EP0716592A1

EP0716592A1 - Compositions against skin impurities and mild forms of acne containing lanolinic acid or lanolinic acid components as active substance

Info

Publication number: EP0716592A1
Application number: EP94924207A
Authority: EP
Inventors: Sven Gohla; Manfred Klier; Florian Wolf
Original assignee: Beiersdorf AG
Current assignee: Beiersdorf AG
Priority date: 1993-09-01
Filing date: 1994-08-23
Publication date: 1996-06-19
Also published as: JPH09501937A; WO1995006457A1; DE4329379C1

Abstract

Mixtures of natural lanolinic acids or mixtures of lanolinic acids prepared by distillation are used as active substances against skin impurities, mild forms of acne and Propionibacterium acnes.

Description

Preparation effective against blemished skin and mild forms of acne with a content of wool wax acid or wool wax acid components as an effective principle

description

Preparations which are effective against impure skin and mild forms of acne and contain wool wax acid or wool wax acid components as an effective principle

The present invention relates to active substances and preparations containing active substances which are effective against impure skin and mild forms of acne.

In the case of blemished skin and mild forms of acne, bacterial secondary infections are of etiological importance in addition to other influences. One of the main microorganisms associated with blemished skin is Propionibacterium acnes.

Impure skin and / or comedones affect the well-being of those affected, even in mild cases. Since practically everyone or every adolescent is affected by impure skin of any kind, there is a need for many people to remedy this condition.

It was therefore the object of the present invention to find mild forms of acne or Propionibacterium acnes active against impure skin.

It has surprisingly been found, and this is the solution to the problem that the use of natural wool wax acid mixtures or wool wax acid mixtures prepared by distillation is effective Principle against blemished skin, mild forms of acne and against Propionibacterium acnes fulfills this task.

In particular, the use of natural wool wax acid mixtures or wool wax acid mixtures prepared by distillation for the production of cosmetic or dermatological preparations effective against impure skin, mild forms of acne or against Propionibacterium acnes is an advantageous embodiment of the present invention.

Wool wax or wool fat is the fat-to-wax-like component of raw sheep's wool that arises during raw wool washing. The wool wax consists of a mixture of fatty acid esters of higher alcohols and free fatty acids.

The main components of wool wax acids are

(a) saturated unsubstituted carboxylic acids, according to the formula

CH ₃ - (CH ₂ ) _n CH ₂ -COOH,

(b) Cu-hydroxycarboxylic acids, according to the formula

CH ₃ - (CH ₂ ) _n CH

COOH,

(c) Ω-hydroxycarboxylic acids, according to the formula

HO-CH ₂ - (CH ₂ ) _n CH ₂ -COOH,

(d) Isocarboxylic acids, according to the formula CH3_-C ^* H- (CH2_) nCH2_-COOH,

CH3

(e) cx-hydroxy-isocarboxylic acids, according to the formula

_{/ 0} H

(f) Ω-hydroxy-isocarboxylic acids, according to the formula

H0-CH, -CH- (CH-) CH -C00H

. "> I Z Xi Z

CH ₃

(g) Anteisocarboxylic acids, according to the formula

CH -.- CH ₀ -CH- (CH_) CH -C00H, →. → \ Z Xi z

CH3

(h) Cu-hydroxy-anisocarboxylic acids, according to the formula

OH /

CH, -CH "-CH- (CH.)" CH 3 2 ^* 2 n • -.

CH3 COOH

(i) Ω-hydroxy-anisocarboxylic acids, according to the formula

HO-CH -, - CH_-CH- (CH „) __CH_-COOH 3 2 i 2 n 2

CH ₃

N usually takes values from 7 - 31. Representative compositions of the wool wax acids are described, for example, in "Perfumery and Cosmetics", 59th year, No. 12/78, pages 429, 430 and in the "Lexicon of auxiliaries for pharmacy, cosmetics and adjacent areas" by HPFiedler, 1989 , 3rd edition, Editio Cantor Aulendorf. Although EP-A-273 202 describes that certain α-hydroxycarboxylic acids are to be used as an agent enhancing the effect of antimicrobial agents in the treatment of acne. However, the person skilled in the art could not assume that the use of wool wax acid mixtures according to the invention with the parameters described in the claims themselves would lead to preparations which are effective against impure skin or against Propionibacterium acnes and would have considerable advantages over the prior art.

