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WO2019144979A1 - Procédé de granulation et de recouvrement de probiotiques et noyau granuleux obtenu au moyen de celui-ci - Google Patents

Procédé de granulation et de recouvrement de probiotiques et noyau granuleux obtenu au moyen de celui-ci Download PDF

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Publication number
WO2019144979A1
WO2019144979A1 PCT/CO2018/000004 CO2018000004W WO2019144979A1 WO 2019144979 A1 WO2019144979 A1 WO 2019144979A1 CO 2018000004 W CO2018000004 W CO 2018000004W WO 2019144979 A1 WO2019144979 A1 WO 2019144979A1
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WO
WIPO (PCT)
Prior art keywords
core
granulated
coating
dry
probiotics
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.)
Ceased
Application number
PCT/CO2018/000004
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English (en)
Spanish (es)
Inventor
Sandra Janneth SANTOS ROCHA
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.)
Vallecilla B Y Vallecilla M Y Cia Sca Carval De Colombia
Original Assignee
Vallecilla B Y Vallecilla M Y Cia Sca Carval De Colombia
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 Vallecilla B Y Vallecilla M Y Cia Sca Carval De Colombia filed Critical Vallecilla B Y Vallecilla M Y Cia Sca Carval De Colombia
Priority to PCT/CO2018/000004 priority Critical patent/WO2019144979A1/fr
Publication of WO2019144979A1 publication Critical patent/WO2019144979A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23B—PRESERVATION OF FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES; CHEMICAL RIPENING OF FRUIT OR VEGETABLES
    • A23B2/00—Preservation of foods or foodstuffs, in general
    • A23B2/90—Preservation of foods or foodstuffs, in general by drying or kilning; Subsequent reconstitution
    • A23B2/92—Freeze drying
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23B—PRESERVATION OF FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES; CHEMICAL RIPENING OF FRUIT OR VEGETABLES
    • A23B2/00—Preservation of foods or foodstuffs, in general
    • A23B2/90—Preservation of foods or foodstuffs, in general by drying or kilning; Subsequent reconstitution
    • A23B2/93—Spray drying
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23B—PRESERVATION OF FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES; CHEMICAL RIPENING OF FRUIT OR VEGETABLES
    • A23B2/00—Preservation of foods or foodstuffs, in general
    • A23B2/90—Preservation of foods or foodstuffs, in general by drying or kilning; Subsequent reconstitution
    • A23B2/95—Fluidised-bed drying
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/135—Bacteria or derivatives thereof, e.g. probiotics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K35/00—Medicinal preparations containing materials or reaction products thereof with undetermined constitution
    • A61K35/66—Microorganisms or materials therefrom
    • A61K35/74—Bacteria
    • A61K35/741—Probiotics
    • A61K35/744—Lactic acid bacteria, e.g. enterococci, pediococci, lactococci, streptococci or leuconostocs
    • A61K35/747—Lactobacilli, e.g. L. acidophilus or L. brevis
    • 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
    • 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
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N1/00—Microorganisms, e.g. protozoa; Compositions thereof; Processes of propagating, maintaining or preserving microorganisms or compositions thereof; Processes of preparing or isolating a composition containing a microorganism; Culture media therefor
    • C12N1/04—Preserving or maintaining viable microorganisms

