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WO2018034364A1 - Microéponge présentant des propriétés améliorées de régulation de solubilité et de redissolution - Google Patents

Microéponge présentant des propriétés améliorées de régulation de solubilité et de redissolution Download PDF

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Publication number
WO2018034364A1
WO2018034364A1 PCT/KR2016/009093 KR2016009093W WO2018034364A1 WO 2018034364 A1 WO2018034364 A1 WO 2018034364A1 KR 2016009093 W KR2016009093 W KR 2016009093W WO 2018034364 A1 WO2018034364 A1 WO 2018034364A1
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Prior art keywords
microsponge
water
molecular weight
soluble
low molecular
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Ceased
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English (en)
Korean (ko)
Inventor
안종원
최승민
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BLISSPACK Co Ltd
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BLISSPACK Co Ltd
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Priority to PCT/KR2016/009093 priority Critical patent/WO2018034364A1/fr
Publication of WO2018034364A1 publication Critical patent/WO2018034364A1/fr
Anticipated expiration legal-status Critical
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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
    • C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
    • C08K3/20—Oxides; Hydroxides
    • C08K3/22—Oxides; Hydroxides of metals
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/34—Silicon-containing compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/34—Silicon-containing compounds
    • C08K3/36—Silica
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/01—Hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L101/00—Compositions of unspecified macromolecular compounds
    • C08L101/12—Compositions of unspecified macromolecular compounds characterised by physical features, e.g. anisotropy, viscosity or electrical conductivity
    • C08L101/14—Compositions of unspecified macromolecular compounds characterised by physical features, e.g. anisotropy, viscosity or electrical conductivity the macromolecular compounds being water soluble or water swellable, e.g. aqueous gels
    • 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

Definitions

  • the present invention relates to a microsponge with improved solubility control and re-dissolution properties, and more particularly, to a water-soluble or water-dispersible disintegrant which has a water-soluble polymer material as a matrix component and can control solubility and improve re-dissolution properties. It relates to a microsponge containing.
  • a molded product in the form of a microsponge is a step of preliminarily freezing a temperature gradient parallel to the thickness direction inside the solution or gel by cooling the interface side with the air layer of the water-soluble polymer material or the gel, and preliminary freezing thereof. It is prepared through a process of freeze-drying the solution or gel of the frozen water-soluble polymer material.
  • the molded product in the form of a micro sponge is used in various fields such as cosmetics, foods, especially health supplements, medicines such as wound dressings, oral disintegrating agents, industrial products having aroma and deodorant, and industrial products such as pesticides and fertilizers. have.
  • the microsponge-type lyophilized products include natural polymers such as collagen or hyaluronic acid as matrix components.
  • Collagen sponges having no network bonds are prepared from collagen aqueous solution by lyophilization or mixed with water. It is manufactured by removing water from the collagen lumps foamed using, and in particular, a collagen sponge having a crosslinked structure is known to be stable in water (Patent Document 1).
  • the hyaluronic acid microsponge prepared by adding an epoxy-based crosslinking agent to the hyaluronic acid solution to hydrogel, and then expanded to give porosity, and then lyophilized the expanded hyaluronic acid hydrogel to control the pore size. It could be applied as a support (patent document 2).
  • the collagen or hyaluronic acid-based non-crosslinked microsponge has a disadvantage in that the mechanical strength is poor or it is difficult to control the dissolution rate when contacted with water.
  • the mechanical strength is poor or it is difficult to control the dissolution rate when contacted with water.
  • cross-linked microsponge can be expected to improve the mechanical strength, there is a property that does not re-dissolve in water, there is a limitation in the application.
  • Patent Document 3 there is a known method of adjusting the solubility by controlling the pores by pre-freeze drying and electroporation control method, but there is a problem that the manufacturing process is complicated and the economic cost is accompanied by an increase in the production cost (Patent Document 3).
  • the inventors of the present invention have a water-soluble natural polymer or a synthetic polymer as a matrix component, and if a water-soluble or water-dispersible disintegrant is included therein to form a lyophilized microsponge-shaped molded article, water is kept in water while maintaining mechanical strength.
