CA2074873C - Seamless capsule and process for producing the same - Google Patents

Seamless capsule and process for producing the same

Info

Publication number
CA2074873C
CA2074873C CA002074873A CA2074873A CA2074873C CA 2074873 C CA2074873 C CA 2074873C CA 002074873 A CA002074873 A CA 002074873A CA 2074873 A CA2074873 A CA 2074873A CA 2074873 C CA2074873 C CA 2074873C
Authority
CA
Canada
Prior art keywords
viscous liquid
solution
film
seamless capsule
water
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.)
Expired - Lifetime
Application number
CA002074873A
Other languages
French (fr)
Other versions
CA2074873A1 (en
Inventor
Yukio Kikuchi
Ryousei Kamaguchi
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.)
Morishita Jintan Co Ltd
Original Assignee
Morishita Jintan Co Ltd
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 Morishita Jintan Co Ltd filed Critical Morishita Jintan Co Ltd
Publication of CA2074873A1 publication Critical patent/CA2074873A1/en
Application granted granted Critical
Publication of CA2074873C publication Critical patent/CA2074873C/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/11—Encapsulated compositions
    • A—HUMAN NECESSITIES
    • 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
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23F—COFFEE; TEA; THEIR SUBSTITUTES; MANUFACTURE, PREPARATION, OR INFUSION THEREOF
    • A23F5/00—Coffee; Coffee substitutes; Preparations thereof
    • A23F5/24—Extraction of coffee; Coffee extracts; Making instant coffee
    • A23F5/243—Liquid, semi-liquid or non-dried semi-solid coffee extract preparations; Coffee gels; Liquid coffee in solid capsules
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61J—CONTAINERS SPECIALLY ADAPTED FOR MEDICAL OR PHARMACEUTICAL PURPOSES; DEVICES OR METHODS SPECIALLY ADAPTED FOR BRINGING PHARMACEUTICAL PRODUCTS INTO PARTICULAR PHYSICAL OR ADMINISTERING FORMS; DEVICES FOR ADMINISTERING FOOD OR MEDICINES ORALLY; BABY COMFORTERS; DEVICES FOR RECEIVING SPITTLE
    • A61J3/00—Devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms
    • A61J3/07—Devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms into the form of capsules or similar small containers for oral use
    • 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
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
    • A61K9/5089—Processes
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
    • 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
    • A61Q19/10—Washing or bathing preparations
    • 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
    • B01J13/04—Making microcapsules or microballoons by physical processes, e.g. drying, spraying
    • 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
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
    • Y10T428/2982—Particulate matter [e.g., sphere, flake, etc.]
    • Y10T428/2984—Microcapsule with fluid core [includes liposome]
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
    • Y10T428/2982—Particulate matter [e.g., sphere, flake, etc.]
    • Y10T428/2984—Microcapsule with fluid core [includes liposome]
    • Y10T428/2985—Solid-walled microcapsule from synthetic polymer
    • Y10T428/2987—Addition polymer from unsaturated monomers only

Abstract

A seamless capsule comprises a content and a film for coating the content. The content is a hydrophilic substance.
A viscous liquid having a viscosity of no more than 1000 cp at 100°C that is scarcely miscible with water is present between the content and the film. A process for producing this capsule comprises simultaneously extruding a film solution for the capsule, a hydrophilic substance solution and the viscous liquid that is scarcely miscible with water into a cooling solution from a concentrically arranged multiple nozzle assembly composed of at least three nozzles, an outermost nozzle, an innermost nozzle and at least one intermediate nozzle between the inner and outer nozzles, the diameter of the nozzles gradually increasing in that order.

