Combinations of one or more alkylamidothiazoles and one or more alkyl sarcosinates and cosmetic preparations containing such combinations

Abstract

The present invention belongs to the cosmetic field, and specifically relates to combinations of one or more alkylamidothiazoles and one or more alkyl sarcosinates, and cosmetic preparations containing such combinations. It is found that the alkyl sarcosinates significantly enhance the solubility of alkylamidothiazoles in cosmetic preparations.

Description

[0001] Combinations of one or more alkylamidothiazoles and one or more alkyl sarcosinates and cosmetic preparations containing such combinations Technical field The present invention belongs to the cosmetic field, and specifically relates to combinations of one or more alkylamidothiazoles and one or more alkyl sarcosinates, and cosmetic preparations containing such combinations. Background art In general, cosmetic products not only serve to look beautiful and attractive, but with their effect they make a decisive contribution to increased self-esteem and the well-being of people. Accordingly, a wide variety of cosmetic products are used for the daily cleaning and care of human skin. For example, cosmetic preparations for the care of human skin are known from DE 102011083259 A1, which contain alkylamidothiazoles. The alkylamidothiazoles are used in the cosmetic preparations to combat and prevent undesired pigmentation of the skin. In this way, the user's complexion can be decisively improved. It is also known from DE 102013226711 A1 that alkylamidothiazoles can be used in cosmetic or dermatological preparations for the prophylaxis and treatment of sensitive skin, itching, dry skin and inflammatory symptoms of human skin. The document discloses various cosmetic O / W emulsions for application to human skin. Furthermore, DE 102013204110 A1 discloses a large number of cosmetic preparations for the care of human skin containing alkylamidothiazoles. A particularly effective lightening of human skin is achieved by the combined use of alkylamidothiazoles with one or more cyclodextrins. However, the fact that the person skilled in the art knows a large number of cosmetic preparations containing alkylamidothiazoles must not obscure the fact that a large number of problems can arise when formulating cosmetic or dermatological preparations. A disadvantage, for example, is the fact that, alkylamidothiazoles show a relatively low solubility in cosmetically acceptable solvents. This circumstance creates considerable difficulties for manufacturers of cosmetic preparations, since it often requires a large number of emollients, which significantly increase the development costs of cosmetic products and negative sensory feeling. Summary of the invention One object of the present invention was therefore to provide a way of enhancing the solubility of alkylamidothiazoles in cosmetic products. This object is achieved by combinations of a) one or more alkylamidothiazoles and b) one or more alkyl sarcosinates of the general formula R1 and R2 being chosen, independently from each other, from the group of branched, linear or cyclic alkyl groups having from 1 to 18 carbon atoms. Astonishingly the alkyl sarcosinates according to the present invention significantly enhance the solubility of alkylamidothiazoles in comparison to other cosmetically acceptable oil components. It is equally possible and can be advantageous to use one or more alkyl sarcosinates according to the present invention as the only