WO2019135420A1 - Composite utilisant un matériau poreux et un polymère, et son utilisation - Google Patents

Composite utilisant un matériau poreux et un polymère, et son utilisation Download PDF

Info

Publication number
WO2019135420A1
WO2019135420A1 PCT/KR2018/000113 KR2018000113W WO2019135420A1 WO 2019135420 A1 WO2019135420 A1 WO 2019135420A1 KR 2018000113 W KR2018000113 W KR 2018000113W WO 2019135420 A1 WO2019135420 A1 WO 2019135420A1
Authority
WO
WIPO (PCT)
Prior art keywords
polymer
physiologically active
acid
active substance
weight
Prior art date
Application number
PCT/KR2018/000113
Other languages
English (en)
Korean (ko)
Inventor
김배용
이병일
Original Assignee
김배용
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 김배용 filed Critical 김배용
Priority to PCT/KR2018/000113 priority Critical patent/WO2019135420A1/fr
Publication of WO2019135420A1 publication Critical patent/WO2019135420A1/fr

Links

Images

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
    • A61K47/69—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit
    • 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
    • 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
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/67—Vitamins
    • 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
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73—Polysaccharides
    • 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
    • A61K9/10—Dispersions; Emulsions
    • A61K9/127—Liposomes
    • 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

