Thermally stable combinations of one or more alkylamidothiazoles and beta-tocopherol and cosmetic formulations containing such combinations

Abstract

The present invention relates to thermally stable combinations of one or more alkylamidothiazoles and beta-tocopherol and cosmetic formulations containing such combinations. In particular, the present invention relates to an active ingredient combination of a) one or more alkylamidothiazoles and b) beta-tocopherol and c) optionally 3-O-ethyl ascorbic acid.

Description

Technical Field

[0001] The present invention belongs to the field of beauty and particularly relates to a thermally stable combination of one or more alkylamidothiazoles and β-tocopherol, and a beauty preparation containing such a combination. Background Art

[0002] Generally speaking, beauty products not only make people look beautiful and charming, but their effects also make a decisive contribution to enhancing people's self-esteem and well-being. Therefore, a variety of beauty products are used for the daily cleansing and care of human skin. For example, a beauty preparation for human skin care containing alkylamidothiazole is known from DE 102011083259 A1.

[0003] The alkylamidothiazole used is for combating and preventing unwanted skin pigmentation in beauty preparations. In this way, the skin color of users can be decisively improved.

[0004] It is also known from DE 102013226711 A1 that alkylamidothiazole can be used in beauty or dermatological preparations for the prevention and treatment of sensitive skin, itching, dry skin and inflammatory symptoms of human skin. The document discloses various beauty O / W emulsions applied to human skin.

[0005] In addition, DE 102013204110 A1 discloses a large number of beauty preparations for human skin care containing alkylamidothiazole.

[0006] By the combined use of alkylamidothiazole and one or more cyclodextrins, particularly effective whitening of human skin can be achieved.

[0007] However, the fact that a large number of beauty preparations containing alkylamidothiazole are known to those skilled in the art cannot obscure the fact that a large number of problems may occur when formulating beauty or dermatological preparations.

[0008] For example, one drawback is the fact that the color of newly produced beauty or dermatological preparations changes during storage. This situation is more serious when the preparation is exposed to higher temperatures, such as 40 °C and above.

[0009] This situation poses considerable difficulties to the manufacturers of beauty preparations, because it is necessary to study the color stability of beauty preparations.

[0010] This usually requires a large number of methods, which greatly increases the development cost of beauty products.

[0011] Accordingly, there is a desire to provide systems and methods for effectively preventing or minimizing degradation processes in cosmetic or dermatological formulations, thereby minimizing development costs. The problem of degradation processes in cosmetic or dermatological formulations is also relevant to consumers.

[0012] Products are generally selected based on their optical appearance or their outer surface. However, if the white appearance of a product deteriorates during storage, consumers are usually annoyed because it no longer meets the decisive purchase criteria.

[0013] In principle, the color stability of cosmetic or dermatological formulations can be evaluated by specially trained personnel who compare freshly prepared formulations (within 24 hours after preparation) with the color after a corresponding storage time. However, it is always difficult to judge the color change of a product. Therefore, it is advantageous to use a special instrument called Digi-Eye for color change.

[0014] Accordingly, an object of the present invention is to provide a method for preventing or minimizing degradation processes in cosmetic products in a particularly effective manner, thereby ensuring color stability. Summary of the Invention

[0015] This object is achieved by a combination of active ingredients of a) one or more alkylamidothiazoles and b) β-tocopherol.

[0016] Another embodiment of the present invention is a cosmetic formulation containing such a combination.

[0017] Another embodiment of the present invention is a method of using b) β-tocopherol for preventing or reducing the degradation of alkylamidothiazoles caused by oxidation processes and / or heat in cosmetic formulations containing one or more alkylamidothiazoles.

[0018] β-Tocopherol is characterized by the following chemical structure:

[0019]

[0020] Like α-tocopherol, it is a well-known antioxidant.

[0021] A preferred embodiment of the present invention is also a cosmetic or dermatological formulation containing such a combination of active ingredients, and its use for whitening human skin. Detailed Description

[0022] Advantageously, the formulation according to the present invention comprises a formulation in which, in order to provide a cosmetic formulation, the total amount of the one or more alkylamidothiazoles is, for example, from 0.00001% by weight to 10% by weight, preferably from 0.001% by weight to 5% by weight, in particular from 0.005% by weight to 3% by weight, based on the total weight of the formulation.