oil component or components in cosmetic compositions as well as in combination with other oil components. Another embodiment of the present invention is cosmetic preparations containing such combinations. Yet another embodiment of the present invention is use of one or more sarcosinates of the general formula R1 and R2 being chosen, independently from each other, from the group of branched, linear or cyclic alkyl groups having from 1 to 18 carbon atoms to enhance the solubility of one or more alkylamidothiazoles in cosmetic preparations. Advantageous embodiments of the present invention are also cosmetic or dermatological preparations with a content of a) one or more alkylamidothiazoles and b) one or more alkyl sarcosinates of the general formula , and the use thereof for lightening human skin. Preferably R1 can be chosen from the group of branched alkyl groups having up to 10 carbon atoms, more preferably up to 5 carbon atoms. Preferably R2 can be chosen from the group of linear alkyl groups having up to 18 carbon atoms, more preferably up to 15 carbon atoms. Most preferred embodiments of the present invention encompass which is believed to be the chemical formula of Isopropyl Lauroyl Sarcosinate. Advantageously, preparations according to the invention comprise formulations, where the total amount of the one or more alkylamidothiazoles is e.g.0.00001% by weight to 10% by weight, preferably 0.001% by weigh to 5% by weight, in particular 0.005% by weight to 3% by weight, based on the total weight of the preparations, in order to provide cosmetic preparations. Advantageously, preparations according to the invention comprise formulations, where the total amount of one or more alkyl sarcosinates is 0.00008% by weight to 80 % by weight, preferably to preferably 0.008% by weigh to 40% by weight, in particular 0.04% by weight to 12% by weight, based on the total weight of the preparations, in order to provide cosmetic preparations. Advantageous alkylamidothiazoles in the context of the present invention are substances of the general formula: in which R1, R2, X and Y can be different, partly identical or completely identical and, independently of one another, can mean: R1=-C1-C24-alkyl (linear or branched), -C1-C24-alkenyl (linear or branched), -C1-C8-cycloalkyl, - C1-C8-cycloalkyl-alkylhydroxy, -C1-C24-alkylhydroxy (linear or branched), -C1-C24 alkylamine (linear or branched), -C1-C24-alkylaryl (linear or branched), -C1-C24-alkylaryl-alkyl-hydroxy (linear or branched), -C1-C24-alkylheteroaryl (linear or branched), -C1-C24-alkyl-O-C1-C24-alkyl (linear or branched), -C1-C24 alky-morpholino, -C1-C24 alky-piperidino, -C1-C24 alky-piperazino, -C1-C24 alky-piperazino-N-alkyl, R2=H, -C1-C24-alkyl (linear or branched), -C1-C24-alkenyl (linear or branched), -C1-C8- cycloalkyl, -C1-C24-hydroxyalkyl (linear or branched), -C1-C24-alkylaryl (linear or branched), - C1-C24-alkylheteroaryl (linear or branched), X=-H, -C1-C24-alkyl (linear or branched), -C1-C24-alkenyl (linear or branched), -C1-C8- cycloalkyl, -C1-C24-aryl (optionally mono- or polysubstituted with -OH, -F, -Cl, -Br, -I, -OMe, - NH2, -CN), -C1-C24-heteroaryl (optionally mono- or polysubstituted with -OH, -F, -Cl, -Br, -I, - OMe, -NH2, -CN), -C1-C24-alkylaryl (linear or branched), -C1-C24-alkylheteroaryl (linear or branched), -aryl (optionally mono- or polysubstituted with -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 or branched), -C1-C24-alkenyl (linear or branched), -C1-C8- cycloalkyl, -C1-C24-aryl, -C1-C24-heteroaryl, -C1-C24-alkylaryl (linear or branched), -C1-C24- alkylheteroaryl (linear or 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 optionally be condensed aromatic, where X and Y can form with one another aromatic or aliphatic homo- or heterocyclic ring systems with up to n ring-forming atoms, and where the number n can assume values from 5 to 8, and the respective ring systems can in turn be substituted with up to n−1 alkyl groups, hydroxyl groups, carboxyl groups, amino groups, nitrile functions, sulfur-containing substituents, ester groups and / or ether groups. Said thiazoles can either be in the form of the free base or the salt: e.g. fluoride, chloride, bromide, iodide, sulfate, carbonate, ascorbate, acetate or phosphate, in particular in the form of halogen salts, such as e.g. chloride and bromide. Furthermore, there is an advantageous realization of the present invention in cosmetic or dermatological preparations with an effective amount of one or more aforementioned alkylamidothiazoles. Also in accordance with the present invention is the use of the aforementioned alkylamidothiazoles for the treatment and / or prophylaxis of undesired skin pigmentation. Here, treatment and / or prophylaxis of undesired skin pigmentation can be both in the cosmetic sphere and in the pharmaceutical sphere. In this connection, the pharmaceutical (or dermatological) treatment is primarily understood for diseased skin conditions, whereas the cosmetic treatment and / or prophylaxis of undesired skin pigmentation primarily relates to healthy skin. Advantageously, X is selected from the group of substituted phenyls, in which case the substituents (Z) can be selected from the group -H, -OH, -F, -Cl, -Br, -I, -OMe, -NH2, -CN, acetyl and can be identical or different. Particularly advantageously, X is selected from the group of phenyl groups substituted with one or more hydroxy groups, in which case the substituent (Z) can be selected from the group -H, - OH, -F, -Cl, -Br, -I, -OMe, -NH2, -CN, acetyl, and preference is given to the following generic structure in which Y, R1 and R2 can have the properties defined above. Particularly advantageous compounds are those in which X = Y=H R1=-C1-C24-alkyl (linear or branched), -C1-C24-alkenyl (linear or branched), -C1-C8-cycloalkyl, - C1-C8-cycloalkyl-alkylhydroxy, -C1-C24 alkylhydroxy (linear or branched), -C1-C24 alkylamine (linear or branched), -C1-C24-alkylaryl (linear or branched), -C1-C24-alkylaryl-alkyl-hydroxy (linear or branched), -C1-C24-alkylheteroaryl (linear or branched), -C1-C24-alkyl-O-C1-C24-alkyl (linear or branched), -C1-C24-alky-morpholino, -C1-C24 alky-piperidino, -C1-C24 alky- piperazino, -C1-C24 alky-piperazino-N-alkyl, R2=H, -C1-C24-alkyl (linear or branched), Z=-H, -OH, -F, -Cl, -Br, -I, -OMe, -NH2, -CN, acetyl. Particular preference is given to those compounds as follows: R1=-C1-C24-alkyl (linear or branched), -C1-C24-alkenyl (linear or branched), -C1-C8-cycloalkyl, - C1-C8-cycloalkyl-alkylhydroxy, -C1-C24-alkylhydroxy (linear or branched), -C1-C24 alkylamine (linear or branched), -C1-C24-alkylaryl (linear or branched), -C1-C24-alkyl-aryl-alkyl-hydroxy (linear or branched), -C1-C24-alkylheteroaryl (linear or branched), -C1-C24-alkyl-O-C1-C24-alkyl (linear or branched), -C1-C24 alky-morpholino, -C1-C24 alky-piperidino, -C1-C24 alky- piperazino, -C1-C24 alky-piperazino-N-alkyl, R2=H The following compounds are most preferred ones within the scope of the present invention: N-(4-(2,4-dihydroxyphenyl)thiazol-2-yl)pivalamide