Description

~

SEAMLESS CAPSULE AND PROCESS FOR PRODUCING THE SAME
The present invention relates to a seamless capsule containing a hydrophilic substance, and to a process for producing the same.
Regarding seamless capsules that have hitherto been used for various applications, the substances that can be encapsulated are specifically limited to lipophilic substances, such as liquid oil, powder-suspended oil and the like.
Hydrophilic substances are not generally encapsulated, because they employ water as a solvent, which makes the capsules soften on and after encapsulation.
In Japanese Patent Kokai No. 03-52639, there is disclosed a method for encapsulating a hydrophilic substance, wherein a lower fatty acid ester of sucrose is provided between the hydrophilic substance and a film. Although the method produces a seamless capsule containing a hydrophilic substance, there is a problem that the water content of the hydrophilic substance is increasingly transferred to the film in the form of water vapour to soften the capsule or adhere to it, particularly at a high temperature (not less than 30°C). Further, the propagation of mold or bacteria is liable to arise with time due to the water content transferred to the film. There is also a quality problem in design.
One object of the present invention is to provide an excellent method for encapsulating a hydrophilic substance.
Another object of the present invention is to provide a seamless capsule having excellent stability of quality and a high commercial value.
In accordance with one aspect of the present invention there is provided a seamless capsule, comprising: a central core layer comprising a hydrophilic substance dissolved in an alcohol; a film forming an outer wall layer for the capsule;
and a discrete layer of a viscous liquid having a viscosity of not more than 1000 cp at 100°C, said viscous liquid being ~

-la-scarcely miscible with water, wherein said discrete layer of viscous liquid is between said central core and said film.
In accordance with another aspect of the present invention there is provided a process for producing a seamless capsule, comprising: supplying a hydrophilic substance solution to an innermost orifice of a concentrically arranged multiple nozzle comprising at least three orifices; supplying a film solution for the seamless capsule to an outermost orifice of the multiple nozzle;
supplying a viscous liquid which is scarcely miscible with water to an intermediate orifice of the multiple nozzle; and simultaneously extruding the film solution, the viscous liquid and the hydrophilic substance solution into a cooling solution.
These objects as well as other objects and advantages of the present invention will become apparent to those skilled in the art from the following description of an embodiment with reference to the accompanying drawings.
Fig.l is a schematic cross section illustrating one embodiment of a nozzle part of apparatus suitable for producing a seamless capsule according to an embodiment of the present invention.

~o?~~ ~3 The present invention provides a seamless capsule comprising a content and a film for coating said content, said content being a hydrophilic substance dissolved in a solvent having strong hygroscopicity, a viscous liquid having a viscosity of no more than 1000 cp at 100°C that is scarcely miscible with water being present between said content and said film.
Further, the present invention also provides a process for producing a seamless capsule, which process comprises simultaneously extruding a film solution for the capsule, a hydrophilic substance solution and a viscous liquid that is scarcely miscible with water into a cooling solution from a concentrically arranged multiple nozzle assembly composed of at least three nozzles, an outermost nozzle, an innermost nozzle and at least one intermediate nozzle placed between the outer and inner nozzles, the diameter of said nozzles gradually increasing in that order.
In the present invention, the content that can be seamless-encapsulated is not limited to a specific one and can be any one that can dissolve in a solvent having strong hygroscopicity and become a liquid under heating, and can be ejected from a nozzle. Examples thereof include various pharmaceutical solutions, foods, cosmetics, flavours, industrial chemicals and the like.
The solvent having strong hygroscopicity is not specifically limited, and examples thereof include alcohols such as polyethylene glycol, propylene glycol, glycerin, ethanol, methanol and the like.
The film substance of the seamless capsule used in the present invention is not specifically limited and suitable examples thereof include a film-forming substance obtained by treating a composition containing gelatin, agar and low methoxyl pectin or sodium alginate with a compound by which an aqueous solution of low methoxyl pectin or sodium alginate can be gelated: a film-forming substance obtained by subjecting a water-soluble polyvalent alcohol or water-soluble derivative thereof to a gelation treatment; a film-forming substance 3.