Raw wool wax acids are not suitable for cosmetic purposes; instead, distilled wool wax acids are usually used. This fact and corresponding processes for refining the raw wool wax acids are known to the person skilled in the art.

Wool wax acids typically consist of approx. 60% saturated, unsubstituted carboxylic acids, approx. 30% α-hydroxycarboxylic acids and approx. 5% Ω-hydroxycarboxylic acids, the rest of approx. 5% being essentially formed by the other aforementioned carboxylic acid types .

In particular, the wool wax acids according to the invention are advantageously characterized by the following characteristic parameters:

Dropping point 50 - 54 ° C acid number 166 - 170 saponification number 175 - 190 OH number 60 - 80 iodine number 7 - 12

It is known from the article "Antimicrobial Factors in Wool Wax" (Australian Journal of Chemistry, 1971, 24, pages 153 ff.) That some wool wax batches contain antimicrobial factors. A note in However, the direction of the present invention is not found at the specified location.

It is believed that in particular the α-hydroxycarboxylic acids make a significant contribution to the effect according to the invention. The use of mixtures is therefore also in accordance with the invention

I) - α-hydroxycarboxylic acids, according to the formula

CH ₃ - (CH ₂ ) _n CH

COOH and / or

α-Hydroxy-isocarboxylic acids, according to the formula

OH

α-Hydroxy-anteisocarboxylic acids, according to the formula

OH / CH -.- CH_-CH- (CH_) CH

CH3 COOH,

where n represents a number from 7 to 31,

as a principle effective in cosmetic preparations against impure skin, mild forms of acne or Propionibacterium acnes.

For the purposes of the present invention, it is particularly advantageous to use cx-hydroxycarboxylic acids which are C _lf bodies and which therefore carry a branched or unbranched C-.H chain on the α-carbon atom. It is also advantageous to use wool wax acid mixtures in which the content of o-hydroxycarboxylic acids is 20-30% by weight, based on the total composition.

According to a further advantageous embodiment of the present invention, one or more are used as wool wax acid components

(a) saturated unsubstituted carboxylic acids, according to the formula

CH ₃ - (CH ₂ ) _n CH ₂ -COOH, and / or

(b) α-Hydroxycarboxylic acids, according to the formula

CH - (CH ₂ > _n CH

COOH, and / or

(c) Ω-hydroxycarboxylic acids, according to the formula

HO-CH ₂ - (CH ₂ ) _n CH ₂ -COOH, and / or

(d) Isocarboxylic acids, according to the formula

CH ό - CιH- (CH Z „) XiCH Z-C00H,

CH3 and / or

(e) α-hydroxy-isocarboxylic acids, according to the formula

(f) Ω-hydroxy-isocarboxylic acids, according to the formula HO-CH_ - CH- (CH „) CH-. -COOH

-5 1 Z Xi Z

CH-, and / or

(g) Anteisocarboxylic acids, according to the formula

CH ₃ -CH ₂ -CH- (CH ₂ ) _n CH ₂ -COOH,

CH3 and / or

(h) α.-Hydroxy-anteisocarboxylic acids, according to the formula

_{/ 0} H

(i) Ω-hydroxy-anisocarboxylic acids, according to the formula

HO-CH, -CH Z_-C \ H- (CH Z-XiCH z_-COOH

CH ₃

where n assumes values from 7 to 31, used in combination with other active ingredients (substitute ingredients), auxiliaries, blends and / or additives customary in cosmetics.

The blends and / or replacement active ingredients are then advantageously present in a concentration of up to 50 parts by weight, preferably up to 35 parts by weight, based on 100 parts by weight of the total amount, which is the sum of the Wool wax acid components and these substitutes and / or blends.

The cosmetic preparations according to the invention against impure skin or against mild forms of acne are particularly advantageously characterized in that the wool wax acids or the wool wax acid components in concentrations of 0.05-10.00% by weight, preferably 0.1 5.0% by weight are present, in each case based on the total weight of the preparations.

