WO2012084419A2

WO2012084419A2 - Active substance combinations of glucosyl glycerides and one or more substances active against dandruff

Info

Publication number: WO2012084419A2
Application number: PCT/EP2011/071176
Authority: WO
Inventors: Christian Frese; Rainer Kröpke; Cathrin Scherner; Sven Fey; Nicole Maria Krauss
Original assignee: Beiersdorf Ag
Priority date: 2010-12-23
Filing date: 2011-11-28
Publication date: 2012-06-28
Also published as: WO2012084419A3; DE102010055763A1

Abstract

The invention relates to active substance combinations of (i) one or more substances active against dandruff and (ii) one or more glucosyl glycerides.

Description

description

Active ingredient combinations of glucosylglycerides and one or more against

Dandruff effective substances

The present invention relates to active ingredient combinations of glucosylglycerides and one or more anti-dandruff substances and their use in the field of cosmetic and pharmaceutical dermatology.

In particular, the present invention relates to active ingredients and cosmetic or dermatological preparations containing such combinations of active substances.

The present invention preferably relates to washing-active cosmetic preparations.

The outermost layer of the epidermis, the stratum corneum (horny layer), is of particular importance as an important barrier layer, inter alia. for protection against environmental influences and dehydration. The horny layer is constantly worn in contact with the environment and must therefore be renewed continuously.

A skin model widely used today in the art understands the stratum corneum as a two-component system, similar to a brick wall (brick-mortar model). In this model, the corneocytes (horny cells) correspond to the bricks, the complex composite lipid membrane in the intercellular spaces corresponds to the mortar.

In addition to their barrier effect against external chemical and physical influences, the epidermal lipids also contribute to the cohesion of the horny layer and have an influence on the skin smoothness. In contrast to the sebaceous gland lipids, which do not form a closed film on the skin, the epidermal lipids are distributed over the entire horny layer. The extremely complex interaction of the moisture-binding substances and the lipids of the upper skin layers is very important for the regulation of skin moisture. Therefore, cosmetics usually contain, in addition to balanced lipid mixtures and water, water-binding substances. These include polyols such as glycerin, sorbitol and xylitol, ethoxylated polyols and hydrolyzed proteins. Other uses include those contained in the natural moisturizing factor (so-called Natural Moisturizing Factor = NMF), such as urea, carbohydrates (eg glucose) and amino acids (eg serine). These substances are therefore of particular importance for the care performance of a cosmetic product, in particular because of their relatively good skin and mucous membrane compatibility.

The desire for clean skin is probably as old as humanity, because dirt, sweat and remains of dead skin particles provide the ideal breeding ground for pathogens and parasites of all kinds. The desire for personal hygiene was steadily increased, as in the 60s of the 20th century In addition to the "classic" soap and liquid detergents could be formulated with newly developed synthetic surfactants. Since then, bathing and showering have become indispensable in our daily lives. Consumers today have a variety of products available for cleaning the various body parts.

Cleaning means the removal of (environmental) dirt and thus causes an increase in mental and physical well-being. Cleaning the surface of the skin and hair is a very complex process, depending on many parameters. On the one hand, substances coming from outside such as, for example, hydrocarbons or inorganic pigments from a wide variety of environments as well as residues of cosmetics or undesired microorganisms should be removed as completely as possible. On the other hand, the body's excretions such as sweat, sebum, dandruff and hair dandruff are to be washed off without profound interventions in the physiological balance.

In addition to hair care and hair care, hair treatment products play an important role in the treatment of scalp dandruff. In general, anti-dandruff treatment includes the control of the Phytosporum ovale Yeast fungi, which is the cause of excessive dandruff for cosmetic dandruff.

Known antidandruff active ingredients include the compounds (1- (4-chlorophenoxy) -1- (1H-imidazolyl) -3,3-dimethyl-2-butanone (INCI name: Climbazole, trade name: Crinipan AD), (bis ( 1-hydroxy-2- (1H) -pyridinethionato) zinc (INCI name: Zinc Pyrithione, trade name: Zinc Omadine) and 1-hydroxy-4-methyl-6- (2,4,4-trimethylpentyl) -2 ( 1 H) -pyridinone, 2-aminoethanol salt (INCI name: Piroctone Olamine, trade name: octopirox) .These compounds are known and commercially available, for example, refer to International Cosmetic Ingredient Dictionary and Handbook, Vol - 3, Seventh Edition 1997, The Cosmetic, Toiletry, and Fragrance Association, Washington, DC In addition, other anti-dandruff active ingredients are those from the group of synthetic or chemical compounds such as salicylic acid, sulfur, tar preparations, undecenoic acid derivatives and hinokitiol and those from the Group of natural products such as e extracts from arnica, birch, burdock root, poplar, stinging nettle or walnut shell.

