DE10307387A1 - New (omega-1)-hydroxy fatty acid esters useful for preparing cosmetic, pharmaceutical or dermatological compositions, especially anti-acne compositions - Google Patents

Abstract

(omega -1)-Hydroxy fatty acid esters (I) are new. (omega -1)-Hydroxy fatty acid esters of formula CH 3-CH(OH)-(CH 2) n-C(O)OR (I) are new. n : 7-23; and R : an aromatic alcohol residue. An independent claim is also included for an anti-acne composition containing (I). ACTIVITY : Antiseborrheic; Dermatological; Antibacterial; Antiinflammatory. Retinyl (omega -1)-hydroxymyristate (Ia) had MIC values of 0.625 mg/ml against Staphylococcus epidermidis and Propionibacterium acnes and 1.25 mg/ml against Staphylococcus aureus. MECHANISM OF ACTION : None given.

Description

The invention is based on the Field of active pharmaceutical ingredients and relates to new hydroxy fatty acid esters, Anti-acne agents based on these esters and their use for Manufacture of cosmetic, pharmaceutical and dermatological Preparations.

State of technology

The term acne means the Specialist a skin condition that is characterized by inflammatory and not flammable nodule distinction and which can lead to the formation of pustules, abscesses and finally scars. Although the causes are different, acne can ultimately be resolved Return blocked hair follicles (comedones). In addition to a hormonal conditional blockage of the hair follicle mouths by body fat, There is a major cause for the development of acne the development of tissue damaging free fatty acids and enzymes by bacteria, such as Propionibacterium acnes.

A whole series of active ingredients are known from the prior art, which can be used to combat acne with more or less great success. For example, in the Spanish patent ES 9702410 B1 (Vinyals) proposed the use of the zinc salt of glycyrrhetic acid against acne. From the two European patent specifications EP 0336880 B1 and EP 0443413 B1 (Schering) is known to use azelaic acid, its salts and esters for the same purpose. In international patent application WO 98/020834 A2 Tamarkin proposes esters of dicarboxylic acids with "keratolytically active" alcohols to combat dermatological diseases. Other active ingredients which are essentially effective against excessive sebum production include, for example, benzoyl peroxide, hexaclorophene, dodecylbenzenesulfonic acid, 2,2 ', 2'-nitrilotriethanol salts, dexpanthenol or resorcinol, but none of these substances on their own have a satisfactory effect against the germs that are significantly involved in the development of acne, especially acne vulgaris.

The object of the invention is therefore consisted of making new active ingredients available, on the one hand across from improved the bacteria involved in the development of acne Have effect and also preferably through the healing process Support anti-inflammatory properties.

description the invention

in der n für Zahlen von 7 bis 23, vorzugsweise 10 bis 20 und R für den Rest eines aromatischen Alkohols steht, wobei sich dieser Alkohol vorzugsweise ableitet von Benzylalkohol, Salicylalkohol, Sterol, Tocopherol, Retinol sowie deren Gemischen.The invention relates to (ω-1) -hydroxy fatty acid esters according to formula (I),

in which n stands for numbers from 7 to 23, preferably 10 to 20 and R stands for the remainder of an aromatic alcohol, this alcohol preferably being derived from benzyl alcohol, salicyl alcohol, sterol, tocopherol, retinol and mixtures thereof.

Surprisingly it has been found that the aromatic esters of (ω-1) hydroxy fatty acids, in particular the (ω-1) hydroxy fatty acid salicylates and retinates have a particularly high bactericidal activity and have an anti-inflammatory effect at the same time, i.e. wound healing accelerate. This could be caused by across from the acid or their salts facilitated transport of the active ingredients through the Lipid barrier of the stratum corneum, whereby the acidity then passes through enzymatic cleavage in the upper layers of the skin, i.e. right in front the place of inflammation is released. The invention includes the finding that also the mixtures of free fatty acids and aromatic alcohol, especially when it is salicylic alcohol or retinol, show a synergistic anti-acne effect.

Anti-acne agents

Another object of the present invention relates to anti-acne agents that contain an effective content of the new (ω-1) -hydroxy fatty acid esters. The (ω-1) -hydroxy fatty acids on which the esters are based represent constituents of beeswax and can be used, for example, according to the Deut patent application DE 198 32 889 A1 (Beiersdorf) can be isolated and cleaned. The corresponding esters can then be prepared in a manner known per se. In this context, for example, the British patent application GB-A 2 285805 (Marigen), which describes in detail the production of steroid esters and their use against skin cancer.

• – Glyzyrrhetinsäure und deren Salzen, Estern oder Extrakten der Pflanze Glyzyrrhiza glabra,
• – Azelainsäure, deren Salzen und Estern,
• – Salicylsäure, deren Salzen und Estern,
• – Benzoylperoxid,
• – Vitamin B6
• – Vitamin E phosphat (z.B. Vitol^® IEP) sowie
• – Pflanzenextrakten.

In a preferred embodiment of the invention, the agents contain further active ingredients which are selected from the group formed by

• Glycyrrhetic acid and its salts, esters or extracts of the plant Glyzyrrhiza glabra,
• - azelaic acid, its salts and esters,
• - salicylic acid, its salts and esters,
• - benzoyl peroxide,
• - Vitamin B6
• - Vitamin E phosphate (e.g. Vitol ^® IEP) as well
• - plant extracts.

Examples of derivatives of glycyrrhetic acid, salicylic acid or azelaic acid are their alkali, alkaline earth, ammonium, alkylammonium, alkanolammonium, Glucammonium and zinc salts and (if claimed) their esters with linear or branched aliphatic alcohols with 1 to 18 carbon atoms as well as the full or partial esters of the acids Polyols with 2 to 15 carbon atoms and at least 2 hydroxyl groups in question.