Definitions

  • the present invention relates to a composite using a porous material and a polymer and a use thereof. More particularly, the present invention relates to a composite material comprising a porous material, a physiologically active substance supported on the micropores of a volcanic soil and an ionic polymer The present invention relates to a method for protecting a biologically active material from external environment by capping and preventing self aggregation by forming a network due to Van der Waals bonding between an ionic polymer residue exposed on a surface and a nonionic polymer after sealing, Precipitation, and discoloration, and particularly excellent in water dispersibility, and uses thereof.
  • the physiologically active substance is a trace amount of a substance that greatly affects the function and physiological function of the living body, and includes vitamins, hydroxy acids, unsaturated fatty acids, hormones, enzymes, neurotransmitters and the like.
  • Physiologically active substances such as vitamins, salicylic acid, hydroxy acids, unsaturated fatty acids and glutathione (GLT) have functions such as antioxidation, acne treatment, skin whitening, exfoliation, starch removal, skin moisturizing and wrinkle prevention
  • GLT glutathione
  • vitamins including vitamins A (retinol), vitamin C (ascorbic acid), vitamin E (tocopherol) and derivatives thereof are widely used in the field of cosmetics. They are used for preventing skin whitening and pigmentation, promoting collagen synthesis, Prevention of dryness and keratinization of skin, prevention of wrinkles, skin moisturization and so on. Despite these effects, however, it has many limitations in practical applications due to the instability of vitamin, irritation, toxicity, dispersibility and the disadvantage that it is easily destroyed by heat, light, oxygen.
  • the volcanic soil is a soil formed by the formation of the soil after the high and far ash (ash) is deposited on the ground at the time of the volcanic eruption. It is characterized by porosity and low specific density. Therefore, it shows excellent ability to hold moisture, excellent in pollution treatment and antibacterial action.
  • the weight of the soil per unit volume is 0.54 g / cm 3, which is significantly lower than 1.2 g / cm 3 of the land area general soil and the porosity is 75%, which is much larger than about 50% Is fast.
  • the present invention is applied to maintain good water quality by adsorbing power to pesticides of soil using excellent adsorption characteristics of pollutants. That is, the possibility of the ceramic carrier is suggested by using the permeability and adsorption force due to the pores of the clay soil.
  • the present inventors have made efforts to efficiently carry weakly physiologically active substances against the external environment such as air, light, heat, pH, moisture, and the like.
  • volcanic ash as a porous material is selected as an inorganic carrier material
  • the physiologically active substance is supported on the pores, the micropores are enclosed with the ionic polymer to protect the physiologically active substance from the external environment, and due to van der Waals bonding between the ionic polymer residue exposed on the surface and the nonionic polymer substance, To prevent self-agglomeration.
  • there was no dropout, precipitation, discoloration, and in particular, excellent water dispersibility was confirmed, thereby completing the present invention.
  • An object of the present invention is to provide a composite in which a porous material, which is a porous material, is used as an inorganic carrier and a physiologically active substance is stably supported.
  • Another object of the present invention is to provide a cosmetic, food or pharmaceutical field using the same, which has no dropout, settling, discoloration and excellent water dispersibility after the production of the composite.
  • the present invention provides a method for preparing a porous material, comprising the steps of supporting a physiologically active substance on micropores of a porous material, encapsulating the micropores into an ionic polymer, and exposing the surface to ionic polymer residues and non- To form a network due to van der Waals bonding and to stabilize the water dispersibility.
  • the complex of the present invention contains 10 to 30 parts by weight of the physiologically active substance per 100 parts by weight of the volcanic ash, 1 to 10 parts by weight of the ionic polymer and 1 to 10 parts by weight of the nonionic polymer, .
  • the physiologically active substance may be selected from the group consisting of vitamin A, vitamin C, vitamin E, salicylic acid, kojic acid, alpha-lipoic acid, elacydic acid, resveratrol, docohexaenoic acid (DHA), eicosapentaenoic acid (EPA), linoleic acid and glutathione Or a mixed form of them may be applied.
  • the ionic polymer is any one selected from the group consisting of alginic acid, pectin, carrageenan, xanthan gum, hyaluronic acid, gum Arabic, karaya gum and tragacanth gum.
  • nonionic polymer is selected from the group consisting of starch or cyclotin.
  • the present invention provides a functional product in which the complex is applied to any one selected from the group consisting of cosmetics, foods, and medicines, and is embodied by a physiologically active substance.
  • the present invention can provide a physiologically active substance complex using a porous material and a polymer. That is, not only is it possible to effectively support various physiologically active substances in the micropores of the clay soil, but also to increase the stability by enclosing the physiologically active substances carried on micropores of the clayey soil with ionic polymers, It is possible to protect the physiologically active substance enclosed in the micropores from the external environment and prevent coagulation and precipitation between physiologically active substances, thereby maintaining the inherent physiological activity of the substance as it is.
  • the complex of the present invention is not only environmentally friendly but also skin-friendly and has high stability to aqueous solution, so that it can be applied not only to raw materials for functional cosmetics but also to industrial fields such as foods and pharmaceuticals, .
  • Fig. 1 schematically shows a composite structure of the present invention.
  • the present invention provides a composite using a porous material and a polymer.
  • Figure 1 schematically shows the composite structure of the present invention.
  • the composite of the present invention is characterized in that the composite of the present invention is formed by supporting a physiologically active substance in micropores of a porous material, sealing the micropores with an ionic polymer, And forms a network due to Van der Waals bonding between the exposed ionic polymer residue and the nonionic polymer.
  • the porous material to be used can be applied as long as it can be used as a conventional inorganic carrier having a micropore.
  • volcanic soil has been selected and described in the embodiments of the present invention, it will be understood that silica, zeolite and the like can also be applied.
  • a complex using a volcanic ash selected as a porous material will be described in detail.
  • 10 to 50 parts by weight of a physiologically active substance is supported on 100 parts by weight of a volcanic ash, 1 to 10 parts by weight of an ionic polymer 1 to 10 parts by weight of a non-ionic polymer is contained and stabilized.
  • the ionic polymer binds to the entrance of the micropores to protect and stabilize the physiologically active substances from the external environment.
  • the hydrophobic residues of the ionic polymer exposed to the surface of the complex due to not being incorporated into the micropores form a network due to the interaction of non-ionic polymers with Van der Waals, thereby causing self-aggregation between the complexes And to increase the dispersion of the aqueous solution.
  • the volcanic ash used in the present invention is a stabilized colloidal solution by stirring or ultrasonicating 0.01 to 1% by weight in distilled water at room temperature.
