WO2008040456A1 - Préparations cosmétiques ou dermatologiques comprenant de l'ester éthylique de la 2-isopropyl-5- méthyl-cyclohexanecarbonyl-d-alanine et un ou plusieurs agents d'hydratation de la peau - Google Patents

Préparations cosmétiques ou dermatologiques comprenant de l'ester éthylique de la 2-isopropyl-5- méthyl-cyclohexanecarbonyl-d-alanine et un ou plusieurs agents d'hydratation de la peau Download PDF

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Publication number
WO2008040456A1
WO2008040456A1 PCT/EP2007/008229 EP2007008229W WO2008040456A1 WO 2008040456 A1 WO2008040456 A1 WO 2008040456A1 EP 2007008229 W EP2007008229 W EP 2007008229W WO 2008040456 A1 WO2008040456 A1 WO 2008040456A1
Authority
WO
WIPO (PCT)
Prior art keywords
preparations
cosmetic
isopropyl
skin
ethyl ester
Prior art date
Application number
PCT/EP2007/008229
Other languages
German (de)
English (en)
Inventor
Julia Eckert
Ludger Kolbe
Gitta Neufang
Original Assignee
Beiersdorf Ag
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Beiersdorf Ag filed Critical Beiersdorf Ag
Publication of WO2008040456A1 publication Critical patent/WO2008040456A1/fr

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Classifications

    • 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
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated 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
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A61K8/20—Halogens; Compounds 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
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A61K8/345—Alcohols containing more than one hydroxy group
    • 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
    • A61K8/365—Hydroxycarboxylic acids; Ketocarboxylic 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
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/42—Amides
    • 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
    • A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
    • A61K8/466—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfonic acid derivatives; Salts
    • 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
    • A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
    • A61K8/4913—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid
    • 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
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73—Polysaccharides
    • A61K8/735—Mucopolysaccharides, e.g. hyaluronic acid; Derivatives thereof
    • 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
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/005—Preparations for sensitive skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/20—Chemical, physico-chemical or functional or structural properties of the composition as a whole
    • A61K2800/24—Thermal properties
    • A61K2800/244—Endothermic; Cooling; Cooling sensation

