DE1248016B - 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 liquidInfo
- Publication number
- DE1248016B DE1248016B DEU6758A DEU0006758A DE1248016B DE 1248016 B DE1248016 B DE 1248016B DE U6758 A DEU6758 A DE U6758A DE U0006758 A DEU0006758 A DE U0006758A DE 1248016 B DE1248016 B DE 1248016B
- Authority
- DE
- Germany
- Prior art keywords
- emulsion
- oil
- hydrophilic liquid
- microcapsules
- production
- 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
Links
- 239000000839 emulsion Substances 0.000 title claims description 13
- 238000000034 method Methods 0.000 title claims description 8
- 239000007788 liquid Substances 0.000 title claims description 4
- 239000003094 microcapsule Substances 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title description 4
- 239000002562 thickening agent Substances 0.000 claims description 7
- 238000005354 coacervation Methods 0.000 claims description 6
- 238000001246 colloidal dispersion Methods 0.000 claims description 2
- 239000003921 oil Substances 0.000 description 9
- 235000019198 oils Nutrition 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- 239000012071 phase Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 239000000203 mixture Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 241000416162 Astragalus gummifer Species 0.000 description 2
- 241000238631 Hexapoda Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 229920001615 Tragacanth Polymers 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 229930182830 galactose Natural products 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229920000609 methyl cellulose Polymers 0.000 description 2
- 239000001923 methylcellulose Substances 0.000 description 2
- 235000010981 methylcellulose Nutrition 0.000 description 2
- 239000007764 o/w emulsion Substances 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000196 tragacanth Substances 0.000 description 2
- 235000010487 tragacanth Nutrition 0.000 description 2
- 229940116362 tragacanth Drugs 0.000 description 2
- 239000011782 vitamin Substances 0.000 description 2
- 229940088594 vitamin Drugs 0.000 description 2
- 229930003231 vitamin Natural products 0.000 description 2
- 235000013343 vitamin Nutrition 0.000 description 2
- DTCCVIYSGXONHU-CJHDCQNGSA-N (z)-2-(2-phenylethenyl)but-2-enedioic acid Chemical compound OC(=O)\C=C(C(O)=O)\C=CC1=CC=CC=C1 DTCCVIYSGXONHU-CJHDCQNGSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 229920000623 Cellulose acetate phthalate Polymers 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 239000005662 Paraffin oil Substances 0.000 description 1
- 241000283984 Rodentia Species 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- SNAAJJQQZSMGQD-UHFFFAOYSA-N aluminum magnesium Chemical compound [Mg].[Al] SNAAJJQQZSMGQD-UHFFFAOYSA-N 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 229940081734 cellulose acetate phthalate Drugs 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000002285 corn oil Substances 0.000 description 1
- 235000005687 corn oil Nutrition 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000000122 growth hormone Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- -1 nematoxides Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229940080817 rotenone Drugs 0.000 description 1
- JUVIOZPCNVVQFO-UHFFFAOYSA-N rotenone Natural products O1C2=C3CC(C(C)=C)OC3=CC=C2C(=O)C2C1COC1=C2C=C(OC)C(OC)=C1 JUVIOZPCNVVQFO-UHFFFAOYSA-N 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
Classifications
-
- 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
- A61K9/5089—Processes
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Agronomy & Crop Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Dispersion Chemistry (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Toxicology (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Manufacturing Of Micro-Capsules (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
DEUTSCHESGERMAN
PATENTAMTPATENT OFFICE
Deutsche Kl.. 12 c - 3German Kl. 12 c - 3
Nummer:
Aktenzeichen:
Anmeldetag.
Auslegetag.Number:
File number:
Filing date.
Display day.
