FR2570604A1 - New method of encapsulation of volatile substances and phyto-aromatic compositions thereby obtained - Google Patents

New method of encapsulation of volatile substances and phyto-aromatic compositions thereby obtained Download PDF

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Publication number
FR2570604A1
FR2570604A1 FR8414653A FR8414653A FR2570604A1 FR 2570604 A1 FR2570604 A1 FR 2570604A1 FR 8414653 A FR8414653 A FR 8414653A FR 8414653 A FR8414653 A FR 8414653A FR 2570604 A1 FR2570604 A1 FR 2570604A1
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Prior art keywords
micro
granules
solution
essence
gelatin
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FR8414653A
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French (fr)
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FR2570604B1 (en
Inventor
Daniele Fredj
Francois Dietlin
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PHARMEDIS SA
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PHARMEDIS SA
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    • 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
    • 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
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/70—Fixation, conservation, or encapsulation of flavouring agents
    • A23L27/72—Encapsulation
    • 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
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/92—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
    • A61K8/922—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof of vegetable origin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q13/00—Formulations or additives for perfume preparations
    • 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
    • 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

Abstract

The invention relates to the field of aromatic products, and especially to that of aromatherapy. The invention relates to a new method of encapsulation of solid or liquid volatile products, which consists in dispersing one or more volatile products in a solution of gelatin, in carrying out coacervation of the globules and in tanning the shell of these globules with formaldehyde. The microgranules thereby obtained find application as an aromatising agent or as a means of preservation of volatile products.

Description

Nouveau procédé d'encapsulation de substances volatiles et compositions phyto-aromatiques ainsi obtenues.New process for encapsulating volatile substances and phyto-aromatic compositions thus obtained.

La présente invention se rapporte à un nouveau procédé permettant d'amener des produits volatils sous une forme stable facilement manipulable et utilisable.The present invention relates to a new process for bringing volatile products in a stable form which is easy to handle and use.

Elle a plus particulièrement pour objet un procédé permettant d'amener des produits volatils , notamment des produits liquides, sous une forme pulvérulente qui peut ensuite être répartie en doses unitaires.It relates more particularly to a process for bringing volatile products, in particular liquid products, in a pulverulent form which can then be divided into unit doses.

Elle a spécifiquement pour objet un nouveau procédé d'encapsulation de produits volatils qui consiste à disperser dans une solution de gelatine le produit ou les produits volatils à la température la plus basse possible, à réaliser la coacervation des globules de gelatine par addition d'une solution ionique, à éliminer l'excès de la phase organique non retenue, à tanner l'enveloppe extérieure des globules de gélatine par une solution de formol et à secher les micro-granules ainsi formés à une température égale ou inférieure à 40". It specifically relates to a new process for encapsulating volatile products which consists in dispersing in a gelatin solution the product or volatile products at the lowest possible temperature, in carrying out the coacervation of the gelatin globules by adding a ionic solution, to remove the excess of the organic phase not retained, to tan the outer envelope of the gelatin globules with a formalin solution and to dry the micro-granules thus formed at a temperature equal to or less than 40 ".

Les micro-granules ainsi obtenus se présentent sous forme pulvérulente, fluide. Les micro-granules ne sont pas gras et ne tachent pas le papier. Ils présentent une odeur faible, perceptible seulement en grande quantité.The micro-granules thus obtained are in powder, fluid form. The micro-granules are not greasy and do not stain the paper. They have a weak odor, noticeable only in large quantities.

Les micro-granules peuvent être répartis en doses unitaires, comme dans des gélules ou des cachets, ou mélangés à une poudre inerte.The micro-granules can be distributed in unit doses, as in capsules or cachets, or mixed with an inert powder.

Par pression, ou par compression, ils relâchent leur contenu et dégagent une forte odeur aromatique.By pressure, or by compression, they release their content and give off a strong aromatic odor.

Les produits volatils introduits dans ces micro-granules possèdent une bonne stabilité, puisque l'analyse montre qu'au bout de 18 mois on retrouve encore 70 à 90 7 de la quantité d'essence introduite et que la qualité du produit aromatique ainsi inclus, ne se modifie pas.The volatile products introduced into these micro-granules have good stability, since analysis shows that after 18 months there are still 70 to 90% of the amount of gasoline introduced and that the quality of the aromatic product thus included, does not change.