  • the present invention has been completed by focusing on the fact that not only the solubility can be controlled, but also the microsponge having remarkably improved re-dissolution properties when contacted with water.
  • Patent Document 1 Korean Laid-Open Patent Publication No. 10-2007-0064329
  • Patent Document 2 Korean Patent Publication No. 10-2007-0108062
  • Patent Document 3 International Publication WO 2001/057121
  • the present invention has been made in view of the above problems, and an object of the present invention is to control the solubility, to easily control the density and strength of the sponge, not only to excellent re-dissolution characteristics, but also without adding a preservative. It is also to provide a micro sponge having a long-term storage and distribution stability.
  • the present invention for achieving the above object is a water-soluble polymer material; And a water-soluble or water-dispersible disintegrant.
  • the water-soluble polymer material is beta glucan, hyaluronic acid, hydroxypropylmethyl cellulose, carboxymethyl cellulose, hydroxyethyl cellulose, chitosan, gelatin, polyvinyl alcohol, polyethylene oxide, polyvinylpyrrolidone, polyacrylamide, xanthan gum, polymer It is characterized by at least one member selected from the group consisting of collagen, carrageenan, pullulan, pectin, chondroitin sulfate, dextran and alginic acid.
  • the content of the water-soluble polymer material is characterized in that 0.1 to 50% by weight based on the micro sponge.
  • the water-soluble disintegrant is a low molecular weight carboxymethyl cellulose, low molecular weight hydroxypropyl methyl cellulose, low molecular weight hydroxyethyl cellulose, low molecular weight chitin, low molecular weight chitosan, low molecular weight collagen, low molecular weight polyacrylic acid, low molecular weight polyacrylamide, low It is characterized by at least one member selected from the group consisting of molecular weight polyvinyl alcohol and low molecular weight polyethylene oxide.
  • the water-soluble disintegrant is characterized in that at least one selected from the group consisting of glucose, sucrose, maltose and lactose.
  • the water-soluble disintegrant is one selected from the group consisting of alpha cyclodextrin, beta cyclodextrin, gamma cyclodextrin, hydroxypropyl cyclodextrin, hydroxyethyl cyclodextrin, carboxymethyl cyclodextrin, methyl cyclodextrin and glucosyl cyclodextrin. It is characterized by the above.
  • the water dispersible disintegrant is characterized in that at least one selected from microcolloidal silica, nanoclay, titanium oxide, talc, or mica inorganic particles, or organic particles of acrylic powder, nylon powder, polyethylene powder or polypropylene powder.
  • the weight ratio of the water-soluble polymer material and the water-soluble or water-dispersible disintegrant in the micro sponge is characterized in that 1: 0.5 to 100.
  • the microsponge is characterized in that it further comprises a functional imparting material.
  • the microsponge is characterized in that it further comprises one or more additives selected from the group consisting of surfactants, colorants, flavors, sweeteners, oils, waxes and antioxidants.
  • microsponge is characterized in that it is in the form of a sphere or a sheet can be formulated in a spherical, heart-shaped, tablet form or sheet form.
  • the micro-sponge prepared according to the present invention can control the solubility, control the density and strength of the sponge, not only excellent re-dissolution characteristics, but also excellent long-term storage and distribution stability without adding a preservative.
  • Formulated in spherical, heart, tablet or sheet form it can be applied to food, medicine, quasi-drugs, cosmetics, household goods, animal drugs, pesticides and industrial products.
  • FIG. 1 is a schematic diagram showing the collapse of the sponge according to the manufacture and re-dissolution of the micro-sponge according to the present invention.
  • Figure 2 is a photograph observing the state of hydration of the microsponge prepared from Example 1 of the present invention.
  • Figure 3 is a scanning electron microscope (SEM) photograph taken of the microsponge prepared from Example 1 of the present invention.
