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DE2660069C2 - - Google Patents

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DE2660069C2
DE2660069C2 DE2660069A DE2660069A DE2660069C2 DE 2660069 C2 DE2660069 C2 DE 2660069C2 DE 2660069 A DE2660069 A DE 2660069A DE 2660069 A DE2660069 A DE 2660069A DE 2660069 C2 DE2660069 C2 DE 2660069C2
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lipid
phase
aqueous phase
liposomes
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German (de)
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Guy Montjay-La-Tour Fr Vanlerberghe
Geb. Villa Rose-Marie Paris Fr Handjani
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LOreal SA
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LOreal SA
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C09K23/34—Higher-molecular-weight carboxylic acid esters
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/10—Dispersions; Emulsions
    • A61K9/127—Synthetic bilayered vehicles, e.g. liposomes or liposomes with cholesterol as the only non-phosphatidyl surfactant
    • A61K9/1277—Preparation processes; Proliposomes
    • 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
    • A61K8/14—Liposomes; Vesicles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/10—Dispersions; Emulsions
    • A61K9/127—Synthetic bilayered vehicles, e.g. liposomes or liposomes with cholesterol as the only non-phosphatidyl surfactant
    • A61K9/1271—Non-conventional liposomes, e.g. PEGylated liposomes or liposomes coated or grafted with polymers
    • A61K9/1272—Non-conventional liposomes, e.g. PEGylated liposomes or liposomes coated or grafted with polymers comprising non-phosphatidyl surfactants as bilayer-forming substances, e.g. cationic lipids or non-phosphatidyl liposomes coated or grafted with polymers
    • 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
    • A61Q19/04—Preparations for care of the skin for chemically tanning the skin
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
    • C09K19/54—Additives having no specific mesophase characterised by their chemical composition
    • C09K19/542—Macromolecular compounds
    • C09K19/544—Macromolecular compounds as dispersing or encapsulating medium around the liquid crystal
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
    • C09K2019/523—Organic solid particles
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
    • C09K2019/528—Surfactants

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Materials Engineering (AREA)
  • Veterinary Medicine (AREA)
  • Organic Chemistry (AREA)
  • Public Health (AREA)
  • Engineering & Computer Science (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • Dermatology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Dispersion Chemistry (AREA)
  • Biophysics (AREA)
  • Birds (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Molecular Biology (AREA)
  • Medicinal Preparation (AREA)
  • Manufacturing Of Micro-Capsules (AREA)
  • Cosmetics (AREA)
  • Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
  • Colloid Chemistry (AREA)
  • Fats And Perfumes (AREA)
  • Liquid Crystal Substances (AREA)

Description

Die Erfindung betrifft ein Verfahren zur Herstellung einer Dispersion von Liposomen.The invention relates to a method for producing a Dispersion of liposomes.

Es ist bekannt, daß gewisse Lipide die Eigenschaft besit­ zen, in Anwesenheit von Wasser mesomorphe Phasen zu bilden, deren Anordnungszustand bzw. Aufbau zwischen dem kristallinen und dem flüssigen Zustand liegt. Es ist bekannt, daß gewisse Lipide, die mesomorphe Phasen bilden können, in wäßriger Lösung quellen können, wobei in dem wäßrigen Milieu disper­ gierte Kügelchen entstehen, die aus multimolekularen Schichten und vorzugsweise aus bimolekularen Schichten mit einer Dicke von etwa 3 bis 10 nm bestehen (vgl. insbesondere Bangham, Standish und Watkins, J. Mol. Biol., 13, 238 (1965)).Certain lipids are known to possess the property zen to form mesomorphic phases in the presence of water, their state of arrangement or structure between the crystalline and the liquid state. It is known that certain Lipids that can form mesomorphic phases in aqueous Can swell solution, disper in the aqueous environment Balls are formed from multimolecular layers and preferably of bimolecular layers with a thickness  of about 3 to 10 nm (see in particular Bangham, Standish and Watkins, J. Mol. Biol., 13, 238 (1965)).