Le procédé, objet de la présente invention, présente de gros avantages par rapport aux procédés déjà décrits dans la littérature. En particulier, le procédé qui utilise la formation de complexes d'inclusion avec une cyclodextrine, (voir brevet Français 2.496.460), comporte la nécessité d'opérer dans des solvants mixtes où les cyclodextrines sont peu solubles, et où les quantités de produit volatil inclus est faible et souvent variable.The process which is the subject of the present invention has great advantages over the processes already described in the literature. In particular, the process which uses the formation of inclusion complexes with a cyclodextrin (see French patent 2,496,460), involves the need to operate in mixed solvents where the cyclodextrins are not very soluble, and where the quantities of product volatile included is low and often variable.

Le présent procédé se différencie également de celui décrit par Takafumi Ishizaka dans J. Pharm. Sci 72 (1983) 1057.The present process also differs from that described by Takafumi Ishizaka in J. Pharm. Sci 72 (1983) 1057.

Dans ce procédé, la concentration en principe actif occlus dans les micro-sphères est entièrement dépendante de la solubilité dans la solution aqueuse de gélatine. Si le principe actif est peu soluble dans le milieu aqueux, la concentration est toujours faible.- En outre, la coagulation de l'albumine se fait par immersion dans un bain-mar-ie à 85". Ce traitement est incompatible avec la présence d'un produit volatil.In this process, the concentration of active ingredient occluded in the microspheres is entirely dependent on the solubility in the aqueous gelatin solution. If the active principle is poorly soluble in the aqueous medium, the concentration is always low. In addition, the coagulation of albumin is done by immersion in a 85 "water bath. This treatment is incompatible with the presence of a volatile product.

Les micro-granules obtenus selon le procédé de l'invention, trouvent un emploi en aromathérapie, c'est-à-dire dans le traitement des maladies au moyen de produits aromatiques ou d'essences végétales. Ils conviennent en particulier pour le traitement des infections pulmonaires, dans le traitement des rhinopharyngites ou dans le traitement des infections urinaires. Grâce à une posologie simple et facile à appliquer, l'observance du traitement est entièrement satisfaisante.The micro-granules obtained according to the process of the invention find use in aromatherapy, that is to say in the treatment of diseases by means of aromatic products or plant essences. They are particularly suitable for the treatment of pulmonary infections, in the treatment of nasopharyngitis or in the treatment of urinary tract infections. Thanks to a simple and easy to apply dosage, adherence to treatment is entirely satisfactory.

Parmi les essences ou produits aromatiques qu'il est possible d'incorporer dans les micro-granules, selon le procédé de l'invention, on pourra citer : l'essence de Romarin, l'essence de Menthe, l'ssence de Thym, l'essence d'Eucalyptus, l'essence de Sauge, l'essence de Basilic, l'essence de
Bergamote, l'essence de Marjolaine, l'essence d'Estragon, les essences de Lavande, l'essence de Lavandin, l'essence de
Géranium, l'essence de Citron, l'essence de Sarriette, l'essence de Sassafras, l'essence de Cannelle, les essences d'Orange, l'essence de Pin de Sibérie, l'essence de Niouli, l'essence de Santal, l'extrait de Kawa-kawa, l'essence de
Serpolet ou l'essence de Verveine. On peut également y incorporer des huiles comme l'huile d'olive, ou des produits aromatiques comme l'eucalyptol, le santalol, l'essence de chenopode, l'extrait de fougère mâle ou le
Gomenol.Among the essences or aromatic products which it is possible to incorporate into the micro-granules, according to the process of the invention, there may be mentioned: the essence of Rosemary, the essence of Mint, the essence of Thyme, the essence of Eucalyptus, the essence of Sage, the essence of Basil, the essence of
Bergamot, the essence of Marjoram, the essence of Tarragon, the essences of Lavender, the essence of Lavandin, the essence of
Geranium, the essence of Lemon, the essence of Savory, the essence of Sassafras, the essence of Cinnamon, the essences of Orange, the essence of Siberian Pine, the essence of Niouli, the essence of Sandalwood, Kawa-kawa extract, the essence of
Serpolet or the essence of Verbena. It is also possible to incorporate oils such as olive oil, or aromatic products such as eucalyptol, santalol, chenopod essence, male fern extract or
Gomenol.

Les micro-granules peuvent, en outre, contenir un autre principe actif d'action similaire, synergique ou complémentaire et de préférence un principe actif soluble en milieu aqueux qu'il sera possible de dissoudre dans la-solution de gélatine.The micro-granules can, in addition, contain another active principle of similar, synergistic or complementary action and preferably an active principle soluble in aqueous medium which it will be possible to dissolve in the gelatin solution.