  • Figure 4 is a photograph observing the state of hydration of the microsponge prepared from Comparative Example 1 of the present invention.
  • Figure 5 is a scanning electron microscope (SEM) photograph taken of the microsponge prepared from Comparative Example 1 of the present invention.
  • Figure 6 is a scanning electron microscope (SEM) photograph taken of the microsponge prepared from Comparative Example 2 of the present invention.
  • Figure 7 is a photograph observing the state of hydration of the microsponge prepared from Example 3 of the present invention.
  • SEM scanning electron microscope
  • the present invention is a water-soluble polymer material; And a water-soluble or water-dispersible disintegrant.
  • beta glucan as a matrix component of the micro sponge, beta glucan, hyaluronic acid, hydroxypropylmethyl cellulose, carboxymethyl cellulose, hydroxyethyl cellulose, chitosan, gelatin, polyvinyl alcohol, polyethylene oxide, polyvinylpyrrolidone, and polyacryl Amide, xanthan gum, polymeric collagen, carrageenan, pullulan, pectin, chondroitin sulfate, dextran and alginic acid are used.
  • the water-soluble polymer material is conventionally used at room temperature or when heated to dryness. The thing of the high molecular weight which has film-like or blocky strength is preferable.
  • the content of the water-soluble polymer material is preferably 0.1 to 50% by weight, and more preferably 0.2 to 30% by weight with respect to the micro sponge. At this time, if the content of the water-soluble polymer material is less than 0.1% by weight with respect to the micro sponge, the content as a matrix component is too low may decrease the mechanical strength of the micro sponge, the content of the water-soluble polymer material is 50% by weight relative to the micro sponge If exceeded, the content of the water-soluble or water-dispersible disintegrant is relatively low, and there is a concern that the re-solubility of the micro sponge is lowered when contacted with water.
  • the present invention serves to improve the dissolution rate when reducing the viscosity of the water-soluble polymer solution as a matrix component in the process of manufacturing the micro sponge or redissolved in the water again to the water-soluble or water dispersible It is characterized by including a disintegrant.
  • low molecular weight carboxymethyl cellulose low molecular weight hydroxypropylmethyl cellulose, low molecular weight hydroxyethyl cellulose, low molecular weight chitin, low molecular weight chitosan, low molecular weight collagen, low molecular weight polyacrylic acid, low molecular weight polyacrylamide, low molecular weight At least one selected from the group consisting of molecular weight polyvinyl alcohol and low molecular weight polyethylene oxide is used.
  • a water-soluble polymer may be used as long as it has a high solubility in water and a dissolution rate in a fibrous, pulp, powder or solid state having a constant crystal structure at room temperature or when heated to dryness.
  • the water-soluble disintegrant may be one or more selected from the group consisting of glucose, sucrose, maltose and lactose, and may be a low molecular sugar that is powder or crystals upon drying.
  • the water-soluble disintegrant is selected from the group consisting of alpha cyclodextrin, beta cyclodextrin, gamma cyclodextrin, hydroxypropyl cyclodextrin, hydroxyethyl cyclodextrin, methyl cyclodextrin, carboxymethyl cyclodextrin and glucosyl cyclodextrin.
  • the water dispersible disintegrant at least one selected from microcolloidal silica, nanoclay, titanium oxide, talc, mica inorganic particles or organic particles such as acrylic powder, nylon powder, polyethylene powder or polypropylene powder, In order to improve the dispersibility or surface properties of the inorganic particles or organic particles, inorganic particles or organic particles surface-treated with organic or inorganic components may be used.
  • the water-soluble disintegrant or water-dispersible disintegrant may be used alone or in combination, but the weight ratio of the water-soluble polymer material and the water-soluble or water-dispersible disintegrant in the micro sponge is 1: 0.5 to 100 with the solubility of the micro sponge. Density and strength can be easily adjusted, it is preferable to maximize the re-dissolution properties when in contact with water, and more preferably 1: 1 to 30.