[0023] In advantageous cases, the preparation according to the invention comprises a formulation, wherein, for providing a cosmetic preparation, the total amount of the β-tocopherol is, for example, from 0.00001% by weight to 10% by weight, preferably from 0.001% by weight to 5% by weight, in particular from 0.005% by weight to 3% by weight, based on the total weight of the preparation.

[0024] In advantageous cases, the preparation according to the invention comprises a formulation which additionally contains 3-O-ethylascorbic acid, wherein, for providing a cosmetic preparation, the total amount of the 3-O-ethylascorbic acid is, for example, from 0.00001% by weight to 10% by weight, preferably from 0.001% by weight to 5% by weight, in particular from 0.005% by weight to 3% by weight, based on the total weight of the preparation.

[0025] In the context of the present invention, advantageous alkylamidothiazoles are substances of the following general formula:

[0026]

[0027] wherein R1, R2, X and Y can be different, partly identical or completely identical, and can independently of one another denote:

[0028] R1 = —C1-C24-alkyl (linear and branched), —C1-C24-alkenyl (linear and branched), —C1-C8-cycloalkyl, —C1-C8-cycloalkyl-alkyl-hydroxy, —C1-C24-alkyl-hydroxy (linear and branched), —C1-C24-alkylamine (linear and branched), —C1-C24-alkylaryl (linear and branched), —C1-C24-alkylaryl-alkyl-hydroxy (linear and branched), —C1-C24-alkylheteroaryl (linear and branched), —C1-C24-alkyl-O—C1-C24-alkyl (linear and branched), —C1-C24-alkyl-morpholinyl, —C1-C24-alkyl-piperidinyl, —C1-C24-alkyl-piperazinyl, —C1-C24-alkyl-piperazinyl-N-alkyl,

[0029] R2 = H, —C1-C24-alkyl (linear and branched), —C1-C24-alkenyl (linear and branched), —C1-C8-cycloalkyl, —C1-C24-hydroxyalkyl (linear and branched), —C1-C24-alkylaryl (linear and branched), —C1-C24-alkylheteroaryl (linear and branched),

[0030] X = —H, —C1-C24-alkyl (linear and branched), —C1-C24-alkenyl (linear and branched), —C1-C8-cycloalkyl, —C1-C24-aryl (optionally mono- or polysubstituted by —OH, —F, —Cl, —Br, —I, —OMe, —NH2, —CN), —C1-C24-heteroaryl (optionally mono- or polysubstituted by —OH, —F, —Cl, —Br, —I, —OMe, —NH2, —CN), —C1-C24-alkylaryl (linear and branched), —C1-C24-alkylheteroaryl (linear and branched), -aryl (optionally mono- or polysubstituted by —OH, —F, —Cl, —Br, —I, —OMe, —NH2, —CN), -phenyl, -2,4-dihydroxyphenyl, -2,3-dihydroxyphenyl, -2,4-dimethoxyphenyl, -2,3-dimethoxyphenyl, Y = H, —C1-C24-alkyl (linear and branched), —C1-C24-alkenyl (linear and branched), —C1-C8-cycloalkyl, —C1-C24-aryl, —C1-C24-heteroaryl, —C1-C24-alkylaryl (linear and branched), —C1-C24-alkylheteroaryl (linear and branched), -aryl, -phenyl, -2,4-dihydroxyphenyl, -2,3-dihydroxyphenyl, -2,4-dimethoxyphenyl, -2,3-dimethoxyphenyl, —COO-alkyl, —COO-alkenyl, —COO-cycloalkyl, —COO-aryl, —COO-heteroaryl, and X, Y can also optionally = fused aromatic, where X and Y can form with each other an aromatic or aliphatic homocyclic or heterocyclic system having at most n ring atoms, and where the number n can take values from 5 to 8, and the corresponding ring system can in turn be substituted by at most n - 1 alkyl, hydroxy, carboxy, amino, nitrile functional groups, sulfur-containing substituents, ester groups and / or ether groups.

[0031] The thiazole can be in the form of the free base or a salt, such as fluoride, chloride, bromide, iodide, sulfate, carbonate, ascorbate, acetate or phosphate. In particular, in the form of a halogen salt, such as chloride and bromide.

[0032] Furthermore, an advantageous embodiment of the invention is a cosmetic or dermatological preparation having an effective content of one or more of the above alkylamidothiazoles.

