FR2859479A1 - CHITOSAN GRANULE FOR DIETETIC, FOOD OR PHYTOSANITARY PURPOSES - Google Patents

CHITOSAN GRANULE FOR DIETETIC, FOOD OR PHYTOSANITARY PURPOSES Download PDF

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Publication number
FR2859479A1
FR2859479A1 FR0310538A FR0310538A FR2859479A1 FR 2859479 A1 FR2859479 A1 FR 2859479A1 FR 0310538 A FR0310538 A FR 0310538A FR 0310538 A FR0310538 A FR 0310538A FR 2859479 A1 FR2859479 A1 FR 2859479A1
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granule
chitosan
active ingredient
food
natural polymer
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FR2859479B1 (en
Inventor
Yann Gourdel
Jacqueline Tronel
Bernard Grandmontagne
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OLIGOCAPS LAB
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OLIGOCAPS LAB
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Priority to FR0310538A priority Critical patent/FR2859479B1/en
Priority to EP04787303A priority patent/EP1730217A2/en
Priority to PCT/FR2004/002248 priority patent/WO2005023929A2/en
Publication of FR2859479A1 publication Critical patent/FR2859479A1/en
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J3/00—Processes of treating or compounding macromolecular substances
    • C08J3/12—Powdering or granulating
    • 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
    • A01N25/08—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 containing solids as carriers or diluents
    • A01N25/10—Macromolecular compounds
    • 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
    • A01N25/12—Powders or granules
    • 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
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
    • A23L29/20—Foods or foodstuffs containing additives; Preparation or treatment thereof containing gelling or thickening agents
    • A23L29/275—Foods or foodstuffs containing additives; Preparation or treatment thereof containing gelling or thickening agents of animal origin, e.g. chitin
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L5/00—Compositions of polysaccharides or of their derivatives not provided for in groups C08L1/00 or C08L3/00
    • C08L5/08—Chitin; Chondroitin sulfate; Hyaluronic acid; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
    • 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
    • A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
    • A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
    • A61K9/167—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction with an outer layer or coating comprising drug; with chemically bound drugs or non-active substances on their surface
    • 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
    • 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
    • A61K9/5073—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 having two or more different coatings optionally including drug-containing subcoatings
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2305/00—Characterised by the use of polysaccharides or of their derivatives not provided for in groups C08J2301/00 or C08J2303/00
    • C08J2305/08—Chitin; Chondroitin sulfate; Hyaluronic acid; Derivatives thereof

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  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Zoology (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Agronomy & Crop Science (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Toxicology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Dentistry (AREA)
  • Wood Science & Technology (AREA)
  • Dispersion Chemistry (AREA)
  • Medicinal Chemistry (AREA)
  • Food Science & Technology (AREA)
  • Nutrition Science (AREA)
  • Medicinal Preparation (AREA)
  • Jellies, Jams, And Syrups (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Cosmetics (AREA)

Abstract

La présente invention concerne une granule composée d'un hydrogel de chitosan séché. Selon l'invention, la granule est recouverte d'une couche d'enrobage constituée d'un polymère naturel.The present invention relates to a granule composed of a dried chitosan hydrogel. According to the invention, the granule is covered with a coating layer consisting of a natural polymer.

Description

La présente invention concerne une granule d'un polymère tel qu'unThe present invention relates to a granule of a polymer such as a

polysaccharide, et en particulier du polyglucosamine ou chitosan.  polysaccharide, and in particular polyglucosamine or chitosan.

Le chitosan est un composé issu du polyacétylglucosamine ou chitine que l'on trouve notamment dans la carapace des crustacés. La chitine est connue pour former des composés complexes avec des molécules organiques ou inorganiques telles que des protéines, du carbonate de calcium, du phosphate de calcium, etc. Cependant, la chitine n'est pas un composé soluble, ce qui limite en général ses applications.  Chitosan is a compound derived from polyacetylglucosamine or chitin found especially in the shell of crustaceans. Chitin is known to form complex compounds with organic or inorganic molecules such as proteins, calcium carbonate, calcium phosphate, and the like. However, chitin is not a soluble compound, which generally limits its applications.

Le chitosan est obtenu en extrayant le groupement acétyle de la chitine par hydrolyse. Le chitosan est un polymère cationique dont la caractéristique majeure est d'être soluble à pH acide situé entre 1 et 6, 5. Le chitosan étant biocompatible et biodégradable, le corps humain ou animal tolère son introduction le temps de son action puis l'élimine. En outre, son action cicatrisante et anticholestérol a également été démontrée. De ce fait, le chitosan trouve application dans des domaines aussi divers que la pharmacie, la médecine et la diététique notamment.  Chitosan is obtained by extracting the acetyl group from chitin by hydrolysis. Chitosan is a cationic polymer whose major characteristic is to be soluble at an acidic pH between 1 and 6.5. Chitosan being biocompatible and biodegradable, the human or animal body tolerates its introduction for the duration of its action and then eliminates it. . In addition, its healing and anticholesterol action has also been demonstrated. As a result, chitosan finds application in fields as diverse as pharmacy, medicine and dietetics in particular.