  • the physiologically active substance there may be mentioned retinoic acid, ascorbic acid, vitamin E (tocopherol), salicylic acid, kojic acid, alpha-lipoic acid lipoic acid, ellagic acid, resveratrol, docohexaenoic acid (DHA), eicosapentaenoic acid (EPA), linoleic acid (LA) , Glutathione, or a mixed form thereof.
  • DHA docohexaenoic acid
  • EPA eicosapentaenoic acid
  • LA linoleic acid
  • Glutathione or a mixed form thereof.
  • the present invention is not limited thereto, and may be changed depending on the application field.
  • the physiologically active substance is supported on 100 parts by weight of the volcanic ash.
  • the ionic polymers used in the present invention may be selected from the group consisting of alginic acid, pectin, carrageenans, xanthan gum, hyaluronic acid, Arabic gum, Karaya gum, and Tragacanth gum.
  • the ionic polymer is used in an amount of 1 to 10 parts by weight, more preferably 2 to 3 parts by weight, based on 100 parts by weight of the volcanic ash. At this time, if the ionic polymer content is less than 1 part by weight, hwasanto to the stabilization after the carry of a biomolecule lack the micro pores and the storage period 4 weeks elapsed time, the precipitation occurs in the third week, or a problem of discoloration Table 2 ]. On the other hand, when the amount is more than 10 parts by weight, precipitation or discoloration is not observed. However, when the excess amount is insufficient, the effect improvement effect is insufficient, and the more the remaining unbonded amount is, the more the nonionic polymer content is increased.
  • starch or cyclodextrin is used as the nonionic polymeric substance.
  • a natural polymer which has little or no bio-toxicity and which can be skin-friendly and environmentally friendly.
  • a physiologically active substance supported on a volcanic soil is stabilized, So as to have a stable dispersion degree.
  • the nonionic polymer is preferably used in an amount of 1 to 10 parts by weight, more preferably 1 to 3 parts by weight, based on 100 parts by weight of the volcanic ash. At this time, or the ionic polymer content is less than 1 part by weight, when the weight exceeds 10 parts, the precipitation or color change occurred in the storage period Week 4 [Table 3].
  • the present invention relates to a method for preparing a stable colloid by stirring or ultrasonically dispersing a volcanic ash, mixing 100 parts by weight of a volcanic ash and 10 to 30 parts by weight of a physiologically active substance to carry a biologically active substance on the micropores of the volcanic ash,
  • the present invention provides a method for producing a composite comprising three steps of inhibiting self-aggregation of a complex through a network of a non-ionic polymer and a residue of an anionic polymer exposed on the surface of the composite.
  • the step 1 is a step of stably supporting a physiologically active substance on the micropores of a porous material, which is a porous material.
  • the physiologically active substance is mixed with 100 parts by weight of the volatile earth by stirring or ultrasonication at 0 to 4 ⁇ , Separate and wash and re-disperse in distilled water.
  • the volcanic ash is mixed with distilled water at a rate of 0.01 to 1 wt% at room temperature or by ultrasonication to produce a stable colloidal solution.
  • stirring is performed for more than 24 hours for 1 hour or more, and the colloid solution is centrifuged to remove the precipitate, thereby finally obtaining a stable volcanic colloid.
  • the physiologically active substance is prepared by dissolving the selected physiologically active substance to 0.1 wt% in distilled water at 4 to 20 ° C.
  • sodium hydroxide is added in an equivalent ratio of 1: Dissolve.
  • step 2 the micropores are sealed with an anionic polymer to protect the supported physiologically active substance from the external environment such as air, light, heat, pH, moisture, and the like, thereby preparing a stabilized complex.
  • step 3 1 to 10 parts by weight of a nonionic polymer is added to the redispersed composite solution in step 2, and the mixture is stirred or ultrasonicated at 4 to 20 ° C, followed by centrifugation and washing with distilled water. .
  • the polymer selected in the second and third steps is used in distilled water in an amount of 0.01 to 1% by weight.
  • the weight ratio of the polymer to water is too high, the viscosity of the solution is excessively increased or difficult to be dissolved by the polymer, so that the preparation of the complex is not easy.
  • the weight ratio of the polymer to the distilled water is too low, Lowering the effect of enclosing the physiologically active substance and the stability of the egg / insoluble complex.
  • the average molecular weight of the polymer is preferably 1,000 to 100,000.
  • the temperature of the polymer solution is preferably 20 to 80 DEG C, and the pH of the solution is preferably 5 to 8.
  • the complex of the present invention is not only environmentally friendly but also skin-friendly and highly stable to an aqueous solution, so that it can be applied to foods and medicines which are required to stabilize a target substance as well as a raw material for functional cosmetics.
  • the present invention provides a functional cosmetic comprising the above-mentioned complex and having a functional property by the supported physiologically active substance.
  • the present invention also provides functional foods or medicines based on physiologically active substances including the complex.
  • a solution of 0.1% vitamin C in 100 g of a 0.1% volcanic acid dispersion was mixed in the amounts shown in Table 1 below. Thereafter, the mixture was stirred at 4 ° C for 24 hours, centrifuged and washed, lyophilized, and the mass of the powder was measured. The amount of physiologically active substance loaded on the volcanic soil was calculated by the following equation.
  • reaction is carried out by stirring the redispersed physiologically active substance / volcanic acid solution and the anionic polymer solution at 4 ° C for 24 hours, centrifuging and washing, and adding the nonionic polymer solution to 100 g of the prepared composite dispersion solution followeded by stirring at 4 ° C for 24 hours for centrifugation and washing.
  • the final product was dispersed in 100 g of distilled water.
  • a complex was prepared as shown in Table 2 below using 0.1% hyaluronic acid as an anionic polymer and 0.1% starch as a nonionic polymer.
  • the composites prepared in each Example were stored at 50 < 0 > C and observed for sedimentation and discoloration.
  • the stabilization of the complex supports that the anionic polymer and the non-ionic polymer form a network to improve the stability of the egg / insoluble substance in the aqueous solution.
  • the anionic polymer shown in the following Table 3 was added to the redispersed solution, stirred at 4 DEG C for 24 hours, centrifuged and washed, and redispersed in 100 g of distilled water.
  • the non-ionic polymer was added to 100 g of the redispersed composite redispersion solution, followed by centrifugation and washing at 4 DEG C for 24 hours with stirring.
  • the final product was dispersed in 100 g of distilled water and stored at 50 ° C to observe sedimentation and discoloration. The results are shown in Table 3 below.
  • the ionic polymer when physiologically active substances are supported by physical interaction with micropores of a porous material, which is a porous material, the ionic polymer is bound to the entrance of micropores to protect and stabilize physiologically active substances from the external environment.
  • the hydrophobic residues of the ionic polymer exposed on the surface of the composite of the present invention form a network by interaction of non-ionic polymers with Van der Waals, thereby suppressing self-agglomeration between the complexes and enhancing water dispersibility, Since it is not only environmentally friendly but also skin-friendly and highly stable to aqueous solution, it can be applied not only to raw materials for functional cosmetics but also to industrial fields such as foods and medicines that require stabilization of the target substance.

