Combination of one or more alkylamide thiazoles and octadecyl di-tert-butyl-4-hydroxyhydrocinnamate and cosmetic formulations containing such combination

Abstract

The present invention relates to a combination of the following active ingredients: c) in cosmetic excipients a) one or more alkylamide thiazoles and b) diethylhexyl clove subunit malonates.

Description

[0001] Technical Field and Background Technology

[0002] Generally speaking, cosmetics not only enhance appearance and attractiveness, but their effects also play a decisive role in improving people's self-esteem and sense of well-being. Therefore, a wide variety of cosmetics are used for the daily cleansing and care of human skin. For example, DE 102011083259 A1 discloses a cosmetic formulation for human skin care containing alkylamide thiazoles.

[0003] The alkylamide thiazole used is employed in cosmetic formulations to combat and prevent unwanted skin pigmentation. This results in a significant improvement in the user's skin tone.

[0004] DE 102013226711 A1 also discloses that alkylamide thiazoles can be used in cosmetic or dermatological preparations for the prevention and treatment of sensitive skin, pruritus, dry skin, and inflammatory symptoms on human skin. This document discloses various oil-in-water (O / W) emulsions for use on human skin in cosmetic applications.

[0005] In addition, DE 102013204110 A1 discloses a large number of cosmetic formulations for human skin care containing alkylamide thiazole.

[0006] The combination of alkylamide thiazole with one or more cyclodextrins can be particularly effective in whitening human skin.

[0007] However, the fact that those skilled in the art are aware of the large number of cosmetic formulations containing alkylamide thiazoles should not obscure the fact that many problems may arise when formulating cosmetic or dermatological preparations.

[0008] For example, one drawback is that newly manufactured cosmetic or dermatological preparations can change color during storage. This change is more pronounced when the preparation is exposed to light.

[0009] This situation presents considerable challenges for manufacturers of cosmetic formulations, as it necessitates research into the color stability of cosmetic formulations.

[0010] This typically requires extensive research, which significantly increases the cost of cosmetic development.

[0011] Therefore, there is a need for systems and methods that can effectively prevent or minimize degradation processes in cosmetics or dermatological preparations to minimize development costs. The issue of degradation processes in cosmetics or dermatological preparations is also of great concern to consumers.

[0012] People typically choose products based on their optical appearance or skin texture. However, if a product's white appearance deteriorates during storage, consumers are usually dissatisfied because it no longer meets their decisive purchasing criteria.

[0013] In principle, specially trained personnel can assess the color stability of cosmetic or dermatological preparations by comparing the color of freshly formulated formulations (within 24 hours of formulation) with the color after a corresponding storage period. However, color changes in products are often difficult to determine. Therefore, using a specialized instrument called a Digi-Eye to monitor color changes is highly advantageous. Summary of the Invention

[0014] Therefore, one object of the present invention is to provide a method that prevents or minimizes the degradation process of cosmetics in a particularly effective manner, thereby ensuring color stability.

[0015] This objective is achieved through the following combination of active ingredients: a) One or more alkylamide thiazoles and b) Octadecyl di-tert-butyl-4-hydroxyhydrocinnamate c) In cosmetic excipients.

[0016] Surprisingly, compared to the single substance, the combination of octadecyl di-tert-butyl-4-hydroxyhydrocinnamate and 3-O-ethyl ascorbic acid works synergistically to prevent or reduce the deterioration of alkylamide thiazoles caused by oxidation processes and / or heat and / or ultraviolet radiation.

[0017] Octadecyl di-tert-butyl-4-hydroxyhydrocinnamate is a well-known antioxidant. It is characterized by the following chemical structure: .

[0018] Another embodiment of the present invention is a cosmetic formulation containing this combination.

[0019] Another embodiment of the present invention is a method for preventing or reducing the deterioration of alkylamide thiazoles in cosmetic formulations containing one or more alkylamide thiazoles due to oxidation processes and / or heat and / or ultraviolet radiation, c) the use of b) octadecyl di-tert-butyl-4-hydroxyhydrocinnamate in cosmetic excipients.

[0020] Advantageous embodiments of the invention also include cosmetic or dermatological preparations containing such combinations of active ingredients, and their use for whitening human skin.