L'introduction dans le corps humain ou animal de ce polymère nécessite cependant une formulation spécifique. Dans les domaines de l'alimentaire, de la diététique et de la pharmacie, le chitosan est habituellement introduit dans le corps par voie orale sous forme de poudre conditionnée ou sous la forme de gel aqueux.  The introduction into the human or animal body of this polymer, however, requires a specific formulation. In the food, dietetic and pharmacy fields, chitosan is usually introduced into the body orally in the form of a powdered form or in the form of an aqueous gel.

Toutefois, on a pu remarquer que ces formulations du chitosan sont peu efficaces dans certains cas et leurs applications sont limitées.  However, it has been noted that these formulations of chitosan are inefficient in some cases and their applications are limited.

Le but de l'invention est donc de proposer une nouvelle formulation du chitosan n'ayant pas les inconvénients précédemment cités.  The object of the invention is therefore to propose a novel formulation of chitosan that does not have the disadvantages mentioned above.

A cet effet, la présente invention concerne une granule composée d'un hydrogel de chitosan séché et caractérisée en ce qu'elle est recouverte d'une couche d'enrobage 25 constituée d'un polymère naturel.  To this end, the present invention relates to a granule composed of a dried chitosan hydrogel and characterized in that it is covered with a coating layer 25 made of a natural polymer.

Selon une autre caractéristique de l'invention, ladite granule est recouverte d'une couche d'enrobage constituée d'alginate.  According to another characteristic of the invention, said granule is covered with a coating layer consisting of alginate.

Selon une autre caractéristique de l'invention, ladite granule incorpore un principe actif dans l'hydrogel de chitosan.  According to another characteristic of the invention, said granule incorporates an active ingredient in the chitosan hydrogel.

Selon une autre caractéristique de l'invention, ladite granule incorpore un principe actif dans la couche de polymère naturel.  According to another characteristic of the invention, said granule incorporates an active ingredient in the natural polymer layer.

Selon une autre caractéristique de l'invention, un principe actif est déposé entre l'hydrogel de chitosan et la couche de polymère naturel.  According to another characteristic of the invention, an active ingredient is deposited between the chitosan hydrogel and the natural polymer layer.

Selon une autre caractéristique de l'invention, un principe actif est déposé sur la couche de polymère naturel.  According to another characteristic of the invention, an active ingredient is deposited on the natural polymer layer.

Selon une autre caractéristique de l'invention, l'épaisseur des couches de ladite granule est ajustée en fonction du milieu dans lequel ladite granule est destinée à agir de manière à optimiser la libération de son contenu.  According to another characteristic of the invention, the thickness of the layers of said granule is adjusted according to the medium in which said granule is intended to act so as to optimize the release of its contents.

L'invention concerne également l'utilisation d'une granule composée de chitosan recouvert d'alginate et incorporant un principe actif à des fins diététiques, 10 alimentaires ou phytosanitaires.  The invention also relates to the use of a granule composed of chitosan coated with alginate and incorporating an active ingredient for dietary, food or phytosanitary purposes.

Les caractéristiques de l'invention mentionnées ci-dessus, ainsi que d'autres, apparaîtront plus clairement à la lecture de la description suivante d'un exemple de réalisation.  The characteristics of the invention mentioned above, as well as others, will appear more clearly on reading the following description of an exemplary embodiment.

Une granule selon l'invention comporte un coeur composé d'hydrogel de chitosan recouvert sur toute sa surface externe d'une couche d'un polymère naturel, de préférence de l'alginate. D'autres polymères naturels sont par exemple de la carraghénane, de l'agare ou de la cellulose. Cette granule est de préférence fabriquée de la manière suivante. On dispose au départ d'une solution de chitosan de concentration pouvant varier de 0,2 à 10 % du volume total, d'une solution basique de condensation, par exemple une solution de soude caustique et d'une solution d'acide alginique. On fait goutter la solution de chitosan dans la solution basique de condensation. Le milieu basique qui entoure la goutte rend la solution de chitosan qu'elle contient insoluble et provoque sa condensation. Au cours de cette condensation, la goutte forme une granule ou bille d'hydrogel physique de chitosan.  A granule according to the invention comprises a core composed of chitosan hydrogel coated on its entire outer surface with a layer of a natural polymer, preferably alginate. Other natural polymers are, for example, carrageenan, agar or cellulose. This granule is preferably manufactured in the following manner. Initially, a solution of chitosan with a concentration ranging from 0.2 to 10% of the total volume, of a basic solution of condensation, for example a solution of caustic soda and an alginic acid solution, is available. The chitosan solution is dripped into the basic condensation solution. The basic environment surrounding the drop makes the chitosan solution it contains insoluble and causes its condensation. During this condensation, the drop forms a granule or ball of physical hydrogel of chitosan.

