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WO1995006457A1 - Compositions against skin impurities and mild forms of acne containing lanolinic acid or lanolinic acid components as active substance - Google Patents

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

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Publication number
WO1995006457A1
WO1995006457A1 PCT/DE1994/000979 DE9400979W WO9506457A1 WO 1995006457 A1 WO1995006457 A1 WO 1995006457A1 DE 9400979 W DE9400979 W DE 9400979W WO 9506457 A1 WO9506457 A1 WO 9506457A1
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Prior art keywords
wool wax
wax acid
acids
acid mixtures
acne
Prior art date
Application number
PCT/DE1994/000979
Other languages
German (de)
French (fr)
Inventor
Sven Gohla
Manfred Klier
Florian Wolf
Original Assignee
Beiersdorf Ag
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Beiersdorf Ag filed Critical Beiersdorf Ag
Priority to EP94924207A priority Critical patent/EP0716592A1/en
Priority to JP7507866A priority patent/JPH09501937A/en
Publication of WO1995006457A1 publication Critical patent/WO1995006457A1/en

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/92—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
    • A61K8/925—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof of animal origin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/0216—Solid or semisolid forms
    • A61K8/0229—Sticks
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/10—Washing or bathing preparations

Definitions

  • the present invention relates to active substances and preparations containing active substances which are effective against impure 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.
  • 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:
  • 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.
  • EP-A-273 202 describes that certain ⁇ -hydroxycarboxylic acids are to be used as an agent enhancing the effect of antimicrobial agents in the treatment of acne.
  • 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% ⁇ -hydroxycarboxylic acids and approx. 5% ⁇ -hydroxycarboxylic acids, the rest of approx. 5% being essentially formed by the other aforementioned carboxylic acid types .
  • the wool wax acids according to the invention are advantageously characterized by the following characteristic parameters:
  • n represents a number from 7 to 31
  • cx-hydroxycarboxylic acids which are C lf bodies and which therefore carry a branched or unbranched C-.H chain on the ⁇ -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.
  • one or more are used as wool wax acid components
  • n assumes values from 7 to 31, used in combination with other active ingredients (substitute ingredients), auxiliaries, blends and / or additives customary in cosmetics.
  • 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.
  • one or more wool wax acids or wool wax acid components in particular one or more wool wax acids or wool wax acid components, in particular
  • n represents a number from 7 to 31
  • 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.
  • 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.
  • oleic acid decyl ester oleic acid decyl ester
  • cetyl alcohol cetylstearyl alcohol
  • 2-octyldodecanol skin-caring fatty or fat-like substances
  • skin-caring fatty or fat-like substances such as oleic acid decyl ester, cetyl alcohol, cetylstearyl alcohol and 2-octyldodecanol
  • skin-caring fatty or fat-like substances such as oleic acid decyl ester, cetyl alcohol, cetylstearyl alcohol and 2-octyldodecanol
  • 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 polymethylphenylsiloxa
  • 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
  • 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.
  • BHT butylated hydroxytoluene
  • 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.
  • 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.
  • 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.
  • 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%
  • 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.
  • the ingredients are melted at approx. 75 ° C, mixed well and poured into suitable molds.
  • 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.
  • 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.
  • 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.

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  • Pharmacology & Pharmacy (AREA)
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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

Gegen unreine Haut und milde Formen der Akne wirksame Zubereitung mit einem Gehalt an Wollwachssäure oder Wollwachssäurekomponenten als wirksames PrinzipPreparation 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
Beschreibungdescription
Gegen unreine Haut und milde Formen der Akne wirksame Zu¬ bereitungen mit einem Gehalt an Wollwachssäure oder Woll¬ wachssäurekomponenten als wirksames PrinzipPreparations 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
Die vorliegende Erfindung betrifft Wirkstoffe und Zubereitungen, solche Wirkstoffe enthaltend, welche gegen unreine Haut und milde Formen der Akne wirksam sind.The present invention relates to active substances and preparations containing active substances which are effective against impure skin and mild forms of acne.
