WO2023109209A1 - Microcapsule antibactérienne de structure bionique, son procédé de préparation, et son utilisation - Google Patents

Microcapsule antibactérienne de structure bionique, son procédé de préparation, et son utilisation Download PDF

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WO2023109209A1
WO2023109209A1 PCT/CN2022/117969 CN2022117969W WO2023109209A1 WO 2023109209 A1 WO2023109209 A1 WO 2023109209A1 CN 2022117969 W CN2022117969 W CN 2022117969W WO 2023109209 A1 WO2023109209 A1 WO 2023109209A1
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antibacterial
microcapsule
microcapsules
core material
emulsion
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PCT/CN2022/117969
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Chinese (zh)
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曹馨文
沈轲
李桂华
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合肥芯能相变新材料科技有限公司
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    • 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
    • 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
    • B01J13/06—Making microcapsules or microballoons by phase separation
    • B01J13/14—Polymerisation; cross-linking

Definitions

  • the invention relates to the field of antibacterial products, in particular to an antibacterial microcapsule with a bionic structure and its preparation method and application.
  • Antibacterial agents are generally divided into three types: inorganic antibacterial agents, organic antibacterial agents and natural antibacterial agents.
  • metals such as silver, copper, and zinc
  • metals such as silver, copper, and zinc (or their Ions) are fixed on the surface of porous materials such as fluorspar and silica gel to make antibacterial agents, and then added to corresponding products to obtain materials with antibacterial capabilities.
  • Metals such as mercury, cadmium, and lead also have antibacterial capabilities, but they are harmful to the human body. Harmful; at the same time, copper, nickel, lead and other ions are colored, which will affect the appearance of the product.
  • Zinc has certain antibacterial properties, but its antibacterial strength is only 1/1000 of silver ions;
  • the prior art Chinese patent CN201910842257 proposes an antibacterial phase-change microcapsule and its formulation technology.
  • This prior art uses the in-situ reduction of silver on the surface of the microcapsule to obtain a phase-change microcapsule with antibacterial function;
  • another example of the prior art Chinese patent CN108686262A provides a pretreated expanded perlite as a carrier, vacuum absorbs a liquid phase change material, and then adsorbs a silver-containing chitosan layer on the surface, and then forms a sodium alginate porous gel layer to obtain a double-wall slow release
  • the method of antibacterial phase-change microcapsules but the method process is more complicated; the above-mentioned method mostly uses the antibacterial ability of silver itself to carry out antibacterial.
  • organic antibacterial agents vanillin or ethyl vanillin compounds, which are often used in polyethylene food packaging films to play an antibacterial role.
  • organic antibacterial agents such as quaternary ammonium salts, biquats, and phenols is still under study.
  • Most organic antibacterial agents have poor heat resistance, are easily hydrolyzed, and have a short validity period.
  • Such as the prior art Chinese patent CN200880018078.9 proposes a polymer microcapsule containing quaternary ammonium salt and its manufacturing method, the core of the method is to use cetylpyridinium chloride as the representative antibacterial agent as the core material , and then encapsulated with polymers to form microcapsules.
  • Natural antibacterial agents mainly come from the extraction of natural plants, such as chitin, mustard, castor oil, horseradish, etc., which are easy to use, but have limited antibacterial effect, poor heat resistance, low bactericidal rate, cannot be used for broad-spectrum and long-term use, and the quantity is very large few.
  • the prior art Chinese patent CN201510287717.3 proposes a preparation method of essential oil microcapsules with chitosan as the wall material.
  • the essential oil with antibacterial function is selected as the core material to realize the antibacterial function.
  • the antibacterial rate reaches 85%.
  • the present invention proposes a kind of antibacterial microcapsule of bionic structure and its preparation method and application.
  • the present invention proposes a bionic structure antibacterial microcapsule and its preparation method and application.
  • An antibacterial microcapsule with a bionic structure comprises a core material and a capsule wall material wrapped on the surface of the core material, the capsule wall material has a through-hole structure, and the surface of the capsule wall material is negatively charged.
  • antibacterial microcapsules are spherical or spheroidal, with a D50 diameter of 0.8-10 microns.
  • the inner shell surface of the core material wrapped by the capsule wall material is lipophilic
  • the outer shell surface of the capsule wall material is hydrophilic
  • the core material includes phase change materials, fat-soluble essences, plant essential oils, and fat-soluble vitamins. at least one.
  • a preparation method of bionic structure antibacterial microcapsules comprising the steps of:
  • the second mixture with the first shell is formed after 4h-8h, and then the temperature of the second mixture is raised to 60-80°C and the initiator is added to keep the temperature constant After 5h-12h, the second layer of shell is formed by polymerization to obtain antibacterial microcapsules.