[0021] Advantageously, the formulation according to the invention comprises a formulation in which the total amount of one or more alkylamide thiazoles is, for example, 0.00001% to 10% by weight, preferably 0.001% to 5% by weight, and especially 0.005% to 3% by weight, based on the total weight of the formulation, thereby providing a cosmetic formulation.

[0022] Advantageously, the formulation according to the invention comprises a formulation wherein the total amount of octadecyl di-tert-butyl-4-hydroxyhydrocinnamate is, for example, 0.00001% by weight to 10% by weight, preferably 0.001% by weight to 5% by weight, and especially 0.005% by weight to 3% by weight, based on the total weight of the formulation, thereby providing a cosmetic formulation.

[0023] Advantageously, the formulation according to the invention comprises a compound that may further contain an active amount of α-tocopherol, preferably, the total amount of α-tocopherol is, for example, 0.00001% by weight to 10% by weight, more preferably 0.001% by weight to 5% by weight, and especially 0.005% by weight to 3% by weight, based on the total weight of the formulation, thereby providing a cosmetic formulation.

[0024] Advantageously, the formulation according to the invention comprises a compound that may further contain an active amount of β-tocopherol, preferably, the total amount of β-tocopherol is, for example, 0.00001% by weight to 10% by weight, preferably 0.001% by weight to 5% by weight, and especially 0.005% by weight to 3% by weight, based on the total weight of the formulation, thereby providing a cosmetic formulation.

[0025] Advantageously, the formulation according to the invention comprises a formulation which may further contain an active amount of dimethylmethoxychromol, preferably, the total amount of dimethylmethoxychromol is based on the total weight of the formulation and is, for example, from 0.00001% by weight to 10% by weight, preferably from 0.001% by weight to 5% by weight, and especially from 0.005% by weight to 3% by weight, thereby providing a cosmetic formulation.

[0026] Dimethylmethoxychromol is a well-known antioxidant. It is characterized by the following chemical structure: .

[0027] Advantageously, the formulation according to the invention includes a formulation which may further contain an active amount of nicotinamide, preferably, the total amount of nicotinamide is, for example, 0.00001% by weight to 10% by weight, preferably 0.001% by weight to 5% by weight, especially 0.005% by weight to 3% by weight, based on the total weight of the formulation, thereby providing a cosmetic formulation.

[0028] Nicotinamide (or nicotinamide) is a form of vitamin B3, found in food and used as a dietary supplement and medication. As a supplement, nicotinamide is taken orally for the prevention and treatment of pellagra (niacin deficiency). Nicotinamide is characterized by the following structural formula: .

[0029] On the other hand, the formulation may contain one or more hydrocolloids at less than about 1.5% by weight of the total weight of the formulation, for example, no more than about 1.0% by weight of one or more hydrocolloids, and / or at least about 0.1% by weight of one or more hydrocolloids.

[0030] In another aspect of the formulation, the one or more hydrocolloids may comprise one or more of the following: a) Organically synthesized compounds of polyacrylic acid; b) Copolymers and crosslinked polymers of polyacrylic acid derivatives; c) Ammonium dimethyltaurate / vinylformamide copolymer; d) Copolymers / crosslinked polymers containing acryloyldimethyl taurate; e) Hydrophilic adhesives and their hydrophilic derivatives; f) Cellulose, cellulose derivatives and microcrystalline cellulose.

[0031] On the other hand, the one or more hydrocolloids may include one or more polyacrylates selected from carbomer 980, 981, 1382, 2984 and 5984 types and carbomer ULTREZ.

[0032] On the other hand, the one or more hydrocolloids may include one or more of polymethyl methacrylate, acrylate copolymer, alkyl acrylate copolymer, polyacrylamide, alkyl acrylate crosspolymer, propylene nitrogen copolymer, and polyacrylamide dimethyl taurine.

[0033] On the other hand, the one or more hydrocolloids may include one or more of agar, alginic acid, carrageenan, gelatin, gum arabic, pectin and tragacanth, and / or one or more of guar gum, locust bean powder, xanthan gum, polyvinyl alcohol, polyvinylpyrrolidone, propylene glycol alginate and starch.