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • Birds (AREA)
  • Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Dermatology (AREA)
  • Dispersion Chemistry (AREA)
  • Medicinal Preparation (AREA)
  • Cosmetics (AREA)

Abstract

La présente invention concerne un composite utilisant un matériau poreux et un polymère, et son utilisation. Le composite de la présente invention comprend une substance bioactive supportée dans les micropores d'un sol volcanique, qui est un matériau poreux, les micropores étant coiffés d'un polymère ionique de façon à protéger la substance bioactive de l'environnement extérieur, et le composite comprenant un réseau formé par des liaisons de Van der Waals entre des fractions polymères ioniques, qui sont visibles à la surface après le coiffage, et un polymère non ionique de façon à empêcher l'auto-agrégation, ce qui évite la séparation, la précipitation et la décoloration après la préparation du composite et ce qui permet, en particulier, d'obtenir une remarquable dispersibilité dans l'eau. Ce composite trouve, par conséquent, de nombreuses applications dans les domaines des produits cosmétiques, alimentaires ou médicaux et la substance bioactive supportée peut présenter diverses fonctionnalités.
PCT/KR2018/000113 2018-01-03 2018-01-03 Composite utilisant un matériau poreux et un polymère, et son utilisation WO2019135420A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
PCT/KR2018/000113 WO2019135420A1 (fr) 2018-01-03 2018-01-03 Composite utilisant un matériau poreux et un polymère, et son utilisation

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/KR2018/000113 WO2019135420A1 (fr) 2018-01-03 2018-01-03 Composite utilisant un matériau poreux et un polymère, et son utilisation

Publications (1)

Publication Number Publication Date
WO2019135420A1 true WO2019135420A1 (fr) 2019-07-11

Family

ID=67143755

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2018/000113 WO2019135420A1 (fr) 2018-01-03 2018-01-03 Composite utilisant un matériau poreux et un polymère, et son utilisation

Country Status (1)

Country Link
WO (1) WO2019135420A1 (fr)