The requirements for a hair cosmetic agent, which is to prevent or reduce dandruff, are versatile. On the one hand, the scalp and thus also the hair should be freed from dandruff. On the other hand, the agent should be compatible not only for the scalp but also the hair should not be damaged when using an anti-dandruff agent and retain its shine and combability.

A problem in this connection is that a lasting liberation of the scalp from dandruff can only be achieved if the anti-dandruff active ingredients are used in a sufficiently high concentration. However, a high concentration of anti-dandruff active ingredients deteriorates the compatibility of the preparation and adversely affects both the sensory properties (in particular the foaming behavior) and the care properties of the preparation (gloss, combability of the hair). There is therefore a need for preparations which contain anti-dandruff agents in effective concentration and at the same time have good compatibility, good care performance and good sensory properties.

After all this it was surprising and unpredictable that drug combinations made

(i) one or more dandruff active substances

and

(ii) one or more glucosylglycerides

or cosmetic preparations containing such Rukstoffkombinationen eliminate the disadvantages of the prior art.

Surprisingly, the problem could be solved by the use of glucosylglycerides in anti-dandruff agents containing one or more anti-scale agents. These preparations are characterized by a high dandruff resistance, very good care properties and good sensory properties even at high levels of anti-dandruff active ingredients.

According to the invention, the substance (s) active against dandruff can be selected from the group of the compounds (1- (4-chlorophenoxy) -1- (1H-imidazolyl) -3,3-dimethyl-2-butanone (INCI name: Climbazole, Trade name: Crinipan AD), (bis (1-hydroxy-2- (1H) -pyridinethionato) zinc (INCI name: Zinc Pyrithione, trade name: Zinc Omadine) and 1-hydroxy-4-methyl-6- (2, 4,4-trimethylpentyl) -2 (1H) -pyridinone, 2-aminoethanol salt (INCI name: Piroctone Olamine, trade name: Octopirox), furthermore from the group of synthetic or chemical compounds such as salicylic acid, sulfur, tar preparations, undecenoic acid derivatives and Hinokitiol and those from the group of natural products such as extracts of arnica, birch, burdock root, poplar, stinging nettle or walnut shell.

Preferred antidandruff active ingredients are climbazoles, piroctone olamine, undecylenamidopropyl betaine and zinc pyrithione. Particularly preferred are climbazoles and piroctone olamine.

Preferred concentration of the antidandruff agent is 0.001 to 10%, particularly preferably 0.01-5%, particularly preferably 0.1 to 3%. Furthermore, the rinse-off preparations contain surfactants, thickeners, preservatives, perfume, oils and possibly other cosmetic ingredients.

For the purposes of the present invention, glucosylglycerides of the general formula are advantageous

and / or the general formula

and / or the general formula

and / or the general formula

are preferred according to the invention. It is advantageous according to the invention to choose the molar ratio of one or more glucosylglycerides to one or more anti-dandruff active ingredients in the range from 100: 1 to 1: 100, preferably 50: 1 to 1:50, particularly preferably 20: 1 to 1:20 ,

According to the invention, those preparations are particularly advantageous, which are characterized in that the glucosylglyceride or in the water and / or oil phase in concentrations of 0.001 to 40.00 wt .-%, preferably 0.005 to 15.00 wt .-%, especially preferably 0.01 to 12.00 wt .-%, each based on the total weight of the composition.

According to the use according to the invention, the preparations are particularly advantageously characterized in that the one or more anti-dandruff active ingredients in concentrations of 0.01-10.00% by weight, preferably 0.05-5.00% by weight, particularly preferably 0.1 to 3.00% by weight, in each case based on the total weight of the composition, is present or present.

The use of the preparation according to the invention as a cosmetic hair cleansing or hair care preparation is advantageous according to the invention. In this case, the preparation according to the invention is preferably used as a shampoo and / or conditioner.

It is advantageous according to the invention if the cosmetic preparation according to the invention is stored in a bottle, squeeze bottle, pump spray or aerosol can and applied out of it. Correspondingly, bottles, squeeze bottles, double-chamber packing, pump spray or aerosol cans containing a preparation according to the invention are also suitable according to the invention.

