DE1248015B - Process for the production of microcapsules from an emulsion of oil in a hydrophilic liquid - Google Patents

Process for the production of microcapsules from an emulsion of oil in a hydrophilic liquid

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Publication number
DE1248015B
DE1248015B DE1959U0006753 DEU0006753A DE1248015B DE 1248015 B DE1248015 B DE 1248015B DE 1959U0006753 DE1959U0006753 DE 1959U0006753 DE U0006753 A DEU0006753 A DE U0006753A DE 1248015 B DE1248015 B DE 1248015B
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DE
Germany
Prior art keywords
emulsion
oil
coacervate
water
hydrophilic
Prior art date
Legal status (The legal status 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 status listed.)
Pending
Application number
DE1959U0006753
Other languages
German (de)
Inventor
Everett Nelson Hiestand
Erik Hugo Jensen
Peter Dietrich Meister
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
NCR Voyix Corp
Original Assignee
NCR Corp
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 NCR Corp filed Critical NCR Corp
Publication of DE1248015B publication Critical patent/DE1248015B/en
Pending legal-status Critical Current

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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
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/11—Encapsulated compositions
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/26—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests in coated particulate form
    • A01N25/28—Microcapsules or nanocapsules
    • 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
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
    • A61K9/5005—Wall or coating material
    • A61K9/5021—Organic macromolecular compounds
    • A61K9/5052—Proteins, e.g. albumin
    • A61K9/5057—Gelatin
    • 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
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
    • A61K9/5089—Processes
    • 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
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J13/00—Colloid chemistry, e.g. the production of colloidal materials or their solutions, not otherwise provided for; Making microcapsules or microballoons
    • B01J13/02—Making microcapsules or microballoons
    • B01J13/06—Making microcapsules or microballoons by phase separation
    • B01J13/10—Complex coacervation, i.e. interaction of oppositely charged particles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/41—Particular ingredients further characterized by their size
    • A61K2800/412—Microsized, i.e. having sizes between 0.1 and 100 microns

Description

DEUTSCHESGERMAN

PATENTAMTPATENT OFFICE

AUSLEGESCHRIFTEDITORIAL

Deutsche Kl. 12 c - 3German class 12 c - 3

Nummer. 1 248 015Number. 1 248 015

Aktenzeichen U 6753IV c/12 cFile number U 6753IV c / 12 c

Anmeldetag 18 Dezember 1959 Filing date December 18, 1959

Auslegetag 24 August 1967Opened on August 24, 1967

Es ist bekannt, Oltropfchen als solche und Öltropfchen, die geloste oder dispergierte Stoffe enthalten, durch komplexe bzw einfache Koazetvierung einzukapseln (vgl. USA.-Patentschnften 2 800 457, 2 800 458) Zwar beschreiben diese Patentschriften die Bildung von Koazervaten aus einer Ol-in-Wasser-Emulsion, es wird jedoch lediglich die Olphase vom Koazervat eingekapselt. Die Einkapselung einer Emulsion war bisher nicht versucht worden, und die bedeutenden Vorteile einer mit einem Koazervat überzogenen Emulsion, deren Phasen geloste oder suspendierte Bestandteile enthalten, waren bisher nicht erkannt worden. Außerdem war bisher kein Verfahren bekannt, durch das ein Koazervat auf einer hydrophilen Oberfläche gebildet werden konnteIt is known to use oil droplets as such and oil droplets, which contain dissolved or dispersed substances, encapsulate by complex or simple coacetivation (See USA.-Patentschnften 2 800 457, 2 800 458) It is true that these patents describe the formation of coacervates from an oil-in-water emulsion, however, only the oil phase is encapsulated by the coacervate. The encapsulation of a Emulsion had not been tried before, and the significant advantages of one with a coacervate Coated emulsions, the phases of which contain dissolved or suspended constituents, were previously not recognized. In addition, no method was previously known by which a coacervate on a hydrophilic surface could be formed