Bei der unreinen Haut sowie bei milden Formen der Akne sind neben anderen Einflüssen bakterielle Sekundärinfek¬ tionen von ätiologischer Bedeutung. Einer der wichtigsten Mikroorganismen, der in Zusammenhang mit unreiner Haut steht, ist Propionibacterium acnes.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.
Unreine Haut und/oder Komedonen beeinträchtigen das Wohl¬ befinden der Betroffenen aber selbst in leichten Fällen. Da praktisch jeder oder jede Jugendliche von unreiner Haut irgendeiner Ausprägung betroffen ist, besteht bei vielen Personen Bedarf, diesem Zustande abzuhelfen.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.
Aufgabe der vorliegenden Erfindung war es also, gegen un¬ reine Haut, milde Formen der Akne bzw. Propionibacterium acnes wirksamen Stoff zu finden.It was therefore the object of the present invention to find mild forms of acne or Propionibacterium acnes active against impure skin.
Es wurde überraschend gefunden, und darin liegt die Lösung der Aufgabe, daß die Verwendung von natürlichen Wollwachssäuregemischen oder durch Destillation aufbereiteten Wollwachssäuregemischen als wirksames Prinzip gegen unreine Haut, milde Formen der Akne sowie gegen Propionibacterium acnes diese Aufgabe erfüllt.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.
Insbesondere ist die Verwendung von natürlichen Wollwachssäuregemischen oder durch Destillation aufbereiteten Wollwachssäuregemischen zur Herstellung von gegen unreine Haut, milde Formen der Akne bzw. gegen Propionibacterium acnes wirksamen kosmetischen oder dermatologischen Zubereitungen eine vorteilhafte Verkörperung der vorliegenden Erfindung.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.
Wollwachs oder Wollfett wird der bei der Rohwollwäsche anfallende fett- bis wachsartige Bestandteil der Rohschafwolle bezeichnet . Das Wollwachs besteht aus aus einem Gemisch von Fettsäureestern höherer Alkohole und aus freien Fettsäuren.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.
Die Hauptbestandteile der Wollwachssäuren sindThe main components of wool wax acids are
(a) gesättigte unsubstituierte Carbonsäuren, gemäß der Formel(a) saturated unsubstituted carboxylic acids, according to the formula
CH3- (CH2)nCH2-COOH,CH 3 - (CH 2 ) n CH 2 -COOH,
(b) cü-Hydroxycarbonsäuren, gemäß der Formel(b) Cu-hydroxycarboxylic acids, according to the formula
CH3-(CH2)nCHCH 3 - (CH 2 ) n CH
COOH,COOH,
(c) Ω-Hydroxycarbonsäuren, gemäß der Formel(c) Ω-hydroxycarboxylic acids, according to the formula
HO-CH2- (CH2) nCH2-COOH,HO-CH 2 - (CH 2 ) n CH 2 -COOH,
(d) Isocarbonsäuren, gemäß der Formel CH3_-C*H-(CH2_)nCH2_-COOH,(d) Isocarboxylic acids, according to the formula CH3_-C * H- (CH2_) nCH2_-COOH,
CH3CH3
(e) cx-Hydroxy-isocarbonsäuren, gemäß der Formel(e) cx-hydroxy-isocarboxylic acids, according to the formula
/0H / 0 H
Figure imgf000005_0001
Figure imgf000005_0001
(f) Ω-Hydroxy-isocarbonsäuren, gemäß der Formel(f) Ω-hydroxy-isocarboxylic acids, according to the formula
H0-CH,-CH- (CH-) CH -C00HH0-CH, -CH- (CH-) CH -C00H
."> I Z Xi Z. "> I Z Xi Z
CH3 CH 3
(g) Anteisocarbonsäuren, gemäß der Formel(g) Anteisocarboxylic acids, according to the formula
CH-.-CH0-CH- (CH_) CH -C00H, →. → \ Z Xi zCH -.- CH 0 -CH- (CH_) CH -C00H, →. → \ Z Xi z
CH3CH3
(h) cü-Hydroxy-anteisocarbonsäuren, gemäß der Formel(h) Cu-hydroxy-anisocarboxylic acids, according to the formula
OH /OH /
CH, -CH„ -CH- (CH. ) „CH 3 2 * 2 n •-.CH, -CH "-CH- (CH.)" CH 3 2 * 2 n • -.