Typical examples are the sodium, Potassium, ammonium, triethanolammonium, glucammonium and zinc salts glycyrrhetic acid, azelaic acid and salicylic acid, the esters of salicylic acid or azelaic acid with methanol, ethanol, the isomeric propanols and butanols as well Capronic alcohol, caprylic alcohol, 2-ethylhexyl alcohol, capric alcohol, Lauryl alcohol, isotridecyl alcohol, myristyl alcohol, cetyl alcohol, Palmoleyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, Elaidyl alcohol, petroselinyl alcohol, linolyl alcohol, linolenyl alcohol, Elaeostearyl alcohol, arachyl alcohol, gadoleyl alcohol, behenyl alcohol, Erucyl alcohol and brassidyl alcohol and their mixtures. Further Examples are the full or partial esters of salicylic acid or azelaic acid glycerol; Alkylene glycols, such as, for example, ethylene glycol, diethylene glycol, Propylene glycol, butylene glycol, hexylene glycol and polyethylene glycols with an average molecular weight of 100 to 1,000 Dalton; technical oligoglycerol mixtures with a degree of self-condensation from 1.5 to 10 such as technical diglycerin mixtures with one Diglycerol content of 40 to 50% by weight; Me thyol compounds, like in particular trimethylolethane, trimethylolpropane, trimethylolbutane, Pentaerythritol and dipentaerythritol; Lower alkyl glucosides, in particular those with 1 to 8 carbons in the alkyl radical, such as Methyl and butyl glucoside; Sugar alcohols with 5 to 12 carbon atoms, such as sorbitol or mannitol; Sugars with 5 to 12 carbon atoms, such as glucose or sucrose; Amino sugars such as glucamine; or dialcohol amines, such as diethanolamine or 2-amino-1,3-propanediol.

Typical examples of suitable ones Plant extracts are the active substances of the following plants Aesculus hippocastanum (Horse chestnut), Argania spinosa, Babtista tinctoria (wild indigo), Cantella asiatica, Camelilla sinensis (green tea), Chamonella recutita (Chamomile), ginkgo biloba (ginkgo), oleo europea (olive), lychee chinensis (Litchi), Melissa officinalis (lemon balm), Panax ginseng (Ginseng), Passiflora incarnata (passion flower), Prunus dulcis (sweet almond), Pterocarpus marsupium, Ruscus aculeatus, Trifolium pratense (Red Clover), Uva ursi (bear grape), Vaccinium myrtillus (blueberry), Vigna acontifolia, and Vitis vinifera (wild Wine).

The final preparations can hydroxy fatty acid esters and contain the other active ingredients in a weight ratio of 90:10 to 10:90, being considerable Synergies in the range of 75: 25 to 25: 75 and especially 60 : 40 to 40: 60.

microcapsules and pro-liposomes

In a special embodiment of the present invention the active ingredients are in the form of microcapsules or pro-liposms. The term "microcapsule" is used by a person skilled in the art spherical Aggregates with a diameter in the range of about 0.0001 to about 5 mm understood the at least one solid or liquid core included, which is enclosed by at least one continuous shell. More precisely, they are finely dispersed with film-forming polymers liquid or solid phases, in the production of which the polymers change Emulsification and coacervation or interfacial polymerization on the be enveloped Knock down material. Another process involves melting Waxes recorded in a matrix ("microsponge"), which act as microparticles additionally coated with film-forming polymers could be. Leave the microscopic capsules, also called nanocapsules drying like powder. In addition to mononuclear microcapsules multinuclear aggregates, also called microspheres, known, the two or contain more cores distributed in the continuous shell material. Single or multi-core Microcapsules can also from an additional second, third etc.

shell be enclosed. The case can from natural, semi-synthetic or synthetic materials exist. Wrapping materials, of course are for example gum arabic, agar agar, agarose, maltodextrins, alginic acid or their salts, e.g. Sodium or calcium alginate, fats and fatty acids, cetyl alcohol, collagen, Chitosan, lecithins, gelatin, albumin, shellac, polysaccharides, like strength or dextran, polypeptides, protein hydrolyzates, sucrose and waxes. Semi-synthetic envelope materials include chemically modified celluloses, in particular Cellulose esters and ethers, e.g. Cellulose acetate, ethyl cellulose, hydroxypropyl cellulose, Hydroxypropylmethyl cellulose and carboxymethyl cellulose, as well as starch derivatives, in particular starch and esters. Synthetic cover materials are, for example, polymers such as polyacrylates, polyamides, polyvinyl alcohol or polyvinyl pyrrolidone.

Examples of prior art microcapsules Technology are the following commercial products (indicated in parentheses each the shell material) : Hallcrest Microcapsules (gelatin, gum arabic), Coletica Thalaspheres (maritime collagen), Lipotec millicapsules (alginic acid, agar-agar), Induchem Unispheres (lactose, microcrystalline cellulose, hydroxypropylmethyl cellulose); Unicerin C30 (lactose, microcrystalline cellulose, hydroxypropylmethyl cellulose), Kobo Glycospheres (modified starch, fatty acid esters, phospholipids), soft spheres (modified agar) and Kuhs Probiol Nanospheres (phospholipids) as well as Primaspheres and Primasponges (Chitosan, Alginate) and Primasys (Phospholipids).

Chitosan microcapsules and process for their manufacture are the subject of earlier patent applications by Patent applicant [WO 01/01926, WO 01/01927, WO 01/01928, WO 01/01929].

• (a1) aus Gelbildnern, Chitosanen und den Wirkstoffen eine Matrix zubereitet,
• (a2) gegebenenfalls die Matrix in einer Ölphase dispergiert,
• (a3) die gegebenenfalls dispergierte Matrix mit wässrigen Lösungen anionischer Polymere behandelt und gegebenenfalls dabei die Ölphase entfernt. oder
• (b1) aus Gelbildnern, anionischen Polymeren und den Wirkstoffen eine Matrix zubereitet,
• (b2) gegebenenfalls die Matrix in einer Ölphase dispergiert,
• (b3) die gegebenenfalls dispergierte Matrix mit wässrigen Chitosanlösungen behandelt und gegebenenfalls dabei die Ölphase entfernt.

oder

• (c1) wässrige Zubereitungen der Wirkstoffe mit Ölkörpern in Gegenwart von Emulgatoren zu O/W-Emulsionen verarbeitet,
• (c2) die so erhaltenen Emulsionen mit wässrigen Lösungen anionischer Polymere behandelt,
• (c3) die so erhaltene Matrix mit wässrigen Chitosanlösungen in Kontakt bringt und
• (c4) die so erhaltenen Verkapselungsprodukte von der wässrigen Phase abtrennt.