Erfindungsgegenstand ist em Verfahren zum Herstellen von Mikrokapseln, die eme Emulsion von Ol m einer hydrophilen Flüssigkeit enthalten, durch einfache Koazervierung mit einem gelierbaren hydrophilen Kolloid durch Zugabe einer waßngen Elektrolytlosung oder einer wasserlöslichen Flüssigkeit, in der das Kolloid weniger löslich ist als in Wasser Das erfindungsgemaße Verfahren ist dadurch gekennzeichnet, daß man der hydrophilen Phase der Emulsion und gegebenenfalls der waßngen Elektrolytlosung em übliches Verdickungsmittel zusetzt und koazerviertThe subject of the invention is a method of production of microcapsules, which contain an emulsion of oil in a hydrophilic liquid, by simple Coacervation with a gellable hydrophilic Colloid by adding an aqueous electrolyte solution or a water-soluble liquid, in which the colloid is less soluble than in water that The method according to the invention is characterized in that that the hydrophilic phase of the emulsion and optionally the aqueous electrolyte solution The usual thickener is added and coacervated

Das erfindungsgemaße Verfahren eröffnet neue Wege bei der Herstellung von impermeablen Überzügen hoher Starke oder solchen, welche eme langsame Freisetzung von wasserlöslichen Stoffen gestatten, em Problem, das mit den bisher bekannten Methoden der Koazervierung nicht gelost werden konnte So können beispielsweise eingekapselte Emulsionspartikeln hergestellt werden, die in den Emulsionsphasen Stoffe als Düngemittel zu langsamer Freisetzung enthalten, Pflanzenwuchshormone und Schädlingsbekämpfungsmittel, wie Pilzmittel, Nematozide, Bakterizide, Virizide u dgl, zur Verwendung in der Landwirtschaft. Weiterhm können Bestandteile vorgemischten Nahrungsmitteln zugesetzt werden, welche infolge des Trocknungsverfahrens fur Nahrungsmittel normalerweise nicht beigemischt werden können, wobei die eingekapselten Ingredienzen infolge der Scherkraft m einer Mischungsstufe vor der tatsachlichen Verwendung freigesetzt werden. Gleicherweise können Vitamine, besonders Zusammensetzungen von wasserlöslichen und olloshchen Vitaminen, trockenen Zereahenpraparaten zur Freisetzung im Korpei zugesetzt werden Es können kosmetische Mittel hergestellt werden, m welchen das zur lokalen Anwendung bestimmte Mittel in einer Verfahren zur Herstellung von Mikrokapseln aus einer Emulsion von Ol in einer hydrophilen
FlüssigkeitThe inventive method opens up new ways in the production of impermeable coatings of high strength or those which allow eme slow release of water-soluble substances, a problem that could not be solved with the previously known methods of coacervation. For example, encapsulated emulsion particles can be produced which in the emulsion phases contain substances as slow-release fertilizers, plant growth hormones and pesticides such as fungicides, nematocides, bactericides, viricides and the like, for use in agriculture. Furthermore, ingredients can be added to premixed foods which normally cannot be mixed due to the drying process for foods, the encapsulated ingredients being released due to the shear force in a mixing step prior to actual use. Similarly, vitamins, especially compositions of water-soluble and oil-soluble vitamins, dry cereal preparations can be added for release in the body
liquid

Anmelder.Applicant.

The National Cash Register Company,The National Cash Register Company,

Dayton, Ohio (V St A.)Dayton, Ohio (V St A.)

Vertreterrepresentative

Dr W Beil, A Hoeppener und Dr. H. J. Wolff,Dr W Beil, A Hoeppener and Dr. H. J. Wolff,

Rechtsanwälte,Lawyers,

Frankfurt/M -Höchst, Adelonstr 58Frankfurt / M -Hochst, Adelonstr 58

Als Erfinder benannt·
Everett Nelson Hiestand,
Erik Hugo Jensen,
Peter Dietrich Meister,
Kalamazoo, Mich (V St A)Named as inventor
Everett Nelson Hiestand,
Erik Hugo Jensen,
Peter Dietrich Master,
Kalamazoo, Me (V St A)

