EP1613423A1 - Systeme d'encapsulation - Google Patents

Systeme d'encapsulation

Info

Publication number
EP1613423A1
EP1613423A1 EP04727809A EP04727809A EP1613423A1 EP 1613423 A1 EP1613423 A1 EP 1613423A1 EP 04727809 A EP04727809 A EP 04727809A EP 04727809 A EP04727809 A EP 04727809A EP 1613423 A1 EP1613423 A1 EP 1613423A1
Authority
EP
European Patent Office
Prior art keywords
encapsulation system
polysaccharide
encapsulation
matrix
active ingredient
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.)
Withdrawn
Application number
EP04727809A
Other languages
German (de)
English (en)
Inventor
Rolf Müller
Federico Innerebner
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.)
Innogel AG
Original Assignee
Innogel AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Innogel AG filed Critical Innogel AG
Publication of EP1613423A1 publication Critical patent/EP1613423A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • 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
    • 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
    • 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
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23P—SHAPING OR WORKING OF FOODSTUFFS, NOT FULLY COVERED BY A SINGLE OTHER SUBCLASS
    • A23P10/00—Shaping or working of foodstuffs characterised by the products
    • A23P10/30—Encapsulation of particles, e.g. foodstuff additives
    • 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
    • A61K9/5036—Polysaccharides, e.g. gums, alginate; Cyclodextrin
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
    • A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin

Definitions

  • the invention describes encapsulation systems consisting of particles consisting of a matrix or shell and a phase enclosed therein, the shell being able to be obtained from very low-viscosity, highly concentrated solutions or melts with a varying crystalline fraction and with a varying network density.
  • the encapsulation system is suitable for the encapsulation of medium to low-viscosity liquids, in particular of hydrophobic active ingredients such as, for example.
  • Aromas, fragrances and active pharmaceutical ingredients and, compared to previous encapsulation systems, allows a significantly increased scope of the process parameters, more stable envelopes of the encapsulation systems and a targeted influence on the release characteristics.
  • Flavors and fragrances are usually relatively thin oily liquids, but this condition is unsuitable for many industrial applications. Processes for the encapsulation of these substances have therefore been developed, as a result of which they can be converted into a solid, easily metered form which is readily miscible with other components and, in addition, protection of the sensitive active substances can be obtained. These active ingredients are to be protected from the atmosphere, in particular from oxygen, since oxidation or the like. can lead to rancidity and, conversely, escape of the active substances from the encapsulation system should be prevented as completely as possible. In the case of aromas and fragrances, the loss of even the smallest fraction can have a massive impact on quality, especially the so-called and beloved top notes, which make the active ingredient attractive, are lost too quickly.
  • An encapsulation system is ideally expected to have this form of consistent quality over a longer period of time, to be stable during a storage period and during transport, later processing steps such as preparation with other components, whereby the particles are solid to liquid substances, temperature, pressure and can be subjected to shear forces, can pass through unimpaired and the active substance is released exactly when the consumer expects it and in particular is released in a manner that the consumer desires.
  • a soup or should then fully develop its aroma when it is served and does not lose its charm while cooking, chewing gum should keep freshness and taste over a longer period of time and not become unattractive after a minute. Fragrances are also expected to please us freshly and pleasantly over a longer period of time. The release of the active ingredient from the particle should therefore be able to take place in a controlled manner, the spectrum of the requirements ranging from fast and intensive to slow and constant.
  • the matrix or coating materials mentioned are extremely hydrophilic, so that their water content increases with the air humidity and tackiness arises, which leads to lump formation and impairment of the free-flowing properties.
  • Other problems with standard technology are that the emulsions have very high water content have to be evaporated, the often heat-sensitive active ingredients suffering or escaping and porosity arises.
  • the high water content of the emulsions is due to the fact that the generally low viscosity of the dispersed phase of the active ingredient in emulsions must be of the same order of magnitude in comparison with the viscosity of the matrix. Since the matrix consists of a solution or melt of polysaccharides, i.e. macromolecules, their viscosity is comparatively high.
  • polysaccharides and sugars As with most previous encapsulation systems, a matrix consisting of polysaccharides and sugars is obtained.
  • the polysaccharides used differ from the polysaccharides used hitherto in that they partially crystallize and form networks in that various crystallites are connected to one another by macromolecule segments.
  • the property for forming networks or gels is a typical property of many polysaccharides, but longer-chain polysaccharides are required for this, which have at least a proportion of linear chain segments. With the chain length, however, the viscosity of aqueous solutions and melts of such polysaccharides increases disproportionately, while the encapsulation technologies require the lowest possible viscosity.
  • the encapsulation systems according to the invention have the common feature that the matrix has at least one specific type of polysaccharides.
  • a polysaccharide P1 which has a low degree of branching, is most preferably completely linear and has a degree of polymerization DP> 7 and ⁇ 100, preferably ⁇ 70, more preferably ⁇ 50, most preferably ⁇ 30.
  • Such polysaccharides can crystallize very well.
  • the solutions bsw. at a DP of 50 even very low at concentrations of 50% and more Viscosities and they are at least metastable at moderate temperatures.
  • setting low viscosities of the matrix is unproblematic even at high concentrations, ie with advantageously low water contents.
  • the polysaccharide P1 crystallizes in the form of nano- and microcrystallites, which agglomerate and form a shell around the enclosed active ingredient phase.
  • the sorption isotherm of the nano- and microcrystalline agglomerates is much flatter than the sorption isotherms of predominantly amorphous polysaccharides, with increasing humidity, much less water is absorbed and no stickiness occurs even at very high humidity levels.
  • the agglomerates of the nano- and microscrystallites disintegrate, which releases the active ingredient.
  • the atmosphere and active ingredient are largely determined by the parameters of the drying process of the aqueous matrix, in particular the temperature and the drying speed, on the other hand, the use of other substances can be used to influence it, which enables specific control of the quality of the encapsulation systems. These other substances are divided into three groups.
  • At least one further polysaccharide P2 can be used for the matrix having at least one polysaccharide P1, which is preferably short-chain, that is to say low-viscosity in the solution or melt, such as, for example.
  • Dextrins or maltodextrins with a correspondingly high dextrose equivalent DE and is characterized in that it forms a predominantly amorphous phase in the solid state.
  • the polysaccharide P2 for example, From the range of polysaccharides previously used for encapsulation systems, those types are selected which are preferred with regard to the requirement for a low viscosity of the matrix in the state of the solution or melt.