To produce such microcapsules with average diameters in the range from 0.0001 to 5, preferably 0.001 to 0.5 and in particular 0.005 to 0.1 mm, consisting of an envelope membrane and a matrix containing the active ingredients, the procedure is preferably such that

• (a1) a matrix is prepared from gel formers, chitosans and the active ingredients,
• (a2) optionally dispersing the matrix in an oil phase,
• (a3) the optionally dispersed matrix is treated with aqueous solutions of anionic polymers and, if appropriate, the oil phase is removed in the process. or
• (b1) a matrix is prepared from gel formers, anionic polymers and the active ingredients,
• (b2) optionally dispersing the matrix in an oil phase,
• (b3) the optionally dispersed matrix is treated with aqueous chitosan solutions and, if appropriate, the oil phase is removed in the process.

or

• (c1) processed aqueous preparations of the active compounds with oil bodies in the presence of emulsifiers to form O / W emulsions,
• (c2) treating the emulsions thus obtained with aqueous solutions of anionic polymers,
• (c3) brings the matrix thus obtained into contact with aqueous chitosan solutions and
• (c4) the encapsulation products thus obtained are separated from the aqueous phase.

gelling agent

For the purposes of the invention are considered Gelling agents are preferably considered such substances that the Show property in watery solution at temperatures above 40 ° C To form gels. Typical examples are heteropolysaccharides and proteins. Preferred thermogelating heteropolysaccharides are Agaroses in question, which in the form of red algae Agar also together with up to 30% by weight of non-gel-forming Agaropectins can be present. The main constituent of the agaroses are linear polysaccharides from D-galactose and 3,6-anhydro-L-galactose, which are alternately β-1,3- and β-1,4-glycosidic connected are. The heteropolysaccharides preferably have a molecular weight in the range of 110,000 to 160,000 and are both color and tasteless. Pectins, xanthans (also xanthan Gum) and their mixtures in question. They are still such types preferred, which still form gels in 1% by weight aqueous solution, which do not below 80 ° C melt and solidify again above 40 ° C. From the The group of thermogelating proteins is exemplary Called gelatin types.

chitosan

Chitosans are biopolymers and belong to the group of hydrocolloids. From a chemical point of view, these are partially deacetylated chitins of different molecular weights that contain the following - idealized - monomer unit:

Unlike most hydrocolloids, that are negatively charged in the range of biological pH values Chitosans represent cationic biopolymers under these conditions. The positively charged chitosans can be charged with oppositely charged ones surfaces interact and are therefore used in cosmetic hair and personal care products as well as pharmaceutical preparations. To make the Chitosane is believed to be chitin, preferably the remains of the shell Crustaceans that are considered cheap raw materials in large quantities to disposal stand. The chitin is produced in a process that was first developed by Hackmann et al. has been described, usually first by Addition of bases deproteinized, demineralized by adding mineral acids and finally deacetylated by adding strong bases, the molecular weights over a wide range can be distributed. Such types are preferably used as the average Molecular weight from 10,000 to 500,000 or 800,000 to 1,200,000 Dalton and / or a Brookfield viscosity (1 wt .-% in glycolic acid) below 5000 mPas, a degree of deacetylation in the range of Have 80 to 88% and an ash content of less than 0.3 wt .-%. For reasons the better solubility in water Chitosans are usually preferred in the form of their salts used as glycolates.

oil phase

The matrix can optionally be dispersed in an oil phase before the membrane is formed. Suitable oils for this purpose are, for example, Guerbet alcohols based on fatty alcohols having 6 to 18, preferably 8 to 10 carbon atoms, esters of linear C ₆ -C ₂₂ fatty acids with linear C ₆ -C ₂₂ fatty alcohols, esters of branched C ₆ -C ₁₃ carboxylic acids with linear C ₆ -C ₂₂ -fatty alcohols, such as myristyl myristate, myristyl palmitate, myristyl stearate, Myristylisostearat, myristyl, Myristylbehenat, Myristylerucat, cetyl myristate, cetyl palmitate, cetyl stearate, Cetylisostearat, cetyl oleate, cetyl behenate, Cetylerucat, Stearylmyristat, stearyl palmitate, stearyl stearate, Stearylisostearat , stearyl oleate, stearyl behenate, Stearylerucat, isostearyl, isostearyl palmitate, Isostearylstearat, isostearyl isostearate, Isostearyloleat, isostearyl behenate, Isostearyloleat, oleyl myristate, oleyl palmitate, oleyl stearate, oleyl isostearate, oleyl oleate, Oleylbehenat, oleyl erucate, behenyl myristate, behenyl palmitate, behenyl, Behenylisostearat, behenyl oleate, behenyl behenate, Behenyleru cat, erucyl myristate, erucyl palmitate, erucyl stearate, erucyl isostearate, erucyl oleate, erucyl behenate and erucylerucate. In addition, esters of linear C ₆ -C ₂₂ fatty acids with branched alcohols, in particular 2-ethylhexanol, esters of hydroxycarboxylic acids with linear or branched C ₆ -C ₂₂ fatty alcohols, in particular dioctyl malates, esters of linear and / or branched fatty acids are also suitable polyhydric alcohols (such as propylene glycol, dimer diol or trimer triol) and / or Guerbet alcohols, triglycerides based on C ₆ -C ₁₀ fatty acids, liquid mono- / di- / triglyceride mixtures based on C ₆ -C ₁₈ fatty acids, esters of C ₆ -C ₂₂ fatty alcohols and / or Guerbet alcohols with aromatic carboxylic acids, in particular benzoic acid, esters of C ₂ -C ₁₂ dicarboxylic acids with linear or branched alcohols with 1 to 22 carbon atoms or polyols with 2 to 10 carbon atoms and 2 to 6 hydroxyl groups, vegetable oils, branched primary alcohols, substituted cyclohexanes, linear and branched C ₆ -C ₂₂ fatty alcohol carbonates, Guerbet carbonates, esters of benzoic acid with l Inearic and / or branched C ₆ -C ₂₂ alcohols (e.g. Finsolv ^® TN), linear or branched, symmetrical or asymmetrical dialkyl ethers with 6 to 22 carbon atoms per alkyl group, ring opening products of epoxidized fatty acid esters with polyols, silicone oils and / or aliphatic or naphthenic Hydrocarbons, such as squalane, squalene or dialkylcyclohexanes.

anionic polymers

The anionic polymers have the task of forming membranes with the chitosans. Salts of alginic acid are preferably suitable for this purpose. Alginic acid is a mixture of carboxyl-containing polysaccharides with the following idealized monomer unit:

The average molecular weight of alginic acids or the alginate is in the range 5 from 150,000 to 250,000. there are as salts of alginic acid both their complete as well as to understand their partial neutralization products, in particular the alkali salts and among these preferably the sodium alginate ("Algin") and the ammonium and alkaline earth salts. Mixed alginates, such as e.g. Sodium / magnesium or sodium / calcium alginates. In an alternative embodiment the invention come for this purpose, however, also anionic chitosan derivatives, e.g. carboxylation and especially succinylation products in question. Alternatively come also poly (meth) acrylates with average molecular weights in the range of 5,000 to 50,000 daltons as well as the various carboxymethyl celluloses in question. Instead of the anionic polymers for the formation of the envelope membrane also anionic surfactants or low molecular weight inorganic salts, such as pyrophosphates.