The preparation according to the invention advantageously contains one or more anionic surfactants. These are according to the invention advantageously in a concentration of 1 to 20% by weight, and according to the invention preferably in a concentration of 5 to 12% by weight, in each case based on the total weight of the preparation, in the preparation. Particularly preferred according to the invention is the use of narium lauryl ether sulfate as anionic surfactant.

According to the invention, the preparation advantageously contains one or more amphoteric surfactants. These are according to the invention advantageously in one Concentration of 1 to 20% by weight, and according to the invention preferably in a concentration of 3 to 8% by weight, in each case based on the total weight of the preparation, in the preparation. Particularly preferred according to the invention is the use of cocamidopropylbetaine as the amphoteric surfactant.

In addition, the preparation according to the invention may advantageously also contain nonionic surfactants. Particularly preferred according to the invention is the use of PEG-7 glyceryl cocoate and / or PEG-40 hydrogenated castor oil as nonionic surfactant.

It is likewise advantageous to add cationic polymers to the preparations for the purposes of the present invention. Suitable cationic polymers are, for example

quaternized cellulose derivatives, e.g. Polyquaternium-10, as are commercially available under the names Celquat and Polymer JR cationic guar derivatives, in particular those sold under the trade names Cosmedia Guar and Jaguar products

polymeric dimethyldiallylammonium salts and their copolymers with esters and amides of acrylic acid and methacrylic acid, in particular the products sold under the names Merquat 100 and Merquat 550 commercially available.

In the context of the present invention, it is advantageous, in particular, cationic polymer or mixtures of cationic polymers in a concentration of 0.01 to 2% by weight, preferably in a concentration of 0.05 to 1.5% by weight and more preferably of 0.1 to 1.0% by weight, in each case based on the total weight of the preparation to use.

The compositions according to the invention optionally contain, in addition to the aforementioned substances, the additives customary in cosmetics, for example perfume, dyes, antimicrobials, moisturizing agents, complexing and sequestering agents, pearlescing agents, plant extracts, vitamins, active ingredients, preservatives, bactericides, pigments containing a have coloring, thickening, softening, wetting and / or moisturizing substances, or other conventional ingredients of a cosmetic or dermatological formulation such as alcohols, polyols, polymers, foam stabilizers, electrolytes, organic solvents or silicone derivatives. The inventively advantageous usable active ingredients, auxiliaries and additives are by no means limited to the substances and compounds mentioned here by name.

Niacinamide, panthenol, polidocanol, [gamma] -Oryzanol, ubiquinones (especially Q-10) creatine, creatinine, biotin (vitamin H), vitamin E and vitamin E acetate, plant extracts, such as, for example, are particularly advantageous active ingredients according to the invention. Bamboo extract, water-lily extract, alpha-hydroxy acids, e.g. Citric acid, tartaric acid, malic acid, salts, e.g. Calcium salts or marine minerals, BHT, propyl gallate, and UV filters (e.g., particularly favorably benzophenone-4).

According to the invention, such active ingredients may advantageously be present in concentrations (individual concentration of an active substance) of from 0.001 to 5% by weight, based in each case on the total weight of the preparation, in the preparations.

It is furthermore advantageous according to the invention if effect substances (for example color and / or bulking beads, glitter substances and the like) are added to the preparations according to the invention and / or the preparation is provided with stable air bubbles and bubbles.

Opacifying agents / pearlescing agents or mixtures which are advantageous according to the invention include:

PEG-3 distearate (e.g., CUTINA TS from Cognis),

a combination of glycol distearate, glycerol, laureth-4 and

Cocamidopropylbetaine (e.g., Euperlan PK 3000 and Euperlan PK 4000 the

Company Cognis),

a combination of glycol distearate, coco glucosides, glyceryl oleate and glyceryl stearate (e.g., Lamesoft ™ Benz from Cognis).

Styrene / acrylate copolymers (e.g., Acusol OP 301 from Rohm & Haas)

It is likewise advantageous to add conventional antioxidants to the preparations for the purposes 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 Wt .-%, in particular 1 - 10 wt .-%, based on the total weight of the preparation.

