WO2021104770A1

WO2021104770A1 - Active substance combinations of ubichinol und glyceryl stearate citrate and cosmetic or dermatological preparations containing said active substance combinations

Info

Publication number: WO2021104770A1
Application number: PCT/EP2020/079990
Authority: WO
Inventors: Sebastian Rosenbaum; Thomas Raschke; Sabrina Breitkreutz; Helga Biergiesser
Original assignee: Beiersdorf Ag
Priority date: 2019-11-26
Filing date: 2020-10-26
Publication date: 2021-06-03
Also published as: DE102019218240A1

Abstract

The invention relates to active substance combinations comprising a) ubidecarenol and b) glyceryl stearate citrate.

Description

description

Active ingredient combinations of ubiquinol and glyceryl stearate citrate and cosmetic or dermatological preparations containing such active ingredient combinations

The present invention relates to cosmetic and dermatological preparations with an effective content of physiologically compatible active ingredient combinations, preferably those which are used in skin care cosmetic or dermatological preparations.

Mainly, antioxidants are used as protective substances against spoilage of the preparations containing them. Nevertheless, it is known that undesirable oxidation processes can also occur in human and animal skin. Such processes play an essential role in skin aging.

In the article "Skin Diseases Associated with Oxidative Injury" in "Oxidative Stress in Dermatology", p. 323 ff. (Marcel Decker Inc., New York, Basel, Hong Kong, editors: Jürgen Fuchs, Frankfurt, and Lester Packer , Berkeley / California), oxidative damage to the skin and its more detailed causes are listed.

Some antioxidants and radical scavengers are known. For example, US Patents 4,144,325 and 4,248,861, as well as numerous other documents, suggest using vitamin E, a substance with a known antioxidant effect, in light protection formulations, but here too the effect achieved remains far below the hoped-for effect.

One object of the present invention was to eliminate the disadvantages of the prior art. In particular, active ingredients or preparations containing such active ingredients should be made available which, when used, can at least reduce, if not completely prevent, damage to the skin and / or hair due to oxidative influence. Another object of the present invention was to provide cosmetic preparations which, before or after treatment of the hair with hair coloring preparations, even those containing strong oxidizing agents such as hydrogen peroxide, counteract their damaging oxidizing effect.

Ubiquinols or their oxidized form, the ubiquinones, play an important role in the transport of electrons in the respiratory chain of living things. Ubiquinols are characterized by the following chemical structure:

In naturally occurring ubiquinols or their oxidized form, the ubiquinones, n can assume values from 0 to 50. In mammals, especially humans, n = 10 predominates (ubidecarenol), which according to the invention is the preferred ubiquinol.

The cosmetic use of ubiquinols is known per se, for example from WO 2017/045034, DE 4228871 and other publications.

One problem, however, was that ubiquinol, in particular ubidecarenol, is very sensitive to water and oxygen and is therefore preferably presented in anhydrous preparations, and is preferably also stored in the absence of air or in the presence of antioxidants. Apart from the fact that the active ingredient as such is lost during the oxidation of the active ingredient, the preparation turns yellowish or even brownish in the course of a short time. The object of the present invention was therefore to remedy this problem.

It was surprising and could not be foreseen by the person skilled in the art that combinations of active ingredients comprising a) ubidecarenol b) glyceryl stearate citrate or cosmetic or dermatological preparations containing such active ingredient combinations represent the solution to these problems and remedy the disadvantages of the prior art.

Glyceryl stearate citrate (2-hydroxy-1, 2,3-propanetricarboxylic acid-1, 2,3-propanetriol monooctadecanoate or INCI name Glyceryl Stearate Citrate or CAS 39175-72-9) is available under the name Imwitor 370 from Sasol im Commercially available and is characterized by the following molecular structure:

Preparations, especially O / W emulsions containing glyceryl stearate citrate, stabilize ubidecarenol significantly better than other, comparable preparations.

It is advantageous according to the invention to choose the molar ratio of ubidecarenol on the one hand to glyceryl stearate citrate on the other hand from the range from 10: 1 to 1: 1000, preferably 5: 1 to 1: 500, particularly preferably 2: 1 to 1: 200.

According to the invention, the preparations are particularly advantageously characterized in that ubidecarenol, in concentrations of 0.001-10.00% by weight, preferably 0.05- 5.00% by weight, particularly preferably 0.1-3.00% by weight, based in each case on the total weight of the composition.

According to the invention, the preparations are particularly advantageously characterized in that glyceryl stearate citrate in total concentrations of 0.001-10.00% by weight, preferably 0.05-5.00% by weight, particularly preferably 0.1-3.00% by weight. -%, based in each case on the total weight of the composition, is present.