emulsifiers

• – Anlagerungsprodukte von 2 bis 30 Mol Ethylenoxid und/oder 0 bis 5 Mol Propylenoxid an lineare Fettalkohole mit 8 bis 22 C-Atomen, an Fettsäuren mit 12 bis 22 C-Atomen, an Alkylphenole mit 8 bis 15 C-Atomen in der Alkylgruppe sowie Alkylamine mit 8 bis 22 Kohlenstoffatomen im Alkylrest;
• – Alkyl- und/oder Alkenyloligoglykoside mit 8 bis 22 Kohlenstoffatomen im Alk(en)ylrest und deren ethoxylierte Analoga;
• – Anlagerungsprodukte von 1 bis 15 Mol Ethylenoxid an Ricinusöl und/oder gehärtetes Ricinusöl;
• – Anlagerungsprodukte von 15 bis 60 Mol Ethylenoxid an Ricinusöl und/oder gehärtetes Ricinusöl;
• – Partialester von Glycerin und/oder Sorbitan mit ungesättigten, linearen oder gesättigten, verzweigten Fettsäuren mit 12 bis 22 Kohlenstoffatomen und/oder Hydroxycarbonsäuren mit 3 bis 18 Kohlenstoffatomen sowie deren Addukte mit 1 bis 30 Mol Ethylenoxid;
• – Partialester von Polyglycerin (durchschnittlicher Eigenkondensationsgrad 2 bis 8), Polyethylenglycol (Molekulargewicht 400 bis 5000), Trimethylolpropan, Pentaerythrit, Zuckeralkoholen (z.B. Sorbit), Alkylglucosiden (z.B. Methylglucosid, Butylglucosid, Laurylglucosid) sowie Polyglucosiden (z.B. Cellulose) mit gesättigten und/oder ungesättigten, linearen oder verzweigten Fettsäuren mit 12 bis 22 Kohlenstoffatomen und/oder Hydroxycarbonsäuren mit 3 bis 18 Kohlenstoffatomen sowie deren Addukte mit 1 bis 30 Mol Ethylenoxid;
• – Mischester aus Pentaerythrit, Fettsäuren, Citronensäure und Fettalkohol und/oder Mischester von Fettsäuren mit 6 bis 22 Kohlenstoffatomen, Methylglucose und Polyolen, vorzugsweise Glycerin oder Polyglycerin.
• – Mono-, Di- und Trialkylphosphate sowie Mono-, Di- und/oder Tri-PEG-alkylphosphate und deren Salze;
• – Wollwachsalkohole;
• – Polysiloxan-Polyalkyl-Polyether-Copolymere bzw. entsprechende Derivate;
• – Block-Copolymere z.B. Polyethylenglycol-30 Dipolyhydroxystearate;
• – Polymeremulgatoren, z.B. Pemulen-Typen (TR-1,TR-2) von Goodrich;
• – Polyalkylenglycole sowie
• – Glycerincarbonat.
• – Ethylenoxidanlagerungsprodukte Die Anlagerungsprodukte von Ethylenoxid und/oder von Propylenoxid an Fettalkohole, Fettsäuren, Alkylphenole oder an Ricinusöl stellen bekannte, im Handel erhältliche Produkte dar. Es handelt sich dabei um Homologengemische, deren mittlerer Alkoxylierungsgrad dem Verhältnis der Stoffmengen von Ethylenoxid und/ oder Propylenoxid und Substrat, mit denen die Anlagerungsreaktion durchgeführt wird, entspricht. C_{12/ 18}-Fettsäuremono- und -diester von Anlagerungsprodukten von Ethylenoxid an Glycerin sind als Rückfettungsmittel für kosmetische Zubereitungen bekannt.
• – Alkyl- und/oder Alkenylogoglykoside Alkyl- und/oder Alkenyloligoglycoside, ihre Herstellung und ihre Verwendung sind aus dem Stand der Technik bekannt. Ihre Herstellung erfolgt insbesondere durch Umsetzung von Glucose oder Oligosacchariden mit primären Alkoholen mit 8 bis 18 Kohlenstoffatomen. Bezüglich des Glycosidrestes gilt, daß sowohl Monoglycoside, bei denen ein cyclischer Zuckerrest glycosidisch an den Fettalkohol gebunden ist, als auch oligomere Glycoside mit einem Oligomerisationsgrad bis vorzugsweise etwa 8 geeignet sind. Der Oligomerisierungsgrad ist dabei ein statistischer Mittelwert, dem eine für solche technischen Produkte übliche Homologenverteilung zugrunde liegt.
• – Partialglyceride Typische Beispiele für geeignete Partialglyceride sind Hydroxystearinsäuremonoglycerid, Hydroxystearinsäurediglycerid, Isostearinsäuremonoglycerid, Isostearinsäurediglycerid, Ölsäuremonoglycerid, Ölsäurediglycerid, Ricinolsäuremoglycerid, Ricinolsäure diglycerid, Linolsäuremonoglycerid, Linolsäurediglycerid, Linolensäuremonoglycerid, Linolensäurediglycerid, Erucasäuremonoglycerid, Erucasäurediglycerid, Weinsäuremonoglycerid, Weinsäurediglycerid, Citronensäuremonoglycerid, Citronendiglycerid, Äpfelsäuremonoglycerid, Äpfelsäurediglycerid sowie deren technische Gemische, die untergeordnet aus dem Herstellungsprozeß noch geringe Mengen an Triglycerid enthalten können. Ebenfalls geeignet sind Anlagerungsprodukte von 1 bis 30, vorzugsweise 5 bis 10 Mol Ethylenoxid an die genannten Partialglyceride.