L'enveloppe constituant la surface externe de la granule forme une couche protectrice pour l'hydrogel de chitosan qu'elle contient. L'épaisseur de cette enveloppe est déterminée par la concentration de la solution de soude caustique. Cette concentration sera choisie en fonction de la souplesse souhaitée pour les granules et de leurs applications.  The envelope constituting the outer surface of the granule forms a protective layer for the chitosan hydrogel it contains. The thickness of this envelope is determined by the concentration of the caustic soda solution. This concentration will be chosen according to the desired flexibility for the granules and their applications.

Ensuite, la granule formée est plongée dans la solution d'acide alginique afin de la recouvrir d'une seconde enveloppe, en l'occurrence constituée par une couche d'alginate. L'épaisseur de la couche d'alginate va dépendre de la concentration de la solution d'acide alginique. L'épaisseur de la couche sera choisie en fonction de l'application visée. Ces couches donnent à la granule une enveloppe qui peut varier de souple à rigide. Le procédé se poursuit notamment par un séchage de granules ainsi produites.  Then, the granule formed is immersed in the alginic acid solution in order to cover it with a second envelope, in this case consisting of an alginate layer. The thickness of the alginate layer will depend on the concentration of the alginic acid solution. The thickness of the layer will be chosen according to the intended application. These layers give the granule an envelope that can vary from soft to rigid. The process is continued in particular by drying granules thus produced.

Une granule peut incorporer un ou plusieurs principes actifs. L'incorporation d'un principe actif peut être réalisée de quatre manières différentes. La première consiste à incorporer le principe actif, dès le départ, à la solution de chitosan. La seconde consiste à faire migrer par diffusion des principes actifs hydrosolubles dans l'hydrogel de chitosan. La troisième consiste à déposer le principe actif, soit à la surface de l'hydrogel de chitosan, soit à la surface de la granule bicouche. La quatrième méthode consiste à incorporer le principe actif à la solution d'acide alginique de manière à lui faire incorporer la couche d'alginate.  A granule may incorporate one or more active ingredients. The incorporation of an active ingredient can be carried out in four different ways. The first is to incorporate the active ingredient, from the beginning, in the chitosan solution. The second is to diffuse migration of water-soluble active ingredients in the chitosan hydrogel. The third is to deposit the active ingredient, either on the surface of the chitosan hydrogel or on the surface of the bilayer granule. The fourth method consists of incorporating the active ingredient into the alginic acid solution so as to incorporate the alginate layer.

Ainsi, la granule est formée d'une bicouche qui favorise une libération contrôlée d'un ou plusieurs principes actifs incorporés dans les diverses couches ou déposés sur ces couches. A titre d'exemple, on peut choisir de placer un principe actif uniquement dans l'hydrogel de chitosan de manière à ce qu'il soit libéré tardivement après dégradation de la couche d'alginate.  Thus, the granule is formed of a bilayer which promotes a controlled release of one or more active ingredients incorporated in the various layers or deposited on these layers. By way of example, it is possible to choose to place an active ingredient only in the chitosan hydrogel so that it is released late after degradation of the alginate layer.

Une granule selon l'invention trouve application dans les domaines de la diététique, de l'alimentaire et phytosanitaire.  A granule according to the invention finds application in the fields of dietetics, food and phytosanitary.

Claims (1)