CH3 COOHCH3 COOH
(i) Ω-Hydroxy-anteisocarbonsäuren, gemäß der Formel(i) Ω-hydroxy-anisocarboxylic acids, according to the formula
HO-CH-,-CH_-CH- (CH„) __CH_-COOH 3 2 i 2 n 2HO-CH -, - CH_-CH- (CH „) __CH_-COOH 3 2 i 2 n 2
CH3 CH 3
Dabei nimmt n gewöhnlich Werte von 7 - 31 an. Repräsenta¬ tive Zusammensetzungen der Wollwachssäuren werden z.B. in "Parfümerie und Kosmetik", 59. Jahrgang, Nr.12/78, S.429, 430 sowie im "Lexikon der Hilfsstoffe für Pharmazie, Kos¬ metik und angrenzende Gebiete" von H.P.Fiedler, 1989, 3. Auflage, Editio Cantor Aulendorf, beschrieben. Zwar beschreibt EP-A-273 202, daß gewisse α-Hydroxycarbonsäuren als die Wirkung antimikrobiell wirksamer Agentien verstärkendes Agens bei der Therapie von Akne zu verwenden sind. Der Fachmann konnte aber nicht davon ausgehen, daß die erfindungsgemäße Verwendung von Wollwachssäuregemischen mit den in den Ansprüchen geschilderten Parametern selbst zu gegen unreine Haut bzw. gegen Propionibacterium acnes wirksamen Zubereitungen führen und erhebliche Vorteile gegenüber dem Stande der Technik aufweisen würde.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.
Rohwollwachssäuren sind für kosmetische Zwecke nicht ge¬ eignet, statt ihrer werden für gewöhnlich destillierte Wollwachssäuren eingesetzt. Dieser Umstand und entspre¬ chende Verfahren zur Raffinierung der Rohwollwachssäuren sind dem Fachmann bekannt.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.
Typischerweise bestehen Wollwachssäuren aus ca. 60 % ge¬ sättigten, unsubstituierten Carbonsäuren, ca. 30 % αr-Hy- droxycarbonsäuren und ca. 5 % Ω-Hydroxycarbonsäuren, wobei der Rest von ca. 5 % im wesentlichen von den anderen vorgenannten Carbonsäuretypen gebildet wird.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 .
Insbesondere zeichnen sich die erfindungsgemäßen Woll- wachssäuren vorteilhaft durch folgende kennzeichnende Parameter aus:In particular, the wool wax acids according to the invention are advantageously characterized by the following characteristic parameters:
Tropfpunkt 50 - 54° C Säurezahl 166 - 170 Verseifungszahl 175 - 190 OH - Zahl 60 - 80 Jodzahl 7 - 12Dropping point 50 - 54 ° C acid number 166 - 170 saponification number 175 - 190 OH number 60 - 80 iodine number 7 - 12
Zwar ist aus dem Aufsatz "Antimicrobial Factors in Wool Wax" (Australian Journal of Chemistry, 1971, 24, Seiten 153 ff.) bekannt, daß in manchen Wollwachschargen antimi- krobielle Faktoren enthalten sind. Ein Hinweis in Richtung der vorliegenden Erfindung findet sich am angegebenen Orte jedoch nicht.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.
Es wird angenommen, daß insbesondere die α-Hydroxycarbon- säuren einen wesentlichen Beitrag zur erfindungsgemäßen Wirkung leisten. Erfindungsgemäß ist daher auch die Ver¬ wendung von Gemischen ausIt 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-Hydroxycarbonsäuren, gemäß der FormelI) - α-hydroxycarboxylic acids, according to the formula
CH3-(CH2)nCHCH 3 - (CH 2 ) n CH
COOH und/oderCOOH and / or
α-Hydroxy-isocarbonsäuren, gemäß der Formelα-Hydroxy-isocarboxylic acids, according to the formula
OHOH
Figure imgf000007_0001
Figure imgf000007_0001
α-Hydroxy-anteisocarbonsäuren, gemäß der Formelα-Hydroxy-anteisocarboxylic acids, according to the formula
OH / CH-.-CH_-CH- (CH_) CHOH / CH -.- CH_-CH- (CH_) CH
CH3 COOH,CH3 COOH,
wobei n jeweils eine Zahl von 7 bis 31 darstellt,where n represents a number from 7 to 31,
als gegen unreine Haut, milde Formen der Akne bzw. Propionibacterium acnes wirksames Prinzip in kosmetischen Zubereitungen.as a principle effective in cosmetic preparations against impure skin, mild forms of acne or Propionibacterium acnes.