[0034] On the other hand, the one or more hydrocolloids may include alkyl-modified cellulose derivatives and / or alkyl hydroxycellulose, such as at least one of methylcellulose, hydroxypropyl methylcellulose and hydroxyethylcellulose.

[0035] On the other hand, the formulation may contain at least about 0.1% by weight and / or no more than about 1.0% by weight of one or more hydrocolloids.

[0036] In another aspect, the one or more hydrocolloids may include at least one of carbomer ULTREZ and / or agar, alginic acid, carrageenan, gelatin, gum arabic, pectin and tragacanth, and / or at least one of guar gum, locust bean powder, xanthan gum, gellan gum, polyvinyl alcohol, polyvinylpyrrolidone, propylene glycol alginate and starch, and / or at least one of methylcellulose, hydroxypropyl methylcellulose and hydroxyethylcellulose.

[0037] In the context of this invention, advantageous alkylamide thiazoles are substances having the following general formula:

[0038] R1, R2, X, and Y can be different, partially the same, or completely identical, and can be represented independently as follows: R1 can be any of the following: -C1-C24-alkyl (straight-chain and branched), -C1-C24-alkenyl (straight-chain and branched), -C1-C8-cycloalkyl, -C1-C8-cycloalkyl-alkylhydroxy, -C1-C24-alkylhydroxy (straight-chain and branched), -C1-C24-alkylamine (straight-chain and branched), -C1-C24-alkylaryl (straight-chain and branched), -C1-C24-alkylaryl-alkyl-hydroxy (straight-chain and branched), -C1-C24-alkylheteraryl (straight-chain and branched), -C1-C24-alkyl-O-C1-C24-alkyl (straight-chain and branched), -C1-C24-alkyl-morpholinyl, -C1-C24-alkyl-piperidinyl, -C1-C24-alkyl-piperazinyl, -C1-C24-alkyl-piperazinyl-N-alkyl. R2 can be H, -C1-C24-alkyl (straight-chain and branched), -C1-C24-alkenyl (straight-chain and branched), -C1-C8-cycloalkyl, -C1-C24-hydroxyalkyl (straight-chain and branched), -C1-C24-alkylaryl (straight-chain and branched), or -C1-C24-alkylheteraryl (straight-chain and branched). X is -H, -C1-C24-alkyl (straight-chain and branched), -C1-C24-alkenyl (straight-chain and branched), -C1-C8-cycloalkyl, -C1-C24-aryl (optionally mono- or poly-substituted with -OH, -F, -Cl, -Br, -I, -OMe, -NH2, -CN), or -C1-C24-heteroaryl (optionally substituted with -OH, -F, -Cl, -Br, -I, -OMe, -NH2). -CN monosubstituted or polysubstituted), -C1-C24-alkylaryl (straight chain and branched chain), -C1-C24-alkylheteroaryl (straight chain and branched chain), -aryl (optionally monosubstituted 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 represents H, -C1-C24-alkyl (straight-chain and branched), -C1-C24-alkenyl (straight-chain and branched), -C1-C8-cycloalkyl, -C1-C24-aryl, -C1-C24-heteroaryl, -C1-C24-alkylaryl (straight-chain and branched), -C1-C24-alkylheteroaryl (straight-chain 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 and Y can also optionally be fused aromatics, wherein X and Y can form an aromatic or aliphatic allotropic or heterocyclic system with each other, wherein the aromatic or aliphatic allotropic or heterocyclic system has at most n cyclic atoms, and wherein the value of n can be in the range of 5 to 8, and the corresponding cyclic system can be substituted by at most n-1 alkyl, hydroxyl, carboxyl, amino, nitrile functional groups, sulfur-containing substituents, ester groups and / or ether groups.

[0039] The thiazole can be in the form of a free base or a salt: for example, fluoride, chloride, bromide, iodide, sulfate, carbonate, ascorbate, acetate, or phosphate. Particularly, halide forms, such as chlorides and bromides.

[0040] Furthermore, an advantageous embodiment of the present invention also lies in a cosmetic or dermatological preparation containing an effective amount of one or more of the above-mentioned alkylamide thiazoles.