• – Sorbitanester Als Sorbitanester kommen Sorbitanmonoisostearat, Sorbitansesquiisostearat, Sorbitandiisostearat, Sorbitantriisostearat, Sorbitanmonooleat, Sorbitansesquioleat, Sorbitandioleat, Sorbitantrioleat, Sorbitanmonoerucat, Sorbitansesquierucat, Sorbitandierucat, Sorbitantrierucat, Sorbitanmonoricinoleat, Sorbitansesquiricinoleat, Sorbitandiricinoleat, Sorbitantriricinoleat, Sorbitanmonohydroxystearat, Sorbitansesquihydroxystearat, Sorbitandihydroxystearat, Sorbitantrihydroxystearat, Sorbitanmonotartrat, Sorbitansesquitartrat, Sorbitanditartrat, Sorbitantritartrat, Sorbitanmonocitrat, Sorbitansesquicitrat, Sorbitandicitrat, Sorbitantricitrat, Sorbitanmonomaleat, Sorbitansesquimaleat, Sorbitandimaleat, Sorbitantrimaleat sowie deren technische Gemische. Ebenfalls geeignet sind Anlagerungsprodukte von 1 bis 30, vorzugsweise 5 bis 10 Mol Ethylenoxid an die genannten Sorbitanester.
• – Polyglycerinester Typische Beispiele für geeignete Polyglycerinester sind Polyglyceryl-2 Dipolyhydroxystearate (Dehymuls^® PGPH), Polyglycerin-3-Diisostearate (Lameform^® TGI), Polyglyceryl-4 Isostearate (Isolan^® GI 34), Polyglyceryl-3 Oleate, Diisostearoyl Polyglyceryl-3 Diisostearate (Isolan^® PDI), Polyglyceryl-3 Methylglucose Distearate (Tego Care^® 450), Polyglyceryl-3 Beeswax (Cera Bellina^®), Polyglyceryl-4 Caprate (Polyglycerol Caprate T2010/90), Polyglyceryl-3 Cetyl Ether (Chimexane^® NL), Polyglyceryl-3 Distearate (Cremophor^® GS 32) und Polyglyceryl Polyricinoleate (Admul^® WOL 1403) Polyglyceryl Dimerate Isostearate sowie deren Gemische. Beispiele für weitere geeignete Polyolester sind die gegebenenfalls mit 1 bis 30 Mol Ethylenoxid umgesetzten Mono-, Di- und Triester von Trimethylolpropan oder Pentaerythrit mit Laurinsäure, Kokosfettsäure, Talgfettsäure, Palmitinsäure, Stearinsäure, Ölsäure, Behensäure und dergleichen.
• – Anionische Emulgatoren Typische anionische Emulgatoren sind aliphatische Fettsäuren mit 12 bis 22 Kohlenstoffatomen, wie beispielsweise Palmitinsäure, Stearinsäure oder Behensäure, sowie Dicarbonsäuren mit 12 bis 22 Kohlenstoffatomen, wie beispielsweise Azelainsäure oder Sebacinsäure.
• – Amphotere und kationische Emulgatoren Weiterhin können als Emulgatoren zwitterionische Tenside verwendet werden. Als zwitterionische Tenside werden solche oberflächenaktiven Verbindungen bezeichnet, die im Molekül mindestens eine quartäre Ammoniumgruppe und mindestens eine Carboxylat- und eine Sulfonatgruppe tragen. Besonders geeignete zwitterionische Tenside sind die sogenannten Betaine wie die N-Alkyl-N,N-dimethylammoniumglycinate, beispielsweise das Kokosalkyldimethylammoniumglycinat, N-Acylaminopropyl-N,N-dimethylammoniumglycinate, beispielsweise das Kokosacylaminopropyldimethylammoniumglycinat, und 2-Alkyl-3-carboxylmethyl-3-hydroxyethylimidazoline mit jeweils 8 bis 18 C-Atomen in der Alkyl- oder Acylgruppe sowie das Kokosacylaminoethylhydroxyethylcarboxymethylglycinat. Besonders bevorzugt ist das unter der CTFA-Bezeichnung Cocamidopropyl Betaine bekannte Fettsäureamid-Derivat. Ebenfalls geeignete Emulgatoren sind ampholytische Tenside. Unter ampholytischen Tensiden werden solche oberflächenaktiven Verbindungen verstanden, die außer einer C_8/18-Alkyl- oder Acylgruppe im Molekül mindestens eine freie Aminogruppe und mindestens eine -COOH- oder -SO₃H-Gruppe enthalten und zur Ausbildung innerer Salze befähigt sind. Beispiele für geeignete ampholytische Tenside sind N-Alkylglycine, N-Alkylpropionsäuren, N-Alkylaminobuttersäuren, N-Alkyliminodipropionsäuren, N-Hydroxyethyl-N-alkylamidopropylglycine, N-Alkyltaurine, N-Alkylsarcosine, 2-Akylaminopropionsäuren und Alkylaminoessigsäuren mit jeweils etwa 8 bis 18 C-Atomen in der Alkylgruppe.. Besonders bevorzugte ampholytische Tenside sind das N-Kokosalkylaminopropionat, das Kokosacylaminoethylaminopropionat und das C_12/18-Acylsarcosin. Schließlich kommen auch Kationtenside als Emulgatoren in Betracht, wobei solche vom Typ der Esterquats, vorzugsweise methylquaternierte Difettsäuretriethanolaminester-Salze, besonders bevorzugt sind.