  • phase separation of P1 and P2 takes place at least partially in the matrix.
  • the extent of phase separation depends on the structure sizes of P2, on the ratio of the molecular weights of P1 and P2, and on the drying parameters.
  • a high irregularity of the steric structure of P2, such as a high degree of branching, the bsw. with dextrins can be »5% or modifications such as substitution of hydroxyl groups, a large difference in molecular weights and a low drying rate promote phase separation, which can be controlled using these parameters.
  • a portion of an amorphous phase consisting of P2 is obtained.
  • This proportion can be determined by the recipe with the proportion A2 to P2.
  • the compactness of the particle shell can be positively influenced by lowering the porosity of the nano- and microcrystalline agglomerates of P1 and the amorphous phase acting as an adhesive between P1 crystallites and crystallite agglomerates.
  • the sensitivity of the matrix to temperature and humidity increases with the proportion of P2.
  • polysaccharides can be included in crystallites of P1, but sequences S2 of P2 are preferably incorporated regularly into the crystallites of P1.
  • the condition for this is the presence of sequences S2 with a degree of polymerization DP> 7, preferably> 10, more preferably> 12, these sequences being linear, composed of the same monomer units as P1 and not modified.
  • This condition is for bsw. fulfilled by many dextrins and maltodextrins, whereby the sequences mostly represent regular side chains.
  • the part of the P2 macromolecule leading away from the side chain or the two parts of P2 leading away from the sequence S2 are then components of the amorphous phase consisting of further macromolecules P2.
  • At least one further polysaccharide P3 can be used for the matrix having at least one polysaccharide P1, optionally at least one second polysaccharide P2, which is characterized in that it has a sequence with DP> 100 and / or at least two sequences of the type S2.
  • P3 can thus be a long chain amylose (LCA) with DP> 100 or a dextrin or maltodextrin with at least two side chains of type S2.
  • LCA long chain amylose
  • the relationships explained above can also be applied analogously to mixtures of P1 and P3, apart from an essential difference.
  • the stability to the temperature and the humidity is increased in systems containing a polysaccharide P3 in addition to the polysaccharide P1 compared to systems containing a polysaccharide P2 in addition to the polysaccharide P1, in particular with regard to the stickiness.
  • the properties of network matrices are in turn primarily determined by the drying conditions, in particular the drying speed, the degree of coupling decreasing with the same formulation as the drying speed increases.
  • the degree of coupling increases with the proportion of prerequisite sequences of P3.
  • gelling dextrins also meet the specified conditions. LCA is preferably used in small proportions, since solutions of it quickly become unstable with increasing concentration at moderate temperatures and, in addition, the viscosity increases disproportionately quickly at DP> 100.
  • Gelling dextrins form relatively stable solutions and melts even at high concentrations at moderate temperatures, but their molecular weight and thus their viscosity in the solution or melt is generally higher than the viscosity of non-gelling, conventional dextrins and their proportion must therefore be kept low ,
  • the P3 polysaccharides do not necessarily have to be able to gel with themselves, as is the case with LCA and gelling dextrins.
  • polysaccharides P1 are used and, in combination with dextrins and maltodextrins, which do not show any gelation even in high concentrations, advantageous networks can be obtained for the present invention of novel encapsulation systems, the outstanding feature of which is that they also consist of very low-viscosity solutions and melts with high concentrations of P1 and P2 and / or P3 can be obtained, the viscosity of which can be adjusted to a few cP at room temperature. So that the basic requirement regarding the viscosity in the production of emulsions, according to which the viscosities of the two phases must be of approximately the same order of magnitude must be met well.
  • the active ingredients used for the encapsulation typically have viscosities in the range of 0.1-100 cP at room temperature.
  • the statements regarding encapsulation systems are basically valid for any polysaccharides P1, P2 and P3, provided that they each belong to the same group or at least closely related groups of polysaccharides, meet the specified conditions and can be usefully used in solution or melt due to their low viscosity.
  • the polysaccharides P1, P2 and P3 are preferably selected from the range of starches, since the types required are commercially available in various grades, in particular also in food quality. In addition, these starches are significantly cheaper than other polysaccharides.
  • starches of the types P2 and P3 are also available, which are partially lipophilically modified (octenyl succinates), thus the emulsifier is already contained in the starch for the production of emulsions with oily active ingredients.
  • the encapsulation systems according to the invention are notable for high stability with respect to temperature and atmospheric humidity and with respect to the stress during processing with further components.
  • the stickiness of the particles can be significantly reduced and shifted to significantly higher atmospheric humidity, so that under most conditions measures to protect against moisture and / or temperature are no longer necessary or at least significantly facilitated.
  • the barrier effect of the matrix against the active ingredient can be increased compared to previous methods and can be optimized in a targeted manner due to the flexibility of the system.
  • the requirement for a very low viscosity of the aqueous solution or melt forming the matrix has massively restricted the scope of the formulation and process, this requirement even accommodates the circumstances of the invention in that the most important component of formulations according to the invention, the polysaccharide 1, naturally has a deep one Molecular weight in the range of mono- and oligomers and thus highly concentrated aqueous solutions from P1 to above 50% are possible at moderate temperatures in the range of a few cP. The scope for further components could thus be increased.