obtained by treating a mixture of a composition containing gelatin and agar and a composition containing gelatin and low methoxyl pectin or sodium alginate with a compound by which an aqueous solution of low methoxyl pectin and sodium alginate can be Belated, and the like. Gelatin, agar and water-soluble polyvalent alcohol or a water-soluble derivative thereof having the same grade as that used for producing a conventional capsule may be employed as is.
The water-soluble polyvalent alcohol or water-soluble derivative thereof is not specifically limited and examples thereof include glycerin, polyglycerin, sorbitol, ethylene glycol, polyethylene glycol, propylene glycol, polypropylene glycol, ethylene oxide-propylene oxide copolymer, oligo-saccharide, sugar ester, glyceride, sorbitan ester and the like.
The amount of gelatin to be used is normally 60 to 90% by weight based on the total weight of the capsule film. The amount of agar is 60 to 90% by weight based on the total weight of the capsule film. Suitable low methoxyl pectin is that having a molecular weight of not less than 200,000 and a methoxylation degree of 1 to 6% (preferably 3.5 to 5%) and the amount thereof is 5 to 20% by weight, preferably 10 to 15% by weight based on the total weight of the film. The amount of the water-soluble polyvalent alcohol or water-soluble derivative thereof is l0 to 30% by weight, preferably 15 to 25% by weight based on the total weight of the film. The amount of gelatin is 65 to 75% by weight (in the case of using with agar), 65 to 75% by weight (in the case of using with low methoxyl pectin) and 65 to 85% by weight (in the case of using with sodium alginate), respectively, based on the total weight of the mixture. When using sodium alginate, the amount of gelatin is 1 to 10% by weight, preferably 3 to 5% by weight based on the total weight of the film. As the compound by which an aqueous solution of low methoxyl pectin or sodium alginate can be Belated, for example, there are salts of polyvalent metal having at least two valences. In the case of low methoxyl pectin, water-soluble salts of calcium, magnesium and the like may be suitably used. In the case of sodium alginate, water-soluble calcium salts such as calcium chloride, calcium phosphate and the like may be used.
In the seamless capsule of the present invention, a viscous liquid that is scarcely miscible with water is present between the above film and content.
The viscous liquid that is scarcely miscible with water may be any one having a viscosity of no more than 1000 cp at 100°C. Examples thereof include emulsifiers, oils, resins and the like, and they may be used alone or in combination thereof. Examples of the emulsifier include nonionic emulsifiers having HLB value of 2 to 8, such as sucrose fatty acid ester, propylene glycol fatty acid ester, glycerin fatty acid ester (e. g. long chain fatty acid triglyceride, medium chain fatty acid triglyceride, etc.), ampho-ionic emulsifiers such as lecithin or a mixture thereof. Examples of oils include vegetable fats and oils, animal fats and oils and mineral oil of which solubility in 100 g of absolute alcohol at 150°C is not more than 50 g, for example, sesame oil, coffee oil, rapeseed oil, brown rice oil, liquid paraffin or mixture thereof are preferred. Further, dl-a-tocopherol, isobutylene polymers (e. g. polybutylene, polybutene, etc.), resins (e.g. silicone resin, vinyl acetate resin, etc.) and the like can be used. Further, as described above, the viscous liquid is present between the content and film when producing the capsule. However, it is not necessarily required that the viscous liquid be present between the content and film, since it may be present in the content in a separate state.
Hereinafter, a process for producing a seamless capsule of the present invention will be explained with reference to the accompanying drawing.
A capsule content 4 which is supplied into a nozzle part is extruded from an inner nozzle (first nozzle) 1, and a viscous liquid that is scarcely miscible with water is extruded from an annular tip of an intermediate nozzle (second nozzle) 2. At the same time, a film solution for a seamless J- o '~ l~ O I _J
capsule 6 is extruded from an annular tip part of an outer nozzle (third nozzle) 3, and then the three-phase composite jet thus obtained is ejected into a cooling solution 8 to obtain a seamless capsule 7 of the present invention.
In this case, when the content jet is a two-phase jet, a triplex soft capsule is obtained, and, when it is a three-phase jet, a quadruplex soft capsule is obtained. Similarly, a desired multiplex soft capsule 7 is produced. Further, the other nozzle, for example, the medium nozzle may itself be multiplex.
The filler is liquid and, therefore, by providing suitable vibration to the composite jet flow by using a vibration means, the dropping of the jet flow can be improved, whereby, the encapsulation is easily conducted, which results in a uniform particle size.
The seamless capsule thus produced above may be dried and then washed.
In general, as the film of the seamless capsule, water-soluble film substances such as gelatin may be used.
Particularly, in the production of the seamless capsule by a dropping method, an aqueous solution of the film substance is extruded out from a nozzle and, therefore, the water content of the film substance is large (not less than 70%).
Accordingly, when a hydrophilic substance containing alcohols as a solvent is used as the content, the film solution is reacted with alcohol and, therefore, no capsule can be formed.
However, according to the present invention, the reaction of the film solution with alcohol can be prevented by providing a viscous liquid that is scarcely miscible with water between the film and the content (hydrophilic substance), and a seamless capsule of a hydrophilic substance containing alcohol as a solvent can be easily obtained by the dropping method.
Further, by using alcohol as the solvent of the content, softening of the film and propagation of mold or bacteria due to water transferred to the film can be prevented and stable quality obtained.