Bisher war es nur möglich, Lipidkügelchen, die aus konzentri­ schen Blättchen bzw. Lamellen bestehen, unter Anwendung von Lipiden herzustellen, die eine ionische hydrophile Gruppe und eine lipophile Gruppe aufweisen, und die beschriebenen Her­ stellungsverfahren führen zu Kügelchen mit einem mittleren Durchmesser unter 100 nm. Das Herstellungsverfahren für diese Kügelchen besteht darin, eine Dispersion zu bilden, deren dis­ perse Phase die zur Bildung der Kügelchen geeignete lipide Sub­ stanz enthält und diese Dispersion einer Ultraschallbehandlung zu unterziehen. Zur Erzielung der einer Ultraschallbehandlung zu unterziehenden Dispersion kann man zunächst an einer Wand bzw. Fläche durch Verdampfen einen dünnen Film der zu disper­ gierenden lipiden Substanz bilden, anschließend die kontinuier­ liche Phase der zu bildenden Dispersion in Kontakt mit der so überzogenen Fläche bringen und schließlich rühren bzw. bewegen, um die der Ultraschallbehandlung zu unterziehende Dispersion zu erhalten. Gemäß einem anderen in der französischen Patentschrift 22 21 122 beschriebenen Verfahren kann man auch zur Herstellung der der Ultraschallbehandlung zu unterziehenden Dispersion das zur Bildung der Wände der Kügelchen bestimmte Lipid einer wäß­ rigen Phase zuführen und anschließend leicht erwärmen und kräf­ tig unter Schütteln rühren. Die aus konzentrischen Blättchen bzw. Lamellen bestehenden Kügelchen, die man so erhält und die einen maximalen Durchmesser von etwa 100 nm aufweisen, werden im allgemeinen Liposome genannt.So far, it has only been possible to concentrate lipid beads that consist of leaflets or lamellae exist, using To produce lipids that have an ionic hydrophilic group and have a lipophilic group, and the described Her Positioning procedures lead to beads with a medium Diameter under 100 nm. The manufacturing process for this Beads consist of forming a dispersion, the dis perse phase the lipid sub suitable for the formation of the beads punch contains and this dispersion of an ultrasound treatment to undergo. To achieve an ultrasound treatment The dispersion to be subjected can first be applied to a wall or surface by evaporation to thin the disper forming lipid substance, then the continuous Liche phase of the dispersion to be formed in contact with the so bring coated surface and finally stir or move, to the dispersion to be subjected to the ultrasonic treatment receive. According to another in the French patent 22 21 122 described methods can also be used to manufacture the dispersion to be subjected to ultrasonic treatment to form the walls of the beads determined lipid an aq phase and then warm gently and vigorously Stir thoroughly while shaking. The concentric leaves or lamellae existing spheres that are obtained in this way and have a maximum diameter of about 100 nm generally called liposomes.

Man hat auch bereits empfohlen, Liposome zum Einschluß von wäßrigen Lösungen zu verwenden, die in den zwischen den Lipid­ doppelschichten enthaltenen wäßrigen Räumen aktive Substanzen enthalten, und so die eingekapselten Substanzen gegen Einwirkun­ gen von außen zu schützen (vgl. insbesondere Sessa und Weismann, J. Lipid Res., 9, 310 (1968) und Magee und Miller, Nature, Vol. 235 (1972)).It has also been recommended that liposomes be included to use aqueous solutions in between the lipid double layers contain aqueous spaces active substances contain, and so the encapsulated substances against action protect from outside (see in particular Sessa and Weismann, J. Lipid Res., 9, 310 (1968) and Magee and Miller, Nature,  Vol. 235 (1972)).

Auch die DE-OS 22 49 552 beschreibt ein Verfahren zur Her­ stellung von Liposomen mit einem maximalen Durchmesser von 100 nm. Dieses Verfahren besteht darin, daß man nach einer ersten Variante ein Lipid zu einer wäßrigen Phase gibt und leicht erwärmt, heftig schüttelt und anschließend mit Ultra­ schall behandelt. Nach einer zweiten Variante überführt man eine in einem Lösungsmittel gelöste disperse Phase in einen dünnen Film durch Verdampfen des Lösungsmittels und bringt diesen dünnen Film anschließend mit einer wäßrigen oder nicht wäßrigen Phase unter starker Agitation in Kontakt. Daran schließt sich eine Ultraschallbehandlung an. Die auf diese Weise erhaltenen Liposomen sind dazu geeignet, Lösungen che­ mischer Substanzen einzuschließen.DE-OS 22 49 552 also describes a process for the manufacture position of liposomes with a maximum diameter of 100 nm. This method consists in that after a first variant gives a lipid to an aqueous phase and slightly warmed, shaken vigorously and then with Ultra treated sound. According to a second variant, you transfer a disperse phase dissolved in a solvent into a thin film by evaporation of the solvent and brings this thin film then with an aqueous or not aqueous phase in contact with strong agitation. That is followed by an ultrasound treatment. The on this Liposomes obtained in this way are suitable for che solutions include mixing substances.

Da die Liposome variable Größen im Bereich unter 100 nm aufweisen können, kann man ihr Penetrationsver­ mögen in den menschlichen Körper variieren, wodurch zahlreiche Anwendungen auf dem Gebiet der Pharmazie in Betracht gezogen wurden, um so mehr als es ihre äußere elektrische Ladung ermög­ lichen kann, ihr Fixierungsgebiet auszuwählen (Biochem. J. (1971), 124, S. 58 P). Auf dem Gebiet der Kosmetik jedoch können durch die Anwendung von Kügelchen mit Durchmessern unter 100 nm Nach­ teile entstehen, da die Gefahr des Eindringens der Produkte durch die Haut besteht. Es ist daher ersichtlich, daß zumindest für diesen Anwendungszweck die Erzielung von Liposomen aus kon­ zentrischen Lipidblättchen bzw. Lamellen mit einem Durchmesser über 100 nm wünschenswert wäre. Because the liposomes have variable sizes in the range Can have less than 100 nm, you can Penetrationsver may vary in the human body, causing numerous Applications in the field of pharmacy considered the more so as their external electrical charge allowed can choose their fixation area (Biochem. J. (1971), 124, p. 58 P). In the field of cosmetics, however, can by the use of beads with diameters below 100 nm Parts arise because of the risk of product penetration through the skin. It can therefore be seen that at least for this purpose the achievement of liposomes from kon centric lipid flakes or lamellae with a diameter over 100 nm would be desirable.  

