalline, schwer flüchtige Verbindungen ohne Geruch und auffallenden Geschmack. Sie entstehen als Verbindungen des pflanzlichen Sekundärstoffwechsels wahrscheinlich durch radikalisch-oxidative Kupplung von zwei Phenylpropanderivaten.Hydroxymatairesinol is a so-called lignan. Lignans are dimers of phenylpropane derivatives which are linked to one another via the C-2 atom of the propane chain (2,2'-linkage). These are mostly colorless, crystalline, hardly volatile compounds without odor and striking taste. They are formed as compounds of plant secondary metabolism probably by radical-oxidative coupling of two phenylpropane derivatives.
Hydroxymatairesinol als solches kommt in der Fichte (Picea abies) vor und ist beispielsweise erhältlich nach Verfahren, wie sie vonEklund, Lindholm, Mikkola, Smeda, Lehtilä und Söholm im Aufsatz „Synthesis of (-)-matairesinol, (-)-enterolactone, and (-)-enterodiol from the natural lignan hydroxymatairesinol" in Org.Lett.2003, 5, S.491 - 493 beschrieben werden.Hydroxymatairesinol as such occurs in the spruce (Picea abies) and is obtainable, for example, by methods as described by Eklund, Lindholm, Mikkola, Smeda, Lehtilä and Söholm in the essay "Synthesis of (-) - matairesinol, (-) - enterolactone, and (-) - enterodiol from the natural lignan hydroxymatairesinol "in Org. Lett.2003, 5, pp. 491-493.
Die erfindungsgemäßen kosmetischen Zubereitungen gegen unreine Haut bzw. gegen milde Formen der Akne sind besonders vorteilhaft dadurch gekennzeichnet, daß das Hydroxymatairesinol in Konzentrationen von 0,05 - 10,00 Gew.-%, bevorzugt 0,1 - 5,0 Gew.-%, vorliegt, jeweils bezogen auf das Gesamtgewicht der Zubereitungen.The cosmetic preparations according to the invention against blemished skin or against mild forms of acne are particularly advantageously characterized in that the hydroxymatairesinol is present in concentrations of 0.05-10.00% by weight, preferably 0.1-5.0% by weight. , in each case based on the total weight of the preparations.
Die erfindungsgemäßen gegen unreine Haut bzw. milde Formen der Akne wirksamen Zubereitungen können in Form von mittels Pinseln oder Abstreifern oder Roll-on-Vorrichtungen auftragbaren flüssigen Zusammensetzungen, als Stifte und in Form von aus normalen Flaschen und Behältern auftragbaren W/O- oder O/W-Emulsionen, z.B. Cremes oder Lotionen. Weiterhin können die erfindungsgemäßen gegen unreine Haut wirksamen Zubereitungen vorteilhaft in Form von Gesichtswässern, Tinkturen oder Reinigungsformulierungen vorliegen.The preparations according to the invention which are active against blemished skin or mild forms of acne may be in the form of liquid compositions which can be applied by means of paint brushes or wipers or roll-on devices, as pens and in the form of W / O or O can be applied from normal bottles and containers. W emulsions, eg Creams or lotions. Furthermore, the preparations according to the invention which are active against impure skin can advantageously be in the form of face lotions, tinctures or cleansing formulations.
Als übliche Trägerstoffe zur Herstellung der erfindungsgemäßen gegen unreine Haut bzw. milde Formen der Akne wirksamen Zubereitungen können neben Wasser, Ethanol und Isopropanol, Glycerin und Propylenglykol hautpflegende Fett- oder fettähnliche Stoffe, wie Ölsäuredecylester, Cetylalkohol, Cetylstearylalkohol und 2-Octyldodecanol, in den für solche Präparate üblichen Mengenverhältnissen eingesetzt werden sowie schleimbildende Stoffe und Verdickungsmittel, z.B. Hydroxyethyl- oder Hydroxypropylcellulose, Polyacrylsäure, Polyvinylpyrrolidon, daneben aber auch in kleinen Mengen cyclische Silikonöle (Polydimethylsiloxane) sowie flüssige Polymethylphenylsiloxane niedriger Viskosität.As usual carriers for the preparation according to the invention effective against blemished skin or mild forms of acne preparations in addition to water, ethanol and isopropanol, glycerol and propylene glycol skin-care fat or fat-like substances, such as Oleic acid decyl ester, cetyl alcohol, cetylstearyl alcohol and 2-octyldodecanol, are used in the usual ratios for such preparations and slime forming substances and thickeners, eg hydroxyethyl or hydroxypropyl cellulose, polyacrylic acid, polyvinylpyrrolidone, but also in small amounts cyclic silicone oils (polydimethylsiloxanes) and liquid polymethylphenylsiloxanes lower Viscosity.