[0041] The present invention also relates to the use of the above-mentioned alkylamide thiazole for the treatment and / or prevention of unwanted skin pigmentation.

[0042] Here, the treatment and / or prevention of unwanted skin pigmentation can fall under either the cosmetics or pharmaceutical fields.

[0043] In this regard, drug (or dermatological) treatments are primarily aimed at the diseased skin condition, while cosmetic treatments and / or prevention of unwanted skin pigmentation are primarily aimed at healthy skin.

[0044] Advantageously, X is selected from substituted phenyl groups, in which case the substituent (Z) can be selected from -H, -OH, -F, -Cl, -Br, -I, -OMe, -NH2, -CN, acetyl, and can be the same or different.

[0045] .

[0046] Particularly advantageous is that X is selected from a phenyl group substituted with one or more hydroxyl groups. In this case, the substituent (Z) can be selected from -H, -OH, -F, -Cl, -Br, -I, -OMe, -NH2, -CN, acetyl, and preferably the following general formula, wherein Y, R1, and R2 can have the above definitions. .

[0047] Particularly advantageous compounds are those that are: X is , Y is H, R1 can be any of the following: -C1-C24-alkyl (straight-chain and branched), -C1-C24-alkenyl (straight-chain and branched), -C1-C8-cycloalkyl, -C1-C8-cycloalkyl-alkylhydroxy, -C1-C24-alkylhydroxy (straight-chain and branched), -C1-C24-alkylamine (straight-chain and branched), -C1-C24-alkylaryl (straight-chain and branched), -C1-C24-alkylaryl-alkyl-hydroxy (straight-chain and branched), -C1-C24-alkylheteraryl (straight-chain and branched), -C1-C24-alkyl-O-C1-C24-alkyl (straight-chain and branched), -C1-C24-alkyl-morpholinyl, -C1-C24-alkyl-piperidinyl, -C1-C24-alkyl-piperazinyl, -C1-C24-alkyl-piperazinyl-N-alkyl. R2 is H, -C1-C24-alkyl (straight chain and branched chain), and Z is -H, -OH, -F, -Cl, -Br, -I, -OMe, -NH2, -CN, or acetyl.

[0048] The compounds shown below are particularly preferred.

[0049] X is , Y is H, R1 can be any of the following: -C1-C24-alkyl (straight-chain and branched), -C1-C24-alkenyl (straight-chain and branched), -C1-C8-cycloalkyl, -C1-C8-cycloalkyl-alkylhydroxy, -C1-C24-alkylhydroxy (straight-chain and branched), -C1-C24-alkylamine (straight-chain and branched), -C1-C24-alkylaryl (straight-chain and branched), -C1-C24-alkyl-aryl-alkyl-hydroxy (straight-chain and branched), -C1-C24-alkylheteroaryl (straight-chain and branched), -C1-C24-alkyl-O-C1-C24-alkyl (straight-chain and branched), -C1-C24-alkyl-morpholinyl, -C1-C24-alkyl-piperidinyl, -C1-C24-alkyl-piperazinyl, -C1-C24-alkyl-piperazinyl-N-alkyl. R2 is H.

[0050] The most preferred compounds within the scope of this invention are the following compounds: .

[0051] Cosmetic or dermatological preparations containing alkylamide thiazoles and their use for the treatment and / or prevention of unwanted skin pigmentation are also advantageous embodiments of the present invention.

[0052] It is particularly advantageous that such formulations contain one or more alkylamide thiazoles used according to the invention, based on 0.000001% to 10% by weight, particularly 0.0001% to 3% by weight, and very particularly 0.001% to 1% by weight of the total weight of the formulation.

[0053] The cosmetic and dermatological preparations of the present invention can be in various forms. Therefore, they can be, for example, solutions, anhydrous formulations, water-in-oil (W / O) or oil-in-water (O / W) emulsions or microemulsions, multiple emulsions (e.g., water-in-oil-in-water (W / O / W)), gels, solid bars, ointments, or aerosols. According to the invention, it is also advantageous to apply the substances used according to the invention and / or their derivatives in an encapsulated form, for example, in a collagen matrix and other commonly used encapsulating materials, such as cellulose, gelatin, or liposomes.

