WO2009115165A2

WO2009115165A2 - Cooling preparations for contact with human skin and/or mucous membranes, containing (1r,2s,5r)-2-isopropyl-5-methyl-n-(2-(pyridin-2-yl)ethyl-cyclohexane carboxamide and/or (1r,2s,5r)-n-(4-(cyanomethyl)-phenyl)-2-isopropyl-5-methylcyclohexane carboxamide

Info

Publication number: WO2009115165A2
Application number: PCT/EP2009/000719
Authority: WO
Inventors: Stefan Biel; Julia Eckert; Björna Windisch; Gitta Neufang; Stefanie Knaupmeier; Stefanie Höltkemeier
Original assignee: Beiersdorf Ag
Priority date: 2008-03-20
Filing date: 2009-02-04
Publication date: 2009-09-24
Also published as: DE102008015428A1; WO2009115165A3

Abstract

The invention relates to cooling preparations for contact with human skin and/or mucous membranes, containing (1R,2S,5R)-2-isopropyl-5-methyl-N-(2-(pyridin-2-yl)ethyl-cyclohexane carboxamide and/or (1R,2S,5R)-N-(4-(cyanomethyl)-phenyl)-2-isopropyl-5-methylcyclohexane carboxamide.

Description

Beiersdorf AG

description

Cooling preparations for human skin and / or mucous membrane contact with a

Content of (1R, 2S, 5R) -2-isopropyl-5-methyl-N- {2- (pyridin-2-yl) ethylcyclohexanecarboxamide and / or (1R, 2S, 5R) -N- (4 - (Cyanomethyl) phenyl) -2-isopropyl-5-methylcyclohexanecarboxamide

The present invention relates to consumer preparations, in particular skin care cosmetic and dermatological preparations.

The cooling of the skin can be something very pleasant. This is especially so when the skin feels hot, hurts, itches or is freshly shaved. Often this is associated with sunburn or bath. In insect bites or inflammatory skin, acne cooling the skin can also be felt soothing.

Examples of cooling substances known hitherto are menthol, menthoxypropanediol, menthone, ethyl menthane carboxamido acetate (WS-5), isopulegol (Coolact P), menthanediol (co-lact 38D), N, 2,3-trimethyl-2-isopropylbutanamide ( WS-23), ethyl menthane carboxamide (WS-3), menthone glycerine acetal (Frescolate MGA) or mono-menthyl succinate (Physcool).

But even with drinks or food, a cold sensation on the skin or mucous membranes may be desirable. The taste impression of many beverage or food preparations depends on the temperature of the preparation or a cold impression is desired. Some drinks are often drunk cold. An example is cocktails, alcoholic or not. There are also cooling pastilles, such as those with menthol. These evoke a fresh feeling in the mouth. Also conceivable are Too-Much-Chillies-Pain-Release-Products.

Furthermore, preparations are known which cause a refreshing cooling sensation in the nose. Such consumer products can be applied to the nasal mucosa or inhaled.

There has been no lack of attempts to effect the cooling of the skin or mucosa by contact with a preparation. It was also trying to find preparations that cool.

This was especially tried for skin after shaving or skin after sunburn or bath. Known products are called After-Shave or After-Sun. Menthol- Containing toothpaste, dragees, pastilles are also known, but not always beneficial in every way.

It was an object of the present invention to remedy the drawbacks of the prior art and to provide cooling of the skin or mucous permitting preparations which are easy to prepare, exert no irritating effect on the skin or mucous membranes and donate pleasant cooling when used as intended.

However, it was surprising and unpredictable to those skilled in the art that refrigerated preparations for human skin and / or mucosal contact containing

(1R, 2S, 5R) -2-isopropyl-5-methyl-N- (2- (pyridin-2-yl) -ethyl-cyclohexanecarboxamide and / or (1R, 2S, 5R) -N- (4- ( Cyanomethyl) -phenyl) -2-isopropyl-5-methylcyclohexanecarboxamide eliminate the disadvantages of the prior art .:

(1R, 2S, 5R) -2-isopropyl-5-methyl-Λ / - (2- (pyridin-2-yl) ethyl) -cyclohexanecarboxamide is characterized by the following structural formula:

(1R, 2S, 5R) -Λ / - (4- (cyanomethyl) -phenyl) -2-isopropyl-5-methylcyclohexanecarboxamide is characterized by the following structural formula:

The preparations are easy to formulate and do not place great demands on manufacturing processes.