1248016
U6758IVC/12C
19 Dezember 1959
24 August 19671248016
U6758IVC / 12C
19 December 1959
August 24, 1967
Es ist bereits bekannt, sehr kleine, im tnnern Ol enthaltende Teilchen durch Koazervierung einer Mischung, die aus einem wäßrigen Gelatinesol und einer Öl-in-Wasser-Emulsion besteht, herzustellen In dem Ol können noch andere Stoffe gelost oder dispergiert sein. Die USA -Patentschriften 2 800 457 und 2 800 458 beschreiben Verfahren zur Einkapselung von Oltropfchen durch einfache bzw komplexe Koazervierung Obwohl diese Patente die Bildung von Koazervaten aus einer Öl-in-Wasser-Emulsion beschreiben, wird tatsachlich nur die Ölphase vom Koazervat eingekapselt Die Einkapselung einer Emulsion wai bisher nicht versucht worden, und die bedeutenden Vorteile einer mit einem Koazervat überzogenen Emulsion, deren Phasen geloste oder suspendierte Bestandteile enthalten, bis jetzt nicht ei kannt wordenIt is already known, very small, inside oil containing particles by coacervation of a mixture consisting of an aqueous gelatin sol and an oil-in-water emulsion consists in the production of other substances can be dissolved or dissolved in the oil be dispersed. U.S. Patent 2,800,457 and 2,800,458 describe methods for encapsulating oil droplets by simple or complex Coacervation Although these patents involve the formation of coacervates from an oil-in-water emulsion describe, actually only the oil phase is dated Encapsulated coacervate The encapsulation of an emulsion has not yet been attempted and the significant advantages of an emulsion coated with a coacervate, the phases of which are dissolved or contain suspended constituents, not previously known
Erfindungsgegenstand ist ein Verfahren zum Herstellen von Mikrokapseln, die eine Emulsion von Ol in einer hydrophilen Flüssigkeit enthalten, durch emfache Koazervierung Das erfindungsgetnaße Verfahren ist dadurch gekennzeichnet, daß man der hydrophilen Phase der Emulsion ein Verdickungsmittel zusetzt und diese dann in Gegenwart einer wäßrigen kolloidalen-Dispersion eines Styiol-Maleinsaure- oder StyroH\iaJiansauxeamid-tMischpolymerisats oder eines Kohlehydrat-Acetatphthalats koazerviert The subject of the invention is a process for producing microcapsules which contain an emulsion of oil in a hydrophilic liquid, by simple coacervation. The process according to the invention is characterized in that a thickener is added to the hydrophilic phase of the emulsion and this is then added in the presence of an aqueous colloidal dispersion of a styrene-maleic acid or StyroH \ iaJiansauxeamid- t copolymer or a carbohydrate-acetate phthalate coacervated
Das beschriebene Verfahren eröffnet neue Wege bei der Herstellung von impermeablen Überzügen
hoher Starke oder solchen, welche eme langsame Freisetzung von wasserlöslichen Stoßen gestatten, em
Problem, das mit den bisher bekannten Methoden der Koazervierung nicht gelost werden konnte So können
eingekapselte Emulsionspartikeln hergestellt werden, welche in den Emulsionsphasen Stofie als
Düngemittel zu langsamer Freisetzung enthalten, Pflanzenwuchshormone und Schädlingsbekämpfungsmittel,
wie Pilzmittel, Nematoxide, Bakterizide, Virizide u. dgl zur Verwendung in der Landwirtschaft
Weiterhin können Bestandteile vorgemischten Nahrungsmitteln zugesetzt werden, welche infolge
des Trocknungsverfahrens den Nahrungsmitteln normalerweise
nicht beigemischt werden können, wobei die eingekapselten Ingredienzen infolge der Scherkraft
in einer Mischungsstufe vor der tatsachlichen Verwendung freigesetzt werden Gleicherweise können
Vitamine, besonders Zusammensetzungen von wasserlöslichen und olloslichen Vitaminen, trockenen
Zerealienpraparaten zur Freisetzung im Korper zugesetzt
werden Es können kosmetische Mittel hergestellt werden, m weichen das zur lokalen Anwen-Verfahren
zur Herstellung von Mikrokapseln aus einer Emulsion von Öl in einer hydrophilen
Flüssigkeit 1The method described opens up new ways in the production of impermeable coatings of high strength or those which allow eme slow release of water-soluble impacts, a problem that could not be solved with the previously known methods of coacervation the emulsion phases contain substances as fertilizers that are released too slowly, plant growth hormones and pesticides such as fungicides, nematoxides, bactericides, viricides and the like for use in agriculture. the encapsulated ingredients being released due to the shear force in a mixing step prior to actual use. Likewise, vitamins, especially compositions of water-soluble and oil-soluble n Vitamins, dry cereal preparations are added for release in the body. Cosmetic agents can be produced, m soft for local application. Process for the production of microcapsules from an emulsion of oil in a hydrophilic one