Besonders vorteilhaft im Sinne der vorliegenden Erfindung ist, cx-Hydroxycarbonsäuren zu verwenden, welche Clf--Körper darstellen, die also am α-Kohlenstoffatom eine verzweigte oder unverzweigte C-.H -Kette tragen. Vorteilhaft ist weiter, Wollwachssäuregemische zu verwen¬ den, in welchen der Gehalt an o;-Hydroxycarbonsäuren 20 - 30 Gew.-%, bezogen auf die Gesamtzusammensetzung beträgt.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.
Nach einer weiteren vorteilhaften Ausführungsform der vorliegenden Erfindung werden als Wollwachssäurekomponen¬ ten ein oder mehrereAccording to a further advantageous embodiment of the present invention, one or more are used as wool wax acid components
(a) gesättigte unsubstituierte Carbonsäuren, gemäß der Formel(a) saturated unsubstituted carboxylic acids, according to the formula
CH3- (CH2)nCH2-COOH , und/oderCH 3 - (CH 2 ) n CH 2 -COOH, and / or
(b) α-Hydroxycarbonsäuren, gemäß der Formel(b) α-Hydroxycarboxylic acids, according to the formula
CH--(CH2>nCHCH - (CH 2 > n CH
COOH, und/oderCOOH, and / or
(c) Ω-Hydroxycarbonsäuren, gemäß der Formel(c) Ω-hydroxycarboxylic acids, according to the formula
HO-CH2- (CH2)nCH2-COOH, und/oderHO-CH 2 - (CH 2 ) n CH 2 -COOH, and / or
(d) Isocarbonsäuren, gemäß der Formel(d) Isocarboxylic acids, according to the formula
CH ό--CιH- (CH Z„) XiCH Z-C00H,CH ό - CιH- (CH Z „) XiCH Z-C00H,
CH3 und/oderCH3 and / or
(e) α-Hydroxy-isocarbonsäuren, gemäß der Formel(e) α-hydroxy-isocarboxylic acids, according to the formula
Figure imgf000008_0001
Figure imgf000008_0001
(f) Ω-Hydroxy-isocarbonsäuren, gemäß der Formel HO-CH_ - CH- (CH„ ) CH-. -COOH(f) Ω-hydroxy-isocarboxylic acids, according to the formula HO-CH_ - CH- (CH „) CH-. -COOH
-5 1 Z Xi Z-5 1 Z Xi Z
CH-, und /oderCH-, and / or
(g) Anteisocarbonsäuren, gemäß der Formel(g) Anteisocarboxylic acids, according to the formula
CH3-CH2-CH- (CH2)nCH2-COOH,CH 3 -CH 2 -CH- (CH 2 ) n CH 2 -COOH,
CH3 und/oderCH3 and / or
(h) α.-Hydroxy-anteisocarbonsäuren, gemäß der Formel(h) α.-Hydroxy-anteisocarboxylic acids, according to the formula
/0H / 0 H
Figure imgf000009_0001
Figure imgf000009_0001
(i) Ω-Hydroxy-anteisocarbonsäuren, gemäß der Formel(i) Ω-hydroxy-anisocarboxylic acids, according to the formula
HO-CH,-CH Z_-C \H- (CH Z- XiCH z_-COOHHO-CH, -CH Z_-C \ H- (CH Z-XiCH z_-COOH
CH3 CH 3
wobei n Werte von 7 - 31 annimmt, in Kombination mit anderen in Kosmetika üblichen Wirkstoffen (Ersatzwirkstoffe), Hilfs-, Verschnitt- und/oder Zusatzstoffen eingesetzt.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.