D'une manière préférée, chaque présentation unitaire des micro-granules obtenus selon le procédé de l'invention renferme quatre essences végétales différentes et au total 20 mg de produits aromatiques.Preferably, each unit presentation of the micro-granules obtained according to the process of the invention contains four different plant essences and in total 20 mg of aromatic products.

Les exemples suivants illustrent l'invention sans toutefois la limiter.The following examples illustrate the invention without, however, limiting it.

EXEMPLE I
Micro-granules renfermant de l'essence de Romarin.EXAMPLE I
Micro-granules containing Rosemary essence.

On prépare à froid 100 ml d'une solution de gélatine à 5 dans un récipient muni d'un dispositif d'agitation mécanique. On ajoute à cette solution par petites portions 2 g50 d'essence de Romarin, et on maintient l'agitation jusqu'à obtention d'une emulsion fine. On réalise la coacervation des gouttelettes de gélatine par addition d'une solution de sulfate d'ammonium à 25 %. On filtre pour séparer l'excès de phase essentielle qui n'a pas été incluse dans la gelatine et la solution saline. Les micro-granules sont mis ensuite en suspension dans une solution de formol à 40 % pendant 30 mn sous forte agitation puis séparés et sêchés en étuve à une température inférieure à 40 . Cold preparation is made of 100 ml of a 5-gelatin solution in a container fitted with a mechanical stirring device. 2 g50 of Rosemary essence are added to this solution in small portions, and the stirring is continued until a fine emulsion is obtained. The gelatin droplets are coacerved by adding a 25% ammonium sulphate solution. It is filtered to separate the excess essential phase which has not been included in the gelatin and the saline solution. The micro-granules are then suspended in a 40% formalin solution for 30 min with vigorous stirring, then separated and dried in an oven at a temperature below 40.

Les micro-granules se présentent sous forme de petits grains aisèment fluides, de faible odeur aromatique et incolores. The micro-granules are in the form of small, easily flowing grains, with a weak aromatic and colorless odor.

Ils sont mélangés avec 10 % de lactose et sont répartis en gelules renfermant 100 mg de micro-granules
EXEMPLE II
En opérant comme à l'exemple I en utilisant successivement de l'essence de Thym, de l'essence de Menthe poivrée et de l'essence d'Eucalyptus on réalise des micro-granules renfermant les trois essences. On les répartit en gélules d'un poids moyen de 150 mg.They are mixed with 10% lactose and are divided into capsules containing 100 mg of micro-granules
EXAMPLE II
By operating as in Example I using successively the essence of Thyme, the essence of Peppermint and the essence of Eucalyptus, micro-granules containing the three essences are produced. They are divided into capsules with an average weight of 150 mg.

EXEMPLE III
En opérant comme à l'exemple I en utilisant de l'essence de
Chenopode on obtient des micro granules d'essence de Chenopode que l'on répartit en gelules de manière à obtenir une préparation à 10 mg de principe actif par prise unitaire.EXAMPLE III
By operating as in Example I using gasoline of
Chenopode is obtained micro granules of Chenopode essence which are divided into capsules so as to obtain a preparation of 10 mg of active principle per unit dose.

EXEMPLE IV
En opérant comme à l'exemple I en utilisant successivement de l'essence de Thym, l'essence de Sarriette, l'essence de
Marjolaine et l'essence de Basilic on obtient des microgranules que l'on répartit dans des capsules de gélatine à raison de 200 mg de micro-granules par prise unitaire.EXAMPLE IV
By operating as in Example I, successively using the essence of Thyme, the essence of Savory, the essence of
Marjoram and the essence of Basil, we obtain microgranules which are distributed in gelatin capsules at the rate of 200 mg of micro-granules per unit dose.

EXEMPLE V
Dans 100 ml d'une solution de gelatine à 5 % préparée à froid et filtrée on ajoute 1 g50 de Thiocol et 0 g25 de phosphate de codéine hemi-hydraté. On homogènéise jusqu'à complète dissolution. A cette solution on ajoute 1 g75 d'essence d'Eucalyptus sous forte agitation mécanique.EXAMPLE V
In 100 ml of a 5% gelatin solution prepared cold and filtered, 1 g50 of Thiocol and 0 g25 of hemihydrated codeine phosphate are added. It is homogenized until complete dissolution. To this solution is added 1 g75 of Eucalyptus essence with strong mechanical stirring.