Liquid 1
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 the 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
(781926)Claimed priority
V. St ν America of December 22, 1958
(781926)
dung bestimmte Mittel sich in einer undurchlässigen, aber leicht zerstörbaren Koazervatschale befindet Pharmazeutische Stoffe können eingekapselt werden zu langsamer Dauerfreisetzung im Korper nach Kontakt mit einem bestimmten pH-Milieu oder Fermentsystem, oder wo Stabilität, Geruch, Geschmack oder Unvereinbarkeit das Problem bilden Solche Stoffe können in Deckschichten zu oraler, lokaler oder Injektionsverabreichung eingeschlossen werden, indem Partikelgroße, Deckschichtdicke, Permeabilität und Harte oder die Zusammensetzung der Deckschicht entsprechend gewählt werden Insektenvertilgungsmittel, welche gegenüber Insekten selektiv giftig wirken, fur Menschen aber relativ nicht-toxisch sind, können ζ B mit einer Koazervatschicht überzogen werden, welche sehr impermeabel ist, mit Ausnahme gegenüber Insektenfermentencertain means are in an impermeable, but easily destructible coacervate shell located Pharmaceutical substances can be encapsulated too slow sustained release in the body after contact with a certain pH environment or fermentation system, or where stability, smell, taste or Incompatibility form the problem. Such substances can be oral, local or overcoats Injection administration can be included by particle size, coating thickness, permeability and the hardness or the composition of the top layer are chosen accordingly insecticides, which are selectively toxic to insects, but relatively non-toxic to humans B can be coated with a coacervate layer which is very impermeable, with the exception of insect ferments
Mittel gegen Nagetiere, welche bei deren Einnahme wirksam werden, aber durch ihren Geruch abstoßend^ oder warnend wirken, können ebenfalls mit KoaziAgents against rodents, which become effective when ingested, but repellant due to their odor can also act as a warning with Koazi
709 e709 e
vatmembranen überzogen werden, welche praktisch fur den Gebrauch total undurchlässig sindvatmembranen are coated, which are practically completely impermeable for use
Die erfindungsgemaß benutzten Verdickungsmittel sind Stoffe, die im wesentlichen in der Olphase der primären Emulsion unlöslich und befähigt smd, der äußeren hydrophilen Flussigkeitsphase Oberflacheneigenschaften zu verleihen, welche dem Koazervat die Ablagerung darauf erlaubt Die Gegenwart eines oder mehrerer Verdickungsmittel in der erwähnten externen Phase ist eme notwendige Voraussetzung der vorliegenden ErfindungThe thickeners used according to the invention are substances that are essentially in the oil phase of the primary emulsion is insoluble and enables the outer hydrophilic liquid phase to have surface properties which allows the coacervate to deposit on it. The presence of an or several thickeners in the mentioned external phase is a necessary requirement of the present invention
Um aber die Koazervierung erleichtern zu können, verlangen diese Verdickungsmittel die Gegenwart von Ol in der inneren Phase, da eine noch unbekannte Beziehung oder gegenseitige Abhängigkeit zwischen Verdickungsmitteln und den Ölen besteht Verdikkungsmittel sind z. B die natürlichen und kunstlichen Verdickungsmittel, wie Akaziengummi, Tragant, Methylcellulose, Carboxymethylcellulose, Magnesiumaluminiumsihkat, Polyglykole, Glycerin, Syrups Die spezifischen Mengen dieser Stoffe tonnen je nach dem betreffenden Mittel und System variiert werden und können ohne Schwierigkeit mittels Routmeexperunenten bestimmt werden Ein Bereich von 1 bis etwa 20 Gewichtsprozent, bezogen auf das Volumen der hydrophilen Flussigkeitsphase, bildet das praktische Maß, wobei 5 bis etwa 10 Gewichtsprozent in den meisten Fallen bevorzugt werdenBut in order to be able to facilitate coacervation, these thickeners require the presence of oil in the internal phase, as an as yet unknown one There is a relationship or interdependence between thickeners and the oils are z. B the natural and artificial thickeners, such as acacia gum, tragacanth, Methyl cellulose, carboxymethyl cellulose, magnesium aluminum silicate, Polyglycols, glycerin, syrups The specific amounts of these substances depend on the the means and system in question and can be varied without difficulty by means of routine experts A range from 1 to about 20 percent by weight, based on volume the hydrophilic liquid phase, forms the practical level, being 5 to about 10 percent by weight are preferred in most cases