The invention also includes the use of (1R, 2S, 5R) -2-isopropyl-5-methyl-N- (2- (pyridin-2-yl) -ethyl-cyclohexanecarboxamide and / or (1R, 2S, 5R) -N- (4- (cyanomethyl) phenyl) - 2-isopropyl-5-methylcyclohexanecarboxamide to create a sensation of coldness on the skin or mucosa.

It is preferred if the preparations contain 0.001-10% by weight, particularly preferably 0.01-1% by weight, of (1R, 2S, 5R) -2-isopropyl-5-methyl-N- (2- (2-one) pyridin-2-yl) ethylcyclohexanecarboxamide and / or (1R, 2S, 5R) -N- (4- (cyanomethyl) -phenyl) -2-isopropyl-5-methylcyclohexanecarboxamide, based on the total composition of the preparations It is preferred for the preparation or use according to the invention to be cosmetic, for the preparation according to the invention to be edible or drinkable, for the preparations according to the invention to contain vitamins, and for the preparations according to the invention to contain antioxidants ,

For example, but not exclusively, cosmetic and dermatological skin and hair care products as well as mouthwash, chewing gum, toothpaste, and medicated ointments, lotions, and sprays are applications of the present invention.

For use, the cosmetic and dermatological preparations are applied according to the invention in the usual manner for cosmetics on the skin and / or hair in sufficient quantity.

The cosmetic and dermatological preparations according to the invention may contain cosmetic adjuvants such as are commonly used in such preparations, e.g. Preservatives, bactericides, perfumes, foaming inhibitors, dyes, pigments having a coloring effect, thickeners, moisturizing and / or moisturizing substances, fats, oils, waxes or other common ingredients of a cosmetic or dermatological formulation such as alcohols, polyols, Polymers, foam stabilizers, electrolytes, tooth polishes or abrasives, vitamins, propellants, antioxidants, alcohols, diols or polyols, organic solvents, UVA filters and / or UVB filters or silicone derivatives.

Food or beverage preparations may contain sweeteners, thickeners, food additives, flavors, colors, flavor enhancers, chelants, antioxidants, plant extracts, and nutrients.

Cosmetic and / or dermatological preparations according to the present invention may also be present as gels which, in addition to an effective content of compounds according to the invention and solvents used therefor, usually and preferably water, nor organic and / or inorganic thickeners. Furthermore, these thickeners are part of cosmetic emulsions.

The amounts of auxiliaries 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.

As emulsifiers for the preparation of the preparations according to the invention, which are to be applied advantageously as liquid or solid preparations to the desired skin areas, and in the preparations in a small amount, e.g. from about 1 to 6% by weight, based on the total composition, of 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. In addition, of course, a whole range of other emulsifiers or emulsifier mixtures are suitable, which are commonly used in cosmetic preparations. Non-limiting examples of these include glyceryl stearate citrate, PEG-40 stearate or also polyglyceryl (3) -methylglucose distearate, stearic acid, steareth-2, steareth-21, glyceryl isostearate isoceteth-20 or also ceteareth-20.

The oil phase of the inventively preferred preparations 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 Chain length of 3 to 30 C-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. Accordingly, such ester oils may, for example, 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 synthetic, semi-synthetic and natural mixtures of such esters, eg Jojoba oil.

Furthermore, the oil phase can advantageously be selected from the group of branched and unbranched hydrocarbons and waxes, silicone oils, dialkyl ethers, the group of saturated or unsaturated, branched or unbranched alcohols, and fatty acid triglycerides, in particular 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, for example olive oil, sunflower oil, soybean oil, peanut oil, rapeseed oil, almond oil, palm oil, coconut oil, palm kernel oil and the like.

Any mixtures of such oil and wax components are advantageously used in the context of the present invention.

Advantageously, the oil phase may further contain 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. Advantageously, cyclomethicone (octamethylcyclotetrasiloxane) or dimethicone is used as silicone oil to be used according to the invention. However, other silicone oils are also advantageously usable for the purposes of the present invention, for example hexamethylcylotrisiloxane, polydimethylsiloxane or poly (methylphenylsiloxane).

Advantageously, the content of the oil phase is between about 1 and 50 wt .-%, based on the total weight of the preparations, preferably about 2.5 to 30 wt .-%, more preferably about 5 to 15 wt .-%.