Darüber hinaus besitzen die bisher zur Erzielung von Liposomen bekannten Verfahren, die zwischen ihren konzentrischen Lipid­ blättchen aktive Substanzen einschließen, beträchtliche Nach­ teile: in erster Linie wird die in der kontinuierlichen Phase der Dispersion, die man der Ultraschallbehandlung unterzieht, enthaltene aktive Substanz nur zu einem sehr geringen Aus­ maß zwischen die Lipidblättchen der Liposomen eingeschlossen, da sich zwischen den genannten Blättchen nur ein sehr geringer Teil der kontinuierlichen Phase der Dispersion eingeschlossen befindet. Wünscht man die Einkapselungs-Liposome zu isolieren, so ist es notwendig, die Dispersion, die man einer Ultraschall­ behandlung unterzogen hat, über eine Trennkolonne vom Typ "Sephadex" zu leiten, wobei man die Liposome in Form einer äu­ ßerst verdünnten Dispersion wieder erhält. Hieraus ergibt sich einerseits, daß es praktisch nicht möglich ist, mit bekannten Verfahren eine große Konzentration an Liposomen zu erhalten und andererseits, daß die aktive Substanz nur zu einem geringen Aus­ maß umkapselt ist und beim Eluieren der Trennkolonne verloren geht, ohne daß es praktisch möglich ist, sie in einfacher Weise wiederzugewinnen, wodurch sich die Gestehungskosten der in die Liposome eingeschlossenen aktiven Substanzen stark erhöhen. Es besteht daher ein Bedürfnis nach einem Herstellungsverfahren für Liposome aus konzentrischen Blättchen bzw. Lamellen, das die Herstellung einer hohen Konzentration an Liposomen mit einem verringerten Verlust an zwischen den Blättchen bzw. La­ mellen der Liposomen eingekapselten Produkt ermöglicht.In addition, they have been used to achieve liposomes known procedures between their concentric lipid include active substance leaflets, considerable after parts: in the first place is in the continuous phase the dispersion to be subjected to ultrasound treatment, contained active substance only to a very small extent measured between the lipid leaflets of the liposomes, since there is only a very small one between the mentioned papers Part of the continuous phase of the dispersion included located. If you want to isolate the encapsulation liposomes, so it is necessary to use the dispersion that is an ultrasound has undergone treatment via a separation column of the type "Sephadex" to conduct, the liposomes in the form of an external extremely dilute dispersion. It follows from this on the one hand that it is practically not possible with known ones Procedures to maintain a high concentration of liposomes and on the other hand, that the active substance only to a small extent dimension is encapsulated and lost when eluting the separation column goes without it being practically possible in a simple manner regain, which increases the cost of ownership in the Liposome trapped active substances greatly increase. It  there is therefore a need for a manufacturing process for liposomes from concentric leaflets or lamellae, the producing a high concentration of liposomes a reduced loss of between the leaflets or La Mellowing the liposome encapsulated product allows.

Darüber hinaus ist es bei den bisher bekannten Herstellungsver­ fahren von Liposomen so, daß man nur bestimmte Kategorien von Lipiden verwenden kann: so wurde bisher die Ver­ wendung von Phospho-lipiden, Lipiden mit einer hydrophilen ionischen und einer lipophilen Gruppe und von ungesättigten Fett­ säuren verwendet.In addition, it is in the known Ver drive from liposomes in such a way that only certain Can use categories of lipids: So far, the Ver Use of phospho-lipids, lipids with a hydrophilic ionic and a lipophilic group and of unsaturated fat acids used.

Ziel der vorliegenden Erfindung ist die Schaffung eines Ver­ fahrens zur Herstellung einer wäßrigen Dispersion von Liposomen mit einem Durchmesser unter oder über 100 nm mit erhöhten Konzentrationen und mit hoher Stabilität und geringer Permeabilität, wobei die Kügelchen aktive Substanzen mit einer großen Einschlußausbeute umkapseln können.The aim of the present invention is to create a ver driving for the preparation of an aqueous dispersion of liposomes with a diameter below or above 100 nm with increased Concentrations and with high stability and low permeability, the beads being active substances with a can encapsulate large inclusion yield.

Der hier verwendete Ausdruck "einschließen" bzw. "umkapseln" soll anzeigen, daß man über eine wäßrige Phase im Inneren einer Kapsel verfügt, die aus Lipidkügelchen gebildet wird.The one used here The expression "enclose" or "encapsulate" is intended to indicate that one has an aqueous phase inside a capsule which is formed from lipid beads.