  • the core material includes at least one of phase change materials, fat-soluble flavors, plant essential oils, and fat-soluble vitamins;
  • the silane coupling agent includes aminopropyltrimethoxysilane, aminopropyltriethoxysilane, phenyltriethoxysilane, 3-(methacryloxy)propyltrimethoxysilane, orthosilane At least two of tetraethyl orthosilicate and tetramethyl orthosilicate;
  • the monomers include at least one of styrene, divinylbenzene, acrylate monomers, acrylic monomers, and diisocyanate prepolymers;
  • Described composite emulsifier is the composition of anionic surfactant and nonionic surfactant.
  • the complex emulsifier includes polyethylene-maleic anhydride copolymer or its hydrolyzed salt, polystyrene-maleic anhydride copolymer or its hydrolyzed salt, block copolymer of epoxy resin and polyethylene glycol, Sodium lauryl sulfate, sodium dodecylbenzene sulfonate, sorbitan monooleate polyoxyethylene ether, fatty alcohol polyoxyethylene ether, alkylphenol polyoxyethylene ether, fatty alcohol polyoxypropylene At least one of ether, glycerol monofatty acid ester, polyoxyethylene sorbitan fatty acid ester, sorbitan fatty acid ester and/or fatty acid pentaerythritol ester.
  • each component includes: 25-60 parts of core material, 0.6-8 parts of silane coupling agent, 1.2-10 parts of monomer and 0.19-3 parts of composite emulsifier.
  • An antibacterial product which contains the above antibacterial microcapsule with bionic structure or the antibacterial microcapsule prepared by the above preparation method.
  • antibacterial microcapsules with bionic structure in transportation or storage of food, medicine, textiles or cosmetics, are the above antibacterial microcapsules with bionic structure or the antibacterial microcapsules prepared by the above preparation method.
  • the antibacterial microcapsules with a bionic structure possess efficient antibacterial properties;
  • the preparation process of the microcapsules of the present invention is simple, relatively universal, and the core material can be replaced conveniently. It is an excellent carrier of functional substances such as drugs, and can realize microstructure transfer, transportation or controlled release of functional substances;
  • the antimicrobial microcapsules prepared by the method of the present invention can provide composite functional microcapsules with at least two functions, that is, the core material of the microcapsules provides a kind of functionality, and the core material can release the self-performance of the core material through the through holes on the surface of the microcapsules. , At the same time, the microcapsules have high antibacterial properties.
  • the present invention obtains an antibacterial microcapsule with a bionic structure, and the microcapsule has a pore structure that runs through the shell.
  • Staphylococcus, Candida albicans, Escherichia coli, etc. have a diameter of several microns in size, and the surface of the bacteria is negatively charged.
  • the present invention itself is a beneficial and important attempt in the design and synthesis of micro-nano structural units.
  • Fig. 1 is the scanning electron microscope (SEM) photo of a kind of bionic structure antibacterial microcapsule described in the embodiment of the present invention 1;
  • Fig. 2 is the transmission electron microscope (TEM) photo of a kind of bionic structure antibacterial microcapsule described in embodiment 1;
  • Fig. 3 is the laser particle size test curve of a kind of biomimetic structure antibacterial microcapsule of embodiment 1 gained;
  • Fig. 4 is the scanning electron microscope (SEM) photograph of a kind of biomimetic structure antibacterial microcapsule of embodiment 2 gained;
  • Fig. 5 is the transmission electron microscope (TEM) photograph of a kind of biomimetic structure antibacterial microcapsule of embodiment 2 gained;
  • Fig. 6 is the laser particle size test curve of a kind of biomimetic structure antibacterial microcapsule of embodiment 2 gained;
  • Fig. 7 is the DSC test curve of a kind of biomimetic structure antibacterial microcapsule of embodiment 2 gained;
  • Fig. 8 is the scanning electron microscope (SEM) photograph of a kind of biomimetic structure antibacterial microcapsule of embodiment 3 gained;
  • SEM scanning electron microscope
  • the present invention adopts following technical scheme:
  • a preparation method of bionic structure antibacterial microcapsules characterized in that the preparation method comprises the following steps:
  • the core material includes at least one of phase change material, n-docosane, industrial paraffin, n-octadecane, pink rose essential oil, fat-soluble essence, plant essential oil, and fat-soluble vitamin;
  • the core material is the core component, endowing the material with functionality, such as heat storage, temperature response, release of fragrance or functional substances, etc.;
  • the core material and the continuous phase are often incompatible. At the interface between the two, a place for the formation of the microcapsule wall material is provided.