On procède ensuite à la réalisation des micro-granules selon le mode opératoire décrit à l'exemple I. Les micro-granules après dilution par du lactose sont répartis dans des gélules. The micro-granules are then produced according to the procedure described in Example I. The micro-granules after dilution with lactose are distributed in capsules.

Claims (7)

REVENDICATIONS 1") Un nouveau procédé d'encapsulation de produits volatils qui consiste à disperser dans une solution de gelatine un ou des produits volatils à la température la plus basse possible, à réaliser la coacervation des globules de gelatine par addition d'une solution ionique, à éliminer l'excès de phase organique non retenue, puis à effectuer le tannage de l'enveloppe externe des globules de gelatine par une solution de formol et à sêcher les micro-granules ainsi formés à une température égale ou inférieure à 40".  1 ") A new process for encapsulating volatile products which consists in dispersing one or more volatile products in a gelatin solution at the lowest possible temperature, in carrying out the coacervation of the gelatin globules by adding an ionic solution, to eliminate the excess of organic phase not retained, then to carry out the tanning of the external envelope of the gelatin globules with a formalin solution and to dry the micro-granules thus formed at a temperature equal to or lower than 40 ". 2") Un procédé selon la revendication 1") dans lequel la solution ionique est une solution concentrée d'un sulfate, d'un phosphate ou d'un nitrate de métal alcalin. 2 ") A method according to claim 1") wherein the ionic solution is a concentrated solution of an alkali metal sulfate, phosphate or nitrate. 3 ) Un procédé selon la revendication 1") dans lequel le tannage est effectué par une solution aqueuse de formol à 40 %. 3) A method according to claim 1 ") in which the tanning is carried out with an aqueous 40% formalin solution. 4 ) Un procédé selon la revendication 1") dans lequel le sêchage des micro-granules est effectué dans une enceinte sous pression réduite à une température comprise entre 35 et 40".  4) A method according to claim 1 ") in which the drying of the micro-granules is carried out in an enclosure under reduced pressure at a temperature between 35 and 40". 5 ) Les micro granules obtenus selon le procédé de la revendication 1").  5) The micro granules obtained according to the process of claim 1 "). 6 ) Les micro granules obtenus selon le procédé de la revendication 1") renfermant de un à quatre principes aromatiques. 6) The micro granules obtained according to the process of claim 1 ") containing from one to four aromatic principles. 7 ) Les micro granules selon l'une des revendications 5 ) ou 6 ) renfermant en outre un autre principe actif soluble en milieu aqueux d'action similaire, synergique ou complémentaire.  7) The micro granules according to one of claims 5) or 6) further containing another active ingredient soluble in an aqueous medium of similar, synergistic or complementary action.
FR8414653A 1984-09-25 1984-09-25 NEW PROCESS FOR THE ENCAPSULATION OF VOLATILE SUBSTANCES AND THE PHYTO-AROMATIC COMPOSITIONS THUS OBTAINED Expired FR2570604B1 (en)

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Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4914084A (en) * 1984-05-09 1990-04-03 Synthetic Blood Corporation Composition and method for introducing heme, hemoproteins, and/or heme-hemoprotein complexes into the body
FR2676361A1 (en) * 1991-05-17 1992-11-20 Oreal Process for enhancing the activity of a rosemary extract constituting an active ingredient in a composition for cosmetic and/or dermopharmaceutical use and composition for carrying out the aforementioned process
WO1993019622A2 (en) * 1992-03-30 1993-10-14 Tastemaker Heat-stable and fracturable spray-dried free-flowing flavor oil capsules, method of making and using in foods
WO1993019621A2 (en) * 1992-03-30 1993-10-14 Tastemaker Aqueous liquid flavor oil capsules, method of making and using in foods
US5286496A (en) * 1991-12-11 1994-02-15 The Procter & Gamble Company Breath protection microcapsules
US5300305A (en) * 1991-09-12 1994-04-05 The Procter & Gamble Company Breath protection microcapsules
WO1995005838A1 (en) * 1993-08-20 1995-03-02 Scottish Agricultural College Beneficial effects of plant volatile oils
WO1997040702A1 (en) * 1996-04-29 1997-11-06 K.U. Leuven Research & Development Oral delivery form having a high absorption efficiency and method for making same
US5759599A (en) * 1992-03-30 1998-06-02 Givaudan Roure Flavors Corporation Method of flavoring and mechanically processing foods with polymer encapsulated flavor oils
WO2004034791A1 (en) * 2002-10-21 2004-04-29 Givaudan Sa Pesticidal compositions
WO2004098318A1 (en) * 2003-05-09 2004-11-18 Givaudan Sa Alginate matrix particles