  • the use of higher molecular weight and higher viscous substances than previously customary has become possible, which gives the optimization of various other properties new degrees of freedom.
  • an encapsulation system can be set by means of the selection of P1 and / or P2 and the proportion of these polysaccharides in such a way that a developed network gives the particle shell greater strength and the solubility in water is reduced by the crystalline proportion.
  • a later thermal treatment such as. better protection of the aroma can then be ensured in a cooking extrusion process.
  • Networks of the matrix that are less developed are suitable, for example. for encapsulation systems from aromas in use for bag soups with an improved aroma experience by triggering the release of the aroma by optimizing the swelling time of the network forming the particle shell to the period after cooking. In this way, aroma intensity and freshness can be gained.
  • Matrices with a high degree of coupling and low degree of swelling are suitable, for example.
  • the degree of crosslinking of the matrix can even be increased to such an extent that release is not possible even after the particle shell has swelled, since the degree of swelling is too deep and the shell is too hard.
  • a matrix of 0.5 mm in diameter such as “Max-Trix” can even withstand digestion for about an hour.
  • the digestion time in the mouth can be varied over a wide range by controlling the Network density and particle size can be set.
  • the aroma set and a spectrum of a particle size distribution of the encapsulation system can thus produce a rapid aroma flash, which is followed by an increasingly surprising because of the unusually long lasting reverberation, in the end the aroma experience could say goodbye with a last wave.
  • the encapsulation material system according to the invention can be produced using the various existing manufacturing processes. Previous process limits can be expanded, improved protective properties of the active ingredient, more homogeneous distributions and / or higher loading levels can be achieved. In addition, new, simpler and cheaper methods can be used which, due to the viscosity problem, could previously only be used to a very limited extent, for example droplet granulation (Droppo method).
  • the condition for the viscosity of the emulsion is ⁇ 500 cP. This condition can easily be met with the emulsions used for the encapsulation systems according to the invention.
  • Another possibility for encapsulation opens up with the Centrifugal Extrusion Device bsw. described in US 3,015,128.
  • Short chain amylose with DP ⁇ 20 was dissolved in a concentration of 50% in one; with regard to advantageous solution methods, reference is made to patent application WO 03/035026 A2, which is hereby included.
  • the clear solution obtained was then brought to a temperature of 70 ° C., the viscosity was determined by pouring the solution through a funnel heated to 70 ° C. The flow time for 25 ml of the solution was 3.1 seconds. The flow time of water through the same funnel heated to 25 ° C was stopped at 1.8 seconds. From this, the known viscosity of water of 0.89cP at 25 ° C was obtained in good approximation for the viscosity of the solution of P1 with 0.89x (3.1 / 1.8) cP ⁇ 1.5cP.
  • the solution remained stable at 70 ° C for a few minutes, ie clear and transparent. Then cloudiness set in. As it cooled further, the solution became increasingly opaque and finally a white paste. By diluting this paste with water, crystallites and crystallite agglomerates could be seen under the microscope to be watched. The size of the crystallites decreased with increasing cooling rate.
  • solutions of various dextrins and maltodextrins as well as of octenyl succinates could sometimes be prepared at room temperature.
  • Potato starch, tapioca starch, waxy corn starch examined. The solutions were tempered at 60 ° C. and then cooled to 25 ° C. Analog solutions were produced with different proportions of solutions in SCA, the SCA solution being stirred into the P2 and / or P3 solution using a magnetic stirrer.
  • the corresponding starch derivatives could thus be identified as type 3 polysaccharides.
  • the gel formation times could be varied within a period of seconds to days by the proportion of SCA.
  • the gel formation times were also heavily dependent on the starch derivative, with the proportion of SCA remaining the same.
  • the gel formation times were shorter for starch derivatives with higher viscosity, but exceptions were also found for starch derivatives which showed structural properties that are advantageous for heterocrystallization with SCA.
  • the gels could also be obtained in a wide range of gel strengths, resulting in delicate gels that could already be damaged by touch and various intermediate stages up to gels with strengths in the range of 1 Pa.
  • the correlation between the SCA content of gels and their stickiness could be clearly determined, even with a water content of 50% practically no stickiness could be found with the stronger gels.
  • the digestion kinetics experiments were carried out with a standardized solution (Megazyme) of porcine pancreatic alpha amylase on dried particles ground to a range of grain sizes in a shaking bath at 37 ° C, the weight loss of the particles being examined as a function of the digestion time. As an extreme value, a weight loss of 50% was measured after around 4 hours with a grain size of 0.7 - 1.0mm. Overall, a clear correlation with the proportion of SCA and the gel strength was found.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Environmental Sciences (AREA)
  • Dispersion Chemistry (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Toxicology (AREA)
  • Dentistry (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Agronomy & Crop Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Medicinal Chemistry (AREA)
  • Epidemiology (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • General Preparation And Processing Of Foods (AREA)
  • Jellies, Jams, And Syrups (AREA)
  • Cosmetics (AREA)
  • Manufacturing Of Micro-Capsules (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)