The cosmetic or dermatological formulations according to the invention can have the usual composition and serve for the treatment, care and cleaning of the skin and / or hair and as a make-up product in decorative cosmetics. They contain th preferably 0.01 wt .-% to 10 wt .-%, preferably 0.05 wt .-% to 5 wt .-%, in particular 0.1-2.0 wt .-%, based on the Total weight of the agent, one or more active ingredient combinations according to the invention.

For use, the cosmetic and dermatological preparations according to the invention are applied to the skin and / or hair in a sufficient amount in the manner customary for cosmetics.

The active ingredient combinations according to the invention can advantageously be incorporated into customary cosmetic and dermatological preparations, which can be in various forms. So you can z. B. a solution, an emulsion of the water-in-oil (W / O) type or of the oil-in-water (O / W) type, or a multiple emulsions, for example of the water-in-oil-in-water type (W / O / W) or oil-in-water-in-oil (O / W / O), a hydrodispersion or lipodispersion, a Pickering emulsion, a gel, a solid stick or an aerosol.

Emulsions according to the invention for the purposes of the present invention, e.g. B. in the form of a cream, a lotion, a cosmetic milk are advantageous and contain z. B. fats, oils, waxes and / or other fatty substances, as well as water and one or more emulsifiers, as they are usually used for such a type of formulation. It is also possible and advantageous for the purposes of the present invention to incorporate the active compound combinations according to the invention into aqueous systems or surfactant preparations for cleaning the skin and hair.

It is of course known to the person skilled in the art that sophisticated cosmetic compositions are mostly inconceivable without the customary auxiliaries and additives. These include, for example, consistency enhancers, fillers, perfumes, dyes, emulsifiers, additional active ingredients such as vitamins or proteins, light protection agents, stabilizers, insect repellants, alcohol, water, salts, antimicrobial, proteolytic or keratolytic substances, etc.

Mutatis mutandis, corresponding requirements apply to the formulation of medical preparations.

Medical topical compositions for the purposes of the present invention generally contain one or more medicaments in effective concentrations. For the sake of simplicity, reference is made to the statutory provisions of the Federal Republic of Germany (e.g. Cosmetics Ordinance, Food and Drugs Act) to clearly distinguish between cosmetic and medical applications and corresponding products.

It is also advantageous to add the active ingredient combinations according to the invention as an additive to preparations which already contain other active ingredients for other purposes.

Accordingly, cosmetic or topical dermatological compositions for the purposes of the present invention, depending on their structure, can be used, for example, as skin protection cream, cleansing milk, sun protection lotion, nutritional cream, day or night cream, etc. It is optionally possible and advantageous to use the compositions according to the invention as a basis for to use pharmaceutical formulations.

For use, the cosmetic and dermatological preparations are applied according to the invention to the skin and / or hair in a sufficient amount in the manner customary for cosmetics. Those cosmetic and dermatological preparations which are in the form of a sunscreen agent are particularly preferred. These can advantageously also contain at least one further UVA filter and / or at least one further UVB filter and / or at least one inorganic pigment, preferably an inorganic micropigment.

According to the invention, the cosmetic and dermatological preparations can contain cosmetic auxiliaries such as are customarily used in such preparations, for example preservatives, bactericides, perfumes, substances to prevent foaming, dyes, pigments that have a coloring effect, thickeners, and moisturizers / or moisture-retaining substances, fats, oils, waxes or other common constituents of a cosmetic or dermatological formulation such as alcohols, polyols, polymers, foam stabilizers, electrolytes, organic solvents or silicone derivatives.

An additional content of customary antioxidants is generally preferred. According to the invention, all antioxidants suitable or customary for cosmetic and / or dermatological applications can be used as favorable antioxidants.

The amount of the aforementioned antioxidants (one or more compounds) in the preparations is preferably 0.001 to 30% by weight, particularly preferably 0.05-20% by weight, in particular 1-10% by weight, based on the total weight the preparation.

If the cosmetic or dermatological preparation in the sense of the present invention is a solution or emulsion or dispersion, the following solvents can be used:

Water or aqueous solutions

Oils, such as triglycerides of capric or caprylic acid, but preferably castor oil; Fats, waxes and other natural and synthetic fatty substances, preferably esters of fatty acids with alcohols of low carbon number, for example with isopropanol, propylene glycol or glycerol, or esters of fatty alcohols with alkanoic acids of low carbon number or with fatty acids; Alcohols, diols or polyols with a low carbon number and their ethers, preferably ethanol, isopropanol, propylene glycol, glycerol, ethylene glycol, ethylene glycol monoethyl or monobutyl ether, propylene glycol monomethyl, monoethyl or monobutyl ether, diethylene glycol monomethyl ether or analogues Products.