4 REVENDICATIONS4 CLAIMS 1) Granule composée d'un hydrogel de chitosan séché, caractérisée en ce qu'elle est recouverte d'une couche d'enrobage constituée d'un polymère naturel.  1) Granule composed of a dried chitosan hydrogel, characterized in that it is covered with a coating layer consisting of a natural polymer. 2) Granule selon la revendication 1, caractérisée en ce qu'elle est recouverte d'une couche d'enrobage constituée d'alginate.  2) Granule according to claim 1, characterized in that it is covered with a coating layer consisting of alginate. 3) Granule selon la revendication 1 ou 2, caractérisée en ce qu'elle incorpore un principe actif dans l'hydrogel de chitosan.  3) Granule according to claim 1 or 2, characterized in that it incorporates an active ingredient in the hydrogel of chitosan. 4) Granule selon l'une des revendications précédentes, caractérisée en ce qu'elle incorpore un principe actif dans la couche de polymère naturel.  4) Granule according to one of the preceding claims, characterized in that it incorporates an active ingredient in the natural polymer layer. 5) Granule selon l'une des revendications précédentes, caractérisée en ce qu'un principe actif est déposé entre l'hydrogel de chitosan et la couche de polymère naturel.  5) Granule according to one of the preceding claims, characterized in that an active ingredient is deposited between the chitosan hydrogel and the natural polymer layer. 6) Granule selon l'une des revendications précédentes, caractérisée en ce qu'un principe actif est déposé sur la couche de polymère naturel.  6) Granule according to one of the preceding claims, characterized in that an active ingredient is deposited on the natural polymer layer. 7) Granule selon l'une des revendications précédentes, caractérisée en ce que l'épaisseur de ses couches est ajustée en fonction du milieu dans lequel ladite granule est destinée à agir de manière à optimiser la libération de son contenu.  7) Granule according to one of the preceding claims, characterized in that the thickness of its layers is adjusted according to the medium in which said granule is intended to act so as to optimize the release of its contents. 8) Utilisation d'une granule composée de chitosan recouvert d'alginate et incorporant un principe actif à des fins diététiques, alimentaires ou phytosanitaires.  8) Use of a granule composed of chitosan coated with alginate and incorporating an active ingredient for dietary, food or phytosanitary purposes.
FR0310538A 2003-09-05 2003-09-05 CHITOSAN GRANULE FOR DIETETIC, FOOD OR PHYTOSANITARY PURPOSES Expired - Fee Related FR2859479B1 (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
FR0310538A FR2859479B1 (en) 2003-09-05 2003-09-05 CHITOSAN GRANULE FOR DIETETIC, FOOD OR PHYTOSANITARY PURPOSES
EP04787303A EP1730217A2 (en) 2003-09-05 2004-09-03 Granule
PCT/FR2004/002248 WO2005023929A2 (en) 2003-09-05 2004-09-03 Granule

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FR0310538A FR2859479B1 (en) 2003-09-05 2003-09-05 CHITOSAN GRANULE FOR DIETETIC, FOOD OR PHYTOSANITARY PURPOSES

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FR2859479A1 true FR2859479A1 (en) 2005-03-11
FR2859479B1 FR2859479B1 (en) 2008-09-19

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Citations (3)

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Publication number Priority date Publication date Assignee Title
WO1999002252A1 (en) * 1997-07-07 1999-01-21 Fmc Biopolymer As Improvements in or relating to capsules
WO2001032751A1 (en) * 1999-10-29 2001-05-10 Cognis Deutschland Gmbh & Co. Kg Method for producing nanoparticulate chitosans or chitosan derivatives
DE10058221A1 (en) * 1999-12-03 2001-07-26 Maik Nicklisch Producing alginate round beads of controlled size or strength for use in detergents, by dripping an alginate solution into a metal ion solution

Family Cites Families (1)

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Publication number Priority date Publication date Assignee Title
IL100096A (en) * 1991-11-20 1996-03-31 Univ Ramot Method for entrapment of active materials in chitosan

Patent Citations (3)

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Publication number Priority date Publication date Assignee Title
WO1999002252A1 (en) * 1997-07-07 1999-01-21 Fmc Biopolymer As Improvements in or relating to capsules
WO2001032751A1 (en) * 1999-10-29 2001-05-10 Cognis Deutschland Gmbh & Co. Kg Method for producing nanoparticulate chitosans or chitosan derivatives
DE10058221A1 (en) * 1999-12-03 2001-07-26 Maik Nicklisch Producing alginate round beads of controlled size or strength for use in detergents, by dripping an alginate solution into a metal ion solution

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
KAZUAKI YAMAGIWA ET AL.: "Formation of Calcium-Alginate on Biocatalyst Immobilization Carrier", JOURNAL OF CHEMICAL INGINEERING OF JAPAN, vol. 25, no. 6, 1992, pages 723 - 728, XP001161189 *
OHYA Y: "RELEASE BEHAVIOUR OF 5-FLUOROURACIL FROM CHITOSAN-GEL MICROSPHERES IMMOBILIZING 5-FLUOROURACIL DERIVATIVE COATED WITH POLYSACCHARIDES AND THEIR CELL SPECIFIC RECOGNITION", JOURNAL OF MICROENCAPSULATION, TAYLOR AND FRANCIS INC. LONDON, GB, vol. 10, no. 1, 1993, pages 1 - 9, XP000334990, ISSN: 0265-2048 *

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