[0002] Cosmetic or dermatological preparations containing alkylamidothiazoles and their use for the treatment and / or prophylaxis of undesired skin pigmentation are likewise advantageous embodiments of the present invention. It is particularly advantageous if such preparations comprise 0.00001 to 10% by weight, in particular 0.001 to 5% by weight, very particularly 0.005 to 3% by weight, of one or more alkylamidothiazoles according to the invention (e.g., N-(4-(2,4-dihydroxyphenyl)thiazol-2- yl)isobutyramide, namely isobutylamide thiazolyl resorcinol), based on the total weight of the preparation. It is particularly advantageous if such preparations comprise 0.00008 to 80 % by weight, in particular 0.008 to 40% by weight, very particularly 0.04 to 12% by weight, of one or more alkyl sarcosinates (e.g., isopropyl lauroyl sarcosinate), based on the total weight of the preparations. Cosmetic and dermatological preparations according to the invention can be in various forms. Thus, they can be e.g. a solution, an anhydrous preparation, an emulsion or micro-emulsion of the water-in-oil (W / O) type or of the oil-in-water (O / W) type, a multiple emulsions, for example of the water-in-oil-in-water (W / O / W) type, a gel, a solid stick, a balm or else an aerosol. It is also advantageous according to the invention to administer the substances used according to the invention and / or their derivatives in encapsulated form, e.g. in collagen matrices and other customary encapsulation materials, e.g. as cellulose encapsulations, in gelatin or liposomally encapsulated. It is also possible and advantageous in the context of the present invention to add the substances used according to the invention and / or their derivatives in aqueous systems or surfactant preparations for cleaning the skin and the hair. The cosmetic and dermatological preparations according to the invention can comprise cosmetic auxiliaries as are customarily used in such preparations, e.g. preservatives, bactericides, perfumes, substances for preventing foaming, dyes, pigments which have a coloring effect, thickeners, surface-active substances, emulsifiers, softening, moisturizing and / or humectant substances, fats, oils, waxes or other customary constituents of a cosmetic or 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 acid or of caprylic acid, also natural oils such as e.g. castor oil; fats, waxes and other natural and synthetic fatty bodies, preferably esters of fatty acids with alcohols of low carbon number, e.g. with isopropanol, propylene glycol or glycerol, or esters of fatty alcohols with alkanoic acids of low carbon number or with fatty acids; alkyl benzoates; silicone oils such as dimethylpolysiloxanes, diethylpolysiloxanes, diphenylpolysiloxanes and mixtures thereof. The oil phase of the emulsions, oleogels or hydrodispersions or lipodispersions within 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 of chain length from 3 to 30 C atoms and saturated and / or unsaturated, branched and / or unbranched alcohols of chain length from 3 to 30 C atoms, from the group of esters of aromatic carboxylic acids and saturated and / or unsaturated, branched and / or unbranched alcohols of chain length from 3 to 30 C 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 synthetic, semisynthetic and natural mixtures of such esters, e.g. jojoba oil. The aqueous phase of the preparations according to the invention optionally advantageously comprises humectants such as e.g. propylene glycol, panthenol or hyaluronic acid, and in particular one or more thickeners which can advantageously be selected from the group silicon dioxide, aluminum silicates, hydroxypropylmethylcellulose, particularly advantageously a polyacrylate such as, for example, carbopol grade 980, in each case individually or in combination. In particular, mixtures of the aforementioned solvents are used. In the case of alcoholic solvents, water can be a further constituent. Emulsions according to the invention are advantageous and comprise e.g. the specified fats, oils, waxes and other fatty bodies, as well as water and an emulsifier, as is customarily used for such a type of formulation. Gels according to the invention usually comprise alcohols of low carbon number, e.g. ethanol, propylene glycol, and water or an aforementioned oil in the presence of a thickener which, in the case of oily-alcoholic gels, is preferably silicon dioxide or an aluminum silicate, and in the case of aqueous-alcoholic or alcoholic gels is preferably a polyacrylate. Suitable propellants for preparations according to the invention that can be sprayed from aerosol containers are the customary known readily volatile, liquefied propellants, for example hydrocarbons (propane, butane, isobutane), which can be used on their own or in a mixture with one another. Compressed air is also to be used advantageously. Advantageously, preparations according to the invention can furthermore advantageously comprise substances which absorb UV radiation in the UVB region, the total amount of the filter substances being e.g.0.1% by weight to 30% by weight, preferably 0.5 to 10% by weight, in particular 1.0 to 6.0% by weight, based on the total weight of the preparations, in order to provide cosmetic preparations which protect the hair and / or the skin from the entire range of ultraviolet radiation. They can also serve as sunscreens for the hair or the skin. Furthermore, preparations according to the invention can advantageously additionally comprise substances which conceal the troublesome intrinsic odor of the remaining raw materials used, the total amount of the perfume ingredients being e.g.0.001% by weight to 30% by weight, preferably 0.05 to 10% by weight, in particular 0.1 to 5.0% by weight, based on the total weight of the preparations, in order to provide cosmetic preparations. Examples The examples below are intended to illustrate the present invention without limiting it. Unless stated otherwise, all of the quantities, fractions and percentages stated are based on the weight and the total amount or on the total weight of the preparations. Effect examples Isobutylamido Thiazolyl Resorcinol + Isopropyl Lauroyl Sarcosinate (solubility 12.5%) Isobutylamido Thiazolyl Resorcinol + Diisopropyle Adipate (solubility 5%) Isobutylamido Thiazolyl Resorcinol + PPG-3 Capry ether (solubility 5%) Isobutylamido Thiazolyl Resorcinol + Dibutyl Adipate (solubility 4.4%) Isobutylamido Thiazolyl Resorcinol + Lauryl Lactate (solubility 2.5%) Isobutylamido Thiazolyl Resorcinol + Diisopropyl Sebacate (solubility 2.5%)