Abstract

L'invention concerne des systèmes d'encapsulation obtenus à partir de particules constituées d'une matrice ou d'une enveloppe et d'une phase enfermée dans ces dernières. L'enveloppe peut être obtenue à partir de solutions de très basse viscosité, très concentrées, et de matières fondues présentant une fraction cristalline variable et une densité de réticulation variable. Ce système d'encapsulation est approprié pour l'encapsulation de liquides moyennement à faiblement visqueux, notamment de substances actives hydrophobes, telles que des arômes, des matières odoriférantes et des principes actifs pharmaceutiques. Ledit système d'encapsulation permet, par rapport aux systèmes d'encapsulation connus, d'accroître considérablement la marge de manoeuvre pour les paramètres de procédé, d'améliorer la stabilité des enveloppes et d'influer de manière ciblée sur les caractéristiques de libération.
EP04727809A 2003-04-17 2004-04-16 Systeme d'encapsulation Withdrawn EP1613423A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE10318040 2003-04-17
PCT/CH2004/000235 WO2004091770A1 (fr) 2003-04-17 2004-04-16 Systeme d'encapsulation

Publications (1)

Publication Number Publication Date
EP1613423A1 true EP1613423A1 (fr) 2006-01-11

Family

ID=33185696

Family Applications (1)

Application Number Title Priority Date Filing Date
EP04727809A Withdrawn EP1613423A1 (fr) 2003-04-17 2004-04-16 Systeme d'encapsulation

Country Status (3)

Country Link
US (1) US20060222766A1 (fr)
EP (1) EP1613423A1 (fr)
WO (1) WO2004091770A1 (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102006021280A1 (de) 2006-05-05 2007-11-08 Innogel Ag Modifiziertes Mogul Verfahren
MX2012010554A (es) * 2010-03-31 2012-10-05 Firmenich & Cie Preparacion de capsulas solidas que comprenden sabores.
US8495971B2 (en) * 2010-12-08 2013-07-30 The Clorox Company Animal litter comprising a surfactant encapsulated fragrance nanoemulsion

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5858146A (ja) * 1981-10-05 1983-04-06 Tanabe Seiyaku Co Ltd 速放性マイクロカプセル
US5741521A (en) * 1989-09-15 1998-04-21 Goodman Fielder Limited Biodegradable controlled release amylaceous material matrix
US5215757A (en) * 1991-03-22 1993-06-01 The Procter & Gamble Company Encapsulated materials
US5487419A (en) * 1993-07-09 1996-01-30 Microcell, Inc. Redispersible microdenominated cellulose
WO1999034780A1 (fr) * 1998-01-12 1999-07-15 Bühler AG Procede et dispositif pour encapsuler des principes actifs
SE517421C2 (sv) * 2000-10-06 2002-06-04 Bioglan Ab Mikropartiklar, lämpade för parenteral administration, väsentligen bestående av stärkelse med minst 85 % amylopektin och med reducerad molekylvikt, samt framställning därav

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2004091770A1 *

Also Published As

Publication number Publication date
WO2004091770A1 (fr) 2004-10-28
US20060222766A1 (en) 2006-10-05

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