Vorteilhaft liegen dann die Verschnittstoffe und/oder Er¬ satzwirkstoffe in einer Konzentration bis zu 50 Gew.-Tei¬ len vor, bevorzugt bis zu 35 Gew.-Teilen, bezogen auf 100 Gew.-Teile der Gesamtmenge, welche sich aus der Summe der Wollwachssäurekomponenten und diesen Ersatzwirkstoffen und/oder Verschnittstoffen zusammensetzt.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.
Die erfindungsgemäßen kosmetischen Zubereitungen gegen unreine Haut bzw. gegen milde Formen der Akne sind besonders vorteilhaft dadurch gekennzeichnet, daß die Wollwachssäuren bzw. die Wollwachssäurekomponenten in Konzentrationen von 0,05 - 10,00 Gew.-%, bevorzugt 0,1 - 5,0 Gew.-%, vorliegen, jeweils bezogen auf das Gesamtge¬ wicht der Zubereitungen.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.
Nach einer weiteren vorteilhaften Ausfuhrungsform der vorliegenden Erfindung werden ein oder mehrere Wollwachssäuren oder Wollwachssäurekomponenten, insbesondereAccording to a further advantageous embodiment of the present invention, one or more wool wax acids or wool wax acid components, in particular
I) - α-Hydroxycarbonsäuren, gemäß der FormelI) - α-hydroxycarboxylic acids, according to the formula
/OH CH3-(CH2)nCH / OH CH 3 - (CH 2 ) n CH
COOH und/oderCOOH and / or
α-Hydroxy-isocarbonsäuren, gemäß der Formelα-Hydroxy-isocarboxylic acids, according to the formula
Figure imgf000010_0001
H und/oder
Figure imgf000010_0001
H and / or
o;-Hydroxy-anteisocarbonsäuren, gemäß der Formelo; -Hydroxy-anteisocarboxylic acids, according to the formula
OHOH
//
CH 3-,-CH2-C,H- (CH2_)'„nCHCH 3 -, - CH2-C, H- (CH2 _) '„nCH
CH3 COOH,CH3 COOH,
wobei n jeweils eine Zahl von 7 bis 31 darstellt,where n represents a number from 7 to 31,
in Kombination mit anderen gegen unreine Haut oder milde Formen der Akne wirksamen oder das Wachstum von Propioni¬ bacterium acnes hemmend oder Propionibacterium acnes abtötend wirkenden Stoffen eingesetzt.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.
Die erfindungsgemäßen gegen unreine Haut bzw. milde Formen der Akne wirksamen Zubereitungen können in Form von mittels Pinseln oder Abstreifern oder Roll-on-Vorrichtungen auftragbaren flüssigen Zusammensetzungen, als Stifte und in Form von aus normalen Flaschen und Behältern auftragbaren W/O- oder O/W-Emulsionen, z.B. Cremes oder Lotionen. Weiterhin können die erfindungsgemäßen gegen unreine Haut wirksamen Zubereitungen vorteilhaft in Form von Gesichtswässern, Tinkturen oder Reinigungsformulierungen vorliegen.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.
Als übliche Trägerstoffe zur Herstellung der erfindungsgemäßen gegen unreine Haut bzw. milde Formen der Akne wirksamen Zubereitungen können neben Wasser, Ethanol und Isopropanol, Glycerin und Propylenglykol hautpflegende Fett- oder fettähnliche Stoffe, wie Ölsäuredecylester, Cetylalkohol, Cetylstearylalkohol und 2-Octyldodecanol, in den für solche Präparate üblichen Mengenverhältnissen eingesetzt werden sowie schleimbildende Stoffe und Verdickungsmittel, z.B. Hydroxyethyl- oder Hydroxypropylcellulose, Polyacrylsäure, Polyvinylpyrrolidon, daneben aber auch in kleinen Mengen cyclische Silikonöle (Polydimethylsiloxane) sowie flüssige Polymethyl- phenylsiloxane niedriger Viskosität.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.