Als Emulgatoren zur Herstellung der erfindungsgemäßen gegen unreine Haut bzw. gegen milde Formen der Akne wirksamen Zubereitungen, welche vorteilhaft als flüssige Zubereitungen auf die gewünschten Hautbereiche aufgetragen werden sollen, vorteilhaft mittels eines Wattebausches, und die in den Zubereitungen in geringer Menge, z.B. 2 bis 5 Gewichts. -%, bezogen auf die Gesamt-Zusammensetzung, verwendet werden können, haben sich nichtionogene Typen, wie Polyoxyethylen-Fettalkoholether, z.B. Cetostearyl- alkoholpolyethylenglykolether mit 12 bzw. 20 angelagerten Ethylenoxid-Einheiten pro Molekül, Cetostearylalkohol sowie Sorbitanester und Sorbitanester-Ethylenoxid-Verbindungen (z.B. Sorbitanmonostearat und Polyoxyethylensorbitanmonostearat) und langkettige höhermolekulare wachsartige Polyglykolether als geeignet erwiesen.As emulsifiers for the preparation of the present invention against blemished skin or mild forms of acne effective preparations which are advantageously applied as liquid preparations to the desired areas of the skin, preferably by means of a cotton swab, and in the preparations in a small amount, e.g. 2 to 5 weight. % based on the total composition can be used, nonionic types such as polyoxyethylene fatty alcohol ethers, e.g. Cetostearyl alcohol polyethylene glycol ethers having 12 or 20 ethylene oxide moieties per molecule, cetostearyl alcohol and sorbitan esters and sorbitan ester ethylene oxide compounds (e.g., sorbitan monostearate and polyoxyethylene sorbitan monostearate) and long chain higher molecular weight waxy polyglycol ethers have been found to be suitable.
Zusätzlich zu den genannten Bestandteilen können den gegen unreine Haut bzw. milde Formen der Akne wirksamen Zubereitungen gemäß der Erfindung, deren pH-Wert vorzugsweise z.B. durch übliche Puffergemische auf 4,0 bis 9,0 insbesondere 5,0 bis 6,5, eingestellt wird, Parfüm, Farbstoffe, Antioxidantien (z.B. _-Tocopherol und seine Derivate oder Butylhydroxytoluol (BHT = 2,6-Di-Tert.-butyl-4-methylphenol) in Mengen von 0,01 bis 0,03 %, bezogen auf die Gesamtzusammensetzung), Suspendiermittel, Puffergemische oder andere übliche kosmetische Grundstoffe beigemischt werden.In addition to the constituents mentioned, the preparations according to the invention which are effective against blemished skin or mild forms of the acne, whose pH is preferably e.g. is adjusted to 4.0 to 9.0, in particular 5.0 to 6.5, by customary buffer mixtures, perfume, dyes, antioxidants (for example _-tocopherol and its derivatives or butylhydroxytoluene (BHT = 2,6-di-tert.- butyl-4-methylphenol) in amounts of from 0.01 to 0.03%, based on the total composition), suspending agents, buffer mixtures or other customary cosmetic base materials.
Vorteilhaft wird der pH-Wert der erfindungsgemäßen gegen unreine Haut bzw. gegen milde Formen der Akne wirksamen Zubereitungen im schwach sauren bis neutralen Bereich eingestellt, bevorzugt von 4,0 - 7,0 , besonders bevorzugt von 5,0 - 6,5.The pH of the preparations according to the invention which are active against blemished skin or against mild forms of acne is advantageously adjusted in the weakly acidic to neutral range, preferably from 4.0 to 7.0, particularly preferably from 5.0 to 6.5.
Die jeweils einzusetzenden Mengen an Trägerstoffen können in Abhängigkeit von der Art des jeweiligen Produktes vom Fachmann durch einfaches Ausprobieren leicht ermittelt werden.The amounts of carrier substances to be used in each case can easily be determined by the skilled person by simple trial and error, depending on the nature of the particular product.
Die erfindungsgemäßen kosmetischen und/oder dermatologischen Formulierungen können wie üblich zusammengesetzt sein und zur Behandlung der Haut und/oder der Haare im Sinne einer dermatologischen Behandlung oder einer Behandlung im Sinne der pflegenden Kosmetik die- nen. Sie können aber auch in Schminkprodukten in der dekorativen Kosmetik eingesetzt werden oder in den kosmetischen und dermatologischen Reinigungsprodukten.The cosmetic and / or dermatological formulations according to the invention may be composed as usual and used for the treatment of the skin and / or the hair in the sense of a dermatological treatment or a treatment in the sense of nourishing cosmetics. NEN. But they can also be used in make-up products in decorative cosmetics or in the cosmetic and dermatological cleaning products.