[0054] Within the scope of this invention, it is also possible and advantageous to add substances used according to the invention and / or their derivatives to aqueous systems or surfactant formulations for cleaning skin and hair.

[0055] The cosmetic and dermatological formulations of the present invention may contain cosmetic adjuvants commonly used in such formulations, such as preservatives, bactericides, fragrances, antifoaming substances, dyes, pigments with coloring effects, thickeners, surfactants, emulsifiers, emulsifiers, moisturizing and / or wetting substances, fats, oils, waxes, or other commonly used ingredients in cosmetic or dermatological formulations, such as alcohols, polyols, polymers, foam stabilizers, electrolytes, organic solvents, or organosilicon derivatives.

[0056] The lipid phase may be advantageously selected from the group consisting of: mineral oils, mineral wax oils, such as triglycerides of capric or octanoic acid, and natural oils such as castor oil; fats, waxes and other natural and synthetic fat bodies, preferably esters of fatty acids with lower alcohols, such as esters of fatty acids with isopropanol, propylene glycol or glycerol, or esters of fatty alcohols with lower carbon number alkanes or with fatty acids; alkyl benzoates; and silicone oils, such as dimethylpolysiloxane, diethylpolysiloxane, diphenylpolysiloxane and mixtures thereof.

[0057] In the context of this invention, the oil phase of emulsions, oleogels, or aqueous or lipid dispersions is advantageously selected from esters of saturated and / or unsaturated, branched and / or unbranched alkane carboxylic acids with a chain length of 3 to 30 carbon atoms and esters of saturated and / or unsaturated, branched and / or unbranched alcohols with a chain length of 3 to 30 carbon atoms, as well as esters of aromatic carboxylic acids and saturated and / or unsaturated, branched and / or unbranched alcohols with a chain length of 3 to 30 carbon atoms. Such ester oils may be advantageously selected from isopropyl myristate, isopropyl palmitate, isopropyl stearate, isopropyl oleate, n-butyl stearate, n-hexyl laurate, n-decyl oleate, isooctyl stearate, isononyl stearate, isononyl isononyl oleate, 2-ethylhexyl palmitate, 2-ethylhexyl laurate, 2-hexyldecyl stearate, 2-octyldodecyl palmitate, oleic acid ester, erucic acid ester, oleic acid mustard ester, erucic acid mustard ester, and synthetic, semi-synthetic and natural mixtures of these esters, such as jojoba oil.

[0058] The aqueous phase of the formulation of the present invention optionally and advantageously contains a wetting agent, such as propylene glycol, panthenol or hyaluronic acid, particularly one or more thickeners, which may be advantageously selected from silica, aluminum silicate, hydroxypropyl methylcellulose, and particularly advantageously selected from polyacrylates, such as carbomer 980, each used alone or in combination.

[0059] In particular, mixtures using the solvents described above. If alcoholic solvents are used, water can be used as another component.

[0060] The emulsions of the present invention are advantageous and contain, for example, prescribed fats, oils, waxes and other fatty bodies conventionally used in this type of formulation, as well as water and emulsifiers.

[0061] The gels of the present invention typically contain low-carbon alcohols, such as ethanol, propylene glycol, and water or the aforementioned oils (in the presence of a thickener). For oleo-alcohol gels, silica or aluminum silicate is preferred; for hydro-alcohol gels or alcohol gels, polyacrylate is preferred.

[0062] Suitable propellants for the formulations of this invention (which can be sprayed from an aerosol container) are generally known volatile liquefied propellants, such as hydrocarbons (propane, butane, isobutane), which can be used alone or in mixtures with each other. Compressed air may also be used advantageously.

[0063] Advantageously, the formulations of the present invention may also advantageously contain substances that absorb ultraviolet radiation in the UVB region, with the total amount of the filtering substance being, for example, 0.1% to 30% by weight, preferably 0.5% to 10% by weight, and particularly 1.0% to 6.0% by weight, based on the total weight of the formulation, thereby providing cosmetic formulations that protect hair and / or skin from damage across the entire range of ultraviolet radiation. They can also be used as sunscreens for hair or skin.