Definitions

  • the present invention relates to cosmetic or dermatological preparations containing 2-isopropyl-5-methyl-cyclohexanecarbonyl-D-alanine ethyl ester and one or more skin moisturizers.
  • the present invention relates, in a particular embodiment, to cosmetic or pharmaceutical preparations with a reduced tack feeling, processes for their preparation and the use of active ingredients for reducing the stickiness of cosmetic preparations.
  • the present invention relates to cosmetic and dermatological preparations with a long-lasting cooling effect, in particular skin-care cosmetic and dermatological preparations.
  • the present invention relates to cosmetic and dermatological preparations with reduced skin irritation.
  • cooling agents which interact with the heat receptors of the skin and thus trigger a sensation of cold without generating a measurable physical cooling
  • menthol and various menthol derivatives Rescolate, Physcool, Questice L, etc.
  • high ethanol contents as well as menthol and its derivatives are, apart from the irritative potential, in particular due to their distinct inherent odor not suitable for numerous purposes from an olfactory point of view.Also, such substances often cause an increase in circulation at the same time, on the contrary causes a feeling of warmth.
  • cooling agents in particular ammonium salts
  • cooling preparations are also widely used isopropanolic gels with camphor and menthol additive.
  • a further object of the present invention was to provide preparations which markedly improve the condition of the skin, in particular reduce skin roughness.
  • an object of the invention to develop cosmetic bases for cosmetic preparations, which are characterized by good skin compatibility. Furthermore, an object of the present invention to provide products with the widest possible variety of applications available. For example, principles should be created for preparation forms such as cleansing emulsions, face and body care preparations, but also pronounced medical-pharmaceutical dosage forms, for example preparations for acne and other skin manifestations.
  • cosmetic or dermatological preparations containing 2-isopropyl-5-methylcyclohexanecarbonyl-D-alanine ethyl ester and one or more skin moisturizing agents.
  • Preparations according to the invention are distinguished by outstanding, pleasant cooling effect and elegant cosmetic appearance. They are not unpleasantly sticky and stable against physical decomposition, such as up or down frame of their components.
  • 2-Isopropyl-5-methylcyclohexanecarbonyl-D-alanine ethyl ester is characterized by the following structure:
  • Skin moisturizers are also often referred to as so-called “moisturizers”.
  • Moisturizers are substances or mixtures of substances which confer on cosmetic preparations the property of moisturizing the horny layer (also known as transepidermal water loss (TEWL) after application or spreading on the skin surface ) and / or to positively influence the hydration of the horny layer.
  • TEWL transepidermal water loss
  • moisturizers for the purposes of the present invention are, for example, glycerol, methylpropanediol, hexanediol, octanediol, taurine, sodium chloride, lactic acid and / or lactates, in particular sodium lactate, butylene glycol, propylene glycol, biosaccharide gum-1, ethylhexy-loxyglycerol, pyrrolidonecarboxylic acid, hyaluronic acid and urea.
  • Cosmetic or dermatological preparations according to the invention preferably contain 0.001-10% by weight, particularly preferably 0.01-1% by weight, of one or more skin moisturizing agents, based on the total composition of the preparations.
  • the cosmetic or dermatological preparations may be composed as usual and used for the treatment, care and cleansing of the skin and / or the hair and as a make-up product in decorative cosmetics.
  • They preferably contain from 0.001% by weight to 10% by weight, preferably from 0.05% by weight to 5% by weight, in particular from 0.1% to 2.0% by weight, based on the total weight of the preparations, 2-isopropyl-5-methylcyclohexanecarbonyl-D-alanine ethyl ester.
  • Cosmetic and dermatological preparations according to the invention can be present in various forms.
  • they may contain a solution, an anhydrous preparation, an emulsion or microemulsion of the water-in-oil (W / O) type or of the oil-in-water (O / W) type, a multiple emulsion, for example water-type. in-oil-in-water (W / O / W), a gel, a solid stick, an ointment or even an aerosol.
  • dugsat advantageous to present folic acid and / or derivatives thereof in encapsulated form, for example in collagen matrices and other conventional encapsulating materials, for example as CeIIuioest encapsulations, in gelatin, wax matrices or liposomal encapsulated.
  • wax matrices as described in DE-OS 43 08 282 have been found to be favorable.
  • folic acid and / or derivatives thereof are also possible and advantageous for the purposes of the present invention to incorporate folic acid and / or derivatives thereof into aqueous systems or surfactant preparations for cleaning the skin and hair.
  • the cosmetic and dermatological preparations according to the invention may comprise cosmetic adjuvants such as are conventionally used in such preparations, e.g. Preservatives, bactericides, perfumes, foaming inhibitors, colorants, pigments having a coloring effect, thickeners, surface-active substances, emulsifiers, softening, moistening and / or moisturizing substances, fats, oils, waxes or other conventional ingredients of a cosmetic or cosmetic dermatological formulation such as alcohols, polyols, polymers, foam stabilizers, electrolytes, organic solvents or silicone derivatives.
  • cosmetic adjuvants such as are conventionally used in such preparations, e.g. Preservatives, bactericides, perfumes, foaming inhibitors, colorants, pigments having a coloring effect, thickeners, surface-active substances, emulsifiers, softening, moistening and / or moisturizing substances, fats, oils, waxes or other conventional ingredients of a cosmetic or cosmetic dermatological formulation such as alcohol
  • the lipid phase can advantageously be selected from the following substance group: mineral oils, mineral waxes
  • Oils such as triglycerides of capric or caprylic acid, further natural oils such as e.g. 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; benzoates;
  • Silicone oils such as dimethylpolysiloxanes, diethylpolysiloxanes, diphenylpolysiloxanes and mixed forms thereof.
  • 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 a chain length of 3 to 30 carbon atoms and saturated and / or unsaturated, branched and / or unbranched alcohols of a chain length of 3 to 30 carbon atoms, from the group consisting 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 aqueous phase of the preparations according to the invention may advantageously contain alcohols, 1,2-propanediol, other diols or polyols of low C number, and their ethers, preferably ethanol, isopropanol, ethylene glycol, ethylene glycol monoethyl or -mobutyl nylether, propylene glycol monomethyl, -monoethyl- or monobutyl ether, diethylene glycol monomethyl or monoethyl ether and analogous products, and in particular one or more thickening agents, which or which can be advantageously selected from the group silicon dioxide, aluminum silicates, polysaccharides or their derivatives, for example Hyaluronic acid, xanthan gum, hydroxypropylmethylcellulose, particularly advantageous from the group of polyacrylates, preferably a polyacrylate from the group of so-called Carbopol, for example, Carbopols types 980, 981, 1382, 2984, 5984, each individually
  • mixtures of the abovementioned solvents are used.
  • alcoholic solvents water can be another ingredient.
  • Emulsions of the invention are advantageous and contain e.g. the said fats, oils, waxes and other fatty substances, as well as water and an emulsifier, as commonly used for such a type of formulation.
  • Gels according to the invention usually contain alcohols of low carbon number, for example, ethanol, isopropanol, 1, 2-propanediol and water or an above-mentioned oil in the presence of a thickener, which in oily-alcoholic gels preferably silica or an aluminum silicate, in aqueous-alcoholic or alcoholic gels preferably a polyacrylate.
  • alcohols of low carbon number for example, ethanol, isopropanol, 1, 2-propanediol and water or an above-mentioned oil
  • a thickener which in oily-alcoholic gels preferably silica or an aluminum silicate, in aqueous-alcoholic or alcoholic gels preferably a polyacrylate.
  • Suitable propellants for preparations which can be sprayed from aerosol containers according to the invention are the customary known highly volatile, liquefied propellants, for example hydrocarbons (propane, butane, isobutane), which can be used alone or mixed with one another. Also, compressed air is advantageous to use.
  • preparations according to the invention may also contain substances which absorb UV radiation in the UVB range, the total amount of filter substances being e.g. 0.1 wt .-% to 30 wt .-%, preferably 0.5 to 10 wt .-%, in particular 1, 0 to 6.0 wt .-%, based on the total weight of the preparations to cosmetic preparations for To provide the hair or the skin against the entire range of ultraviolet radiation. They can also serve as a sunscreen for hair or skin.