Definitions

  • the present invention belongs to the field of pharmaceutical chemistry and biotechnology. It reveals a method of coating and encapsulation for probiotics, which allows extended and stable storage of this kind of products without refrigeration.
  • Probiotics represent a prevention and treatment strategy for all these disorders.
  • the clinical use of probiotics is gaining increasing attention worldwide, both in medical practice and in personal care in general (Masi, 2013), attending different gastrointestinal, urogenital, respiratory, oral and immunological conditions (Hathout et al , 2011).
  • probiotics are living microorganisms that, when ingested, promote host health. These microorganisms are considered normal flora of the gastrointestinal tract of animals and humans. Probiotics represent a potential in terms of health and nutritional benefits, since they control pathogenic microorganisms, providing protection to the host, whether human or animal (Hathout et al, 2011).
  • Microencapsulation is the process by which small particles or drops are surrounded by a coating agent producing microcapsules. There are different microencapsulation processes and different purposes. Depending on the application, the coating agents can vary from polysaccharides to lipids. The former have been used in aqueous solution applications such as yogurt and some beverages, while lipids have been applied to matrices such as creamy and related cheeses.
  • the extrusion technology aims to develop beads or gel capsules that are made from hydrocolloids. Powdered probiotics are mixed with the hydrocolloid; then, said mixture is passed through an extruder generating micro drops that fall into a gelling solution under permanent agitation. The size of the microgranules will depend on the orifice of the extruder and the distance between it and the gelling solution. In the end you get a pearl with solid porous center. (Gbassi et al, 2012).
  • the emulsion process consists in the dispersion of the probiotic-hydrocolloid mixture in a vegetable oil.
  • the resulting water-in-oil emulsion is homogenized by permanent agitation. This is the critical stage that generates the size and shape of the drops formed that are then collected by sedimentation. In the end, microcapsules with liquid center are obtained. (Gbassi et al, 2012).
  • Lyophilization is a process in which water is removed from a frozen solution by sublimation under pressure. This generates dry products of good quality, without loss of sensory or nutritional characteristics. These products can be easily rehydrated for later use. This technology is very expensive due to the high energy expenditure and the duration of the process compared to other methods (Barbosa J, 2015)
  • spray drying allows the transformation of a solution into a dry powder in one step.
  • Said solution is fed to a chamber where there is hot dry air and evaporates the water contained in the solution, generating a powder of good characteristics.
  • This technology is cheaper than lyophilization and faster. (Barbosa J, 2015)
  • Drying of the fluid bed consists of liquid spraying in a bed of fluidized particles.
  • the sprayed liquid is absorbed by an inert support or binding agent creating a core that is coated with layers. This occurs while hot air is injected that fluidizes the material and evaporates the liquids.
  • the particles can grow by agglomeration and this is known as granulation. These processes are performed in batches.
  • the resulting product can have different sizes depending on the desired one, since the variables can be modified to achieve it.
  • probiotic bacteria are enclosed in a gelatinous matrix of natural biological materials such as alginates, carrageenans or gums.
  • the main difficulty is that due to its jelly-like consistency they can be stabilized in liquids only. These processes are not easily industrial ladders (Semyonov et al, 2012).
  • lyophilization and spray drying generate microcapsules; while fluid bed drying generates a microcapsule with a core and a true cover.
  • Freeze drying produces microcapsules of probiotics with good viability characteristics; However, it is expensive and its industrial escalation is difficult. Spray drying is widely used, but the temperature characteristics that are handled and the osmotic pressure exerted is so strong that cell viability is affected.
  • the operating conditions further favor the viability and stability of the probiotic due to the temperatures it handles, not exceeding 40 ° C, it occurs in shorter times and is economically more viable.
  • sizes adjusted to the needs of subsequent application are obtained (Semyonov et al, 2012).
  • what is sought with the different methods of encapsulation of probiotics is that these, once introduced to the application matrix, remain viable, retain their probiotic properties and maintain their stability over time, remaining in the final product in the desired quantities, until the end of the useful life of the finished product.
  • microencapsulation methods seek gastrointestinal resistance, which implies that the finished product requires refrigerated storage, a condition that makes storage, transport and final distribution of products more difficult.
  • the patent document W02009 / 070012 A1 of the year 2009 called "Protein-based probiotic encapsulates” teaches an encapsulation that has a protein-based encapsulation matrix, which involves one or more preferably Gram-positive probiotic bacteria; These bacteria have an average mass of 1-5000pm, where the encapsulation matrix contains at least 10% w / w of a protein that has been crosslinked with disulfide bonds.
  • W02009 / 070012 A1 agrees with the present invention because it teaches probiotic compositions that include Lactobacillus acidophilus, L casei, L. rhamnosus; Bifidobacterium breve, B. infantis, B.
  • W02009 / 070012 A1 does not disclose that the process includes the addition of the Opadry product or the incorporation of vitamin E, specifically. Similarly, the granulation and subsequent coating process that are incorporated in the present invention are not suggested or mentioned herein.
  • the objective of W02009 / 070012 A1 is to provide the gastric resistance of the supplied probiotic, while the present invention seeks storage at room temperature and its shelf stability.