Gegenstand der Erfindung ist daher ein Verfahren zur Herstellung einer Dispersion von Liposomen, die aus molekularen Schichten von ionischen Lipidverbindungen der Formel X - Y, worin X eine hydrophile ionische und Y eine lipophile Gruppe bedeuten, bestehen, die eine wäßrige Phase einschließen, wobei man mindestens eine in Wasser dispergierbare flüssige Lipidverbindung der obigen Formel und eine in die Liposomen einzuschlie­ ßende wäßrige Phase vermischt, das dadurch gekennzeichnet ist, daß das Lipophil/Hydrophil-Verhältnis des Lipids so gewählt wird, daß das Lipid in der einzuschließenden wäßrigen Phase quillt und unter Rühren bzw. Bewegen eine lamellenartige Phase bildet, und daß man anschließend eine Dispergierflüssigkeit im Überschuß zur erhaltenen lamellenartigen Phase gibt und 15 Minuten bis 3 Stunden kräftig bewegt oder schüttelt.The invention therefore relates to a process for the preparation of a dispersion of liposomes which consist of molecular layers of ionic lipid compounds of the formula X - Y , in which X is a hydrophilic ionic group and Y is a lipophilic group, which include an aqueous phase, at least one of which comprises a water-dispersible liquid lipid compound of the above formula and an aqueous phase to be enclosed in the liposomes are mixed, which is characterized in that the lipophile / hydrophile ratio of the lipid is selected such that the lipid swells in the aqueous phase to be enclosed and with stirring or moving forms a lamellar phase, and then an excess of dispersing liquid is added to the lamellar phase obtained and vigorously agitated or shaken for 15 minutes to 3 hours.

Gemäß bevorzugten Ausführungsformen beträgt das Gewichtsver­ hältnis von wäßriger einzuschließender Phase, die in Kontakt mit den Lipiden gebracht wird, und der die lamellenartige Phase bildenden Lipide 0,1 bis 3; kann die wäßrige einzuschließende Phase Wasser oder eine wäßrige Lösung des aktiven Produkts sein; liegt das Gewichtsverhältnis von Dispersionsphase, die man zufügt, zu der lamellen­ artigen Phase, die man dispergiert, bei 2 bis 100; sind die Dispersionsphase und die einzuschließende wäßrige Phase isoosmotisch; kann die Dispersionsphase vorteilhaft eine wäßrige Lösung sein; wird das Bewegen bzw. Rühren als letzte Phase des Verfahrens mittels eines Schüttlers durch­ geführt; wird das Verfahren bei Raumtemperatur oder einer höheren Temperatur durchgeführt, wenn das Lipid bei Raum­ temperatur fest ist, vorzugsweise bei einer Temperatur, die mindestens gleich der Schmelztemperatur des Lipids ist.According to preferred embodiments, the weight ver ratio of aqueous phase to be enclosed, which is brought into contact with the lipids, and the the lamellar phase-forming lipids 0.1 to 3; the aqueous phase to be enclosed can be water or an aqueous phase Solution of the active product; is the weight ratio from the dispersion phase to be added to the lamella like phase, which is dispersed at 2 to 100; are the dispersion phase and the aqueous phase to be enclosed isoosmotic; the dispersion phase can advantageously be a be aqueous solution; is moving or stirring as the last phase of the procedure using a shaker guided; the procedure is at room temperature or a higher temperature when the lipid is at room temperature is fixed, preferably at a temperature which is at least equal to the melting temperature of the lipid.

Zur Bildung der Lamellenphase kann man ein einziges Lipid oder eine Mischung von Lipiden verwenden. Das (die) Lipid(e), das bzw. die man verwendet, weist bzw. weisen eine lange lipophile Kette mit 12 bis 30 Kohlenstoffatomen auf, die gesättigt oder ungesättigt, verzweigt oder linear sein kann. Man kann insbesondere Ketten des Olein-, Lanolin-, Tetradecyl-, Hexadecyl-, Isostearyl-, Laurin­ alkohols bzw. Oleyl-, Lanolyl-, Tetradecycl-, Isostearyl-, Lauryl- oder Alkylphenylketten wählen. Vorzugsweise ist die Verbindung X - Y eine zwei lipophile Ketten enthaltende Asparaginverbindung oder eine Assoziation von zwei organi­ schen Ionen mit langer Kette und umgekehrtem Vorzeichen.A single lipid or a mixture of lipids can be used to form the lamella phase. The lipid (s) that are used have a long lipophilic chain with 12 to 30 carbon atoms, which can be saturated or unsaturated, branched or linear. One can choose in particular chains of oleic, lanolin, tetradecyl, hexadecyl, isostearyl, lauric alcohol or oleyl, lanolyl, tetradecycl, isostearyl, lauryl or alkylphenyl chains. The compound X - Y is preferably an asparagine compound containing two lipophilic chains or an association of two organic ions with a long chain and the opposite sign.