If the cosmetic or dermatological preparation in the sense of the present invention is a solution or emulsion or dispersion, it is possible to use as solvent:

Water or aqueous solutions

Oils, such as triglycerides of capric or caprylic acid, but preferably castor oil;

Fats, waxes and other natural and synthetic fats, preferably esters of fatty acids with lower C-number alcohols, e.g. with isopropanol, propylene glycol or glycerol, or esters of fatty alcohols with alkanoic acids of low C number or with fatty acids;

Alcohols, diols or polyols of low C 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 or monoethyl ether and analog products.

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

Cosmetic preparations in the context of the present invention may also be present as gels which, in addition to an effective content of the active ingredient according to the invention and solvents used for this purpose, preferably water, also organic thickening agents, e.g. Gum arabic, xanthan gum, sodium alginate, cellulose derivatives, preferably methylcellulose, hydroxymethylcellulose, hydroxyethylcellulose, hydroxypropylcellulose, hydroxypropylmethylcellulose or inorganic thickening agents, e.g. For example, aluminum silicates such as Benetonite, or a mixture of polyethylene glycol and polyethylene glycol stearate or distearate.

Embodiments of the present invention which are advantageous according to the invention are characterized in that the preparation likewise contains polyacrylates as thickening agent. Polyacrylates which are advantageous according to the invention are polymers of acrylic acid, in particular those selected from the group of the so-called carbomers or carbopols (Carbopol <(R)> is actually a registered trademark of the BF Goodrich Company). Advantageous carbopols are for example the types 907, 910, 934, 940, 941, 951, 954, 980, 981, 1342, 1382, 2984 and 5984 or also the types ETD (Easy-to-disperse) 2001, 2020, 2050, Aqua -SF1 wherein these compounds can be present individually or in any desired combinations with one another.

Also advantageous for the purposes of the present invention, the copolymers of C10-30-alkyl acrylates and one or more monomers of acrylic acid, methacrylic acid or their esters which are comparable to the acrylate-alkyl acrylate copolymers are advantageous. The INCI name for such compounds is "Acrylates / C 10-30 Alkyl Acrylate Crosspolymer". Particularly advantageous are those available under the trade names Pemulen TR1 and Pemulen TR2 from the B.F. Goodrich Company.

It is according to the invention of particular advantage when used as polyacrylates C10 to C30-alkyl acrylate copolymers.

The thickener is present in the gel e.g. in an amount between 0, 1 and 30 wt .-%, preferably between 0.5 and 15 wt .-%, included.

Following are advantageous embodiments of the present invention.

used raw materials

Trade name Name Active content Manufacturer

Amphoram U undecylenamidopropyl betaine -30% CECA

Cetiol HE PEG-7 glyceryl cocoate 100% Cognis

Comperlan KD Cocamide DEA 100% Cognis

Crinipan AD Climbazol 100% Symrise

DC 5-7139 dimethicone + cocamidopropyl- 65% + 1% + Dow Corning betaine + C12-15 pareth-3 + 1% + 0.6% guar hydroxypropyltrimonium chloride

Dehyquart A-CA Cetrimonium chloride -25% Cognis

Dehyton AB 30 Cocobetaine -30% Cognis

Eumulgin HRE PEG-40 Hydrogenated castor oil 100% Cognis 40

Euperlan PK 900 PEG-3 Distearate + Sodium Lime 25% + 14% Cognis

rethsulfat

Genapol LA 090 Laureth-9 -98% Clariant

Jaguar Excel Guar Hydroxypropyltrimonium -90% Rhodia

chloride

Lanette-0 Cetylstearylalcohol 100% Cognis

Merquat 550 Polyquaternium-7 -8% Nalco

Octopirox Piroctonolamine 100% Clariant

Rewoderm LI PEG-200 Hydrogenated -70% Evonik Gold520-70 Glycerylpalmat schmidt

Tego Amide S 18 Stearamidopropyldimethylamine 100% Evonik Goldschmidt

Tego Betain F 50 Cocamidopropylbetaine + Glyce- 36% + -3% Evonik Goldrin schmidt

Texapon N 70 Sodium Laureth Sulfate -70% Cognis

Ucare Polymer Polyquaternium-10 -90% Dow Chemical JR 400 Comparative Experiment Antidandruff Shampoo

The following products were manufactured and compared in a test subject:

all concentration data in% by weight

* Quantity variable for setting a viscosity in the range of 3000 - 4500 mPas

(according to HAAKE viscotester VT02 with rotor 1)

** Quantity variable to set a pH of 4.8 to 5.8 manufacturing

The Inhalststoffe of phase A are mixed together until a homogeneous phase is formed.