  • patent document US2011 / 0268703 A1 of the year 2011, called "Probiotic strain and antimicrobial peptide derived therefrom” shows the study of a strain of Enterococcus mundtii with probiotic characteristics.
  • the E. mundtii strain produces an antimicrobial peptide that exhibits antibiotic activity against a wide range of bacteria.
  • a process is disclosed to provide for the production of a peptide comprising culturing the strain in a nutrient medium under microaerophilic conditions at a temperature between 10 ° C and 45 ° C until a recovery of an important peptide.
  • the isolated peptide can be used as an antimicrobial agent in a liquid formulation or a gel formulation as a topical treatment and also as an antimicrobial agent in an encapsulation polymer.
  • US2011 / 0268703 does not disclose any method of encapsulation or protection of probiotics, nor the use of protective matrices.
  • At least one cover composed of different materials such as fats, fatty acids, emulsifiers, oils, fats, resins, low permeability polymers, hydrocolloids, starches derived from potatoes, corn, wheat, cassava; polyols and cellulose, as well as the mixture of any of these components.
  • hygroscopic salts are dipotassium phosphate, sodium phosphate, sodium hexametaphosphate, anhydrous sodium acetate, lithium chloride, magnesium chloride, sodium acetate, calcium acetate and sodium formate among others. Such granules ensure a stability of 15-40 ° C for two years.
  • the proposed technology is through lyophilization or spray coating, the absorption of the microorganism suspended in oil on an inert porous transporter. It also mentions the possibility of bed drying. This foregoing, however, does not mention the formation of granules and their subsequent coating as proposed in this invention. Similarly, the use of hygroscopic salts is not used in the present invention to achieve the same effect.
  • binding agents microorganisms that have been prepared in a culture medium and that have been exposed to stress processes that give them resistance are used as binding agents.
  • the binding agent is a gum together with stabilizing materials such as Trehalose, Vitamin E, Acetate and whole milk powder. These are the ones that are going to coat the microorganisms that are in a powder mixture and not the opposite as in this patent.
  • microorganisms of the present invention are not subjected to any dilution or mixing process in liquids, nor exposed to stress conditions.
  • Lactobacilli and coconuts remain in the same logarithmic unit, while Bifidobacteria lose two logarithmic units after 12 months.
  • the first outer layer is aimed at resistance to gastrointestinal conditions. And the last layer aims at thermal resistance and is achieved through the incorporation of a fibrous or gelatinous polysaccharide. Opadry can be used on the outer cover.
  • some starting compounds present in the present invention are disclosed in this document and the use of a fluid bed dryer is mentioned, what is sought is to be able to withstand baking and food preparation temperatures, but does not mention stability in time or much less in shelf storage conditions. The above also does not describe the type of spray used in the different drying processes for the formation of the layers.
  • the formation of the first layer or center of the granule containing the probiotics can be similar in terms of the materials used, but without even suggesting the use of whole milk powder which is the main component or support of the present invention. It is then granulated and in the present invention the binder and stabilizer material is used to make the wet granulation.
  • the binder and stabilizer material is used to make the wet granulation.
  • they use a granulation technology called hot melt that is based on the coating with a molten oily layer (grease, oil, wax). Subsequently, they generate two layers whose objective is gastrointestinal protection and resistance to high temperatures.
  • the coating has the objective of protecting moisture so that it can be stored on a shelf at room temperature.
  • the process in question is focused primarily on the stabilization of enzymes for use in animals, although probiotics are mentioned, and seeks stabilization against pelletizing and food processing at temperatures between 70 ° C and 95 ° C.
  • wet and dry granulation is mentioned in the process disclosed above, no specific drying technology is incorporated as part of said process, nor are operating conditions or stability in the finished product described, as It only shows the maintenance of the enzymatic activity of the granules during the granulation process but not after it.
  • the process involves the atomization of a liquid that contains the material of interest with a sugary polymer and a water soluble solvent inside an excipient that is fluidized in a chamber at a temperature greater than the ambient one.
  • the proposed process is carried out in a bed dryer with some modifications both in the spray guns, and in the return of the air, generating a continuous process. Similarly, a bottom spray drying is proposed due to the location of the spray guns.
  • the microorganisms tested are only stable at 2 months.
  • the present invention takes advantage of the spray gun alternatives using top and tangential spray without any modification and ensuring stability for periods longer than the two months mentioned in this reference.
  • the present invention reveals a process that integrates probiotic drying and coating technologies, the application of which allows that the organisms thus microencapsulated and the final products that comprise them, can be stored at room temperature for long periods, without losing their viability and stability, which optimizes their logistic management throughout their distribution process and delivery to the final consumer, even allowing its handling in shelves or gondolas without the need for air conditioning or refrigeration.
  • the present invention describes a method of obtaining microgranules suitable for transporting any type of sensitive microorganism, including but not limited to probiotic microorganisms, in particle sizes between 100 and 800 microns, which includes the stages of drying, granulation and coating, in a fluid bed dryer.