Man kann eine einzuschließende wäßrige Phase verwenden, die aktive Substanzen jeglicher Art und insbesondere Substanzen ent­ hält, die von pharmazeutischem Interesse, von Interesse auf dem Nahrungsmittelgebiet sind oder Substanzen mit einer kosmetischen Wirksamkeit. Die aktiven Substanzen können beispielsweise, was die Kosmetik betrifft, Produkte sein, die zur Pflege der Haut oder der Haare bestimmt sind, beispielsweise Befeuchtungsmittel, wie Glycerin, Sorbit, Pentaerythrit, Inosit, Pyrrolidoncarbonsäure und ihre Salze; künstliche Bräunungsmittel, wie Dihydroxyaceton, Ery­ thrulose, Glycerinaldehyd, die δ-Dialdehyde, wie der der Weinsäure entsprechende Aldehyd (wobei diese Produkte gegebenenfalls zu­ sammen mit Farbstoffen vorliegen können); wasserlösliche Sonnen­ schutzmittel; Antitranspirationsmittel, desodorierende Mittel, adstringierende Mittel, erfrischende, tonisierende, narbenbil­ dende, keratolytische, enthaarende Produkte; wäßrige Parfums, Extrakte von tierischen oder pflanzlichen Geweben, wie Proteine, Polysaccharide, Amnionsflüssigkeiten; wasserlösliche Farbstoffe, Antischuppenmittel, Antiseborrhoemittel, Oxidationsmittel (Ent­ färbungsmittel), wie Wasserstoffperoxid, Reduktionsmittel, wie Thioglykolsäure und deren Salze. Als pharmazeutisch wirksame Substanzen kann man nennen: Vitamine, Hormone, Enzyme (beispiels­ weise Dismutasesuperoxid), Vaccine, antiinflammatorische Mit­ tel (z. B. Hydrocortison), Antibiotika, Bactericide.An aqueous phase to be enclosed can be used which contains active substances of all kinds and in particular substances which are of pharmaceutical interest, are of interest in the food field or substances with a cosmetic activity. As far as cosmetics are concerned, the active substances can, for example, be products intended for the care of the skin or hair, for example moisturizing agents such as glycerol, sorbitol, pentaerythritol, inositol, pyrrolidone carboxylic acid and their salts; artificial tanning agents, such as dihydroxyacetone, erythroulose, glyceraldehyde, the δ -dialdehydes, such as the aldehyde corresponding to tartaric acid (these products may optionally be present together with dyes); water-soluble sunscreen; Antiperspirants, deodorants, astringents, refreshing, toning, scar-forming, keratolytic, depilatory products; aqueous perfumes, extracts from animal or vegetable tissues, such as proteins, polysaccharides, amniotic fluids; water-soluble dyes, anti-dandruff agents, anti-seborrhea agents, oxidizing agents (de-coloring agents) such as hydrogen peroxide, reducing agents such as thioglycolic acid and their salts. The following can be mentioned as pharmaceutically active substances: vitamins, hormones, enzymes (for example dismutase superoxide), vaccines, anti-inflammatory agents (for example hydrocortisone), antibiotics, bactericides.

Die Lipide zur Einkapselung der gewünschten wäßrigen Phase in stabiler Weise wählt man je nach Funktion der in der wäßrigen Phase enthaltenen aktiven Substanzen. Zur Erzielung stabiler Liposomen aus den die lamellenartige Phase bildenden Lipiden sollte eine ausreichende laterale bzw. Seitenkettenwirkung zwischen den Ketten der Lipide vorliegen, die, Seite an Seite liegend, die Schichten oder Blättchen der Kü­ gelchen bilden, so daß die Van-der-Waals-Kräfte zwischen den Ket­ ten eine ausreichende Kohäsion der Blättchen bzw. Lamellen si­ cherstellen. Diese Bedingung ist für die Lipide mit den Charakteristika der vorstehend gegebenen allgemeinen De­ finition erfüllt. Die Lipide, die beim erfindungsgemäßen Verfahren verwendet werden können, gehören der Klasse der Emulgiermittel vom Typ Wasser-in-Öl an. The lipids to encapsulate the desired aqueous phase is selected in a stable manner depending on the function of the active substances contained in the aqueous phase. To achieve stable liposomes from which the lamellar Phase-forming lipids should have sufficient lateral or Side chain effect between the chains of lipids, the, lying side by side, the layers or leaflets of the Kü gelchen form, so that the Van der Waals forces between the Ket sufficient cohesion of the leaflets or lamellae create. This condition is for the lipids with the Characteristics of the general De finition met. The lipids used in the invention Procedures that can be used belong to the class of Water-in-oil emulsifier.  

Gemäß einer bevorzugten Ausführungsform ist die einzukapselnde wäßrige Phase eine wäßrige Lösung einer aktiven Substanz; die aktiven Substanzen der wäßrigen einzukapselnden Phase sind Produkte mit kosmetischer Wirkung; die kontinuierliche Phase der Dispersion ist eine wäßrige Phase; der Gewichtsanteil der Kü­ gelchen, bezogen auf das Gewicht der kontinuierlichen Phase der Dispersion liegt bei etwa 0,01 bis etwa 0,5; die kontinuierliche Phase der Dispersion ist vorteilhaft isoosmotisch mit der in die Liposomen eingeschlossenen wäßrigen Phase.According to a preferred embodiment, the one to be encapsulated aqueous phase an aqueous solution of an active substance; the are active substances of the aqueous phase to be encapsulated Cosmetic products; the continuous phase of Dispersion is an aqueous phase; the weight percentage of the Kü gelchen, based on the weight of the continuous phase of Dispersion is from about 0.01 to about 0.5; the continuous  The dispersion phase is advantageously isoosmotic with the in the liposomes enclosed aqueous phase.