Gel formers, also known as thickeners, are macromolecules which have a largely linear shape and intermolecular interaction forces that allow side and Hauptvalenzbindungen between the individual molecules and thus the formation of a net-like structure. They include partially water-soluble natural or synthetic polymers which form gels or viscous solutions in aqueous systems. They increase the viscosity of the water either by binding water molecules (hydration) or by absorbing and enveloping the water in their intertwined macromolecules, while at the same time restricting the mobility of the water. Such water-soluble polymers represent a large group of chemically very different natural and synthetic polymers whose common feature is their solubility in water or aqueous media. The prerequisite for this is that these polymers have a sufficient number of hydrophilic groups for water solubility and are not too strongly crosslinked. The hydrophilic groups may be nonionic, anionic or cationic in nature.

Advantageous thickeners for cosmetic preparations are, for example, copolymers of C ₁₀ -3o-alkyl acrylates and one or more monomers of acrylic acid, methacrylic acid or esters thereof. The INCI name for such compounds is "Acrylates / C 10-30 Alkyl Acrylate Crosspolymer. "Particularly advantageous are the Pemulen® types TR 1, TR 2 and TRZ from Goodrich (Noveon).

Carbopols are also advantageous gelling agents for preparations according to the invention. Carbopols are polymers of acrylic acid, especially acrylate-alkyl acrylate copolymers. Examples of advantageous carbopols are the types 980, 981, 984 1342, 1382, 2984 and 5984, likewise the ETD types 2001, 2020, 2050 and Carbopol Ultrez 10, PVM / MA decadiene crosspolymer (trade name Stabileze 06), polyglyceryl methacrylate and polyacrylamide , Further advantageous gelling agents for such preparations are xanthan gum, polyvinylpyrrolidone, cellulose derivatives, in particular cellulose ethers such as, for example, hydroxypropylmethylcellulose, starch and starch derivatives, hyaluronic acid locust bean gum, silicon dioxide and aluminum silicates.

The thickening agent is present in the gel, dispersion or emulsion e.g. in an amount of between about 0.01 and 5% by weight, preferably between about 0.1 and 2% by weight.

The acrylamidomethylpropyl sulfonic acid polymers, in short AMPS polymers, may be commercially available as 100% active substance or as inverse thickener. Examples:

• crosslinked AMPS copolymers, powder form: Aristoflex AVC (ammonium acryloyldimethyltaurate / VP Copolymer, Clariant) Aristoflex

HMB (ammonium acryloyldimethyltaurate / beheneth-25 methacrylate copolymer, Clariant)

Crosslinked AMPS copolymers, inverse thickeners:

Simulgel NS (Seppic): hydroxyethyl acrylate / sodium acryloyldimethyl taurate copolymer / squalane / polysorbate

Polymers advantageous according to the invention are described, for example, in DE 100 29 462 A1.

Preferred acrylamidomethylpropylsulfonic acid polymers according to the invention carry the INCI name ammonium acryloyldimethyltaurate / vinylpyrrolidinone copolymers.

It may be preferred according to the invention to add complexing agents to the described preparations. Complexing agents are known auxiliaries of cosmetology or medical galenics. Complexing agents, in particular chelators, form complexes with metal atoms, which in the presence of one or more polybasic complexing agents, ie chelators, represent metallacycles. Chelates are compounds in which a single ligand occupies more than one coordination site on a central atom. In this case, therefore, normally stretched compounds by complexing over a metal atom or ion to Rings closed. The number of bound ligands depends on the coordination number of the central metal. The prerequisite for chelation is that the metal-reactive compound contain two or more atomic groups acting as electron donors.

The complexing agent (s) can advantageously be selected from the group of the customary compounds, preference being given to at least one substance from tartaric acid and its anions, citric acid and its anions, aminopolycarboxylic acids and their anions (such as, for example, ethylenediaminetetraacetic acid (EDTA) and their anions, and nitrilotriacetic acid (NTA) and their anions is selected.

The complexing agent (s) according to the invention are advantageously present in cosmetic or dermatological preparations generally at from about 0.01% by weight to about 10% by weight, preferably from about 0.05% by weight to about 10% by weight, more preferably about 0.1 to 1, 0 wt .-%, based on the total weight of the preparations containing.