Suitable emulsifiers are, for example, nonionic surfactants from at least one of the following groups:

• - Adducts of 2 to 30 moles of ethylene oxide and / or 0 to 5 moles of propylene oxide with linear fatty alcohols with 8 to 22 carbon atoms, with fatty acids with 12 to 22 carbon atoms, with alkylphenols with 8 to 15 carbon atoms in the alkyl group and Alkylamines with 8 to 22 carbon atoms in the alkyl radical;
• - Alkyl and / or alkenyl oligoglycosides with 8 to 22 carbon atoms in the alk (en) yl radical and their ethoxylated analogs;
• - Adducts of 1 to 15 moles of ethylene oxide with castor oil and / or hydrogenated castor oil;
• - Adducts of 15 to 60 moles of ethylene oxide with castor oil and / or hydrogenated castor oil;
• Partial esters of glycerol and / or sorbitan with unsaturated, linear or saturated, branched fatty acids with 12 to 22 carbon atoms and / or hydroxycarboxylic acids with 3 to 18 carbon atoms and their adducts with 1 to 30 mol of ethylene oxide;
• - Partial esters of polyglycerol (average degree of self-condensation 2 to 8), polyethylene glycol (molecular weight 400 to 5000), trimethylolpropane, pentaerythritol, sugar alcohols (e.g. sorbitol), alkyl glucosides (e.g. methyl glucoside, butyl glucoside, lauryl glucoside) and polyglucosides (e.g. cellulose) unsaturated, linear or branched fatty acids with 12 to 22 carbon atoms and / or hydroxycarboxylic acids with 3 to 18 carbon atoms and their adducts with 1 to 30 moles of ethylene oxide;
• - Mixed esters of pentaerythritol, fatty acids, citric acid and fatty alcohol and / or mixed esters of fatty acids with 6 to 22 carbon atoms, methyl glucose and polyols, preferably glycerol or polyglycerol.
• - Mono-, di- and trialkyl phosphates as well as mono-, di- and / or tri-PEG-alkyl phosphates and their salts;
• - wool wax alcohols;
• - Polysiloxane-polyalkyl-polyether copolymers or corresponding derivatives;
• Block copolymers, for example polyethylene glycol 30 dipolyhydroxystearate;
• - polymer emulsifiers, for example Pemulen types (TR-1, TR-2) from Goodrich;
• - Polyalkylene glycols as well
• - glycerine carbonate.
• - Ethylene oxide addition products The addition products of ethylene oxide and / or of propylene oxide with fatty alcohols, fatty acids, alkylphenols or with castor oil are known, commercially available products. These are mixtures of homologs, the average degree of alkoxylation of which is the ratio of the amounts of ethylene oxide and / or propylene oxide and Substrate with which the addition reaction is carried out corresponds. C _12/18 fatty acid monoesters and diesters of addition products of ethylene oxide onto glycerol are known as refatting agents for cosmetic preparations.
• - Alkyl and / or alkenylogoglycosides Alkyl and / or alkenyl oligoglycosides, their preparation and their use are known from the prior art. They are produced in particular by reacting glucose or oligosaccharides with primary alcohols with 8 to 18 carbon atoms. With regard to the glycoside residue, both monoglycosides in which a cyclic sugar residue is glycosidically bonded to the fatty alcohol and oligomeric glycosides with a degree of oligomerization of up to preferably about 8 are suitable. The degree of oligomerization is a statistical mean value which is based on a homolog distribution customary for such technical products.
• - Partial glycerides Typical examples of suitable partial glycerides are hydroxystearic acid monoglyceride, hydroxystearic acid diglyceride, isostearic acid, Isostearinsäurediglycerid, oleic acid monoglyceride, oleic acid diglyceride, Ricinolsäuremoglycerid, ricinoleic acid diglyceride, Linolsäuremonoglycerid, Linolsäurediglycerid, Linolensäuremonoglycerid, Linolensäurediglycerid, Erucasäuremonoglycerid, Erucasäurediglycerid, Weinsäuremonoglycerid, Weinsäurediglycerid, Citronensäuremonoglycerid, Citronendiglycerid, Äpfelsäuremonoglycerid, malic acid diglyceride and their technical mixtures which may still contain small amounts of triglyceride from the manufacturing process. Addition products of 1 to 30, preferably 5 to 10, mol of ethylene oxide onto the partial glycerides mentioned are also suitable.
• - sorbitan as sorbitan esters sorbitan, sorbitan sesquiisostearate, Sorbitan, sorbitan triisostearate, sorbitan monooleate, sorbitan, sorbitan, Sorbitanmonoerucat, Sorbitansesquierucat, Sorbitandierucat, Sorbitantrierucat, Sorbitanmonoricinoleat, Sorbitansesquiricinoleat, Sorbitandiricinoleat, Sorbitantriricinoleat, Sorbitanmonohydroxystearat, Sorbitansesquihydroxystearat, Sorbitandihydroxystearat, Sorbitantrihydroxystearat, Sorbitanmonotartrat, Sorbitansesquitartrat, Sorbitanditartrat , Sorbitan tritartrate, sorbitan monocitrate, sorbitan sesquicitrate, sorbitan citrate, sorbitan tricitrate, sorbitan monomaleate, sorbitan sesquimaleate, sorbitan trimaleate, sorbitan trimaleate and their technical mixtures. Addition products of 1 to 30, preferably 5 to 10, mol of ethylene oxide onto the sorbitan esters mentioned are also suitable.
• - Polyglycerol esters Typical examples of suitable polyglycerol esters are polyglyceryl-2 dipolyhydroxystearates (Dehymuls ^® PGPH), polyglycerol-3-diisostearates (Lameform ^® TGI), polyglyceryl-4 isostearates (Isolan ^® GI 34), polyglyceryl-3 oleates, diisostate-3-diolate (Isolan ^® PDI), Polyglyceryl-3 Methylglucose Distearate (Tego Care ^® 450), Polyglyceryl-3 Beeswax (Cera Bellina ^® ), Polyglyceryl-4 Caprate (Polyglycerol Caprate T2010 / 90), Polyglyceryl-3 Cetyl Ether (Chimexane ^® NL) , Polyglyceryl-3 Distearate (Cremophor ^® GS 32) and Polyglyceryl Polyricinoleate (Admul ^® WOL 1403) Polyglyceryl Dimerate Isostearate and their mixtures. Examples of other suitable polyol esters are the mono-, di- and triesters of trimethylolpropane or pentaerythritol with lauric acid, coconut fatty acid, tallow fatty acid, palmitic acid, stearic acid, oleic acid, behenic acid and the like which are optionally reacted with 1 to 30 mol of ethylene oxide.
• - Anionic emulsifiers Typical anionic emulsifiers are aliphatic fatty acids with 12 to 22 carbon atoms, such as, for example, palmitic acid, stearic acid or behenic acid, and dicarboxylic acids with 12 to 22 carbon atoms, such as, for example, azelaic acid or sebacic acid.
• - Amphoteric and cationic emulsifiers Furthermore, zwitterionic surfactants can be used as emulsifiers. Zwitterionic surfactants are surface-active compounds that contain at least one quaternary ammonium group and at least one carboxylate and one sulfonate group in the molecule. Particularly suitable zwitterionic surfactants are the so-called betaines such as the N-alkyl-N, N-dimethylammonium glycinate, for example the coconut alkyldimethylammonium glycinate, N-acylaminopropyl-N, N-dimethylammonium glycinate, for example the coconut acylaminopropyldimethylammonium glycinate, and 2-alkyl-3-carboxyimide-3-carboxylimide each with 8 to 18 carbon atoms in the alkyl or acyl group and the cocoacylaminoethylhydroxyethylcarboxymethylglycinate. The fatty acid amide derivative known under the CTFA name Cocamidopropyl Betaine is particularly preferred. Suitable emulsifiers are ampholytic surfactants. Ampholytic surfactants are surface-active compounds which, in addition to a C _8/18 alkyl or acyl group, contain at least one free amino group and at least one -COOH or -SO ₃ H group in the molecule and are capable of forming internal salts. Examples of suitable ampholytic surfactants are N-alkylglycines, N-alkylpropionic acids, N-alkylaminobutyric acids, N-alkyliminodipropionic acids, N-hydroxyethyl-N-alkylamidopropylglycines, N-alkyltaurines, N-alkylsarcosines, 2-akylaminopropionic acids and alkylaminoacetic acids each with about 8 to 18 C. -Atoms in the alkyl group .. Particularly preferred ampholytic surfactants are the N-cocoalkylaminopropionate, the cocoacylaminoethylaminopropionate and the C _12/18 acylsarcosine. Finally, cationic surfactants are also suitable as emulsifiers, those of the esterquat type, preferably methylquaternized difatty acid triethanolamine ester salts, being particularly preferred.