Die wäßrigen Dispersionen sind insbesondere interessant auf dem Gebiet der Kosmetik, da die Anwendung von Liposomen mit großen Dimensionen die Gefahren verringert, die sich durch das Eindringen der Präparate durch die Haut ergeben.The aqueous dispersions are special interesting in the field of cosmetics since the application of Liposomes with large dimensions reduce the dangers that result from the penetration of the preparations through the skin.

Die Anwendung der erfindungsgemäßen wäßrigen Dispersionen in der Kosmetik hat einen beträchtlichen Vorteil im Vergleich zur Anwendung von Emulsionen. Wünscht man in der Praxis Präparate anzuwenden, die gleichzei­ tig Fettkörper und Wasser enthalten, so ist es notwendig, zur Sicherstellung der Stabilität der Emulsion amphiphile Emulgier­ mittel zu verwenden. Es ist bekannt, daß bestimmte Emulgier­ mittel eine ziemliche Reizwirkung ausüben können, wenn sie auf die Haut aufgetragen werden. Im Rahmen der vorliegenden Erfin­ dung wurde gefunden, daß diese Wirkung der Emulgiermittel mit gegebener chemischer Struktur beträchtlich von der Form abhängt, in der sie angewendet werden. So konnte bewiesen werden, daß eine Wasser/Öl-Emulsion aus 42% Perhydrosqualen, 8% Emulgier­ mittel und 50% Wasser eine starke Reizwirkung ausübt, wohin­ gegen eine wäßrige Dispersion mit 8% des gleichen Emulgier­ mittels praktisch eine unbedeutende Reizwirkung aufweist und das Perhydrosqualen absolut unschädlich ist. Hieraus ergibt sich ein Synergismus für die Reizwirkung, wenn man ein Emul­ giermittel und eine ölige Phase vorliegen hat. Die erfindungs­ gemäßen wäßrigen Dispersionen ermöglichen es, gleichzeitig ein Emulgiermittel und ein Öl zu verwenden, wodurch sich auf dem Ge­ biet der Kosmetik ein beträchtlicher Vorteil ergibt.The application of the invention aqueous dispersions in cosmetics has a significant advantage in Comparison to the use of emulsions. If one wishes to use preparations in practice that simultaneously fat bodies and water, so it is necessary to Ensuring the stability of the amphiphilic emulsifying emulsion medium to use. It is known that certain emulsifiers can be quite irritating if they are on applied to the skin. Within the scope of the present inven It was found that this effect of the emulsifiers with given chemical structure depends considerably on the shape, in which they are used. So it could be proven that a water / oil emulsion of 42% perhydrosqualene, 8% emulsifier medium and 50% water has a strong irritant effect wherever against an aqueous dispersion with 8% of the same emulsifier has practically an insignificant irritant effect and  the perhydroscalene is absolutely harmless. From this results a synergism for the irritant effect when you have an emul yaw and an oily phase. The fiction modern aqueous dispersions make it possible to simultaneously To use emulsifier and an oil, which is on the Ge offers the cosmetics a considerable advantage.

Es sei festgestellt, daß man zu den erfindungsgemäßen Disper­ sionen von Liposomen verschiedene Hilfsstoffe fügen kann, um das Aussehen oder den organoleptischen Charakter zu modifizie­ ren, wie Trübungsmittel, gelbildende Mittel, aromagebende Mit­ tel, Parfums oder Farbstoffe.It should be noted that the Disper sions of liposomes can add various excipients to to modify the appearance or the organoleptic character such as opacifying agents, gel-forming agents, flavoring agents tel, perfumes or dyes.

Die erfindungsgemäßen Dispersionen ermöglichen die Einarbeitung von hydrophilen Substanzen in ein im wesentlichen lipophiles Medium. Es ergibt sich unter diesen Bedingungen, daß diese in maskierter Form vorliegen, woraus ein Schutzeffekt gegenüber verschiedene mögliche verändernde Einwirkungen, wie Oxidations­ mittel, Verdauungssäfte und allgemein gegenüber den eingekapsel­ ten Substanzen reaktive Verbindungen resultiert. Das Eindringen und/oder die Fixierung der aktiven Substanzen kann durch Variation der Größe der Kügelchen und ihrer elektrischen Ladung modifi­ ziert werden. Ihre Wirkung kann auch aufgeschoben werden (Ver­ zögerungseffekt). Darüber hinaus erlaubt es die Maskierungswir­ kung, ihren organoleptischen Charakter und insbesondere den Ge­ schmack zu unterdrücken oder wesentlich zu verändern. Schließ­ lich weisen die in den Präparaten verwendeten Lipide selbst eine günstige, beispielsweise weichmachende, gleitendmachende oder glänzendmachende Wirkung auf.The dispersions according to the invention enable incorporation of hydrophilic substances into an essentially lipophilic Medium. Under these conditions it follows that these masked form are present, resulting in a protective effect various possible changing effects, such as oxidation medium, digestive juices and generally compared to the encapsulated reactive substances result. The intrusion and / or the fixation of the active substances by variation the size of the beads and their electrical charge modifi be decorated. Their effect can also be postponed (Ver delay effect). It also allows masking kung, their organoleptic character and especially the ge suppress taste or change it significantly. Close Lich the lipids used in the preparations themselves a cheap, for example softening, lubricating or glossing effect.