Kosmetische und dermatologische Zubereitungen gemäß der Erfindung, auch z.B. zum Schütze der Haut vor UV-Strahlen, können in verschiedenen Formen vorliegen, wie sie z.B. üblicherweise für diesen Typ von Zubereitungen eingesetzt werden. So können sie z.B. eine Lösung, eine Emulsion vom Typ Wasser-in-ÖI (W/O) oder vom Typ Öl-in-Wasser (O/W), oder eine multiple Emulsionen, beispielsweise vom Typ Wasser-in-ÖI-in-Wasser (W/O/W), Öl-in- Wasser-in-ÖI (O/W/O), ein Gel, eine Hydrodispersion, eine lamellare Phase, eine flüssige isotrope Lösungsphase, eine micellare Phase, eine solide oder dispergierte ein- oder mehrfach hexagonale Phase, eine solide oder dispergierte ein- oder mehrfach kubische Phase, eine lyotrope Phase, eine kristalline Phase, einen festen Stift oder auch ein Aerosol darstellen.Cosmetic and dermatological preparations according to the invention, also e.g. to protect the skin from UV rays may be in various forms, such as e.g. Usually used for this type of preparations. So they can e.g. a solution, a water-in-oil (W / O) or oil-in-water (O / W) type emulsion, or a multiple emulsions, such as water-in-oil-in-water (W / O / W), oil-in-water-in-oil (O / W / O), a gel, a hydrodispersion, a lamellar phase, a liquid isotropic solution phase, a micellar phase, a solid or dispersed one or more times hexagonal phase, a solid or dispersed single or multi-cubic phase, a lyotropic phase, a crystalline phase, a solid stick or even an aerosol.
Die erfindungsgemäßen Wirkstoffe können auch besonders vorteilhaft in Mikroemulsionen, beispielsweise wie in der deutschen Offenlegungsschrift DE-195 9 079 beschrieben, verwendet werden.The active compounds according to the invention can also be used with particular advantage in microemulsions, for example as described in German Offenlegungsschrift DE-195 9 079.
Die Ölphase der erfindungsgemäßen Zubereitungen wird vorteilhaft gewählt aus der Gruppe der Ester aus gesättigten und/oder ungesättigten, verzweigten und/oder unverzweigten Al- kancarbonsäuren 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-He- xyllaurat, n-Decyloleat, Isooctylstearat, Isononylstearat, Isononylisononanoat, 2-Ethylhe- xylpalmitat, 2-Ethylhexyllaurat, 2-Hexyldecylstearat, 2-Octyldodecylpalmitat, Oleyloleat, Oleyl- erucat, Erucyloleat, Erucylerucat sowie synthetische, halbsynthetische und natürliche Gemische solcher Ester, z.B. Jojobaöl.The oil phase of the preparations according to the invention is advantageously selected from the group of esters of saturated and / or unsaturated, branched and / or unbranched alkanecarboxylic acids having a chain length of 3 to 30 carbon atoms and saturated and / or unsaturated, branched and / or unbranched alcohols a chain length of 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 consisting of 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, as well as synthetic, semi-synthetic 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 Fettsäure- triglyceride, 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 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 the fatty acid triglycerides, namely the triglycerol esters of saturated and / or unsaturated, branched and / or unbranched alkanecarboxylic acids having a chain length of 8 to 24, in particular 12 - 18 C atoms. The fatty acid triglycerides can be selected, for example, advantageously from the group of synthetic, semi-synthetic and natural oils, such as olive oil, sunflower oil, soybean oil, peanut oil, rapeseed oil, almond oil, palm oil, coconut oil, palm kernel oil and the like.
Auch beliebige Abmischungen solcher Öl- und Wachskomponenten sind vorteilhaft im Sinne der vorliegenden Erfindung einzusetzen.Any mixtures of such oil and wax components are also advantageous to use in the context of the present invention.
Vorteilhaft wird die Ölphase gewählt aus der Gruppe 2-Ethylhexylisostearat, Octyldodecanol, Isotridecylisononanoat, Isoeicosan, 2-Ethylhexylcocoat, C12-i5-Alkylbenzoat, Capryl-Caprinsäure- triglycerid, Dicaprylylether.Advantageously, the oil phase selected from the group 2-ethylhexyl isostearate, octyldodecanol, isotridecyl isononanoate, isoeicosane, 2-ethylhexyl cocoate, C 12 -i 5 alkyl benzoate, caprylic-capric acid triglyceride, dicaprylyl ether.