Ucare Polymer JR 400 is interspersed in the water of phase B. The phase B is heated with stirring to about 70 ° C until a clear solution is formed. Subsequently, phase B is cooled and added to phase A.

The water of phase C is mixed with the sodium hydroxide solution. Jaguar Excel is slowly sprinkled while stirring. Subsequently, the mixture is heated to 70 ° C and stirred until a homogeneous phase is formed. With stirring, the citric acid is added. Phase C is cooled and added to phase A.

Genapol LA 090 is heated to about 70 ° C with stirring. Subsequently, the Crinipan AD is added and dissolved with stirring. The mixture is then cooled to 40 ° C and it is added with stirring, the addition of the remaining ingredients of the phase D. It is stirred until a homogeneous phase is formed and added to the phase A.

The addition of the ingredients of phase E is carried out in the order given. It is stirred until a homogeneous shampoo is formed.

Results

Criterion product A no difference product B

better better

Fragrance impression 1 6 0

Consistency 2 5 0

Amount of foam 5 2 0

Foam quality 5 2 0

Rinsability 2 5 0

Nursing benefit 5 2 0

Combability 6 1 0 3 out of 7 subjects found the sensors of the inventive product A better overall than the sensors of the comparative product B. The other subjects were unable to detect any difference.

It can be clearly seen that the inventive product A is superior to the comparison product in terms of all features.

example recipes

shampoo preparations

all concentration data in% by weight

* Variable amount for setting a viscosity in the range of 3000 - 5000 mPas

(according to HAAKE viscotester VT02 with rotor 1)

** Quantity variable to set a pH of 4.8 to 5.8 The Inhalststoffe of phase A are mixed together until a homogeneous phase is formed.

Ucare Polymer JR 400 is interspersed in the water of phase B. The phase B is heated with stirring to about 70 ° C until a clear solution is formed. Phase B is cooled and added to Phase A.

Comperlan KD and DC 5-7139 are added to phase A with stirring.

The raw materials of phase E are heated to about 75 ° C, mixed homogeneously and added to phase A.

Eumulgin HRE 40 is melted at a temperature of about 40 ° C. The remaining phase F raw materials are added to the Eumulgin HRE 40. The phase is mixed homogeneously and added to phase A.

Rinse-off conditioner

all concentration data in% by weight

Amount variable for adjusting a pH of the water phase from 3.8 to 4.8

The raw materials of phase A are mixed together and heated to 80 ° C.

The water of phase B is mixed with the sodium hydroxide solution. Jaguar Excel is slowly sprinkled while stirring. Subsequently, the mixture is heated to 70 ° C and stirred until a homogeneous phase is formed. With stirring, the citric acid is added. Phase B is added to Phase A.

In a Kitchen Aid, the raw materials of phase C are heated to 80 ° C. and mixed homogeneously with stirring. Phase A is added to Phase C.

Phase A and Phase C are mixed and cooled in a Kitchen Aid. Phase D is added at 40 ° C and Phase E at 30 ° C. It is stirred until a homogeneous conditioner is formed. The viscosity of the conditioner is 3000-5000 mPas (measured with HAAKE viscotester VT02 with rotor 1)

Claims

claims:

1. drug combinations from

(i) one or dandruff-active substances

and

(ii) one or more glucosylglycerides.

2. active compound combinations according to claim 1, characterized in that the substance or substances effective against dandruff is selected or are from the group Climbazole, Piroctone Olamine, Undecylenamidopropyl Betaine and Zinc Pyrithione ..

3. Cosmetic preparations, drug combinations according to one of claims 1 - 2 containing.

4. Cosmetic preparations according to claim 3, in which one or more active against dandruff substances in concentrations of 0.001 to 10 wt .-%, particularly preferably 0.01-5 wt .-%, particularly preferably 0, 1% - 3 wt. %, in each case based on the total weight of the preparations, is present or present.

5. Cosmetic preparations according to claim 3 or 4 in which the glucosylglycerides or in the water and / or oil phase in concentrations of 0.001 to 40.00 wt .-%, preferably 0.005 to 15.00 wt .-%, particularly preferably 0 , 01-12.00% by weight, based in each case on the total weight of the composition.

6. Preparations according to one of the preceding claims, characterized in that they contain one or more surface-active substances.

7. Use of preparations according to one of the preceding claims as washing-active preparations.