Die folgenden Beispiele dienen zur Erläuterung der Erfindung. The following examples serve to illustrate the invention.  

Beispiel 1example 1

In einem 50 ml-Rundkolben bringt man 300 mg Sphingomyelin mit 0,350 ml einer 0,3 m-Lösung von Glucose in Kontakt und homogeni­ siert die Mischung bei Raumtemperatur.300 mg of sphingomyelin is brought into a 50 ml round-bottomed flask 0.350 ml of a 0.3 m solution of glucose in contact and homogeneous siert the mixture at room temperature.

Man fügt darauf 5 ml einer 0,145 m-Lösung von NaCl, KCl zu. Der Kolben wird in eine Schüttelvorrichtung eingebracht und zwei Stunden unter kräftiger Bewegung gehalten.5 ml of a 0.145 m solution of NaCl, KCl are then added. The Flask is placed in a shaker and two Held under vigorous motion for hours.

Man erhält eine milchige Dispersion mit einem Durchmesser der Liposomen von etwa 2 µm. A milky dispersion with a diameter of Liposomes of approximately 2 µm.  

Beispiel 2Example 2

In einem 50 ml-Rundkolben bringt man 300 mg Sphingomyelin mit 0,350 ml einer 0,3 m-Lösung von Ascorbinsäure in Kontakt und homogenisiert die Mischung bei Raumtemperatur.300 mg of sphingomyelin are placed in a 50 ml round-bottomed flask in contact with 0.350 ml of a 0.3 m solution of ascorbic acid and homogenizes the mixture at room temperature.

Man fügt darauf 2,650 ml einer 0,145 m-Lösung von NaCl, KCl zu. Man bringt den Kolben in eine Schüttelvorrichtung ein und bewegt kräftig während 4 Stunden.2.650 ml of a 0.145 m solution of NaCl, KCl are then added to. The flask is placed in a shaker and moves vigorously for 4 hours.

Man erhält eine milchige Lösung und einen Durchmesser der Liposomen von etwa 2 µm.A milky solution and a diameter of Liposomes of approximately 2 µm.

Gegebenenfalls kann man die Dispersion über eine Kolonne von "grobem Sephadex G 50", gequollen in einer 0,145 m-Lösung von NaCl, KCl filtrieren. If necessary, the dispersion can be passed through a column of "coarse Sephadex G 50", swollen in a 0.145 Filter m solution of NaCl, KCl.  

Beispiel 3Example 3

In einem 50 ml-Rundkolben löst man 142 mg des Natriumsalzes von N2-(Alkyl-Talg)-N-dodecyl-N-(N′, N′-diäthylaminoäthyl)-asparagin in 2 ml einer Chloroform-Methanolmischung im Verhältnis 2 : 1. Man verdampft das Lösungsmittel mittels eines Rotationsverdampfers und eliminiert letzte Spuren an Lösungsmittel durch einstündige Behandlung des Produkts unter dem verminderten Druck einer Flü­ gelpumpe.142 mg of the sodium salt of N 2 - (alkyl tallow) -N-dodecyl-N- (N ′, N′-diethylaminoethyl) asparagine are dissolved in 2 ml of a chloroform-methanol mixture in a ratio of 2 in a 50 ml round-bottomed flask: 1. The solvent is evaporated using a rotary evaporator and last traces of solvent are eliminated by treating the product for one hour under the reduced pressure of a wing pump.

Man bringt 10 ml einer 0,3 m-Lösung von Glucose mit dem Lipid in Kontakt.10 ml of a 0.3 m solution of glucose are brought with the lipid in contact.

Der auf eine Schüttelvorrichtung aufgebrachte Kolben wird vier Stunden kräftig bewegt, wobei man bei Raumtemperatur arbeitet. Die Größe der Liposomen liegt bei etwa 1 µm. Die Dispersion wird anschließend über eine Kolonne von "grobem Sephadex G 50"-Gel, gequollen in einer Lösung von 0,145 m (NaCl, KCl) filtriert.The piston placed on a shaker is vigorously moved for four hours, taking one at room temperature is working. The size of the liposomes is approximately 1 µm. The dispersion is then over a column of "Coarse Sephadex G 50" gel, swollen in a solution of 0.145 m (NaCl, KCl) filtered.

