WO2008040456A1

WO2008040456A1 - Cosmetic or dermatological preparations with a content of 2-isopropyl-5- methyl-cyclohexancarbonyl-d-alanine ethyl ester and one or more skin moisturising agents

Info

Publication number: WO2008040456A1
Application number: PCT/EP2007/008229
Authority: WO
Inventors: Julia Eckert; Ludger Kolbe; Gitta Neufang
Original assignee: Beiersdorf Ag
Priority date: 2006-09-29
Filing date: 2007-09-21
Publication date: 2008-04-10
Also published as: DE102006047166A1

Abstract

The invention relates to cosmetic or dermatological preparations with a content of 2-isopropyl-5- methyl-cyclohexancarbonyl-D-alanine ethyl ester and one or more skin moisturising agents

Description

description

Cosmetic or dermatological preparations containing 2-isopropyl-5-methylcyclohexanecarbonyl-D-alanine ethyl ester and one or more skin moisturizers

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.

In a very particular embodiment, the present invention relates to cosmetic and dermatological preparations with a long-lasting cooling effect, in particular skin-care cosmetic and dermatological preparations.

In a very particular embodiment, the present invention relates to cosmetic and dermatological preparations with reduced skin irritation.

The cooling effect of cosmetic preparations is based on two basic principles:

Use of components that volatilize after topical application gaseous and the required amount of energy, the so-called evaporation enthalpy, to a large part of the skin surface. Therefore, suitable liquid components are used in corresponding non-occlusive cosmetics. Especially suitable here Ethanol proven, besides, formulations with high water content also show a significant cooling effect.

Use of so-called "cooling agents", which interact with the heat receptors of the skin and thus trigger a sensation of cold without generating a measurable physical cooling, in particular menthol and various menthol derivatives (Frescolate, Physcool, Questice L, etc.) In particular 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.

In the literature, for example, ionic compounds, in particular ammonium salts, are described as cooling agents. As cooling preparations are also widely used isopropanolic gels with camphor and menthol additive.

The use of these substances, especially on irritated skin, is in any case problematic. In addition, many of these compounds are poorly water-soluble. Their use is therefore limited to a few cosmetics and dermatics.

It was therefore an object of the present invention to provide nourishing cosmetic and medical preparations which do not have the disadvantages of the prior art, in particular those which, applied to the skin or mucous membranes, have a moisturizing and / or cooling action.

DE 43 12 656 describes the use of cosmetically or pharmaceutically acceptable substances with positive enthalpy of solution in cosmetic or medical topical preparations, characterized in that the substance or substances in the preparations in a substantially anhydrous medium and / or by a material barrier of a be shielded aqueous medium.

Although this procedure can in principle lead to cosmetically satisfactory preparations, they are galenically extremely expensive to produce. It was therefore the object of the present invention to remedy the evils of the prior art and to provide cooling cosmetic or dermatological preparations which are easy to prepare, exert no irritating effect on skin or mucous membranes - for example, unpleasant tingling or itching - as well as intended Application pleasant cooling donate.

The use of skin moisturizer - often used polyhydric alcohols such as glycerin - is generally desirable. A disadvantage of preparations of the prior art, however, is that they - if polyol amounts are used, which show a certain effectiveness with respect to the skin moisturization - have a significant stickiness and can be distributed only badly on the skin.

In order to reduce the stickiness of polyol-containing O / W emulsions and to achieve a light skin feel (easily dispersible, hardly any residue, rapidly absorbed), it is customary to use very thin oils (ie oils with a viscosity of 1 to 15 mPa.s). , which also have a very high spreading capacity (800 to 1200 mm2 / 10 min).

It was therefore an object of the invention to bring about good skin moisturization without the cosmetic appearance of the preparations suffers.

A further object of the present invention was to provide preparations which markedly improve the condition of the skin, in particular reduce skin roughness.

The task was therefore to remedy all these disadvantages of the prior art. In particular, products with reduced tackiness should be provided. Products in the field of nourishing cosmetics, decorative cosmetics and pharmacological galenics should likewise be freed from the described disadvantages of the prior art.

Furthermore, it was 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.

These objects are achieved according to the invention by 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:

The synthesis of 2-isopropyl-5-methyl-cyclohexanecarbonyl-D-alanine ethyl ester [syn- nom: (R) -2 - [((1 R, 2S, 5R) -2-isopropyl-5-methyl-cyclohexanecarbonyl) -amino ] Propionic acid ethyl ester can be made according to the following instructions:

1, 0 g of D-alanine ethyl ester hydrochloride (from Aldrich Chemical Co received) 1 ml of double distilled water, diethyl ether and in 28 ml and cooled to 0 ⁰ C. A spatula tip of the catalyst diaminopyrimidine was added. 1, 62 ml of p-menthyl chloride was added dropwise, followed by 2 ml of triethylamine. Flakes of a no-mist precipitate formed in the mixture, which was stirred overnight at room temperature has been. The precipitate was dissolved in ethyl acetate, washed with double-distilled water and dried over sodium sulfate. The organic phase was evaporated under reduced pressure to give 2 g of the final product, which crystallized at room temperature. The expected molecular mass and structure were confirmed by mass spectrometer or NMR spectrum.

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.

Advantageous 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.

According to the invention, 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. For example, 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. It is also invented dugsgemäß 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. In particular wax matrices as described in DE-OS 43 08 282, have been found to be favorable.

It is 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.

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. 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.

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 or in combination.

In particular, mixtures of the abovementioned solvents are used. For 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.

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.

Advantageously, 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.

The following examples are intended to illustrate the present invention without limiting it. All amounts, proportions and percentages are, unless otherwise stated, percentages by weight, based on the weight and the total amount or on the total weight of the preparations.

Claims

claims

1. Cosmetic or dermatological preparations containing 2-isopropyl-5-methylcyclohexanecarbonyl-D-alanine ethyl ester and one or more skin moisturizers.

2. Preparations according to claim 1, characterized in that the one or more skin moisturizers is selected or are selected from the group glycerol, methylpropanediol, hexanediol, octanediol, taurine, sodium chloride lactic acid and / or lactates, in particular sodium lactate, butylene glycol, propylene glycol, biosaccharide gums. 1, ethylhexyloxyglycerol, pyrrolidonecarboxylic acid, hyaluronic acid and urea.

3. Preparations according to one of the preceding claims, characterized in that it contains from 0.001% by weight to 10% by weight, preferably from 0.01% by weight to 1.0% by weight, in particular 0.05-0, 5% by weight, based on the total weight of the preparations, of 2-isopropyl-5-methylcyclohexanecarbonyl-D-alanine ethyl ester.

4. Preparations according to one of the preceding claims, characterized in that it contains 0.001 wt .-% to 20 wt .-%, preferably 0.01 wt .-% to 10 wt .-%, in particular 0.1 - 10 wt. %, based on the total weight of the preparations, of one or more skin moisturizers.