[0033] The use of the above alkylamidothiazoles for the treatment and / or prevention of undesired skin pigmentation also falls within the scope of the invention.

[0034] Here, the treatment and / or prevention of undesired skin pigmentation can be in both the cosmetic and the pharmaceutical fields.

[0035] In this context, the pharmaceutical (or dermatological) treatment is mainly understood to be for diseased skin conditions, while the cosmetic treatment and / or prevention of undesired skin pigmentation is mainly related to healthy skin.

[0036] In a preferred case, X is selected from substituted phenyl, in which case the substituents (Z) can be selected from —H, —OH, —F, —Cl, —Br, —I, —OMe, —NH2, —CN, acetyl, and can be the same or different.

[0037]

[0038] In a particularly preferred case, X is selected from phenyl substituted by one or more hydroxyl groups, in which case the substituents (Z) can be selected from —H, —OH, —F, —Cl, —Br, —I, —OMe, —NH2, —CN, acetyl, and preferably the following general structures, where Y, R1, and R2 can have the properties defined above.

[0039]

[0040] Particularly preferred compounds are those that meet the following conditions:

[0041] X =

[0042] Y = H

[0043] R1 = —C1-C24-alkyl (linear and branched), —C1-C24-alkenyl (linear and branched), —C1-C8-cycloalkyl, —C1-C8-cycloalkyl-alkyl-hydroxy, —C1-C24-alkyl-hydroxy (linear and branched), —C1-C24-alkyl-amine (linear and branched), —C1-C24-alkyl-aryl (linear and branched), —C1-C24-alkyl-aryl-alkyl-hydroxy (linear and branched), —C1-C24-alkyl-heteroaryl (linear and branched), —C1-C24-alkyl-O—C1-C24-alkyl (linear and branched), —C1-C24-alkyl-morpholinyl, —C1-C24-alkyl-piperidinyl, —C1-C24-alkyl-piperazinyl, —C1-C24-alkyl-piperazinyl-N-alkyl,

[0044] R2 = H, —C1-C24-alkyl (linear and branched),

[0045] Z = —H, —OH, —F, —Cl, —Br, —I, —OMe, —NH2, —CN, acetyl.

[0046] Particularly preferred are compounds that meet the following conditions, where the pictures can be obtained from the "original literature":

[0047] X =

[0048] Y = H

[0049] R1 = —C1-C24 alkyl (linear and branched), —C1-C24 alkenyl (linear and branched), —C1-C8 cycloalkyl, —C1-C8 cycloalkyl-alkyl hydroxy, —C1-C24 alkyl hydroxy (linear and branched), —C1-C24 alkylamine (linear and branched), —C1-C24 alkylaryl (linear and branched), —C1-C24 alkyl-aryl-alkyl-hydroxy (linear and branched), —C1-C24 alkyl heteroaryl (linear and branched), —C1-C24 alkyl-O—C1-C24 alkyl (linear and branched), —C1-C24 alkyl morpholinyl, —C1-C24 alkyl piperidinyl, —C1-C24 alkyl piperazinyl, —C1-C24 alkyl piperazinyl-N-alkyl,

[0050] R2 = H

[0051] Within the scope of the present invention, the following compounds are the most preferred compounds:

[0052]

[0053] N-(4-(2,4-Dihydroxyphenyl)thiazol-2-yl)pivalamide

[0054]

[0055] N-(4-(2,4-Dihydroxyphenyl)thiazol-2-yl)isobutyramide

[0056]

[0057] N-(4-(2,4-Dihydroxyphenyl)thiazol-2-yl)butyramide

[0058]

[0059] N-(4-(2,4-Dihydroxyphenyl)thiazol-2-yl)heptanamide

[0060]

[0061] N-(4-(2,4-Dihydroxyphenyl)thiazol-2-yl)-6-hydroxyhexanamide

[0062]

[0063] N-(4-(2,4-Dihydroxyphenyl)thiazol-2-yl)-3-hydroxypropanamide

[0064]

[0065] N-(4-(2,4-Dihydroxyphenyl)thiazol-2-yl)-2-methoxyacetamide

[0066]

[0067] 3-Amino-N-(4-(2,4-dihydroxyphenyl)thiazol-2-yl)propanamide

[0068]

[0069] N-(4-(2,4-Dihydroxyphenyl)thiazol-2-yl)acetamide

[0070]

[0071] N-(4-(2,4-Dihydroxyphenyl)thiazol-2-yl)-4-(hydroxymethyl)cyclohexanecarboxamide

[0072]

[0073] N-(4-(2,4-Dihydroxyphenyl)thiazol-2-yl)cyclohexanecarboxamide

[0074] .