According to a further advantageous embodiment of the present invention, one or more wool wax acids or wool wax acid components, in particular

I) - α-hydroxycarboxylic acids, according to the formula

_/ OH CH ₃ - (CH ₂ ) _n CH

COOH and / or

α-Hydroxy-isocarboxylic acids, according to the formula

H and / or

o; -Hydroxy-anteisocarboxylic acids, according to the formula

OH

/

CH 3 -, - CH2-C, H- (CH2 _) '„nCH

CH3 COOH,

where n represents a number from 7 to 31,

used in combination with other substances which are effective against impure skin or mild forms of acne or which inhibit the growth of Propionibacterium acnes or which kill Propionibacterium acnes.

The preparations according to the invention which are effective against impure skin or mild forms of acne can be in the form of liquid which can be applied by means of brushes or scrapers or roll-on devices Compositions, as sticks and in the form of W / O or O / W emulsions which can be applied from normal bottles and containers, for example creams or lotions. Furthermore, the preparations according to the invention which are effective against impure skin can advantageously be present in the form of facial tonics, tinctures or cleaning formulations.

In addition to water, ethanol and isopropanol, glycerol and propylene glycol, skin-caring fatty or fat-like substances such as oleic acid decyl ester, cetyl alcohol, cetylstearyl alcohol and 2-octyldodecanol can be used as usual carriers for the preparation of the preparations according to the invention which are effective against impure skin or mild forms of acne such preparations are used in the usual proportions as well as slime-forming substances and thickeners, for example Hydroxyethyl or hydroxypropyl cellulose, polyacrylic acid, polyvinylpyrrolidone, but also in small quantities cyclic silicone oils (polydimethylsiloxanes) and liquid polymethylphenylsiloxanes with low viscosity.

As emulsifiers for the production of the preparations according to the invention against impure skin or against mild forms of acne, which are advantageously to be applied as liquid preparations to the desired skin areas, advantageously by means of a cotton swab, and which are less in the preparations Amount, e.g. 2 to 5% by weight, based on the total composition, can be used, non-ionic types such as polyoxyethylene fatty alcohol ethers, e.g. Cetostearyl alcohol polyethylene glycol ether with 12 or 20 attached ethylene oxide units per molecule, cetostearyl alcohol and sorbitan esters and sorbitan ester-ethylene oxide compounds (e.g.

Sorbitan monostearate and po- lyoxyethylene sorbitan monostearate) and long-chain higher molecular wax-like polyglycol ethers have been found to be suitable.

In addition to the ingredients mentioned, the preparations according to the invention which are effective against impure skin or mild forms of acne, the pH of which is preferably e.g. is adjusted to 4.0 to 9.0, in particular 5.0 to 6.5, by customary buffer mixtures, perfume, dyes, antioxidants (eg o-tocopherol and its derivatives or butylated hydroxytoluene (BHT = 2,6-di-tert-butyl -4-methylphenol) in amounts of 0.01 to 0.03%, based on the total composition), suspending agents, buffer mixtures or other customary cosmetic basic substances.

The pH of the preparations according to the invention, which are effective against impure skin or against mild forms of acne, is advantageously adjusted in the slightly acidic to neutral range, preferably from 4.0 to 7.0, particularly preferably from 5.0 to 6.5.

Depending on the type of product, the amounts of carrier substances to be used can easily be determined by a person skilled in the art by simply trying them out.

The preparations according to the invention are prepared with the exception of special preparations which. are noted separately in the examples, in the usual way, mostly by simple mixing with stirring, optionally with gentle heating. It has no difficulties. For emulsions, the fat phase and the water phase are, for example, prepared separately, optionally with heating, and then emulsified. Otherwise, the usual measures for the composition of pharmaceutical formulations, which are known to the person skilled in the art, must be observed.

Advantageous exemplary embodiments of the present invention follow. In the examples, the term "WWS" means a wool wax acid fraction which was obtained from raw wool wax acid by short-path distillation at 10 ^~ bar from the distillation temperature interval of 150-200 ° C. The proportion of o ^* -hydroxycarboxylic acids is about 22 - 27%

example 1

Gel I, thin

Weight (a)

1,3-butylene glycol 2.00

Hydroxyethyl cellulose 0.50

(e.g. Tylose 4000, Hoechst)

(b)

Ethyl alcohol 60.00

PEG-40 hydrogenated castor oil 2.00

WWS - 0.80

(c)

Water ad 100.00

The constituents mentioned under (a) are dispersed, water (c) is added, swelled at room temperature, a solution of the constituents mentioned under (b) is added after about 15 minutes. The resulting mixture is homogenized and can be filled.