Als Emulgatoren zur Herstellung der erfindungsgemäßen ge¬ gen unreine Haut bzw. gegen milde Formen der Akne wirksa¬ men Zubereitungen, welche vorteilhaft als flüssige Zube¬ reitungen auf die gewünschten Hautbereiche aufgetragen werden sollen, vorteilhaft mittels eines Wattebausches, und die in den Zubereitungen in geringer Menge, z.B. 2 bis 5 Gewichts.-%, bezogen auf die Gesamt-Zusammensetzung, verwendet werden können, haben sich nichtionogene Typen, wie Polyoxyethylen-Fettalkohol- ether, z.B. Cetostearylalkoholpolyethylenglykolether mit 12 bzw. 20 angelagerten Ethylenoxid-Einheiten pro Molekül, Cetostearylalkohol sowie Sorbitanester und Sorbitanester-Ethylenoxid-Verbindungen (z.B.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.
Sorbitanmonostearat und Po- lyoxyethylensorbitanmonostearat) und langkettige höhermo¬ lekulare wachsartige Polyglykolether als geeignet erwie¬ sen.Sorbitan monostearate and po- lyoxyethylene sorbitan monostearate) and long-chain higher molecular wax-like polyglycol ethers have been found to be suitable.
Zusätzlich zu den genannten Bestandteilen können den gegen unreine Haut bzw. milde Formen der Akne wirksamen Zubereitungen gemäß der Erfindung, deren pH-Wert vorzugsweise z.B. durch übliche Puffergemische auf 4,0 bis 9,0 insbesondere 5,0 bis 6,5, eingestellt wird, Parfüm, Farbstoffe, Antioxidantien (z.B. o.-Tocopherol und seine Derivate oder Butylhydroxytoluol (BHT = 2,6-Di-Tert.-butyl-4-methylphenol) in Mengen von 0,01 bis 0,03 %, bezogen auf die Gesamtzusammensetzung), Suspen¬ diermittel, Puffergemische oder andere übliche kosmetische Grundstoffe beigemischt werden.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.
Vorteilhaft wird der pH-Wert der erfindungsgemäßen gegen unreine Haut bzw. gegen milde Formen der Akne wirksamen Zubereitungen im schwach sauren bis neutralen Bereich eingestellt, bevorzugt von 4,0 - 7,0 , besonders bevorzugt von 5,0 - 6,5.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.
Die jeweils einzusetzenden Mengen an Trägerstoffen können in Abhängigkeit von der Art des jeweiligen Produktes vom Fachmann durch einfaches Ausprobieren leicht ermittelt werden.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.
Die Herstellung der erfindungsgemäßen Zubereitungen er¬ folgt abgesehen von speziellen Zubereitungen, die. in den Beispielen jeweils gesondert vermerkt sind, in üblicher Weise, zumeist durch einfaches Vermischen unter Rühren, gegebenenfalls unter leichter Erwärmung. Sie bietet keine Schwierigkeiten. Für Emulsionen werden Fettphase und die Wasserphase z.B. separat, gegebenenfalls unter Erwärmen hergestellt und dann emulgiert. Ansonsten sind die üblichen Maßregeln für das Zusammen¬ stellen von galenischen Formulierungen zu beachten, die dem Fachmann geläufig sind.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.
Es folgen vorteilhafte Ausführungsbeispiele der vorliegenden Erfindung. In den Beispielen bedeutet der Begriff "WWS" eine Wollwachssäurefraktion, welche gewonnen wurde aus Rohwollwachssäure durch Kurzwegdestillation im bei 10~ bar aus dem Destil¬ lationstemperaturintervall von 150 - 200° C. Der- Anteil an o*-Hydroxycarbonsäuren beträgt dabei ca. 22 - 27 % 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%
Beispiel 1example 1
Gel I, dünnflüssigGel I, thin
Gew. (a)Weight (a)
1,3-Butylenglycol 2,001,3-butylene glycol 2.00
Hydroxyethylcellulose 0,50Hydroxyethyl cellulose 0.50
(z.B. Tylose 4000, Hoechst)(e.g. Tylose 4000, Hoechst)
(b)(b)
Ethylalkohol 60,00Ethyl alcohol 60.00
PEG-40-Hydriertes Ricinusöl 2,00PEG-40 hydrogenated castor oil 2.00
WWS - 0,80WWS - 0.80
(c)(c)
Wasser ad 100,00Water ad 100.00
Die unter (a) genannten Bestandteile werden dispergiert, Wasser (c) wird zugegeben, bei Raumtemperatur quellen ge¬ lassen, eine Lösung der unter (b) genannten Bestandteile wird nach ca. 15 Minuten zugegeben. Die entstanden Mi¬ schung wird homogenisiert und kann abgefüllt werden. 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.