[0075] N-(4-(2,4-Dihydroxyphenyl)thiazol-2-yl)-2-(4-(hydroxymethyl)phenyl)acetamide.

[0076] Cosmetic or dermatological preparations containing alkylamidothiazoles and their use for treating and / or preventing undesired skin pigmentation are likewise advantageous embodiments of the present invention.

[0077] In particularly advantageous cases, such preparations contain, based on the total weight of the preparation, from 0.000001 to 10% by weight, in particular from 0.0001 to 3% by weight, very particularly from 0.001 to 1% by weight of one or more alkylamidothiazoles used according to the invention.

[0078] The cosmetic and dermatological preparations according to the invention can take various forms. Thus, they can be, for example, solutions, anhydrous preparations, emulsions or microemulsions of the water-in-oil (W / O) or oil-in-water (O / W) type, multiple emulsions such as water-in-oil-in-water type (W / O / W), gels, solid sticks, balms or aerosols. According to the invention, it is also advantageous to administer the substances and / or their derivatives used according to the invention in encapsulated form, for example in a collagen matrix and other customary encapsulation materials, such as in the form of cellulose encapsulation, gelatin or liposome encapsulation.

[0079] In the context of the present invention, it is also possible and advantageous to add the substances and / or their derivatives used according to the present invention to aqueous systems or surfactant preparations for cleaning the skin and hair.

[0080] The cosmetic and dermatological preparations according to the present invention can contain cosmetic auxiliaries commonly used in such preparations, such as preservatives, bactericides, fragrances, anti-foaming substances, dyes, pigments with coloring effects, thickeners, surface-active substances, emulsifiers, softening, moisturizing and / or wetting substances, fats, oils, waxes or other commonly used components of cosmetic or dermatological formulations, such as alcohols, polyols, polymers, foam stabilizers, electrolytes, organic solvents or silicone derivatives.

[0081] The lipid phase can advantageously be selected from the following substances: mineral oil, mineral wax oil such as triglycerides of capric acid or caprylic acid, and natural oils such as castor oil; fats, waxes and other natural and synthetic fatty bodies, preferably esters of fatty acids with lower-carbon alcohols such as with isopropanol, propylene glycol or glycerol, or esters of fatty alcohols with lower-carbon chain alkanoic acids or fatty acids; alkyl benzoates; silicone oils, such as dimethylpolysiloxane, diethylpolysiloxane, diphenylpolysiloxane and mixtures thereof.

[0082] In the context of the present invention, the oil phase of an emulsion, oil gel or aqueous or fat dispersion advantageously is selected from esters of saturated and / or unsaturated, branched and / or unbranched alkanoic acids with 3 to 30 C atoms in the chain length and saturated and / or unsaturated, branched and / or unbranched alcohols with 3 to 30 C atoms in the chain length, and esters of aromatic carboxylic acids with saturated and / or unsaturated, branched or unbranched alcohols with 3 to 30 C atoms in the chain length. Thus, such ester oils can advantageously be selected from 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, erucyl oleate, oleyl erucate, erucyl erucate, and synthetic, semi-synthetic and natural mixtures of such esters, such as jojoba oil.

[0083] The aqueous phase of the preparations according to the present invention optionally advantageously contains wetting agents such as propylene glycol, panthenol or hyaluronic acid, and in particular one or more thickeners, which can advantageously be selected from silica, aluminum silicate, hydroxypropylmethyl cellulose, and particularly advantageously polyacrylates, such as Carbopol grade 980, which are used alone or in combination in each case.

[0084] In particular, mixtures of the above solvents are used. In the case of alcohol solvents, water can be another component.

[0085] The emulsion according to the invention is advantageous and contains, for example, specific fats, oils, waxes and other fatty substances, as well as water and emulsifiers, as is commonly used in formulations of this type.

[0086] The gel according to the invention generally contains, in the presence of a thickening agent, a lower-carbon alcohol such as ethanol, propylene glycol and water or the abovementioned oils, and the thickening agent is preferably silica or aluminium silicate in the case of an oil-alcohol gel and polyacrylate in the case of a water-alcohol gel or an alcohol gel.