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE504499C (en) * 1926-10-21 1930-08-04 Curt Von Duhn Process for the representation of liquid bodies in a highly enriched solid form
DE1255081B (en) * 1963-06-10 1967-11-30 Roha Werk Walter Buehner & Co Transfer of oily substances into capsules by spray-drying oil-in-water emulsions
FR2243018A1 (en) * 1973-09-11 1975-04-04 Spiegl Paul Microencapsulation of liquids or solids with gelatine - with addn of aq. tannin solns. to the coacervate to give dry powdery capsules

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE504499C (en) * 1926-10-21 1930-08-04 Curt Von Duhn Process for the representation of liquid bodies in a highly enriched solid form
DE1255081B (en) * 1963-06-10 1967-11-30 Roha Werk Walter Buehner & Co Transfer of oily substances into capsules by spray-drying oil-in-water emulsions
FR2243018A1 (en) * 1973-09-11 1975-04-04 Spiegl Paul Microencapsulation of liquids or solids with gelatine - with addn of aq. tannin solns. to the coacervate to give dry powdery capsules

Cited By (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4914084A (en) * 1984-05-09 1990-04-03 Synthetic Blood Corporation Composition and method for introducing heme, hemoproteins, and/or heme-hemoprotein complexes into the body
FR2676361A1 (en) * 1991-05-17 1992-11-20 Oreal Process for enhancing the activity of a rosemary extract constituting an active ingredient in a composition for cosmetic and/or dermopharmaceutical use and composition for carrying out the aforementioned process
US5300305A (en) * 1991-09-12 1994-04-05 The Procter & Gamble Company Breath protection microcapsules
US5286496A (en) * 1991-12-11 1994-02-15 The Procter & Gamble Company Breath protection microcapsules
US5382424A (en) * 1991-12-11 1995-01-17 The Procter & Gamble Company Breath protection microcapsules
WO1993019621A3 (en) * 1992-03-30 1993-11-25 Tastemaker Aqueous liquid flavor oil capsules, method of making and using in foods
US5759599A (en) * 1992-03-30 1998-06-02 Givaudan Roure Flavors Corporation Method of flavoring and mechanically processing foods with polymer encapsulated flavor oils
WO1993019621A2 (en) * 1992-03-30 1993-10-14 Tastemaker Aqueous liquid flavor oil capsules, method of making and using in foods
WO1993019622A2 (en) * 1992-03-30 1993-10-14 Tastemaker Heat-stable and fracturable spray-dried free-flowing flavor oil capsules, method of making and using in foods
WO1993019622A3 (en) * 1992-03-30 1993-11-25 Tastemaker Heat-stable and fracturable spray-dried free-flowing flavor oil capsules, method of making and using in foods
AU669167B2 (en) * 1992-03-30 1996-05-30 Givaudan-Roure (International) Sa Heat-stable and fracturable spray-dried free-flowing flavor oil capsules, method of making and using in foods
AU669166B2 (en) * 1992-03-30 1996-05-30 Givaudan-Roure (International) Sa Aqueous liquid flavor oil capsules, method of making and using in foods
US5858370A (en) * 1993-08-20 1999-01-12 Scottish Agricultural College Beneficial effects of plant volatile oils
AU693467B2 (en) * 1993-08-20 1998-07-02 Scottish Agricultural College Beneficial effects of plant volatile oils
WO1995005838A1 (en) * 1993-08-20 1995-03-02 Scottish Agricultural College Beneficial effects of plant volatile oils
WO1997040702A1 (en) * 1996-04-29 1997-11-06 K.U. Leuven Research & Development Oral delivery form having a high absorption efficiency and method for making same
WO2004034791A1 (en) * 2002-10-21 2004-04-29 Givaudan Sa Pesticidal compositions
WO2004098318A1 (en) * 2003-05-09 2004-11-18 Givaudan Sa Alginate matrix particles
US8119175B2 (en) 2003-05-09 2012-02-21 Givaudan S.A. Alginate matrix particles

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