Beanspruchte Priorität
V St ν Amerika vom 22 Dezember 1958
(781925)Claimed priority
V St ν America dated December 22, 1958
(781925)

undurchlässigen, aber leicht zerstörbaren Koazervatschale sich befindet Pharmazeutische Stoffe können eingekapselt werden zu langsamer Dauerfreisetzung im Korper nach Kontakt mit einem bestimmten pH-Milieu odei Fermentsystem, oder wo Stabilität, Geruch, Geschmack oder Unvereinbarkeit das Problem bilden. Solche Stoffe können in Deckschichten zu oraler, lokaler oder Injektionsverabreichung emgeschlossen werden, indem Partikelgroße, Deckschichtdicke, Permeabilität und Harte oder die Zusammensetzung der Deckschicht entsprechend gewählt werdenimpermeable, but easily destructible coacervate shell Pharmaceuticals can be encapsulated to slow sustained release in the body after contact with a certain pH environment odei ferment system, or where stability, smell, taste or incompatibility is the problem form. Such substances can be included in top layers for oral, topical or injection administration by particle size, surface layer thickness, permeability and hardness or the composition be selected according to the top layer

So können Insektenmittel, welche gegenubei Insekten selektiv giftig wirken, fur Menschen aber relativ nichttoxisch sind, ζ B. mit einer Koazervatschicht überzogen werden, welche impermeabel ist, mit Ausnahme gegenüber Insektenfermenten Mittel gegen Nagetiere, welche bei deren Einnahme wuksam werden, aber durch ihren Geruch abstoßend oder warnend wirken, können ebenfalls mit Koazervatmembranen überzogen werden, welche praktisch fur den Geruch total undurchlässig sind
Die hier erfindungsgemaß eingesetzten Verdikkungsmittel sind Stoffe, die im wesentlichen m der Olphase der primären Emulsion unlöslich und befähigt sind, der äußeren hydrophilen Flüssigkeit^For example, insecticides, which are selectively toxic to insects but are relatively non-toxic to humans, can e.g. be coated with a coacervate layer which is impermeable, with the exception of insectic ferments, which are effective against rodents when ingested, but because of their smell repellant or warning can also be covered with coacervate membranes, which are practically completely impermeable to the odor
The thickeners used here according to the invention are substances which are essentially insoluble in the oil phase of the primary emulsion and capable of removing the external hydrophilic liquid

709 638,709 638,

phase Oberflacheneigenschaften zu verleihen, welche dem Koazervat die Ablagerung darauf erlaubt Beispiele sind die natürlichen oder kunstlichen Verdickungsmittel, wie Akaziengummi, Tragant, Methylcellulose, Carboxymethylcellulose, Magnesmmalumiuiumsüikat, Polyglykole, Glycerin, Syrupsphase to impart surface properties that allow the coacervate to deposit on it. Examples are the natural or artificial thickeners, like acacia gum, tragacanth, methyl cellulose, Carboxymethylcellulose, Magnesiummmalumiuiumsüikat, Polyglycols, glycerin, syrups

Die spezifischen Mengen dieser Stoffe können je nach dem betreffenden Mittel und System variiert werden und können ohne Schwierigkeit mittels Routmeexperimenten bestimmt werden. Em Bereich von 1 bis etwa 20 Gewichtspiozent, bezogen auf das Volumen der hydrophilen Flussigkeitsphase, bildet das praktische Maß, wobei 5 bis etwa 10 Gewichtspiozent m den meisten Fallen bevorzugt werdenThe specific amounts of these substances can vary can be varied according to the means and system in question and can be used without difficulty Routine experiments are determined. Em range from 1 to about 20 percent by weight based on the Volume of the hydrophilic liquid phase, forms the practical measure, with 5 to about 10 percent by weight m to be preferred in most cases

Beispiel 1example 1

Eine Ol-m-Wasser-Emulsion wird hergestellt, indem bei 50° C 50 ml Maisöl m 50 ml Wasser, das 2,5 g Methylcellulose enthalt, emulgiert weiden Em Gelatmesol, bestehend aus 25 g Gelatme und 250 ml Wasser, wird auf 50° C erwärmt, mit der Emulsion vermischt und langsam zu 250 ml einer 20%igen Natiiumsulfatlosung, welche ebenfalls auf 50° C erwärmt worden war, zugegeben Die Natriumsulfatlosung wird wahrend der ganzen Zugabezeit kraftig gerührt. Die Temperatur des Gemisches wird auf 50C reduziert, um das Koazervat zu gelieren Genügend lO°/oige Natronlaugelosung wird zugegeben, um das pH auf 9,5 zu bringen, gefolgt von Härtung des Koazervats mit 25 ml emer 37°/oigen Formaldehydlosung wahrend einer Stunde Das gehartete Koazervat wird dann abffltnert, gewaschen und luftgetrocknet bei 80° CAn oil-in-water emulsion is prepared by emulsifying 50 ml of corn oil with 50 ml of water containing 2.5 g of methyl cellulose at 50 ° C ° C, mixed with the emulsion and slowly added to 250 ml of a 20% sodium sulfate solution, which had also been heated to 50 ° C. The sodium sulfate solution is vigorously stirred during the entire addition time. The temperature of the mixture is reduced to 5 0 C to the coacervate to gel Sufficient lO ° / o aqueous sodium hydroxide solution is added to bring the pH to 9.5, followed by curing of the coacervate with 25 ml emer 37 ° / o formaldehyde solution while one hour The hardened coacervate is then removed, washed and air-dried at 80 ° C