[0087] Propellants suitable for the formulations according to the invention that can be ejected from an aerosol container are commonly known volatile liquefied propellants, such as hydrocarbons (propane, butane, isobutane), which can be used alone or in admixture with one another. Compressed air can also be advantageously used.

[0088] Advantageously, the formulations according to the invention can also advantageously contain substances that absorb UV radiation in the UVB region, and the total amount of the filtering substances is, for example, from 0.1% by weight to 30% by weight, preferably from 0.5 to 10% by weight, in particular from 1.0 to 6.0% by weight, based on the total weight of the formulation, to provide a cosmetic formulation that protects hair and / or skin from the entire range of ultraviolet radiation. They can also act as a sunscreen for hair or skin.

[0089] Furthermore, the formulations according to the invention can advantageously additionally contain substances that mask the objectionable inherent odours of the remaining raw materials used, and the total amount of the perfume components is, for example, from 0.001% by weight to 30% by weight, preferably from 0.05 to 10% by weight, in particular from 0.1 to 5.0% by weight, based on the total weight of the formulation, in order to provide a cosmetic formulation.

[0090] The following examples are intended to illustrate the invention without limiting it. Unless otherwise stated, all amounts, fractions and percentages are based on the weight and total amount or total weight of the formulation.

[0091] Formulation examples

[0092] Example 1 in the toner

[0093]

[0094] Example 2 in the emulsion

[0095]

Claims

1. An active ingredient combination of a) one or more alkylamidothiazoles and b) beta-tocopherol and c) optionally 3-O-ethylascorbic acid.

2. A cosmetic preparation comprising the combination according to claim 1.

3. A method of using an active ingredient combination of b) β-tocopherol and c) optionally 3-O-ethylascorbic acid for preventing or reducing the thermally induced degradation of alkylamidothiazoles in cosmetic preparations containing one or more alkylamidothiazoles.

4. The cosmetic preparation according to claim 2 or the method of use according to claim 3, characterized in that In order to provide a cosmetic preparation, the total amount of the one or more alkylamidothiazoles is, for example, 0.00001% to 10% by weight, preferably 0.001% to 5% by weight, in particular 0.005% to 3% by weight, based on the total weight of the preparation.

5. The cosmetic preparation according to any one of the preceding claims, characterized in that In order to provide a cosmetic preparation, the total amount of β-tocopherol is, for example, 0.00001 to 10% by weight, preferably 0.001 to 5% by weight, and in particular 0.005 to 3% by weight, based on the total weight of the preparation.

6. The cosmetic preparation according to any one of the preceding claims, characterized in that In order to provide a cosmetic preparation, the total amount of 3-O-ethylascorbic acid is, for example, 0.00001 to 10% by weight, preferably 0.001 to 5% by weight, and in particular 0.005 to 3% by weight, based on the total weight of the preparation.

7. The active ingredient combination or cosmetic preparation according to any one of the preceding claims, characterized in that The one or more alkylamidothiazoles are selected from the following: N-(4-(2,4-dihydroxyphenyl)thiazol-2-yl)pivalamide N-(4-(2,4-dihydroxyphenyl)thiazol-2-yl)isobutyramide N-(4-(2,4-Dihydroxyphenyl)thiazol-2-yl)butanamide N-(4-(2,4-Dihydroxyphenyl)thiazol-2-yl)heptylamide N-(4-(2,4-dihydroxyphenyl)thiazol-2-yl)-6-hydroxyhexanamide N-(4-(2,4-dihydroxyphenyl)thiazol-2-yl)-3-hydroxypropanamide N-(4-(2,4-Dihydroxyphenyl)thiazol-2-yl)-2-methoxyacetamide 3-Amino-N-(4-(2,4-dihydroxyphenyl)thiazol-2-yl)propanamide N-(4-(2,4-Dihydroxyphenyl)thiazol-2-yl)acetamide N-(4-(2,4-dihydroxyphenyl)thiazol-2-yl)-4-(hydroxymethyl)cyclohexanecarboxamide N-(4-(2,4-Dihydroxyphenyl)thiazol-2-yl)cyclohexanecarboxamide N-(4-(2,4-dihydroxyphenyl)thiazol-2-yl)-2-(4-(hydroxymethyl)phenyl)acetamide.

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