Example 2

Crayon I

Wt.

Hydrogenated castor oil 5.00

Beeswax 6.00

Ceresin (hard ozokerite) 30.00

C _{2 5} alcohol benzoates ^" 17.00

WWS 0.90

Octyldodecanol ad 100.00

The ingredients are melted at approx. 75 ° C, mixed well and poured into suitable molds.

Example 3

Crayon II

^" % By weight

Hydrogenated castor oil 5.00

Beeswax 6.00

Ceresin (hard ozokerite) 30.00 ^c ₁₂ _ _i5 alcohol benzoate 17.00

WWS 1.45

Octyldodecanol ad 100.00

The ingredients are melted at approx. 75 ° C, mixed well and poured into suitable molds. Example 4

Cleaning emulsion I

(a)

% By weight

Triceteareth phosphate 0.30

Octyldodecanol 2.00

C _{12 15} alcohol benzoates 2.00

WWS 0.50

C ₁₀ _ ₃₀ -alkyl 0.15

(b)

Ethyl alcohol 10.00

(c)

NaOH 0.05

Water ad 100.00

The components mentioned under (a) and (c) are each heated to 75 ° C. with stirring. Then components (a) are added to (c). The mixture is on

Cooled to 35 ° C. Component (b) is added to the mixture of (a) and (c) with stirring.

Example 5

Skin cleansing gel I

% By weight (a)

1,3-butylene glycol 2.00

Hydroxyethyl cellulose 0.50

(e.g. Tylose 4000, Hoechst)

(b)

Ethyl alcohol 60.00

PEG-40 hydrogenated castor oil 2.00

WWS 1.30

(c)

Water ad 100.00

Example 6

Facial Toner I

Weight

Ethanol 10.00

WWS 1.00

Water ad 100.00

Attempt :

The following experiment is intended to demonstrate the effectiveness of the monocarboxylic acid esters of wool wax acids or preparations containing such esters according to the invention.

Facial lotions corresponding to the formulations according to Examples 6 and 7 were tested for their antimicrobial effectiveness. A solution of 10% ethanol and 90% water was used as a control.

A mixture of AC medium, 3% tween, 0.3% lecithin, 0.1% histidine was used as the disinhibiting medium.

Suspension test:

To carry out a suspension test, propionibacteria were grown under aerobic conditions up to a germ count of 10 germs / ml. A suspension test was then carried out over a period of 1 hour with the germ suspension thus obtained. Then aliquots of the incubation batches were diluted with ten times the amount of disinhibiting medium and plated out on solid nutrient media. After seven days of incubation under anaerobic conditions, the test was evaluated numerically.

Results:

Both the formulation according to Example 6 and the formulation according to Example 7 significantly reduced the number of bacteria. The control formulation did not reduce the bacterial count.

Claims

1. Use of natural wool wax acid mixtures or of wool wax acid mixtures prepared by distillation as an effective principle against impure skin, mild forms of acne and against Propionibacterium acnes.

2. Use of natural wool wax acid mixtures or wool wax acid mixtures prepared by distillation for the production of cosmetic or dermatological preparations which are effective against impure skin, mild forms of acne or against Propionibacterium acnes.

4. Use according to claim 1 or 2, characterized in that the wool wax acid mixture or the wool wax acid mixtures are present in a suitable cosmetic or dermatological carrier.

5. Use according to claim 1 or 2, characterized in that the wool wax acid mixtures consist of approx. 60% saturated, unsubstituted carboxylic acids, approx. 30% α-hydroxycarboxylic acids and approx. 5% Ω-hydroxycarboxylic acids, the rest of approx. 5 % is essentially formed from other carboxylic acids.

6. Use according to claim 1 or 2, wherein the wool wax acid mixture or the wool wax acid mixtures are characterized by the following parameters:

Dropping point 50 - 54 ° C acid number 166 - 170 saponification number 175 - 190 OH number 60 - 80 iodine number 7 - 12 7. Use according to claim 1 or 2, characterized in that wool wax acid mixtures are selected in which the content of α-hydroxycarboxylic acids 20th

30 wt .-%, based on the total composition.

8. Use according to claim 1, characterized in that c-hydroxycarboxylic acids are chosen as wool wax acid component, which are C _lg bodies, which thus carry a branched or unbranched C ₁₄ H _2g chain on the oj carbon atom.