Beispiel 2Example 2

Gemäß dem Verfahren vom Beispiel 1, aber unter Verwendung von Arachidol an Stelle von Maisöl, Tragant an Stelle von Methylcellulose, Kaliumchlorid an Stelle des Natriumsulfats und Fibrinogen an Stelle von Gelatine erhalt man ein Koazervat, welches im wesentlichen die gleichen Eigenschaften wie das im Beispiel 1 hergestellte aufweistFollowing the procedure of Example 1, but using arachidol instead of corn oil, Tragacanth in place of methyl cellulose, potassium chloride in place of sodium sulfate and fibrinogen in place from gelatin one obtains a coacervate which has essentially the same properties as the im Example 1 has produced

Beispiel 3Example 3

Eine Öl-in-Wasser-Emulsion wird hergestellt bei 50° C, indem 33 ml Paraffinol in 25 ml Wasser, das 2 g Magnesiumalummiumsilikat und 0,5 g Alizanncyangrun enthalt, emulgiert werden Em Gelatineso] wird bei 50° C aus 12,5 g Gelatine und 125 ml Wasser hergestellt und gründlich mit der Emulsion vermischt Das erhaltene Gemisch _wird langsam zu 125 ml emer 2O°/oigen TNTatnumsulfatlosung, welche 37 g Akaziengummi enthalt, zugegeben, wobei die Natnumsulfatlosung wahrend der ganzen Zugabezeit kraftig geschüttelt wird, um die Koazervatbildung zu fordern Die Temperatur der Gleichgewichtsflussigkeit, welche die koazervatuberzogene Emulsion enthalt, wird auf 5° C reduziert und 10%ige Natronlaugelosung zugegeben, um ein pH von 9,5 zu erhalten . Dann werden 12,5 ml einer 37°/oigen Formaldehydlosung zugesetzt, um die Koazervatschale zu harten Nach 5 Stunden wird das resultierende Produkt von dem Gemisch abfiltneri, gewaschen und sprühgetrocknet bei 80° C (Auspufftemperatur)An oil-in-water emulsion is made at 50 ° C by adding 33 ml of paraffin oil in 25 ml of water, the 2 g of magnesium aluminum silicate and 0.5 g of Alizanncyangrun contains, are emulsified Em Gelatineso] is made at 50 ° C from 12.5 g of gelatine and 125 ml of water prepared and mixed thoroughly with the emulsion The mixture obtained is slowly increasing 125 ml emer 2O% TNTatum sulfate solution, which Containing 37 g of acacia gum, the sodium sulfate solution was added during the entire addition time is shaken vigorously to prevent coacervate formation demand the temperature of the equilibrium liquid, which contains the coacervate-coated emulsion is reduced to 5 ° C. and 10% sodium hydroxide solution added to obtain a pH of 9.5. Then 12.5 ml of a 37% formaldehyde solution are added added to make the coacervate shell hard. After 5 hours, the resulting product is added filtered off from the mixture, washed and spray-dried at 80 ° C (exhaust temperature)

Wird das oben beschriebene Koazervat Saure- und alkalischen Testlosungen unterzogen, so kann festgestellt werden, daß em hoch impermeabler Überzug erhalten wurdeIf the coacervate described above is subjected to acidic and alkaline test solutions, it can be determined that a highly impermeable coating was obtained

Beispiel 4Example 4

Gemäß dem Verfahren vom Beispiel 3 unter Verwendung von Lanolin an Stelle von Paraffinol als der Olphase in der Öl-in-Wasser-Emulsion, Carboxymethylcellulose an Stelle von Magnesiumalummiumsilikat als Verdickungsmittel fur die Wasserphase derFollowing the procedure of Example 3 using lanolin in place of paraffinol as the Oil phase in the oil-in-water emulsion, carboxymethyl cellulose instead of magnesium aluminum silicate as a thickener for the water phase of the