Advantageous preservatives for the purposes of the present invention are, for example, benzyl alcohol, sorbic acid and its salts, formaldehyde releasers (such as diazolidinyl urea (trade name Germall II from ISP), imidazolidinyl urea (trade name Germall 115) or DMDM hydantoin, which is described, for example, in US Pat the trade name Glydant ™ from the company Lonza), methylisothiazolinone and corresponding derivatives (trade name Kathon CG), iodopropynyl butyl carbamates (for example those available under the trade names Glycacil-L, Glycacil-S from the company Lonza and / or Dekaben LMB by Jan Dekker), parabens (ie, p-hydroxybenzoic acid alkyl esters such as methyl, ethyl, propyl, isopropyl, and / or butylparaben), phenoxyethanol, ethanol, triclosan, benzoic acid, and the like. Usually, the preservation system according to the invention also advantageously also comprises substances which improve the effectiveness of classical preservatives, such as, for example, hexanediol, pentanediol and methylpropanediol.

It is also advantageous to add conventional antioxidants to the preparations of the present invention. According to the invention, all antioxidants which are suitable or customary for cosmetic and / or dermatological applications can be used as favorable antioxidants.

The amount of antioxidants (one or more compounds) in the preparations is preferably from 0.001 to 30% by weight, particularly preferably from 0.05 to 20% by weight, in particular from 1 to 10% by weight, based on the total weight of the preparation , Advantageously, the antioxidants are selected from the group consisting of amino acids (eg glycine, alanine, serine, arginine) and derivatives thereof, peptides such as D, L-carnosine, D-carnosine, L-carnosine and their derivatives (eg anserine), carotenoids ( eg alpha-carotene, beta-carotene, lycopene) and their derivatives, lipoic acid and its derivatives (eg dihydrolipoic acid), thiols (eg thioredoxin, glutathione, cysteine, cystine, cystamine) and their salts,, furthermore (metal) - chelators (eg alpha-hydroxy fatty acids, phytic acid, lactoferrin), alpha-hydroxy acids (eg citric acid, lactic acid, malic acid), unsaturated fatty acids and their derivatives (eg gamma-linolenic acid, linoleic acid, oleic acid), folic acid and its derivatives, ubiquinone and ubiquinol and their derivatives (in particular ubiquinone Q10), glycyrrhetinic acid, vitamin C and derivatives (eg ascorbyl palmitate, Na ascorbyl phosphate), tocopherols and derivatives (eg vitamin E acetate), vitamin A and derivatives (vitamin A palmitate), rutinic acid and their derivatives D derivatives, plant polyphenols with a logP of 1-3, quercetin, isoflavones, genistein, genistin, daidzein, alpha-glycosylrutin, ferulic acid, butylhydroxytoluene

Particularly advantageous for the purposes of the present invention, water-soluble antioxidants can be used, such as vitamins, eg. As ascorbic acid and its derivatives.

Preferred antioxidants are also vitamin E (alpha-tocopherol) and its derivatives as well as vitamin A (retinol) and its derivatives.

If vitamin E and / or its derivatives represent the antioxidant (s), it is advantageous to choose their respective concentrations from the range from 0.001 to 10% by weight, based on the total weight of the formulation.

If vitamin A or vitamin A derivatives, or carotenes or their derivatives or analogs represent the antioxidant (s), it is advantageous if their respective concentrations are in the range from 0.001 to 5% by weight, based on the total weight of the formulation , to choose.

It is particularly advantageous if the cosmetic preparations according to the present invention contain cosmetic or dermatological active ingredients, where preferred active ingredients are antioxidants which can protect the skin against oxidative, photochemical and / or radical stress.

Further particularly advantageous active ingredients in the context of the present invention are natural active ingredients and / or their derivatives, such as. B. D-biotin, coenzyme Q10 (ubiquinone or ubiquinol and its derivatives), alpha-glucosylrutin, carnitine, natural and / or synthetic isoflavotenoids, vitamin B3 (niacin or niacinamide), taurine and 8-hexadecene-1, 16-dicarboxylic acid (Dioic acid, CAS number 20701-68-2, provisional INCI name octadecenedioic acid).

Inventive formulations which z. B. known anti-wrinkle active ingredients such as flavone glycosides (especially alpha-glycosyl rutin), creatine and creatinine, genistein, vitamin A, coenzyme Q10 and the like, are particularly advantageous for the prophylaxis and treatment of cosmetic or dermatological skin changes, as z. Skin aging (such as dryness, roughness, and formation of dryness wrinkles, itching, decreased refatting (eg, after washing), visible vasodilation (telangiectasia, cuperosis), flaccidity, and formation of wrinkles and wrinkles, local Hyper-, hypo- and false pigmentation (eg, age spots), increased susceptibility to mechanical stress (eg, cracking), and the like). Furthermore, they are advantageously suitable against the appearance of dry or rough skin.