Besonders vorteilhaft sind Mischungen aus C12-15-Alkylbenzoat und 2-Ethylhexylisostearat, Mischungen aus C12-15-Alkylbenzoat und Isotridecylisononanoat sowie Mischungen aus C12--I5- Alkylbenzoat, 2-Ethylhexylisostearat und Isotridecylisononanoat.Particularly advantageous are mixtures of C 12-15 -alkyl benzoate and 2-ethylhexyl isostearate, mixtures of C 12-15 -alkyl benzoate and isotridecyl isononanoate and mixtures of C 12 - I5 - benzoate, 2-ethylhexyl isostearate and isotridecyl isononanoate.
Von den Kohlenwasserstoffen sind Paraffinöl, Squalan und Squalen vorteilhaft im Sinne der vorliegenden Erfindung zu verwenden.Of the hydrocarbons, paraffin oil, squalane and squalene are to be used advantageously in the context of the present invention.
Vorteilhaft kann die Ölphase ferner einen Gehalt an cyclischen oder linearen Silikonölen aufweisen oder vollständig aus solchen Ölen bestehen, wobei allerdings bevorzugt wird, außer dem Silikonöl oder den Silikonölen einen zusätzlichen Gehalt an anderen Ölphasenkomponenten zu verwenden.Advantageously, the oil phase may further comprise 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 silicone oils.
Vorteilhaft wird Cyclomethicon (Octamethylcyclotetrasiloxan) als erfindungsgemäß zu verwendendes Silikonöl eingesetzt. Aber auch andere Silikonöle sind vorteilhaft im Sinne der vorliegenden Erfindung zu verwenden, beispielsweise Hexamethylcyclotrisiloxan, Polydimethyl- siloxan, Poly(methylphenylsiloxan).Advantageously, cyclomethicone (octamethylcyclotetrasiloxane) is used as the silicone oil to be used according to the invention. However, other silicone oils are also advantageous for the purposes of the present invention, for example hexamethylcyclotrisiloxane, polydimethylsiloxane, poly (methylphenylsiloxane).
Besonders vorteilhaft sind ferner Mischungen aus Cyclomethicon und Isotridecylisononanoat, aus Cyclomethicon und 2-Ethylhexylisostearat.Also particularly advantageous are mixtures of cyclomethicone and isotridecyl isononanoate, cyclomethicone and 2-ethylhexyl isostearate.
Vorteilhaft beträgt der Gehalt an der Ölphase zwischen 1 und 50 Gew.-%, bezogen auf das Gesamtgewicht der Zubereitungen, bevorzugt 2,5 - 30 Gew.-%, insbesondere bevorzugt 5 - 15 Gew.-%. Zur Anwendung werden die erfindungsgemäßen kosmetischen und/oder dermatologischen Formulierungen in der für Kosmetika und Dermatika üblichen Weise auf die Haut und/oder die Haare in ausreichender Menge aufgebracht.Advantageously, the content of the oil phase is between 1 and 50 wt .-%, based on the total weight of the preparations, preferably 2.5 to 30 wt .-%, particularly preferably 5 to 15 wt .-%. For use, the cosmetic and / or dermatological formulations according to the invention are applied to the skin and / or the hair in a sufficient amount in the manner customary for cosmetics and dermatological agents.
Die folgenden Beispiele sollen die Verkörperungen der vorliegenden Erfindungen verdeutlichen. The following examples are intended to illustrate the embodiments of the present inventions.
Figure imgf000008_0001
Figure imgf000009_0001
Figure imgf000008_0001
Figure imgf000009_0001

Claims

Patentansprüche claims
1. Verwendung von Hydroxymatairesinol als wirksames Prinzip gegen unreine Haut, milde Formen der Akne und/oder gegen Propionibacterium acnes.1. Use of hydroxymatairesinol as an effective principle against blemished skin, mild forms of acne and / or against Propionibacterium acnes.
2. Verwendung nach Anspruch 1 , dadurch gekennzeichnet, daß das Hydroxymatairesinol in Konzentrationen von 0,05 - 10,00 Gew.-%, bevorzugt 0,1 - 5,0 Gew.-%, vorliegt, jeweils bezogen auf das Gesamtgewicht der Zubereitungen. 2. Use according to claim 1, characterized in that the hydroxymatairesinol in concentrations of 0.05 to 10.00 wt .-%, preferably 0.1 to 5.0 wt .-%, is present, in each case based on the total weight of the preparations ,
PCT/EP2007/001352 2006-02-22 2007-02-16 Preparations effective against blemished skin and mild forms of acne with a content of hydroxymatairesinol as active principle WO2007096088A1 (en)

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