  • cyclodextrin and its derivatives, and organic or inorganic compound-treated porous beads such as porous silica
  • the microsponge disintegrates in water and re-dissolves, it can show its efficacy by slowly releasing the impregnated functional impregnated substances, and these sustained-release functions are cosmetics, medicines, deodorants, household goods including fragrances, pesticides and fertilizers. It can be widely used for industrial products, such as these.
  • the present invention may further include a functional imparting substance in the microsponge, wherein the functional imparting substance, when redissolved, is released and exhibits a function, a whitening agent, an anti-depressant agent, a sunscreen agent, a moisturizer, a humectant, a release agent, and an anti-aging agent.
  • Agents anti-wrinkle agents, weight loss agents, weight gain agents, ingredients that improve elasticity, ingredients that stimulate collagen or elastin synthesis, anti acne agents, anti-inflammatory agents, antioxidants, anti-free radical ingredients, pro-colorants, or bleaching
  • the properties of the functional imparting substance are water-soluble, poorly soluble, oil-soluble, or water-dispersible, and may be oil or waxy.
  • an oil- or wax-like functional imparting substance in order to contain an oil- or wax-like functional imparting substance, without using a conventional method such as micro-encapsulation or emulsification, it is dispersed in an aqueous solution of the matrix component and the disintegrant and frozen, and then lyophilized to obtain an oil- or wax-like phase.
  • a microsponge having a functional imparting substance stably included in the pores of the sponge is obtained.
  • the microsponge according to the present invention has one technical feature of having long-term storage and distribution stability without adding a preservative, it is possible to feel a preservative such as a preservative, or color, aroma, and taste as necessary.
  • the micro sponge may further include at least one additive selected from the group consisting of a surfactant, a colorant, a flavoring agent, a sweetener, an antioxidant, and a preservative, so that the physical properties of the microsponge during re-dissolution are further included. Is given.
  • the microsponge may shrink or expand according to the design of the container used in the freeze-drying process and the characteristics of the raw material after freeze-drying, surface properties and colors may be changed, and the spherical, heart-shaped, tablet-type or It is obtained in the form of a sheet or a sheet which can be formulated in a sheet form.
  • the microsponge according to the present invention forms pores with a uniform cross-sectional shape as well as the surface layer, and scans that the water-soluble polymer material, which is a matrix component, and the water-soluble or water-dispersible disintegrant, are uniformly present in the form of a sponge as one material. It was confirmed by an electron microscope (SEM). Furthermore, when hydrated in water, disintegrants, which dissolve or disperse rapidly in water as they rapidly enter the pores by capillary action, first dissolve or disperse rapidly and induce the internal penetration of water much faster. It was confirmed that the water-soluble polymer material, which is a matrix component, was continuously hydrated and dissolved in a sufficient amount of water so as to disintegrate / dissolve at a very high rate.
  • the molded article on the micro-sponge prepared by the conventional water-soluble solid agent has a similar structure, but in the case of the micro sponge made of only the water-soluble solid agent, water is rapidly introduced into the pores by capillary action as in the micro sponge of the present invention.
  • the viscosity rises rapidly to prevent further water from flowing into or transferred to the water-soluble solid agent, which takes a long time until the water-soluble solid agent is hydrated in water and completely dissolved. If you do not dissolve by rubbing or stirring or shaking the container by hydrating the water again with physical force, it is difficult to dissolve completely.
  • Figure 1 shows a schematic diagram showing the collapse of the sponge according to the manufacture and re-dissolution of the micro-sponge according to the present invention.
  • beta glucan 0.5 wt%, which is a water-soluble polymer
  • 3 g of marine collagen low molecular weight collagen
  • 5 g of water-soluble oligo chitosan low molecular weight chitosan
  • the mixed solution was placed in a spherical mold having a diameter of 11 mm, placed in a low temperature freezer, and frozen at -40 ° C. for 1 hour.
  • the frozen balls were removed from the mold and placed in a freeze dryer in an exposed state to dry for 24 hours to prepare a microsponge.