In addition, the use of the cosmetic preparations according to the invention for the prophylaxis and treatment of the symptoms of the sensitive or inflamed skin is advantageous. Preferred active ingredients for this purpose are: ingredients of the milk thistle, in particular silymarin, licochalcone, in particular licochalcone A, dexpanthenol, witch hazel extract, chamomile extract, ingredients of the licorice plant (glycerrhizic acid), acetylsalicylic acid, diclofenac, pentacyclic triterpenes (sericosides, ursolic acid) and panthenol.

In addition, the use of the spherical cosmetic preparations according to the invention for the prophylaxis and treatment of the symptoms of the maligmatized skin is advantageous. Preferred active substances for this purpose are: tyrosinase inhibitors, hydroquinone derivatives, dioic acid, lipoic acid and its derivatives, vitamin C and its derivatives, ellagic acid and kojic acid.

It may be possible and advantageous to use the compositions of the invention as a basis for pharmaceutical formulations. Furthermore, the use of the spherical cosmetic preparations according to the invention for the prophylaxis and treatment of the symptoms of diseased skin is preferred. Relevant but not exclusive pathological skin conditions are psoriasis, acne, atopic dermatitis and other atopic diseases such as atopic dermatitis, skin cancer, herpes, mycoses, ichthyosis, pityriasis, seborrhea, pellagra, contact eczema and allergies. Suitable active ingredients for such purposes are antibiotics such as fusidic acid, erythromycin, sulfadiazine, clindamycin, tetracyclines, tyrothricin aminoglycosides, bacitracin, chloramphenicol, antivirals (eg acyclovir, idoxuridine, penciclovir), antifungals (eg nystatin, amphotericin, clotrimazole, econazole, ketoconazole, naftifine, Terbinafine), allethrin, cytostatics (5-fluorouracil), Antiphlogistics (hydrocortisone, bethamethasone, prednisolone, triamcinolone acetonide, dexamethasone, diclofenac, bufexamac), immunosuppressants (cyclosporin A, interferon-beta), antipsoriatics (dithranol, psoralen, tazarotene), acne agents (retinoic acid, isotretinoin, benzoyl peroxide, adapalene); Capsaicin, azelaic acid, keratolytics (salicylic acid, lactic acid), antihistamines (azelastine, levocabastine, disodium cromoglycine); Antipsoriatics (dithranol, calcitriol, psoralen) and vitamins (especially the A, B and C vitamins).

Humectants and / or skin-moisturizing substances are substances or mixtures of substances which confer on cosmetic or dermatological preparations the property of reducing or eliminating the moisturization of the horny layer (also called transepidermal water ioss (TEWL)) after application or spreading on the skin surface to positively influence the hydration of the horny layer. Advantageous moisturizers for the purposes of the present invention are, for example, glycerol, lactic acid and / or lactates, in particular sodium lactate, panthenol, fucogel, glycine soya, ethylhexyloxyglycerol, pyrrolidonecarboxylic acid and its derivatives, and also urea. Furthermore, it is particularly advantageous to use polymeric moisturizers from the group of water-soluble and / or water-swellable and / or water-gellable polysaccharides. Hyaluronic acid, chitosan and / or a fucose-rich polysaccharide, for example, which are filed in the Chemical Abstracts under the registry number 178463-23-5 and z. B. under the name Fucogel®1000 is available. Moisturizers can also be used advantageously as anti-wrinkle active ingredients for the prophylaxis and treatment of cosmetic or dermatological skin changes, as described, for example, in US Pat. B. occur during skin aging, can be used.

It is also possible and advantageous according to the invention to use a content of UV protective substances. Therefore, preparations according to the invention can advantageously contain substances which absorb UV radiation in the UVB range, the total amount of the filter substances preferably being between about 0.1% by weight and about 30% by weight. Preference is given to commercially available water or oil-soluble UVB filters. It may also be advantageous to use UVA filters in formulations according to the invention which are customarily contained in cosmetic and / or dermatological preparations. It can be used the same amounts, which were called for UVB filter.