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

Abstract

La présente invention concerne des préparations cosmétiques ou dermatologiques comprenant de l'ester éthylique de la 2-isopropyl-5-méthyl-cyclohexanecarbonyl-D-alanine et un ou plusieurs agents d'hydratation de la peau.
PCT/EP2007/008229 2006-09-29 2007-09-21 Préparations cosmétiques ou dermatologiques comprenant de l'ester éthylique de la 2-isopropyl-5- méthyl-cyclohexanecarbonyl-d-alanine et un ou plusieurs agents d'hydratation de la peau WO2008040456A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE200610047166 DE102006047166A1 (de) 2006-09-29 2006-09-29 Kosmetische oder dermatologische Zubereitungen mit einem Gehalt an 2-Isopropyl-5-Methyl-Cyclohexancarbonyl-D-Alaninethylester und einem oder mehreren Hautbefeuchtungsmitteln
DE102006047166.0 2006-09-29

Publications (1)

Publication Number Publication Date
WO2008040456A1 true WO2008040456A1 (fr) 2008-04-10

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Application Number Title Priority Date Filing Date
PCT/EP2007/008229 WO2008040456A1 (fr) 2006-09-29 2007-09-21 Préparations cosmétiques ou dermatologiques comprenant de l'ester éthylique de la 2-isopropyl-5- méthyl-cyclohexanecarbonyl-d-alanine et un ou plusieurs agents d'hydratation de la peau

Country Status (2)

Country Link
DE (1) DE102006047166A1 (fr)
WO (1) WO2008040456A1 (fr)

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2205255A1 (fr) * 1971-02-04 1972-11-30
WO2002030367A2 (fr) * 2000-10-10 2002-04-18 The Procter & Gamble Company Systeme de conditionnement pour objet presentant une forme determinee
WO2002032381A2 (fr) * 2000-10-10 2002-04-25 The Procter & Gamble Company Compositions cosmetiques emballees destinees au cuir chevelu
EP1639993A1 (fr) * 2003-06-17 2006-03-29 Takasago International Corporation Composition de shampooing ou de nettoyage corporel
US20060171912A1 (en) * 2005-01-28 2006-08-03 Schwartz James R Diiodomethyl-p-tolylsulfone as a particulate dispersion in a liquid solvent

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TW544310B (en) * 1998-04-02 2003-08-01 Ajinomoto Kk Amino acid derivatives and anti-inflammatory agents
EP1477155A1 (fr) * 2003-05-16 2004-11-17 The Procter & Gamble Company Compositions conprenant une amidine et un alkane polyol
US20050106194A1 (en) * 2003-11-18 2005-05-19 Mary Kay Inc. Compositions for achieving benefits in skin using key cellular metabolic intermediates

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2205255A1 (fr) * 1971-02-04 1972-11-30
WO2002030367A2 (fr) * 2000-10-10 2002-04-18 The Procter & Gamble Company Systeme de conditionnement pour objet presentant une forme determinee
WO2002032381A2 (fr) * 2000-10-10 2002-04-25 The Procter & Gamble Company Compositions cosmetiques emballees destinees au cuir chevelu
EP1639993A1 (fr) * 2003-06-17 2006-03-29 Takasago International Corporation Composition de shampooing ou de nettoyage corporel
US20060171912A1 (en) * 2005-01-28 2006-08-03 Schwartz James R Diiodomethyl-p-tolylsulfone as a particulate dispersion in a liquid solvent

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
WATSON H R ET AL: "NEW COMPOUNDS WITH THE MENTHOL COOLING EFFECT", JOURNAL OF THE SOCIETY COSMETIC CHEMISTS, SOCIETY OF COSMETIC CHEMISTS,, US, vol. 29, no. 4, 1978, pages 185 - 200, XP009045124, ISSN: 0037-9832 *

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Publication number Publication date
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