50 g Harnstoff und 10 g Methylcellulose werden in 25 ml Wasser dispergiert und auf 80° C erwärmt. 40 ml Paraffinol werden auf 80° C erwärmt und in die wäßrige Dispersion emulgiert mittels dreimaligem Passieren durch eme Handmischmaschine. 40 g Styrolmaleinsaurecopolymer werden mit 10 g Galactosepolysacchand gemischt und in 650 ml Wasser dispergiert und auf 80° C erwärmt. Die Emulsion und das Copolymersol werden in einem Einzelstrom m 175 ml einer 20%igen Natnumsulfatlosung eingeführt, welche zuvor auf 80° C erwärmt worden war Das Gemisch wird bei 80° C unter starkem Ruhren wahrend 15 Minuten gehalten und dann in eme Losung von 20 ml Eisessig m 500 ml Eiswasser geschüttet Das eingekapselte Material wird dann mittels Zentrifugieren abgetrennt, mit kaltem Wasser gewaschen und getrocknet.50 g of urea and 10 g of methyl cellulose are dispersed in 25 ml of water and heated to 80 ° C. 40 ml of paraffin oil are heated to 80 ° C. and emulsified into the aqueous dispersion by means of three times Passed through a hand mixer. 40 grams of styrene maleic acid copolymer are mixed with 10 g of galactose polysacchand and dispersed in 650 ml of water and heated to 80 ° C. The emulsion and the copolymer sol are in a single stream m 175 ml a 20% sodium sulphate solution introduced, which had previously been heated to 80 ° C. The mixture is kept at 80 ° C. with vigorous stirring Hold for 15 minutes and then poured into a solution of 20 ml of glacial acetic acid m 500 ml of ice water The encapsulated material is then separated by centrifugation, washed with cold water and dried.
100 ml Methylsihkonol werden m eme Losung von
30 g Celluloseacetatphthalat in 600 ml Aceton emulgiert.
Die Emulsion wird auf 30° C erwärmt und unter Ruhren 450 ml einer 2%igen Essigsaurelosung
zugetropft Das Gemisch wird auf Raumtemperatur abgekühlt, die Losung mittels Filtnerens getrennt und
mit l%iger Salzsaure gewaschen
ίο Das getrocknete Produkt kann Lotions fur die
Hände und pharmazeutischen Lokalpraparaten zugesetzt werden, um die Wasserabstoßung dieser
Präparate zu vergrößern, wenn sie auf der Haut
angewendet werden100 ml of methylsihkonol are emulsified with a solution of 30 g of cellulose acetate phthalate in 600 ml of acetone. The emulsion is heated to 30 ° C. and 450 ml of a 2% acetic acid solution are added dropwise with stirring. The mixture is cooled to room temperature, the solution is separated by means of a filter and washed with 1% hydrochloric acid
ίο The dried product can be added to hand lotions and topical pharmaceutical preparations to increase the water repellency of these preparations when applied to the skin
25 g Rotenon und 10 g Tragant werden in 100 ml Glycerm dispergiert und auf 80° C erwärmt. 100 ml Maisöl werden auf 80° C erwärmt und in dieGlycerradispersion emulgiert 100 g Styrolmaleinsaurecopolymer werden mit 20g Galactose-polysacchand vermischt und in 1650 ml Wasser dispergiert und auf 80° C erwannt Die Emulsion und das Copolymersol werden in einem Einzelstrom in 450 ml 2O°/oige Ammonsulfatlösung, welche zuvor auf 80° C erhitzt worden war, eingeführt Das Gemisch wird wahrend 20 Minuten bei 80° C gerührt und dann in eme Losung von 50 ml Eisessig in 3000 ml Eiswasser unter konstantem Ruhren gegossen Das emgekapselte Material wird dann mittels Zentnfugieren abgetrennt, mit Wasser gewaschen und bei 80° C sprühgetrocknet (Auspufftemperatur). 25 g of Rotenone and 10 g of tragacanth are dispersed in 100 ml of Glycerm and heated to 80 ° C. 100 ml Corn oil are warmed to 80 ° C and poured into the glycerine dispersion emulsified 100 g of styrene maleic acid copolymer are mixed with 20 g of galactose polysacchand and dispersed in 1650 ml of water and heated to 80 ° C The emulsion and the copolymer sol are in a single stream in 450 ml of 20% ammonium sulfate solution, which had previously been heated to 80 ° C. The mixture is introduced for 20 minutes stirred at 80 ° C and then in a solution of 50 ml Glacial acetic acid is poured into 3000 ml of ice water with constant stirring. The encapsulated material is then separated by means of centrifuging, washed with water and spray-dried at 80 ° C (exhaust temperature).