Advantageous UV-A filter substances for the purposes of the present invention are dibenzoyl methane derivatives, in particular 4- (tert-butyl) -4'-methoxydibenzoylmethane (CAS No. 70356-09-1), which has been sold by Givaudan under the trademark Parsol ^® 1789 and sold by Merck under the trade name Eusolex® 9020. Advantageous further UV filter substances in the context of the present invention are sulfonated, water-soluble UV filters, such as. B .:

• phenylene-1, 4-bis- (2-benzimidazyl) -3,3'-5.5 ^l -tetrasulfonsäure and its salts, particularly the corresponding sodium, potassium or triethanolammonium salts, in particular phenylene-1, 4 bis (2-benzimidazyl) -3,3'-5,5'-tetrasulfonic acid bis-sodium salt with the

INCI name Bisimidazylate (CAS No .: 180898-37-7), which is available, for example, under the trade name Neo Heliopan AP from Haarmann &Reimer;

Salts of 2-phenylbenzimidazole-5-sulfonic acid, such as its sodium, potassium or triethanolammonium salt, and also the sulfonic acid itself with the INCI name phenylbenzimidazole sulfonic acid (CAS No. 27503-81-7), which, for example, under the

Trade name Eusolex 232 available from Merck or Neo Heliopan Hydro from Haarmann &Reimer;

1, 4-di (2-oxo-10-sulfo-3-bornylidenemethyl) benzene (also: 3,3 '- (1,4-phenylenedimethylene) bis (7,7-dimethyl-2-oxo) bicyclo [2.2.1] hept-1-ylmethane sulfonic acid) and its salts (especially the corresponding 10-sulfato compounds, in particular the corresponding sodium, potassium or triethanolammonium salt), which is also known as benzene-1, 4- benzo-1,4-di (2-oxo-3-bornylidenemethyl-10-sulfonic acid) has the INCI name Terephtalidene Dicampher sulfonic acid (CAS. No .: 90457-82-2) and is available, for example, under the trade name Mexoryl SX from Chimex;

Sulfonic acid derivatives of 3-Benzylidencamphers, such as. B. 4- (2-oxo-3-bornylidenme- thyl) benzenesulfonic acid, 2-methyl-5- (2-oxo-3-bomylidenemethyl) sulfonic acid and salts thereof.

Advantageous UV filter substances for the purposes of the present invention are also so-called broadband filters, i. Filter substances that absorb both UV-A and UV-B radiation. Advantageous broadband filters or UV-B filter substances are, for example, triazine derivatives, such as. B.

2,4-bis - {[4- (2-ethyl-hexyloxy) -2-hydroxy] -phenyl} -6- (4-methoxyphenyl) -1, 3,5-triazine (INCI: aniso triazine), which is available under the trade name Tinosorb® S is available from CIBA-Chemikalien GmbH;

Diethylhexylbutylamidotriazone (INCI: diethylhexylbutamidotriazone), which is available under the trade name UVASORB HEB from Sigma 3V;

4,4 ', 4 "- (1,3,5-triazine-2,4,6-tri-triimino) tris-benzoic acid tris (2-ethylhexyl ester), also: 2,4,6-tris [anilino- (p-carbo-2'-ethyl-1'-hexyloxy)] - 1, 3,5-triazine (INCI: ethylhexyl triazone), which is sold by BASF Aktiengesellschaft under the trade name UVINUL® T 150. An advantageous broadband filter for the purposes of the present invention is also the 2,2'-methylenebis (6- (2H-benzotriazol-2-yl) -4- (1,1,3,3-tetramethylbutyl) phenol), which is available under the trade name Tinosorb® M from CIBA-Chemikalien GmbH.

Advantageous broadband filter according to the present invention is further the 2- (2H-benzothiazol-2-yl) -4-methyl-6- [2-methyl-3- [1,3,3,3-tetramethyl-1] [(trimethylsilyl) oxy] disiloxanyl] propyl] phenol (CAS No .: 155633-54-8) with the INCI name Drometrizole Trisiloxane, which is available under the trade name Mexoryl® XL from Chimex.

The other UV filter substances can be oil-soluble or water-soluble.

Advantageous oil-soluble UV-B and / or broadband filter substances in the context of the present invention are, for. B .:

■ 3-benzylidene camphor derivatives, preferably 3- (4-methylbenzylidene) camphor, 3-benzylidene camphor;

Cinnamic acid derivatives, preferably 2-ethylhexyl methoxycinnamate (CAS No .: 5466-77-3), which is available under the trade name Parsol MCX from Givaudan.

■ 4-aminobenzoic acid derivatives, preferably (2-ethylhexyl) -4- (dimethylamino) benzoate, 4- (dimethylamino) benzoic acid amyl ester;

■ Derivatives of benzophenone, preferably 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-methoxy-4'-methylbenzophenone, 2,2'-dihydroxy-4-methoxybenzophenone

■ as well as UV-bound polymers.