manufacturing microcapsules

For the production of the microcapsules you usually ask a 1 to 10, preferably 2 to 5% by weight aqueous solution of the gelling agent, preferably of the agar and heats them under reflux. In the boiling heat preferably at 80 to 100 ° C, becomes a second watery solution added which the chitosan in amounts of 0.1 to 2, preferably 0.25 to 0.5% by weight and the active ingredients in amounts of 0.1 to 25 and in particular contains 0.25 to 10% by weight; this mixture is called Called matrix. The loading of the microcapsules with active ingredients can therefore also 0.1 to 25 wt .-% based on the capsule weight be. If desired, can at this time to adjust the viscosity also insoluble in water Constituents, for example inorganic pigments, are added, where these are usually in the form of aqueous or aqueous / alcoholic Adds dispersions. For emulsifying or dispersing the active ingredients it may also be useful to use the matrix emulsifiers and / or solubilizers should admit. After making the matrix from gelling agent, chitosan and active ingredient mixture, the matrix can optionally be in an oil phase strong shear to be very finely dispersed to the following Encapsulation if possible to produce small particles. It has proven to be particularly advantageous proven to heat the matrix to temperatures in the range of 40 to 60 ° C while the oil phase to 10 to 20 ° C cools. in the The last step, which is now mandatory, is the actual step Encapsulation, i.e. the formation of the envelope membrane by contacting of chitosan in the matrix with the anionic polymers. Recommends this it is the matrix which may be dispersed in the oil phase at a temperature in the range of 40 to 100, preferably 50 up to 60 ° C with an aqueous, about 1 to 50 and preferably 10 to 15% by weight aqueous solution of the anion polymer and, if necessary, simultaneously or later the oil phase to remove. The resulting aqueous preparations have usually a microcapsule content in the range of 1 to 10% by weight on. In some cases it can be advantageous if the solution of the polymers further Ingredients, such as emulsifiers or preservatives contains. After filtration, microcapsules are obtained, which have an average Have diameters in the range of preferably about 1 mm. It it is advisable to sieve the capsules in order to distribute the size as evenly as possible sure. The microcapsules obtained in this way can manufacturing-related frames have any shape, they are preferred, however, approximately spherical. Alternatively, the anion polymers can also be used to produce the matrix insert and encapsulate with the chitosans.

In an alternative procedure to produce the microcapsules according to the invention is first a O / W emulsion prepared, which in addition to the oil body, water and the active ingredients contains an effective amount of emulsifier. To make the matrix this preparation is stirred vigorously with an appropriate Amount of an aqueous anionic polymer added. The membrane is formed by adding the chitosan solution. The entire process preferably takes place in the weakly acidic range pH = 3 to 4 instead. If necessary, the pH is adjusted by adding mineral acid. After membrane formation, the pH is raised to 5 to 6, for example by adding triethanolamine or another Base. This leads to an increase in viscosity caused by Addition of further thickeners, e.g. polysaccharides in particular xanthan gum, guar guar, agar agar, alginates and tyloses, carboxymethyl cellulose and hydroxyethyl cellulose, higher molecular weight Polyethylene glycol mono- and diesters of fatty acids, polyacrylates, polyacrylamides and the like still supported can be. In conclusion the microcapsules from the watery Phase, for example by decanting, filtering or centrifuging separated.

Pro-liposomes

Instead of the described microcapsules come as carriers for the Mixtures of active substances also questionable pro-liposomes. To clarify the term noted that the pro-liposomes do not contain water and only absorb this with the formation of real liposomes if them into a watery Environment. Under the name Lecithine means those skilled in the art those glycerophospholipids which are composed of fatty acids, glycerol, phosphoric acid and form choline by esterification. Lecithins are used in the professional world therefore often referred to as phosphatidylcholine (PC). As examples of natural lecithins, encapsulants are the cephalins, also known as phosphatidic acids are and represent derivatives of 1,2-diacyl-sn-glycerol-3-phosphoric acids. Opposite phospholipids are usually understood to be mono- and preferably Diesters of phosphoric acid with glycerin (glycerin phosphate), which is generally classified as a fat become. In addition, sphingosines are also used for liposomal encapsulation or sphingolipids in question.

Pro-liposomes can be obtained for the purposes of the invention by treating the active ingredients in pharmaceutically or cosmetically acceptable solvents with lecithins and / or phospholipids. For this purpose, the active ingredients are usually either placed in a solvent and mixed with the lecithins or Phospholipids are brought into contact at temperatures in the range from 30 to 70 ° C. or the anhydrous mixtures are stirred into a solution of the lecithins or phospholipids. The active ingredients and the lecithins and / or phospholipids can be used in a weight ratio of 1:20 to 5: 1, preferably 1 2 to 4: 1. Suitable solvents are preferably lower alcohols with 1 to 4 carbon atoms, such as ethanol or polyols, which generally have 2 to 15 carbon atoms and at least two hydroxyl groups; propylene glycol is preferred here.

commercial applicability

Another subject of the present The invention relates to the use of the new (ω-1) -hydroxy fatty acid esters for the production of cosmetic, pharmaceutical and / or dermatological preparations, in which they are present in amounts of 0.01 to 20, preferably 0.1 to 5 and in particular 0.5 to 1 wt .-% - based on the final preparations - included could be.

PREPARATION

Example 1. In a 500 ml three-necked flask with stirrer and reflux condenser, 3 g of agar were dissolved in 200 ml of water at the boiling point. Subsequently, the mixture within about 30 min with vigorous stirring was First a homogeneous dispersion of 10 g of glycerol and 2 g talc in 100 g water and then ig with a preparation of 25 g of chitosan (Hydagen ^® DCMF, 1 wt .-% in glycolic acid, Cognis Germany GmbH & Co. KG), 4 g of salicylic acid, 4 g (ω-1) -Hydroxymyristinsäuresalicylester, Phenonip ^® (preservative mixture containing phenoxyethanol and parabens) and 0.5 g of polysorbate 20 in 100 g water was added. The matrix obtained was filtered, heated to 60 ° C. and dropped into a 0.5% by weight sodium alginate solution. After sieving, an aqueous preparation was obtained which contained 8% by weight of microcapsules with an average diameter of 1 mm.