Beispiel 2Example 2
Wachsstift ICrayon I
Gew.- .Wt.
Hydriertes Ricinusöl 5,00Hydrogenated castor oil 5.00
Bienenwachs 6,00Beeswax 6.00
Ceresin (Hart-Ozokerit) 30,00Ceresin (hard ozokerite) 30.00
C 2 5-Alkohol-Benzoate "17,00C 2 5 alcohol benzoates " 17.00
WWS 0,90WWS 0.90
Octyldodecanol ad 100,00Octyldodecanol ad 100.00
Die Bestandteile werden bei ca. 75° C aufgeschmolzen, gut vermischt und in geeignete Formen gegossen.The ingredients are melted at approx. 75 ° C, mixed well and poured into suitable molds.
Beispiel 3Example 3
Wachsstift IICrayon II
"Gew.-% " % By weight
Hydriertes Ricinusöl 5,00Hydrogenated castor oil 5.00
Bienenwachs 6,00Beeswax 6.00
Ceresin (Hart-Ozokerit) 30,00 c 12_i5-Alkohol-Benzoate 17,00Ceresin (hard ozokerite) 30.00 c 12 _ i5 alcohol benzoate 17.00
WWS 1,45WWS 1.45
Octyldodecanol ad 100,00Octyldodecanol ad 100.00
Die Bestandteile werden bei ca. 75° C aufgeschmolzen, gut vermischt und in geeignete Formen gegossen. Beispiel 4The ingredients are melted at approx. 75 ° C, mixed well and poured into suitable molds. Example 4
Reinigungsemulsion ICleaning emulsion I
(a)(a)
Gew.-%% By weight
Tricetearethphosphat 0,30Triceteareth phosphate 0.30
Octyldodecanol 2,00Octyldodecanol 2.00
C12 15-Alkohol-Benzoate 2,00C 12 15 alcohol benzoates 2.00
WWS 0,50WWS 0.50
C10_30-Alkylacrylate 0,15C 10 _ 30 -alkyl 0.15
(b)(b)
Ethylalkohol 10,00Ethyl alcohol 10.00
(c)(c)
NaOH 0,05NaOH 0.05
Wasser ad 100,00Water ad 100.00
Die unter (a) und (c) genannten Bestandteile werden je¬ weils unter Rühren auf 75° C erwärmt. Sodann werden die Bestandteile (a) zu (c) gegeben. Die Mischung wird aufThe 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
35° C abgekühlt. Komponente (b) wird unter Rühren zur Mischung aus (a) und (c) gegeben. Cooled to 35 ° C. Component (b) is added to the mixture of (a) and (c) with stirring.
Beispiel 5Example 5
Hautreinigungs-Gel ISkin cleansing gel I
Gew.-% (a)% By weight (a)
1,3-Butylenglycol 2,001,3-butylene glycol 2.00
Hydroxyethylcellulose 0,50Hydroxyethyl cellulose 0.50
(z.B. Tylose 4000, Hoechst)(e.g. Tylose 4000, Hoechst)
(b)(b)
Ethylalkohol 60,00Ethyl alcohol 60.00
PEG-40-Hydriertes Ricinusöl 2,00PEG-40 hydrogenated castor oil 2.00
WWS 1,30WWS 1.30
(c)(c)
Wasser ad 100,00Water ad 100.00
Die unter (a) genannten Bestandteile werden dispergiert, Wasser (c) wird zugegeben, bei Raumtemperatur quellen ge¬ lassen, eine Lösung der unter (b) genannten Bestandteile wird nach ca. 15 Minuten zugegeben. Die entstanden Mi¬ schung wird homogenisiert und kann abgefüllt werden. 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.
Beispiel 6Example 6
Gesichtswasser IFacial Toner I
Gew.--Weight
Ethanol 10,00Ethanol 10.00
WWS 1,00WWS 1.00
Wasser ad 100,00 Water ad 100.00
Versuch :Attempt :
Der nachfolgende Versuch soll die Wirksamkeit der erfin¬ dungsgemäßen Monocarbonsäureester der Wollwachssäuren bzw. Präparate, solche Ester enthaltend, demonstrieren.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.