■ 3- (4- (2,2-bis ethoxycarbonylvinyl) phenoxy) propenyl) methoxysiloxane / dimethylsiloxane copolymer, which is available, for example, under the trade name Parsol® SLX from Hoffmann La Roche.

Advantageous water-soluble filter substances are z. B .:

Sulfonic acid derivatives of 3-Benzylidencamphers, such as. B. 4- (2-oxo-3-bomylidenemethyl) benzene sulfonic acid, 2-methyl-5- (2-oxo-3-bomylidenemethyl) sulfonic acid and salts thereof.

A further light protection filter substance according to the invention to be used advantageously is ethylhexyl-2-cyano-3,3-diphenylacrylate (octocrylene), which is available from BASF under the name Uvinul ^® N 539th

Particularly advantageous preparations according to the present invention, which are characterized by a high or very high UV-A and / or UV-B protection, in addition to the or the filter substance (s) according to the invention preferably further UV-A and / or broadband filters, in particular Dibenzoylmethanderivate [for example, the 4- (tert-butyl) -4'-methoxydibenzoylmethan], phenylene-1, 4-bis (2 benzimidazyl) -3,3'-5,5'-tetrasulfonic acid and / or its salts, the 1, 4-di (2-oxo-10-sulfo-3-bomylidenemethyl) benzene and / or its salts and / or the 2,4-bis - {[4- (2-ethyl-hexyloxy) -2-hydroxy] -phenyl} -6- (4-methoxyphenyl) -1,3,5-triazine, individually or in any combination with one another.

The list of said UV filters which can be used in the context of the present invention is of course not intended to be limiting.

Advantageously, the preparations of the invention contain the substances which absorb UV radiation in the UV-A and / or UV-B range, in a total amount of z. B. 0.1 wt .-% to 30 wt .-%, preferably 0.5 to 20 wt .-%, in particular 1, 0 to 15.0 wt .-%, each based on the total weight of the preparations to cosmetic To provide preparations that protect the hair or the skin from the entire range of ultraviolet radiation.

Cosmetic and / or dermatological preparations according to the invention may also contain inorganic pigments which are conventionally used in cosmetics for protecting the skin from UV rays. These are usually oxides of titanium, zinc, iron, zirconium, silicon, manganese, aluminum and mixtures thereof. Particular preference is given to pigments based on titanium dioxide TiO ₂ or zinc oxide ZnO. The quantities mentioned for the previous combinations can be used.

Suitable titanium dioxide particles and predispersions of titanium dioxide particles are available from the following companies under the following trade names:

Suitable propellants for cosmetic and / or dermatological 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. Compressed air is also an advantage.

Of course, the person skilled in the art knows that there are per se nontoxic propellants which would in principle be suitable for the realization of the present invention in the form of aerosol preparations, but which should nevertheless be dispensed with because of harmful effects on the environment or other accompanying circumstances, in particular fluorocarbons and Chlorofluorocarbons (CFCs).

Cosmetic and / or dermatological preparations according to the invention may also contain clay minerals, such as phyllosilicates and / or silicas, as occur, for example, in oily cosmetic deodorants and antiperspirants as suspending aids.

Advantageous phyllosilicates, optionally modified, for the purposes of the present invention can be selected, for example, from the group montmorillonite, kaolinite, mit, beidellite, nontronite, saponite, hectorite, bentonite, smectite.

Examples of phyllosilicates are:

Montmorillonite is the main mineral of the naturally occurring bentonites.

Phyllosilicates are well documented in the literature, eg in "Lehrbuch der Inorganischen Chemie", AF Hollemann, E. Wiberg and N. Wiberg, 91.-100. Ed., Walter de Gruyter-Verlag 1985, passim, as well as "Textbook of Inorganic Chemistry", H. Remy, 12th ed., Akademische Verlagsgesellschaft, Leipzig 1965, passim. The layer structure of montmorillonite is Römpps Chemie-Lexikon, Franckh'sche Verlagshandlung W. Keller & Co., Stuttgart, δ.Aufl., 1985, p 2668f.

Preparations according to the present invention may also be distinguished by a content of surfactants. Surfactants are amphiphilic substances that can dissolve organic, nonpolar substances in water. Due to their specific molecular structure with at least one hydrophilic and one hydrophobic part of the molecule, they provide for a lowering of the surface tension of the water, the wetting of the skin, the facilitation of dirt removal and dissolution, a gentle rinsing and, as desired, for foam regulation.