  • Microsponge was prepared in the same manner as in Example 1, except that 30 g of aqueous solution of beta glucan (1% by weight) and 70 g of aqueous solution of sodium hyaluronate (0.5% by weight) were used to obtain a mixed solution using 2 g of beta cyclodextrin and 2 g of marine collagen. Prepared.
  • aqueous beta glucan solution (1 wt%) and 80 g of aqueous sodium hyaluronate solution (0.5 wt%) were mixed and stirred to obtain a mixed solution.
  • 2 g of hydroxypropyl cyclodextrin and 2 g of marine collagen powder mixture were prepared, and 0.5 g of shea butter was added to an oil mixture of 1 g of rosehip oil and 1 g of tocopherol to dissolve the shea butter at 70 ° C.
  • the oil mixture was then poured into a mixture of hydroxypropyl cyclodextrin and marine collagen powder to form a dough, which was then dispersed again in a mixed solution of aqueous beta glucan solution and aqueous sodium hyaluronate solution.
  • a microsponge was prepared from the dispersion solution in the same manner as in Example 1.
  • a microsponge was prepared in the same manner as in Example 1 only from an aqueous sodium hyaluronate solution in which 1 g of sodium hyaluronate was dissolved in 100 g of water.
  • Microsponge was prepared in the same manner as in Example 1 only from beta glucan aqueous solution in which 1 g of beta glucan was dissolved in 100 g of water.
  • Figure 2 shows a photograph observing the hydration state of the micro-sponge prepared from Example 1 of the present invention, as shown in Figure 2, time after dropping the prepared ball-type microsponge in water Therefore, even though no external force is applied, the pores formed by lyophilization are rapidly introduced into the pores by capillary action, and at the same time, the disintegrant (disintegrant) melts and the microsponge disintegrates rapidly.
  • Example 3 shows a scanning electron microscope (SEM) photograph of the microsponge prepared in Example 1 of the present invention, wherein the water-soluble polymer material and the water-soluble disintegrant do not phase separate from each other to form a uniform wall of the cell. In addition, it can be confirmed that the gap of the regular cells is formed.
  • Figure 4 shows a photograph observing the state of hydration of the microsponge prepared from Comparative Example 1 of the present invention, as shown in Figure 4, the time after dropping the prepared ball-shaped microsponge in water As the elapsed time, the outside is hydrated and dissolved to some extent, but as time passes, the hydration rate is slowed down, and eventually, it takes a considerable time to completely dissolve unless physical external force is applied from the outside.
  • FIG. 5 and 6 show scanning electron microscope (SEM) images of microsponges prepared from Comparative Examples 1 and 2 of the present invention, respectively.
  • the microsponges prepared from Comparative Example 1 were relatively uniform cells. It can be seen that it has a structure, but in the case of the microsponge manufactured from Comparative Example 2, the pores are well formed, while the cell wall has an excessively thin and coarse structure to hydrate well, but the structure is fragile enough to handle. You can check that you have it.
  • Figure 7 shows a photograph observing the hydration state of the microsponge prepared from Example 3 of the present invention, the content of the oil component as a functional imparting substance not included in the microsponge prepared from Example 1 High, despite the structure of the oil dispersed in the pores of the sponge, hydroxypropyl cyclodextrin used as a water-soluble disintegrant and low-molecular weight of marine collagen was rapidly hydrated to confirm that it collapses at almost the same rate as in Example 1 Can be. Therefore, it can be seen again that water-soluble disintegrants play an important role in re-dissolving the sponge in water.
  • Example 8 shows a scanning electron microscope (SEM) photograph of the microsponge prepared in Example 3 of the present invention, in which oil components which are not dissolved in water are uniformly dispersed in the uniformly formed pores. I can confirm that there is.
  • Table 1 shows the re-dissolution time for each hydration solution of the microsponges prepared from Examples 1 to 4 and Comparative Examples 1 and 2, and the feeling of use when applying the skin thereof.