Example 2. In a 500 ml three-necked flask with stirrer and reflux condenser, 3 g of agar were dissolved in 200 ml of water at the boiling point. The mixture was then stirred over a period of about 30 minutes, first with a homogeneous dispersion of 10 g glycerol and 2 g talc in 100 g water and then with a preparation of 25 g chitosan, 4 g (ω-1) hydroxypalmitic acid retinyl ester, 0.5 g of Phenonip ^® and 0.5 g of Polysorbate-20 are added to 100 g of water. The matrix obtained was filtered, heated to 50 ° C. and dispersed with vigorous stirring in 2.5 times the volume of paraffin oil which had previously been cooled to 15 ° C. The dispersion was then washed with an aqueous solution containing 1% by weight sodium lauryl sulfate and 0.5% by weight sodium alginate and then repeatedly with a 0.5% by weight aqueous phenonip solution, the oil phase being removed. After sieving, an aqueous preparation was obtained which contained 8% by weight of microcapsules with an average diameter of 1 mm.

Example 3. In a 500 ml three-necked flask equipped with a stirrer and reflux condenser, 3 g of agar were dissolved in 200 ml of water at the boiling point. The mixture was then stirred over a period of about 30 minutes, first with a homogeneous dispersion of 10 g of glycerol and 2 g of talc in 100 g of water and then with a preparation of 25 g of chitosan, 4 g of (ω-1) tocopheryl hydroxystearate, 0.5 g of Phenonip ^® and 0.5 g of Polysorbate-20 are added to 100 g of water. The matrix obtained was filtered, heated to 60 ° C. and added dropwise to a 15% by weight solution of sodium laureth sulfate. After sieving, an aqueous preparation was obtained which contained 9% by weight of microcapsules with an average diameter of 1 mm.

Antibacterial effectiveness

• A1 (ω-1)-Hydroxymyristinsäure
• A2 Salicylsäure
• B1 (ω-1)-Hydroxymyristinsäuresalicylester
• B2 (ω-1)-Hydroxypalmitinsäureretinylester
• B3 (ω-1)-Hydroxystearinsäuretocopherylester

The following active ingredients or their mixtures were tested in the following:

• A1 (ω-1) hydroxymyristic acid
• A2 salicylic acid
• B1 (ω-1) hydroxymyristic acid salicylic ester
• B2 (ω-1) hydroxypalmitic acid retinyl ester
• B3 (ω-1) hydroxystearic acid tocopheryl ester

The antibacterial effectiveness of the active ingredients and active ingredient mixtures was investigated using the diffusion method on agar plates or the agar dilution method. First, a round filter paper of defined diameter is soaked with the test solution and then applied to the surface of an agar plate which had previously been inoculated with the test microorganisms. The size of the inhibition zones is then determined after defined times. This technique allows in particular to determine the MIC (Minimum Inhibitory Concentration) as the lowest test substance concentration with which a complete inhibition of the microorganisms can be achieved.

Agar diffusion method. The inoculum was prepared using a fresh culture in a stationary growth phase (after approx. 18-24 h) in a BHI solution (Brain Heart Infusion I). The bacterial suspension was adjusted to 0.5 MacFarland units, corresponding to 1.5 10 ⁸ colony-forming units (cfu) / ml; the suspension was then diluted 1/100 with a saline solution in order to set a value of 1.5 10 ⁶ cfu / ml. Mueller-Hinton agar (Staphylococcus epidermis, Staphylococcus aureus) and Wilkins-Chalgrens agar with 5% by weight sheep's blood (Propionobacterium aches) were then sterilized at 121 ° C. for 15 min and then placed in petri dishes. 2 to 4 ml of the bacterial suspensions were added to the petri dishes and dried at room temperature. The filter papers were impregnated with 20 μl of the test substances and applied to the surface of the agar plates. The inoculated Petri dishes were incubated at 37 ° C for 18 to 24 (the Petri dishes with Propionibacterium acnes under anaerobic conditions) and the antimicrobial activity was then determined by determining the growth inhibition zone. The results are summarized in Table 1. The diameter of the inhibition areas is given in mm.

Agar dilution method (MIC determination). As described above, various agars were prepared using different concentrations of test substances added, homogenized and then dried. Subsequently the Petri dishes were inoculated with 2 μl of the bacterial suspensions. To after drying again, the Petri dishes were at 18 to 18 ° C Incubated for 24 h. Table 2 shows the MIC in mg / ml, i.e. the lowest concentrations with which a complete inhibition of the Bacterial growth can be achieved. It is in each case around the mean of duplicate determinations.

Inhibition zones [mm] Table 1

MIC [mg / ml] Table 2:

The results show that the (ω-1) -hydroxy fatty acid esters compared to the free acids via ver have improved antimicrobial properties especially against those germs that are involved in the development of acne. These properties can still be improved when mixed.

Claims (8)

(ω-1) hydroxy fatty acid esters according to formula (I),

in which n stands for numbers from 7 to 23 and R stands for the remainder of an aromatic alcohol. Ester according to claim 1, characterized in that the aromatic alcohol is selected from the group formed by benzyl alcohol, salicyl alcohol, sterol, tocopherol, retinol and mixtures thereof. Anti-acne remedy containing an effective amount of (Ω-1) -Hydroxyfettsäureestern according to claim 1. Agent according to claim 3, characterized in that they continue to contain active ingredients that are selected from the group consisting of is formed by - glycyrrhetic acid and their salts or extracts of the Glyzyrrhiza glabra plant, - Azelaic acid, the Salts and esters, - salicylic acid, the Salts and esters, - benzoyl peroxide, - vitamin B6 - vitamin E phosphate as well - plant extracts. Agent according to claims 3 and / or 4, characterized characterized that they are the active ingredients in the form of microcapsules or contain pro-liposomes. Use of (ω-1) -hydroxy fatty acid ester according to the claims 1 and / or 2 for the production of cosmetic, pharmaceutical or dermatological preparations. Use according to claim 6, characterized in that that the preparations are anti-acne represent. Use according to claims 6 and / or 7, thereby characterized in that the preparations contain the esters in amounts of 0.01 contain up to 20 wt .-%.