Gesichtswässer entsprechend den Formulierungen gemäß den Beispielen 6 und 7 wurden auf ihre antimikrobielle Wirk¬ samkeit getestet. Als Kontrolle wurde eine Lösung von 10 % Ethanol und 90 % Wasser verwendet.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.
Als Enthemmungsmedium wurde ein Gemisch aus AC-Medium, 3% Tween, 0,3% Lecithin, 0,1 % Histidin verwendet.A mixture of AC medium, 3% tween, 0.3% lecithin, 0.1% histidine was used as the disinhibiting medium.
Suspensionstest:Suspension test:
Zur Durchführung eines Suspensionstests wurden Propioni- bakterien unter aeroben Bedingungen bis zu einer Keimzahl von 10 Keimen/ml angezogen. Anschließend wurde mit der so erhaltenen Keimsuspension ein Suspensionstest über einen Zeitraum von 1 Stunde durchgeführt. Anschließend wurden Aliquots der Inkubationsansätze mit der zehnfachen Menge Enthemmungsmedium verdünnt und auf festen Nährmedien ausplattiert. Nach siebentägiger Inkubation unter anaeroben Bedingungen wurde der Test numerisch ausgewertet.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.
Ergebnisse:Results:
Sowohl die Formulierung gemäß Beispiel 6 als auch die Formulierung gemäß Beispiel 7 reduzierten die Keimzahl in signifikanter Weise. Die Kontrollformulierung bewirkte keine Keimzahlreduzierung. 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

PatentansprücheClaims
1. Verwendung von natürlichen Wollwachssäuregemischen oder von durch Destillation aufbereiteten Woll¬ wachssäuregemischen als wirksames Prinzip gegen unreine Haut, milde Formen der Akne sowie gegen Propionibacterium acnes.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. Verwendung von natürlichen Wollwachssäuregemischen oder durch Destillation aufbereiteten Wollwachssäuregemi¬ schen zur Herstellung von gegen unreine Haut, milde Formen der Akne bzw. gegen Propionibacterium acnes wirksamen kosmetischen oder dermatologischen Zube¬ reitungen.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. Verwendung nach Anspruch 1 oder 2, dadurch gekennzeichnet, daß das Wollwachssäuϊregemisch oder die Wollwachssäuregemische in einem geeigneten kosmetischen oder dermatologischen Träger vorliegen.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. Verwendung nach Anspruch 1 oder 2, dadurch gekennzeichnet, daß die Wollwachssäuregemische aus ca. 60 % gesättigten, unsubstituierten Carbonsäuren, aus ca. 30 % α-Hydroxycarbonsäuren und ca. 5 % Ω-Hydroxycarbonsäuren bestehen, wobei der Rest von ca. 5 % im wesentlichen aus anderen Carbonsäuren gebildet wird.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. Verwendung nach Anspruch 1 oder 2, wobei das Wollwachssäuregemisch oder die Wollwachssäuregemische gekennzeichnet sind durch folgende Parameter: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:
Tropfpunkt 50 - 54° C Säurezahl 166 - 170 Verseifungszahl 175 - 190 OH - Zahl 60 - 80 Jodzahl 7 - 12 7. Verwendung nach Anspruch 1 oder 2, dadurch gekennzeichnet, daß Wollwachssäuregemische gewählt werden, in welchen der Gehalt an α-Hydroxycarbonsäuren 20Dropping 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 Gew.-%, bezogen auf die GesamtZusammensetzung beträgt.30 wt .-%, based on the total composition.
8. Verwendung nach Anspruch 1, dadurch gekennzeichnet, daß als Wollwachssaurekomponente c-Hydroxycarbonsäuren gewählt werden, welche Clg-Körper darstellen, die also am oj-Kohlenstoffatom eine verzweigte oder unverzweigte C14H2g-Kette tragen. 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.
PCT/DE1994/000979 1993-09-01 1994-08-23 Compositions against skin impurities and mild forms of acne containing lanolinic acid or lanolinic acid components as active substance WO1995006457A1 (en)

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