2~ ~~~~ 3 The following Examples further illustrate the present invention in detail, but are not to be construed to limit the scope thereof.
A seamless capsule in the following Examples is composed of a content solution (solution I), a viscous liquid (solution II), present between the film solution and the content solution, and the film solution (solution III).
Example 1 By using polyethylene glycol 400 (molecular weight: 380 to 420) as a solvent for solution I and using sucrose fatty acid ester (SAIB) as the viscous liquid (solution II), a mouth refrigerant capsule of 3.2 mm~ containing herb extract was produced.
(Formulation 1) Ingredients Amount j% by weight) Ratio (o) Solution I:
Polyethylene glycol 96.5 Herb extract 2.0 70 Sweetener 1.0 Flavour 0.5 Solution II:
SAIB 80.0 1-Menthol 15.0 20 Flavour 5.0 Solution III:
Gelatin 20.0 D-sorbitol 5.0 10 Water 75.0 By using a concentric triplex nozzle, a herb extract solution containing PEG 400 as a solvent (solution I) was extruded from an inner nozzle and a 1-menthol solution containing SAIB as a main ingredient (solution II) heated to 80°C was extruded from an intermediate nozzle and, at the same time, a gelatin solution (solution III) heated to 60°C
was extruded from an outer nozzle to form a three-phase jet in the ratio shown in Formulation 1, and then the jet was injected into a vegetable oil cooled to 12°C, which was 20~~~~3 _ 7 _ descending at a flow rate of 0.3 m/second, to obtain a seamless capsule. Regarding the capsule after drying, no softening and dissolution were observed at high temperature (not less than 30C), and it was stable. The capsule was transparent and had good mouth feel and taste.

Example 2 By using PEG 400 (molecular weight: 380 to 420) as a solvent for solution I and using sucrose fatty acid ester (SAIB) as the viscous liquid (solution II), a mouth refrigerant capsule f 3.2 mm~ containing herb medicine o extract was produced.

(Formulation 2) Ingredients Amount (% by weight) Ratio (%) Solution I:

Polyethylene glycol 97.0 Gambir extract 1.5 65 Sweetener 1.0 Flavour 0.5 Solution II:

SAIB 80.0 1-Menthol 15.0 Cinnamon oil 1.0 20 Fennel oil 1.6 Clove oil 1.6 Flavour 0.3 Solution III:

Gelatin 20.0 D-sorbitol 5.0 15 Water 75.0 According to the same preparation condition as that described in Example 1, a seamless capsule was obtained.