  • the application of the claimed process provides coated probiotics that are stable and effective at room temperature for long periods of time without affecting their viability, on shelf storage, even at high temperatures without the need for refrigeration or air conditioning, ensuring period stability prolonged time of up to 12 months.
  • the present invention generates a protective layer against moisture and oxygen which allows microorganisms to be stored without affecting their viability and performance.
  • Microencapsulation It is an operation that involves surrounding a solid, liquid or gaseous base (core) with a sufficiently resistant and stable envelope, immiscible but adherent with the core, and that is only altered by releasing its content in certain media.
  • the size of the units varies between 0.5 and 5000 microns.
  • Cover refers to a layer that surrounds the microorganism or granule and is applied in order to protect the inner layer or dry core, as the case may be.
  • Drying fluid bed it is a type of particle drying whose basic principle is the atomization of a suspension in a bed of particles fluidized by hot air injection. During fluidization the water evaporates leaving dry particles. Several drying stages can be generated generating coating layers.
  • Lyophilization is a type of particle drying that aims to remove water from a particle by means of freezing and sublimation at reduced pressures. This process is carried out under vacuum and at low temperatures thus avoiding protein denaturation.
  • Aqueous activity defined as the relationship between the vapor pressure of a food in relation to the vapor pressure of water at the same temperature.
  • Water activity (3w) is the amount of free water in the food, that is, the water available for the growth of microorganisms and so that different chemical reactions can be carried out. It has a maximum value of 1 and a minimum value of 0. The lower this value, the better the product will be preserved.
  • Water activity is related to the texture of food: at a higher activity, the texture is much more juicy and tender; however, the product is altered more easily and more care must be taken.
  • Humidity refers to the total amount of water present in a product, although it may not be free to interact, which makes it different from the water activity.
  • probiotics are "Living microorganisms that, when supplied in adequate amounts, promote health benefits of the host organism.” These microorganisms can be bacteria and yeasts. The best known genera are Lactobacillus sp., Bifidobacterium sp., Streptococcus sp., Bacillus sp., And yeasts of the genus Saccharomyces sp. With the foregoing in mind, it is mentioned that the claimed process is constituted by the following general stages, which are described as an illustration without limiting the scope of the present application: a.
  • Manufacture of a core by wet granulation by fluid bed A dry mixture of probiotics and powdered milk is granulated by the addition of a binder solution (gum arabic) and stabilizing materials (Trehalose, Vitamin E Acetate and whole milk powder). This granulated nucleus is characterized by containing low levels of aqueous activity and moisture. b. Then, the granulate obtained is subjected to a coating process with a film that allows the core to be isolated from environmental conditions such as humidity and oxygen. This coating is also carried out in a fluid bed by atomizing a coating solution. c. At the end of the process, granules coated with probiotic microorganisms with sizes between 100 and 800 microns, a humidity between 3% and 5% and an aqueous activity between 0.3 and 0.5 can be suspended and can be suspended in water.
  • a binder solution gum arabic
  • stabilizing materials Tehalose, Vitamin E Acetate and whole milk powder
  • FIGURE No. 1 Microencapsulated acid lactic acid count
  • FIGURE No. 2 Microencapsulated bacteria count by gender
  • FIGURE No. 3 Survival of microencapsulated probiotics
  • FIGURE No. 4 Survival of microencapsulated probiotics by gender
  • the gum arabic is hydrated for 1 to 6 hours. This is done with water and is brought to a concentration of 25%.
  • the ratio between the rubber and the dry core should be stored at 1: 6.
  • the stabilizers are added: trehalose that can be incorporated in proportions between 1: 50, 1: 40, 1: 30 or 1: 20 in relation to the dry core; whole milk powder that can be incorporated in proportions against the dry core between 1: 5, 1: 7 or 1: 9 and vitamin E acetate that can be incorporated between 1: 40, 1: 50, 1: 60 and up to 1: 80 in proportion to the dry core.
  • Stirring is continued for 30 to 60 minutes until all materials are properly incorporated to obtain a lump-free fluid dispersion.
  • the gentle agitation is continued during the process.
  • the granulation process occurs, consisting of the top spray spray of the binder solution on the probiotic mixture.
  • the granulation process is preferably carried out in a fluid bed equipment with top spray atomization gun arrangement.
  • the core is controlled to grow to an approximate average size between 100 and 800 microns.
  • a temperature in the fluidization chamber is handled between 30 ° C and 40 ° and a total process time of approximately 300 minutes.
  • This process is composed of a stage of heating and fluidization of the dry core, followed by the atomization of the binder solution. After the total addition of binder, it is dried for 30-60 minutes or until a humidity less than or equal to 5% and an aqueous activity less than or equal to 0.5 is reached.
  • the fluidization of materials is carried out with air flow between 700 and 3000 m 3 / h and an inlet air temperature not exceeding 45 ° C.
  • the coating film After the addition of the coating film, it is dried for 30-60 minutes or until a humidity less than or equal to 5% and an aqueous activity less than or equal to 0.5 is reached.
  • the granule maintains its size generated in the granulation, that is 100 to 800 microns.
  • a sample should be taken and the moisture content and the water activity must be verified, which must be a maximum of 5% and a 3w of maximum 0.5 respectively.