[0064] Furthermore, the formulations of the present invention may advantageously include substances for masking the unpleasant inherent odors of the remaining raw materials used, wherein the total amount of fragrance components is, for example, 0.001% to 30% by weight, preferably 0.05% to 10% by weight, particularly 0.1% to 5.0% by weight, based on the total weight of the formulation, thereby providing a cosmetic formulation.

[0065] The highly advantageous composition according to the invention contains: - Isobutyramidothiazolyl resorcinol, in an amount of 0.01% to 0.2%; - Nicotinamide, in amounts ranging from 0.01% to 3%. - Diethylhexyl eugenyl malonate + caprylic / capric triglyceride, in an amount of 0.01% to 0.15%. - Sodium hyaluronate, xanthan gum, and gellan gum, in amounts of 0.01% to 0.2%. - PEG-40 hydrogenated castor oil, in amounts of 0.01% to 5%. - Alcohols, in amounts of 5% to 20%. Detailed Implementation

[0066] The following examples are intended to illustrate the invention and not to limit it. Unless otherwise stated, all quantities, fractions, and percentages are based on weight and total amount or total weight of the formulation.

[0067]

Claims

1. The following combination of active ingredients: a) One or more alkylamide thiazoles and b) Octadecyl di-tert-butyl-4-hydroxyhydrocinnamate c) In cosmetic excipients.

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

3. Method of using octadecyl di-tert-butyl-4-hydroxyhydrocinnamate to prevent or reduce the deterioration of alkylamide thiazoles in cosmetic formulations containing one or more alkylamide thiazoles due to oxidation processes and / or heat and / or ultraviolet radiation.

4. The cosmetic formulation according to claim 2 or the method of use according to claim 3, characterized in that, The total amount of the one or more alkylamide thiazoles is, for example, 0.00001% to 10% by weight, preferably 0.001% to 5% by weight, and especially 0.005% to 3% by weight, based on the total weight of the formulation, thereby providing a cosmetic formulation.

5. The cosmetic formulation according to any one of the preceding claims, characterized in that, The total amount of the octadecyl di-tert-butyl-4-hydroxyhydrocinnamate is, for example, from 0.00001% to 10% by weight, preferably from 0.001% to 5% by weight, and especially from 0.005% to 3% by weight, based on the total weight of the formulation, thereby providing a cosmetic formulation.

6. The cosmetic formulation according to any one of the preceding claims, characterized in that, It also contains nicotinamide, the total amount of which is, for example, 0.00001% to 10% by weight, preferably 0.001% to 5% by weight, and especially 0.005% to 3% by weight, based on the total weight of the formulation, thereby providing a cosmetic formulation.

7. The cosmetic formulation according to any one of the preceding claims, characterized in that, It also contains α-tocopherol, the total amount of which is, for example, 0.00001% to 10% by weight, preferably 0.001% to 5% by weight, and especially 0.005% to 3% by weight, based on the total weight of the formulation, thereby providing a cosmetic formulation.

8. The cosmetic formulation according to any one of the preceding claims, characterized in that, It also contains β-tocopherol, the total amount of which is, for example, 0.00001% to 10% by weight, preferably 0.001% to 5% by weight, and especially 0.005% to 3% by weight, based on the total weight of the formulation, thereby providing a cosmetic formulation.

9. The cosmetic formulation according to any one of the preceding claims, characterized in that, It also contains dimethylmethoxychromol, the total amount of which is, for example, 0.00001% to 10% by weight, preferably 0.001% to 5% by weight, and especially 0.005% to 3% by weight, based on the total weight of the formulation, thereby providing a cosmetic formulation.

10. The cosmetic formulation according to any one of the preceding claims, characterized in that, The formulation comprises one or more hydrocolloids at less than about 1.5% by weight of the total weight of the formulation, for example, no more than about 1.0% by weight of one or more hydrocolloids, and / or at least about 0.1% by weight of one or more hydrocolloids.

11. The active ingredient combination or cosmetic formulation according to any one of the preceding claims, characterized in that, The one or more alkylamide thiazoles are selected from the following substances: 。

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