Regarding the capsule after drying, no softening and dissolution were obse rved at high temperature (not less than 30C), and it wa s stable. The herb medicine capsule was transparent and had ood mouth feel and taste.
g 2~~~~~ 3.
_8_ Example 3 By using ethyl alcohol as a solvent for solution I and using coffee oil as the viscous liquid (solution II), a coffee capsule of 3.2 mm~ containing coffee extract was produced.
(Formulation 3) Ingredients Amount l% by weight) Ratio (%) Solution I:
Ethyl alcohol 60.0 Polyvinyl pyrrolidone (PVP) 25.0 65 Sweetener 1.0 Coffee flavour 14.0 Solution II:
Coffee oil (press oil) 100.0 20 Solution III:
Gelatin 12.0 Lactose 8.0 15 Water 75.0 According to the same preparation condition as that described in Example 1, a seamless capsule was obtained.
Regarding the capsule after drying, no softening and dissolution were observed at high temperature (not less than 30°C), and it was stable. The coffee capsule was transparent and had good mouth feel and taste.

Claims (9)

1. A seamless capsule, comprising:
a central core layer comprising a hydrophilic substance dissolved in an alcohol;
a film forming an outer wall layer for the capsule; and a discrete layer of a viscous liquid having a viscosity of not more than 1000 cp at 100°C, said viscous liquid being scarcely miscible with water, wherein said discrete layer of viscous liquid is between said central core and said film.
2. The seamless capsule according to claim 1, wherein said viscous liquid is a nonionic emulsifier having HLB value of 2 to 8, an ampho-ionic emulsifier or a mixture of these emulsifiers.
3. The seamless capsule according to claim 1, wherein said viscous liquid is selected from the group consisting of vegetable fats and oils, animal fats and oils and mineral oil having a solubility in 100 g of absolute alcohol at 15°C
which is not more than 50 g.
4. The seamless capsule according to claim 1, wherein said viscous liquid is dl-.alpha.-tocopherol.
5. The seamless capsule according to claim 1, wherein said viscous liquid is isobutylene polymer.
6. The seamless capsule according to claim 1, wherein said viscous liquid is silicone resin or vinyl acetate resin.
7. The seamless capsule according to claim 1, wherein said film comprises gelatin.
8. A process for producing a seamless capsule, comprising:
supplying a hydrophilic substance solution to an innermost orifice of a concentrically arranged multiple nozzle comprising at least three orifices;
supplying a film solution for the seamless capsule to an outermost orifice of the multiple nozzle;
supplying a viscous liquid which is scarcely miscible with water to an intermediate orifice of the multiple nozzle;
and simultaneously extruding the film solution, the viscous liquid and the hydrophilic substance solution into a cooling solution.
9. The process of claim 8, wherein the cooling solution is a vegetable oil.
CA002074873A 1991-07-31 1992-07-29 Seamless capsule and process for producing the same Expired - Lifetime CA2074873C (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP19178491A JP3313124B2 (en) 1991-07-31 1991-07-31 SEAMLESS CAPSULES CONTAINING A HYDROPHILIC SUBSTANCE AND PROCESS FOR PRODUCING THE SAME
JP191784/1991 1991-07-31

Publications (2)

Publication Number Publication Date
CA2074873A1 CA2074873A1 (en) 1993-02-01
CA2074873C true CA2074873C (en) 1999-09-28

Family

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Family Applications (1)

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CA002074873A Expired - Lifetime CA2074873C (en) 1991-07-31 1992-07-29 Seamless capsule and process for producing the same

Country Status (6)

Country Link
US (1) US5330835A (en)
EP (1) EP0525731B1 (en)
JP (1) JP3313124B2 (en)
KR (1) KR100240528B1 (en)
CA (1) CA2074873C (en)
DE (1) DE69222591T2 (en)

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CA2074873A1 (en) 1993-02-01
US5330835A (en) 1994-07-19
DE69222591T2 (en) 1998-02-12
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KR100240528B1 (en) 2000-02-01
JP3313124B2 (en) 2002-08-12

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