Claims (8)

1. Verfahren zur Herstellung einer Dispersion von Liposomen, die aus molekularen Schichten von ionischen Lipidverbin­ dungen der Formel X - Y, worin X eine hydrophile ioni­ sche und Y eine lipophile Gruppe bedeuten, bestehen, die eine wäßrige Phase einschließen, wobei man mindestens eine in Wasser dispergierbare flüssige Lipidverbindung der obigen Formel und eine in die Liposomen einzuschlie­ ßende wäßrige Phase vermischt, dadurch gekennzeichnet, daß
das Lipophil/Hydrophil-Verhältnis des Lipids so gewählt wird, daß das Lipid in der einzuschließenden wäßrigen Phase quillt und unter Rühren bzw. Bewegen eine lamellen­ artige Phase bildet, und
daß man anschließend eine Dispergierflüssigkeit im Über­ schuß zur erhaltenen lamellenartigen Phase gibt und 15 Minuten bis 3 Stunden kräftig bewegt oder schüttelt.1. A process for the preparation of a dispersion of liposomes consisting of molecular layers of ionic lipid compounds of the formula X - Y , wherein X is a hydrophilic ionic and Y is a lipophilic group, which include an aqueous phase, wherein at least one in Water-dispersible liquid lipid compound of the above formula and an aqueous phase to be enclosed in the liposomes, characterized in that
the lipophile / hydrophile ratio of the lipid is chosen such that the lipid swells in the aqueous phase to be enclosed and forms a lamellar phase with stirring or agitation, and
that you then add a dispersing liquid in excess to the lamellar phase obtained and vigorously agitated or shaken for 15 minutes to 3 hours. 2. Verfahren gemäß Anspruch 1, dadurch gekennzeichnet, daß man die einzuschließende wäßrige Phase, die in Kontakt mit den Lipiden gebracht wird, und die die lamellenar­ tige Phase bildenden Lipide in einem Gewichtsverhältnis von 0,1 bis 3 verwendet. 2. The method according to claim 1, characterized in that one to include the aqueous phase to be in contact brought with the lipids, and which the lamellenar term phase-forming lipids in a weight ratio from 0.1 to 3 used.   3. Verfahren gemäß einem der Ansprüche 1 oder 2, dadurch gekennzeichnet, daß man als einzuschließende wäßrige Phase Wasser verwendet.3. The method according to any one of claims 1 or 2, characterized characterized in that to be included as an aqueous Phase water used. 4. Verfahren gemäß einem der Ansprüche 1 bis 3, dadurch ge­ kennzeichnet, daß man als einzuschließende wäßrige Phase eine wäßrige Lösung eines aktiven Produktes verwendet.4. The method according to any one of claims 1 to 3, characterized ge indicates that the aqueous phase to be enclosed an aqueous solution of an active product is used. 5. Verfahren gemäß einem der Ansprüche 1 bis 4, dadurch ge­ kennzeichnet, daß man die Dispergierflüssigkeit und die lamellenartige Phase, die dispergiert werden soll, in einem Gewichtsverhältnis von 2 bis 100 verwendet.5. The method according to any one of claims 1 to 4, characterized ge indicates that the dispersing liquid and the lamellar phase to be dispersed in a weight ratio of 2 to 100 used. 6. Verfahren gemäß einem der Ansprüche 1 bis 5, dadurch ge­ kennzeichnet, daß man eine Dispergierflüssigkeit verwen­ det, die mit der wäßrigen einzuschließenden Phase isoosmo­ tisch ist.6. The method according to any one of claims 1 to 5, characterized ge indicates that a dispersing liquid is used det, the isoosmo to be enclosed with the aqueous phase is table. 7. Verfahren gemäß einem der Ansprüche 1 bis 6, dadurch ge­ kennzeichnet, daß man als Dispergierflüssigkeit eine wäßrige Lösung verwendet.7. The method according to any one of claims 1 to 6, characterized ge indicates that a aqueous solution used. 8. Verfahren gemäß einem der Ansprüche 1 bis 7, dadurch ge­ kennzeichnet, daß man bei einer Temperatur arbeitet, die mindestens gleich der Schmelztemperatur des Lipids bzw. der Lipide ist.8. The method according to any one of claims 1 to 7, characterized ge indicates that one works at a temperature that at least equal to the melting temperature of the lipid or the lipid is.
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FR2315991B1 (en) 1977-12-02
AT361893B (en) 1981-04-10
JPS56108528A (en) 1981-08-28
CA1063908A (en) 1979-10-09
AU1539376A (en) 1978-01-05
ES449312A1 (en) 1977-08-16
BE843300A (en) 1976-12-23
JPS526375A (en) 1977-01-18
CH616087A5 (en) 1980-03-14
BR7604270A (en) 1977-04-05
IT1062389B (en) 1984-10-10
DE2629100B2 (en) 1979-11-29
DK291376A (en) 1976-12-31
JPS6156016B2 (en) 1986-12-01
NL168715C (en) 1982-05-17
DE2629100C3 (en) 1980-08-14
AU505843B2 (en) 1979-12-06
JPS588287B2 (en) 1983-02-15
NL7607210A (en) 1977-01-03
FR2315991A1 (en) 1977-01-28
DE2661108C2 (en) 1993-12-16
DK150967C (en) 1988-02-15
ATA470376A (en) 1980-09-15
DK150967B (en) 1987-10-05
CH623236A5 (en) 1981-05-29
GB1539625A (en) 1979-01-31
DE2629100A1 (en) 1977-01-20

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