In particular, mixtures of the abovementioned solvents are used. In the case of alcoholic solvents, water can be another component.

Water or aqueous solutions

Oils, such as triglycerides of capric or caprylic acid, but preferably castor oil; Fats, waxes and other natural and synthetic fatty substances, preferably esters of fatty acids with alcohols of low carbon number, e.g. with isopropanol, propylene glycol or glycerine, or esters of fatty alcohols with alkanoic acids of low carbon number or with fatty acids;

Alcohols, diols or polyols with a low carbon number and their ethers, preferably ethanol, isopropanol, propylene glycol, glycerol, ethylene glycol, ethylene glycol monoethyl or monobutyl ether, propylene glycol monomethyl, monoethyl or monobutyl ether, diethylene glycol monomethyl ether or analogues Products.

Suitable propellants for cosmetic and / or dermatological preparations that can be sprayed from aerosol containers in the context of the present invention are the customary, highly volatile, liquefied propellants, for example hydrocarbons (propane, butane, isobutane), which can be used alone or in a mixture with one another. It is also advantageous to use compressed air.

Of course, the person skilled in the art knows that there are propellant gases which are nontoxic per se which are fundamentally necessary for the implementation of the present invention in the form of aerosol preparations which, however, should be avoided because of their harmful effects on the environment or other accompanying circumstances, in particular fluorocarbons and chlorofluorocarbons (CFCs).

Cosmetic preparations within the meaning of the present invention can also be in the form of gels which, in addition to an effective content of active ingredient combinations according to the invention and solvents usually used for this, preferably water, also organic thickeners, e.g. gum arabic, xanthan gum, sodium alginate, cellulose derivatives, preferably methyl cellulose, hydroxymethyl cellulose , Hydroxyethyl cellulose, hydroxypropyl cellulose, hydroxypropylmethyl cellulose or inorganic thickeners, e.g. B. aluminum miniumsilicates such as bentonite, or a mixture of polyethylene glycol and polyethylene glycol stearate or distearate, contain. The thickening agent is contained in the gel, for example, in an amount between 0.1 and 30% by weight, preferably between 0.5 and 15% by weight.

It is advantageous according to the invention, in addition to the combinations according to the invention, to use further oil-soluble UVA filters and / or UVB filters in the lipid phase and / or further water-soluble UVA filters and / or UVB filters in the aqueous phase.

According to the invention, the light protection formulations can advantageously contain further substances which absorb UV radiation in the UVB range, the total amount of the filter substances being, for example, 0.1% by weight to 30% by weight, preferably 0.5 to 10% by weight. %, in particular 1 to 6% by weight, based on the total weight of the preparations, in order to provide cosmetic preparations which protect the skin from the entire range of ultraviolet radiation. They can also serve as sunscreens.

Experiments on the stability of ubidecarenol in combination with different emulsifiers:

Surprisingly, it was found that some hydrophilic O / W emulsifiers (glyceryl stearate citrate, stearoyl sulfate, cetearyl phosphate) stabilize ubiquinol better than emulsifiers from the prior art (e.g. stearate).

For this purpose, 5 emulsions with different emulsifiers were stored in the light for 4 weeks.

The oil phases are one and the same solution. Accordingly, the initial concentration in all emulsions was exactly the same.

After 4 weeks the following analytical results were obtained:

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

Recipe examples:

pH 5-6

pH 5-6

pH 5-6

Claims

1. Active ingredient combinations, comprising a) ubidecarenol and b) glyceryl stearate citrate.

2. Cosmetic or dermatological preparations, in particular in the form of O / W emulsions, with a content of active ingredient combinations according to Claim 1.

3. Active ingredient combinations or preparations according to one of the preceding claims, characterized in that the molar ratio of ubidecarenol to glyceryl stearate citrate is in the range from 10: 1 to 1: 1000, preferably 5: 1 to 1: 500, particularly preferably 2: 1 up to 1: 100 is selected.

4. Preparations according to one of the preceding claims, characterized in that ubidecarenol, in concentrations of 0.001-10.00% by weight, preferably 0.05-5.00% by weight, particularly preferably 0.1-3.00 % By weight, each based on the total weight of the composition.

5. Preparations according to one of the preceding claims, characterized in that glyceryl stearate citrate in concentrations of 0.001-10.00% by weight, preferably 0.05-5.00% by weight, particularly preferably 0.1-3.00% by weight .-%, each based on the total weight of the composition, is present.