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6391336B1 (en) * 1997-09-22 2002-05-21 Royer Biomedical, Inc. Inorganic-polymer complexes for the controlled release of compounds including medicinals
WO2009113522A1 (fr) * 2008-03-11 2009-09-17 あすか製薬株式会社 Dispersion solide, compositions pharmaceutiques comprenant celle-ci, et procédés de production associés
KR20100120244A (ko) * 2004-10-25 2010-11-12 니뽄 다바코 산교 가부시키가이샤 용해성 및 안정성이 개선된 고형 제제 및 그의 제조 방법
KR20170038679A (ko) * 2015-09-30 2017-04-07 (주)아모레퍼시픽 화산송이 분말 입자가 다공성 고분자에 함침된 복합분체, 이를 함유하는 화장료 조성물 및 이의 제조방법
US20170246111A1 (en) * 2014-09-15 2017-08-31 Pharmasol Gmbh Active-loaded particulate materials for topical administration

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6391336B1 (en) * 1997-09-22 2002-05-21 Royer Biomedical, Inc. Inorganic-polymer complexes for the controlled release of compounds including medicinals
KR20100120244A (ko) * 2004-10-25 2010-11-12 니뽄 다바코 산교 가부시키가이샤 용해성 및 안정성이 개선된 고형 제제 및 그의 제조 방법
WO2009113522A1 (fr) * 2008-03-11 2009-09-17 あすか製薬株式会社 Dispersion solide, compositions pharmaceutiques comprenant celle-ci, et procédés de production associés
US20170246111A1 (en) * 2014-09-15 2017-08-31 Pharmasol Gmbh Active-loaded particulate materials for topical administration
KR20170038679A (ko) * 2015-09-30 2017-04-07 (주)아모레퍼시픽 화산송이 분말 입자가 다공성 고분자에 함침된 복합분체, 이를 함유하는 화장료 조성물 및 이의 제조방법

Similar Documents

Publication Publication Date Title
Lvov et al. Clay nanotube encapsulation for functional biocomposites
Wang et al. Characterization, release, and antioxidant activity of curcumin-loaded sodium alginate/ZnO hydrogel beads
Wang et al. Combination of adsorption by porous CaCO3 microparticles and encapsulation by polyelectrolyte multilayer films for sustained drug delivery
Kevadiya et al. Layered bionanocomposites as carrier for procainamide
GB2030161A (en) Process for stabilizing dyestuffs sensitive to light and/or oxidation
KR870700209A (ko) 즉석 균질마이크로 캎셀 현탁액의 제조방법
WO2004081222A2 (fr) Microparticules et nanoparticules d'encapsulation d'agents, procedes de preparation de celles-ci, et produits contenant celles-ci
CN102199312B (zh) 一种具有缓释功能的介孔氧化硅微粒复合载体及其制备方法和应用
DK161744B (da) Fremgangsmaade til fremstilling af fritstroemmende ethylcellulosemikrokapsler
WO2011071239A2 (fr) Procédé de solubilisation d'une matière active difficilement soluble/insoluble par la formation de composite d'oligomères
Flamminii et al. Alginate-based microparticles structured with different biopolymers and enriched with a phenolic-rich olive leaves extract: A physico-chemical characterization
CN101703480A (zh) 明胶-壳聚糖/蒙脱土载药微球及制备方法
KR20140033122A (ko) 무기 미립자 재료의 제조 방법
Wang et al. Preparation of cellulose based microspheres by combining spray coagulating with spray drying
Hassanpouraghdam et al. In-vitro evaluation of the 5-fluorouracil loaded GQDs@ Bio-MOF capped with starch biopolymer for improved colon-specific delivery
AU2014356854B2 (en) Process for producing inorganic particulate material
WO2019135420A1 (fr) Composite utilisant un matériau poreux et un polymère, et son utilisation
ES2728252T3 (es) Uso de material a base de óxido de silicio para la liberación modificada de agentes biológicamente activos
CN105919978B (zh) 一种阿莫西林微球缓释胶囊制备方法
CA1317547C (fr) Forme anhydre pour application d'huminates de metal alcalin, a faible poids moleculaire
CN103497344B (zh) 用于负载贵金属颗粒的纳米凝胶及其制备方法与应用
WO2018044035A1 (fr) Composition cosmétique de type huile dans l'eau
CN108653239B (zh) 一种表没食子儿茶素没食子酸酯纳米缓释制剂及其制备方法
CN113730374B (zh) 一种甜菜果胶基口服缓释凝胶珠及其制备方法
KR20180006779A (ko) 다공성 물질과 고분자를 이용한 복합체 및 그를 이용한 용도

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 18898048

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 18898048

Country of ref document: EP

Kind code of ref document: A1