  • Cosmetic composition 10 parts butylene glycol, 3 parts glycerin, 0.3 parts sebum / fiji-17 / 6 copolymer, 0.2 parts sebum-75 0.2 parts, xanthan gum, 1 part sebum-60 hydrogenated caster 0.3 parts of oil, 0.1 parts of disodium ethane, 1 part of sodium hyaluronate, 3 parts of chamomile flower / leaf extract, 0.5 parts of sage extract, 0.5 parts of lavender extract, 3 parts of rosemary leaf extract, 0.8 parts of phenoxyethanol, 0.3 parts of fragrances and 76 parts of purified water
  • the microsponge prepared from Examples 1 to 4 of the present invention is significantly shorter re-dissolution time, even if the hydration solution is water or cosmetics compared to the micro sponge prepared in Comparative Example 1 (Comparative Example 2 It has a fragile structure that cannot be handled, so it is not applicable to skin dissolution time because it is not applicable), and it can be seen that it has excellent feeling when applying skin.
  • the microsponge produced from the present invention was confirmed to be excellent in long-term storage and distribution stability even when no conventional preservatives are included.
  • the micro-sponge prepared according to the present invention can control the solubility, easy to control the density and strength of the sponge, excellent re-dissolution properties, excellent long-term storage and distribution stability without addition of preservatives Therefore, it is possible to apply to food, pharmaceuticals, quasi-drugs, cosmetics, household goods, animal medicines, pesticides and industrial products in the form of sphere, heart, tablet or sheet.

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  • Chemical Kinetics & Catalysis (AREA)
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Abstract

La présente invention concerne une microéponge présentant un matériau polymère soluble dans l'eau en tant que constituant de matrice et comprenant un agent de désintégration soluble ou dispersible dans l'eau pouvant réguler la solubilité et d'améliorer les propriétés de redissolution. La microéponge produite selon la présente invention permet non seulement de réguler la solubilité et de réguler facilement la densité et la résistance de l'éponge et présente d'excellentes propriétés de redissolution, mais elle présente également une excellente aptitude au stockage à long terme et une excellente stabilité de distribution sans addition de conservateur. Par conséquent, la microéponge peut être formée sous une forme sphérique, une forme de coeur, une forme de comprimé ou une forme de feuille et appliquée à des aliments, un médicament, des quasi-médicaments, des cosmétiques, des articles ménagers, des médicaments pour animaux, des pesticides agricoles, des produits industriels, etc.
PCT/KR2016/009093 2016-08-18 2016-08-18 Microéponge présentant des propriétés améliorées de régulation de solubilité et de redissolution Ceased WO2018034364A1 (fr)

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CN112043678A (zh) * 2020-09-18 2020-12-08 福州爱建生物科技有限公司 口腔异味自我感受器
CN114632434A (zh) * 2022-03-21 2022-06-17 哈尔滨工业大学 一种纳米SiO2粉体-糖溶液的制备方法

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KR100996106B1 (ko) * 2002-09-05 2010-11-22 킴벌리-클라크 월드와이드, 인크. 압출 세정 제품
KR20070108062A (ko) * 2006-05-04 2007-11-08 재단법인서울대학교산학협력재단 세포 전달 시스템용 다공성 히아루론산 스펀지의 제조방법
KR20070064329A (ko) * 2007-03-23 2007-06-20 군제 가부시키가이샤 콜라겐 스펀지의 제조 방법, 인공 피부의 제조 방법, 인공피부 및 세포 조직 배양 기재
KR20160131487A (ko) * 2015-05-07 2016-11-16 주식회사 블리스팩 용해도 조절 및 재용해 특성이 향상된 마이크로스펀지

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CN112043678A (zh) * 2020-09-18 2020-12-08 福州爱建生物科技有限公司 口腔异味自我感受器
CN114632434A (zh) * 2022-03-21 2022-06-17 哈尔滨工业大学 一种纳米SiO2粉体-糖溶液的制备方法
CN114632434B (zh) * 2022-03-21 2023-01-24 哈尔滨工业大学 一种纳米SiO2粉体-糖溶液的制备方法

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