Claims

Claims 1. Combinations of a) one or more alkylamidothiazoles and b) one or more alkyl sarcosinates of the general formulaR1 and R2 being chosen, independently from each other, from the group of branched, linear or cyclic alkyl groups having from 1 to 18 carbon atoms.

2. Combinations according to claim 1, characterized in that R1 is chosen from the group of branched alkyl groups having up to 10 carbon atoms, preferably up to 5 carbon atoms, and R2 is chosen from the group of linear alkyl groups having up to 18 carbon atoms, preferably up to 15 carbon atoms.

3. Cosmetic preparations containing combinations according to claim 1 or 2.

4. Use of one or more alkyl sarcosinates of the general formulaR1 and R2 being chosen, independently from each other, from the group of branched, linear or cyclic alkyl groups having from 1 to 18 carbon atoms to enhance the solubility of one or more alkylamidothiazoles in cosmetic preparations.

5. Use according to claim 4, characterized in that R1 is chosen from the group of branched alkyl groups having up to 10 carbon atoms, preferably up to 5 carbon atoms, and R2 is chosen from the group of linear alkyl groups having up to 18 carbon atoms, preferably up to 15 carbon atoms.

6. Cosmetic preparations according to claim 2 or 3, or use according to claim 4 or 5, characterised in that the total amount of the one or more alkylamidothiazoles is 0.00001% by weight to 10% by weight, preferably 0.001% by weight to 5% by weight, in particular 0.005% by weight to 3% by weight, based on the total weight of the preparations.

7. Cosmetic preparations according to claim 2 or 3, or use according to claim 4 or 5, characterized in that the total amount of one or more sarcosinates is 0.00008% by weight to 80 % by weight, preferably 0.008% by weight to 40% by weight, in particular 0.04% by weight to 12% by weight, based on the total weight of the preparations.

8. Combinations, cosmetic preparations or use according to one of the preceding claims, characterized in that the alkyl sarcosinate is characterized by the structure.

9. Combinations, cosmetic preparations or use according to one of the preceding claims, characterized in that alkylamidothiazoles are substances of the general formula:Wherein R1=-C1-C24-alkyl (linear or branched), -C1-C24-alkenyl (linear or branched), -C1-C8-cycloalkyl, - C1-C8-cycloalkyl-alkylhydroxy, -C1-C24-alkylhydroxy (linear or branched), -C1-C24 alkylamine (linear or branched), -C1-C24-alkylaryl (linear or branched), -C1-C24-alkylaryl-alkyl-hydroxy (linear or branched), -C1-C24-alkylheteroaryl (linear or branched), -C1-C24-alkyl-O-C1-C24-alkyl (linear or branched), -C1-C24 alky-morpholino, -C1-C24 alky-piperidino, -C1-C24 alky-piperazino, -C1-C24 alky-piperazino-N-alkyl, R2=H, -C1-C24-alkyl (linear or branched), -C1-C24-alkenyl (linear or branched), -C1-C8- cycloalkyl, -C1-C24-hydroxyalkyl (linear or branched), -C1-C24-alkylaryl (linear or branched), - C1-C24-alkylheteroaryl (linear or branched), X=-H, -C1-C24-alkyl (linear or branched), -C1-C24-alkenyl (linear or branched), -C1-C8- cycloalkyl, -C1-C24-aryl (optionally mono- or polysubstituted with -OH, -F, -Cl, -Br, -I, -OMe, - NH2, -CN), -C1-C24-heteroaryl (optionally mono- or polysubstituted with -OH, -F, -Cl, -Br, -I, - OMe, -NH2, -CN), -C1-C24-alkylaryl (linear or branched), -C1-C24-alkylheteroaryl (linear or branched), -aryl (optionally mono- or polysubstituted with -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 or branched), -C1-C24-alkenyl (linear or branched), -C1-C8- cycloalkyl, -C1-C24-aryl, -C1-C24-heteroaryl, -C1-C24-alkylaryl (linear or branched), -C1-C24- alkylheteroaryl (linear or 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 optionally be condensed aromatic, where X and Y can form with one another aromatic or aliphatic homo- or heterocyclic ring systems with up to n ring-forming atoms, and where the number n can assume values from 5 to 8, and the respective ring systems can in turn be substituted with up to n−1 alkyl groups, hydroxyl groups, carboxyl groups, amino groups, nitrile functions, sulfur-containing substituents, ester groups and / or ether groups.

10. Combinations, cosmetic preparations or use according to claim 9, characterized in that X is selected from the group of substituted phenyl, wherein Z is selected from the group -H, -OH, -F, - Cl, -Br, -I, -OMe, -NH2, -CN, acetyl and can be identical or different, and R1, R2 and Y are defined as the same in claim 9,11. Combinations, cosmetic preparations or use according to claim 9, characterized in that X is selected from the group of substituted phenyl, wherein R2 is selected from H or –C1-C24-alkyl (linear or branched), and R1, Y and Z are defined as the same in claim 10,, preferably Y is H, R2 is H, and Z is OH.

12. Combinations, cosmetic preparations or use according to one of the preceding claims, characterized in that the alkylamidothiazole is selected from the group consisting of the following substances:

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