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Abstract

Un procédé de recouvrement et d'encapsulation pour des probiotiques qui comprend deux étapes: l'une de granulation et l'autre de recouvrement postérieur dans un séchoir de lit fluidisé. Ce procédé permet le stockage étandu et stable de cette classe de produits sans nécessiter de réfrigération. Le noyau granuleux ainsi obtenu assure une survie des probiotiques supérieures à 70% jusqu'à 12 mois, à température ambiante jusqu'à 30 °C et sans nécessiter de réfrigération, et peut être intégré à différentes matrices tant alimentaires que pharmaceutiques. Cette technologie combine deux types d'arrosage; une pulvérisation supérieure pour le procédé de granulation, où l'on cherche à produire le granulé de dimension adéquate et fonctionnelle, et postérieurement un arrosage tangentiel, avec pour objectif d'optimiser le procédé de recouvrement du granulé tout en assurant son recouvrement et la protection des probiotiques.
PCT/CO2018/000004 2018-01-25 2018-01-25 Procédé de granulation et de recouvrement de probiotiques et noyau granuleux obtenu au moyen de celui-ci Ceased WO2019144979A1 (fr)

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Cited By (3)

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Publication number Priority date Publication date Assignee Title
CN111661933A (zh) * 2020-06-30 2020-09-15 武汉合缘绿色生物股份有限公司 一种用于调节水体营养及预防病害的生物制剂及其制备方法
WO2022160540A1 (fr) * 2021-02-01 2022-08-04 绍兴同创生物科技有限公司 Microcapsule probiotique et son procédé de préparation
US20220389370A1 (en) * 2019-11-11 2022-12-08 Probiotical S.P.A. Granular bacteria gastroprotected with a coating matrix in crystalline form, process for the preparation thereof and compositions thereof

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WO2008035332A1 (fr) * 2006-09-19 2008-03-27 Technion Research And Development Foundation Ltd. Compositions probiotiques et procédés de fabrication
US20130115334A1 (en) * 2009-07-09 2013-05-09 Adel Penhasi Heat resistant probiotic compositions and healthy food comprising them
WO2013069021A2 (fr) * 2011-11-11 2013-05-16 Keepcool Ltd. Stratification et microencapsulation de matériau biologiquement actif sensible à la chaleur à l'aide de couches de matériaux absorbant la chaleur avec des points de fusion croissants

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SCHELL DANIEL ET AL.: "Fluidized bed microencapsulation of Lactobacillus reuteri with sweet whey and shellac for improved acid resistance and in-vitro gastro-intestinal survival", FOOD RESEARCH INTERNATIONAL, vol. 62, 2014, pages 308 - 314, XP028863542, ISSN: 0963-9969, DOI: 10.1016/j.foodres.2014.03.016 *

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20220389370A1 (en) * 2019-11-11 2022-12-08 Probiotical S.P.A. Granular bacteria gastroprotected with a coating matrix in crystalline form, process for the preparation thereof and compositions thereof
CN111661933A (zh) * 2020-06-30 2020-09-15 武汉合缘绿色生物股份有限公司 一种用于调节水体营养及预防病害的生物制剂及其制备方法
WO2022160540A1 (fr) * 2021-02-01 2022-08-04 绍兴同创生物科技有限公司 Microcapsule probiotique et son procédé de préparation
US12446607B2 (en) 2021-02-01 2025-10-21 Shaoxing Tongchuang Biotechnology Co., Ltd. Probiotic microcapsule and preparation method thereof

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