The hydrophilic fractions of a surfactant molecule are usually polar functional groups, for example -COO ^" , -OSO ₃ ^{2 '} , -SO ₃ ^" , while the hydrophobic parts are generally nonpolar hydrocarbon radicals. Surfactants are generally classified according to the nature and charge of the hydrophilic part of the molecule. Here four groups can be distinguished:

Anionic surfactants,

Cationic surfactants,

• amphoteric surfactants and

• nonionic surfactants.

It has not been foreseen by those skilled in the art that the present invention is particularly suitable for use in cosmetic or dermatological preparations

Care of the dry house

Increase of the barrier performance of the skin - protection of the skin from exogenous pollutants

Protection and prevention of the symptoms of sensitive skin

Reduction of skin roughness

Care of the aging skin

Care of stressed hair - care of the scalp

Improvement of well-being in the application of the invention to skin and

Hair.

Following are advantageous embodiments of the present invention

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

O / W cream

O / W Day Cream

Sunblock

After Sun Lotion

After Shave BaIm

O / W cream

O / W cream

O / W cream

microemulsion

Examples of W / O pins

Deodorant creams macro emulsions

Raw material (INCI)% by weight

Polyethylene glycol (21) stearyl ether 3,000 3,000 3,000 1, 500

Polyethylene glycol (2) stearyl ether 2,000 2,000 2,500 3,000

Polypropylene glycol (15) stearyl ether 2,000 3,000 3,000

Coconut fatty acid 2-ethylhexyl ester - - 1, 000 -

Na ₃ HEDTA (20% aqueous solution) 1, 500 1, 500 1, 500 1, 500

Avocado oil 0.100 0.100 0.100 0.100

Aluminum Chlorohydrate 10,000 15,000 8,000 4,000

Perfume, Antioxidants (EDTA) q.s. q.s. q.s. q.s.

(1R, 2S, 5R) -2-isopropyl-5-methyl-N- (2-05-0,2 (pyridin-2-yl) -ethyl-cyclohexanecarboxamide

(1R, 2S, 5R) -N- (4- (cyanomethyl) -phenyl) -2- 0.1 0.2 isopropyl-5-methylcyclohexanecarboxamide

Water, ad 100,000 100,000 100,000 100,00

Transparent microemulsion - roll-on

Translucent deodorant microemulsion

Deo macro emulsion roll-on

Deodorant aerosol spray type A

The liquid phase obtained by mixing together the respective components is filled with a propane-butane mixture (2.7) in the ratio 39:61 in aerosol containers.

Deodorant aerosol spray type B

The liquid phase obtained by mixing the respective components together with a propane-butane mixture (2.7) in the ratio 17:83 filled in aerosol container.

Deodorant roll-on emulsion

Deo stick

shampoo

shampoo

hair conditioner

hair conditioner

Claims

claims

1. Cooling preparations for human skin and / or mucosal contact containing (1 R, 2S, 5R) -2-isopropyl-5-methyl-N- (2- (pyridin-2-yl) ethyl-cyclohexanecarboxamide and / or (1R, 2S, 5R) -N- (4- (cyanomethyl) -phenyl) -2-isopropyl-5-methylcyclohexanecarboxamide.

2. Use of (1R, 2S, 5R) -2-isopropyl-5-methyl-N- (2- (pyridin-2-yl) ethylcyclohexanecarboxamide and / or (1R, 2S, 5R) -N- (4- (Cyanomethyl) phenyl) -2-isopropyl-5-methylcyclohexanecarboxamide to create a sensation of cold on the skin or mucous membrane.

3. A preparation according to claim 1 or use according to claim 2, characterized marked, that the preparations 0.001 to 10 wt .-%, particularly preferably 0.01 to 1 wt .-%, of (1R, 2S, 5R) -2 -isopropyl-5-methyl-N- (2- (pyridin-2-yl) -ethyl-cyclohexanecarboxamide and / or (1R, 2S, 5R) -N- (4- (cyanomethyl) -phenyl) -2-isopropyl- 5 methylcyclohexanecarboxamide, based on the total composition of the preparations.

4. Preparation or use according to one of the preceding claims, characterized in that it is cosmetically.

5. Preparation or use according to one of the preceding claims, character- ized in that the preparation is edible or drinkable.

6. Preparation or use according to one of the preceding claims, characterized in that the preparations contain vitamins.

7. Preparation or use according to one of the preceding claims, characterized in that the preparations contain antioxidants.