Claims (1)
USA -Patentschriften Nr 2 800 457, 2 800 458Considered print sections:
USA Patent Nos. 2,800,457, 2,800,458
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US78192658A | 1958-12-22 | 1958-12-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1248016B true DE1248016B (en) | 1967-08-24 |
Family
ID=25124400
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEU6758A Pending DE1248016B (en) | 1958-12-22 | 1959-12-19 | Process for the production of microcapsules from an emulsion of oil in a hydrophilic liquid |
Country Status (5)
| Country | Link |
|---|---|
| BR (1) | BR5915727D0 (en) |
| CH (1) | CH393274A (en) |
| DE (1) | DE1248016B (en) |
| FR (1) | FR1280583A (en) |
| GB (1) | GB929227A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6566306B1 (en) | 1998-09-05 | 2003-05-20 | Bayer Aktiengesellschaft | Microcapsule formulations |
| US6653256B1 (en) | 1999-08-24 | 2003-11-25 | Bayer Aktiengesellschaft | Microcapsule formulations |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE628650A (en) * | 1962-02-20 | |||
| DE3237814A1 (en) * | 1982-10-12 | 1984-04-12 | Warner-Lambert Co., 07950 Morris Plains, N.J. | WATER-FREE EMULSIONS AND USE THEREOF |
| JPS59166966A (en) * | 1983-03-14 | 1984-09-20 | Fuji Photo Film Co Ltd | Production of capsule toner |
| DE3702029A1 (en) * | 1987-01-24 | 1988-08-04 | Basf Ag | AQUEOUS OR POWDERED, WATER-DISPERSIBLE PREPARATION OF A PHARMACEUTICAL ACTIVE SUBSTANCE IN WATER-SOLUBLE AND METHOD FOR THE PRODUCTION THEREOF |
| US9364422B2 (en) | 2013-12-19 | 2016-06-14 | Avon Products, Inc | Styrene maleic anhydride polymers in cosmetics and personal care products |
| CN114015271B (en) * | 2021-11-25 | 2022-11-08 | 亚士创能科技(上海)股份有限公司 | Water-in-water multicolor paint capable of scraping in batches, preparation method, construction method and application |
Citations (2)
| 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 |
-
1959
- 1959-11-26 GB GB40226/59A patent/GB929227A/en not_active Expired
- 1959-12-18 BR BR115727/59A patent/BR5915727D0/en unknown
- 1959-12-19 DE DEU6758A patent/DE1248016B/en active Pending
- 1959-12-19 CH CH8205659A patent/CH393274A/en unknown
- 1959-12-21 FR FR813660A patent/FR1280583A/en not_active Expired
Patent Citations (2)
| 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 (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6566306B1 (en) | 1998-09-05 | 2003-05-20 | Bayer Aktiengesellschaft | Microcapsule formulations |
| US6653256B1 (en) | 1999-08-24 | 2003-11-25 | Bayer Aktiengesellschaft | Microcapsule formulations |
Also Published As
| Publication number | Publication date |
|---|---|
| BR5915727D0 (en) | 1973-05-29 |
| CH393274A (en) | 1965-06-15 |
| FR1280583A (en) | 1962-01-08 |
| GB929227A (en) | 1963-06-19 |
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| Hofer | Streitfragen zur altfranzösischen Literatur. |