ίο primären Emulsion, Ammonphosphat an Stelle des Natriumsulfats als Koazervierungsmittel, Agar-Agar an Stelle von Gelatine als Koazervierungskolloid und Tragant an Stelle von Akaziengummi als Verdikkungsimttel fur die Koazervierungslosung, man erhalt em Koazervat, das im wesentlichen die gleichen Eigenschaften wie das im Beispiel 3 hergestellte aufweist ίο primary emulsion, ammonium phosphate in place of the Sodium sulfate as a coacervation agent, agar-agar instead of gelatin as a coacervation colloid and Tragacanth instead of acacia gum as a thickener for the coacervation solution, one obtains a coacervate which is essentially the same Properties like that produced in Example 3 has

Beispiel 5Example 5

Eine Ol-m-Athanol-Emulsion wird hergestellt, indem bei 50° C 33 ml Arachidol in 25 ml Äthanol, welches 2 g Methylcellulose enthalt, emulgiert wird Em Fibrrnogensol wild bei 50° C aus 12,5 g Fibrinogen und 125 ml Wasser hergestellt und grundhch mit der Emulsion vermischt Das entstandene Gemisch wird langsam zu 125 ml emer 20%igen Natnumsultatlosung, welche 37 g Akaziengummi enthalt, zugegeben, wobei die Natriumsulfatlosung wahrend der ganzen Zugabezeit kraftig geschüttelt wird, um die Bildung eines Koazervats zu fordern Die Temperatur wird auf 5° C reduziert, um das Koazervat zu gelieren, und lO°/oige Natronlaugelosung zugegeben, um das pH auf 9,5 zu bringen Dann werden 12,5 ml einer 37°/oigen Formaldehydlosung zugegeben, um die Koazervatschale zu harten Nach Stehenlassen wahrend 5 Stunden wird das erhaltene Produkt vom Gemisch abfiltnert, gewaschen und kaltegetrocknet bei 40° C (wohl - 40° C) und 0,01 mm QuecksilbervakuumAn oil-m-ethanol emulsion is produced by emulsifying 33 ml of arachidol in 25 ml of ethanol containing 2 g of methylcellulose at 50 ° C. Em Fibrrnogensol wild at 50 ° C from 12.5 g of fibrinogen and 125 ml of water and thoroughly mixed with the emulsion. The resulting mixture is slowly added to 125 ml of a 20% sodium resultant solution, which contains 37 g of acacia gum, the sodium sulfate solution being vigorously shaken during the entire time of addition to encourage the formation of a coacervate Reduced to 5 ° C. to gel the coacervate, and 10% sodium hydroxide solution was added to bring the pH to 9.5. Then 12.5 ml of a 37% formaldehyde solution were added to make the coacervate shell harder The product obtained is filtered off from the mixture for 5 hours, washed and cold-dried at 40 ° C. (probably −40 ° C.) and a 0.01 mm mercury vacuum

Die Verfahren der Beispiele 1 bis 5 können auch mit anderen Verdickungsmitteln fur die hydrophile Flüssigkeit, wie früher schon erwähnt, durchgeführt werden, welche der äußeren Phase die Eigenschaften verleihen, welche dem Koazervat die Ablagerung ermöglichen Speziell können beispielsweise äquivalente Mengen von Akaziengummi, Tragant, Carboxymethylcellulose, Magnesiumalummiumsilikat, die Polyglycole, Glycerin, Sirups u dgl. verwendet werdenThe procedures of Examples 1 to 5 can also with other thickeners for the hydrophilic liquid, as mentioned earlier which give the outer phase the properties which give the coacervate the deposit enable Specifically, for example, equivalents Amounts of acacia, tragacanth, carboxymethyl cellulose, magnesium aluminum silicate, the Polyglycols, glycerin, syrups and the like can be used

Claims (1)

PatentanspruchClaim Verfahren zum Herstellen von Mikrokapseln, die eine Emulsion von Ol in emer hydrophilen Flüssigkeit enthalten, durch einfache Koazervierung mit einem gelierbaren hydrophilen Kolloid durch Zugabe emer wäßrigen Elektrolytlosung . oder einer wasserlöslichen Flüssigkeit, in der das Kolloid weniger löslich ist als in Wasser, dadurch gekennzeichnet, daß man der hydrophilen Phase der Emulsion und gegebenenfalls der wäßrigen Elektrolytlosung em übliches Verdickungsmittel zusetzt und koazerviertProcess for producing microcapsules which contain an emulsion of oil in a hydrophilic liquid by simple coacervation with a gellable hydrophilic colloid by adding an aqueous electrolyte solution. or a water-soluble liquid in which the colloid is less soluble than in water, characterized in that a customary thickener is added to the hydrophilic phase of the emulsion and optionally to the aqueous electrolyte solution and coacervated In Betracht gezogene Druckschriften-USA -Patentschriften Nr. 2 800 457, 2 800 458Contemplated Publications USA Patent Nos. 2,800,457, 2,800,458 Bei der Bekanntmachung der Anmeldung sind Mikrophotos und Beschreibung dazu ausgelegt wordenWhen the application was announced, photomicrographs and description were laid out 709 638/481 8 67 © Bundesdruckerei Berlin709 638/481 8 67 © Bundesdruckerei Berlin
DE1959U0006753 1958-12-22 1959-12-18 Process for the production of microcapsules from an emulsion of oil in a hydrophilic liquid Pending DE1248015B (en)

Applications Claiming Priority (1)

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US78192558A 1958-12-22 1958-12-22

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BR (1) BR5915726D0 (en)
CH (1) CH395940A (en)
DE (1) DE1248015B (en)
GB (1) GB929402A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3615514A1 (en) * 1985-05-08 1986-11-13 Lion Corp., Tokio/Tokyo MICROCAPSULES CONTAINING AQUEOUS AGENT AND METHOD FOR THE PRODUCTION THEREOF
US4908233A (en) * 1985-05-08 1990-03-13 Lion Corporation Production of microcapsules by simple coacervation

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS60100516A (en) * 1983-11-04 1985-06-04 Takeda Chem Ind Ltd Preparation of sustained release microcapsule
EP0190833B1 (en) * 1985-02-07 1991-03-27 Takeda Chemical Industries, Ltd. Method for producing microcapsule
TW333456B (en) 1992-12-07 1998-06-11 Takeda Pharm Ind Co Ltd A pharmaceutical composition of sustained-release preparation the invention relates to a pharmaceutical composition of sustained-release preparation which comprises a physiologically active peptide.
DK0730406T3 (en) * 1993-11-15 1999-06-28 Zeneca Ltd Microcapsules containing suspensions of biologically active compounds
US5846554A (en) * 1993-11-15 1998-12-08 Zeneca Limited Microcapsules containing suspensions of biologically active compounds and ultraviolet protectant
US5993842A (en) * 1994-12-12 1999-11-30 Zeneca Limited Microcapsules containing suspensions of biologically active compounds
FR3046088B1 (en) 2015-12-28 2018-01-19 Capsulae MICROCAPSULE COMPRISING A MEMBRANE FROM A COMPLEX COOPERATION MICROENCAPSULATION, AND PROCESS FOR OBTAINING THE SAME

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2800457A (en) * 1953-06-30 1957-07-23 Ncr Co Oil-containing microscopic capsules and method of making them
US2800458A (en) * 1953-06-30 1957-07-23 Ncr Co Oil-containing microscopic capsules and method of making them

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2800457A (en) * 1953-06-30 1957-07-23 Ncr Co Oil-containing microscopic capsules and method of making them
US2800458A (en) * 1953-06-30 1957-07-23 Ncr Co Oil-containing microscopic capsules and method of making them

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3615514A1 (en) * 1985-05-08 1986-11-13 Lion Corp., Tokio/Tokyo MICROCAPSULES CONTAINING AQUEOUS AGENT AND METHOD FOR THE PRODUCTION THEREOF
US4777089A (en) * 1985-05-08 1988-10-11 Lion Corporation Microcapsule containing hydrous composition
US4908233A (en) * 1985-05-08 1990-03-13 Lion Corporation Production of microcapsules by simple coacervation

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GB929402A (en) 1963-06-19
CH395940A (en) 1965-07-31
BR5915726D0 (en) 1973-05-29

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