  • the core material in this plan is mainly based on various staphylococcus and candida albicans during implementation. , Escherichia coli cell fluid investigation, selected materials with similar physical and chemical properties as the main component of the core material.
  • silane coupling agent comprises aminopropyltrimethoxysilane coupling agent, KH550 silane coupling agent (3-aminopropyltriethoxysilane), phenyltriethoxysilane coupling agent, 3-( At least two of methacryloyloxy)propyltrimethoxysilane coupling agent, tetraethyl orthosilicate, and tetramethyl orthosilicate; the silane coupling agent is used as an inorganic silicon source, and the formed Silica is a part of the wall material.
  • the silane coupling agent can effectively modify the interface through the simple and convenient sol-gel process, and the selection range of the silane coupling agent is also relatively large;
  • the method introduces at least two chemical groups with different properties into the wall material by selecting at least two kinds of silane coupling agents, which can regulate the properties of the microcapsule shell to a certain extent;
  • the monomers include at least one of styrene, divinylbenzene, acrylate monomers, acrylic monomers, and diisocyanate prepolymers. After the monomer initiates polymerization, it forms a composite shell with the aforementioned inorganic substances.
  • the organic-inorganic composite shell formed under the method of the present invention can exhibit different properties on both sides of the shell, such as facing the core.
  • the inner shell side of the material is more oleophilic, while the outer shell side facing the water phase is more hydrophilic. These two sides are actually two sides of the same shell;
  • Described compound emulsifier is selected from the block copolymer of polyethylene-maleic anhydride copolymer or its hydrolyzed salt, polystyrene-maleic anhydride copolymer or its hydrolyzed salt, epoxy resin and Polyethylene Glycol, dodecane Sodium Alkyl Sulfate, Sodium Dodecyl Benzene Sulfonate, Fatty Alcohol Polyoxyethylene Ether, Tween 80 (Sorbitan Monooleate Polyoxyethylene Ether), Tween 60 (Polyoxyethylene Sorbitan Stearate ester), triton (polyethylene glycol p-isooctyl phenyl ether), alkylphenol polyoxyethylene ether, fatty alcohol polyoxypropylene ether, glycerin monofatty acid ester, polyoxyethylene sorbitan A composition of at least one anionic surfactant and at least one nonionic surfactant in fatty acid esters, sorbitan fatty acid esters,
  • Surfactants provide the key guarantee for stabilizing the oil-water interface while creating sites for shell formation.
  • the specific phase behavior of surfactants at the oil-water interface can be adjusted by two or more different types of surfactants to achieve different effects;
  • the sum of the consumption of the core material, silane coupling agent and polymer monomer is 10.0%-59.0%wt of the final microcapsule suspension; the nonionic surfactant consumption is no more than 0.8% of the final microcapsule suspension. %wt;
  • the sum of the amount of the core material, silane coupling agent, and polymer monomer is 15.0%-49.0%wt of the final microcapsule suspension, and the amount of the nonionic surfactant is the final microcapsule suspension 0.1%-0.67%wt;
  • the sum of the amount of the core material, silane coupling agent, and polymer monomer is 25.0%-39.0%wt of the final microcapsule suspension, and the amount of the nonionic surfactant is the final microcapsule suspension 0.2%-0.45%wt of liquid.
  • step d represents the sol-gel process
  • step e represents the polymerization process of organic monomers.
  • the two processes can be passed. Conditions such as temperature, pH, initiator ultraviolet light, etc. control the successive start respectively, or start at the same time;
  • sol-gel process is started first, and then the organic monomer polymerization is started, which is more conducive to the formation of the biomimetic structure described in the present invention.
  • the hydrophilic outer shell structure is more conducive to the formation of the through-hole structure.
  • microcapsules are spherical or spheroidal, with a D50 diameter of 0.8 microns to 10 microns; the surface of the microcapsules is negatively charged; the microcapsules have a pore structure that runs through the shell;
  • Staphylococcus, Candida albicans, Escherichia coli, etc. have a diameter of several microns in size, and the surface of the bacteria is negatively charged. At the same time, there are some small pore structures on the surface of the bacteria. These pore structures run through the shell, and the bacteria pass through these negatively charged membrane structures, or pores. structure for nutrition.
  • the biomimetic structure microcapsule of the present invention performs very well in antibacterial aspect, and its reason includes as follows, when the microcapsule of the present invention and bacterium are in the same condition together, this type of biomimetic structure microcapsule can produce competition with some bacteria Food effect, the possibility of bacteria obtaining nutrition is greatly reduced, which hinders bacteria from obtaining nutrition and multiplying, thus achieving antibacterial effect;
  • the biomimetic structure microcapsules performed poorly, because the structure biomimetic microcapsules did not contain any of the above three antibacterial agents, and could not actively kill bacteria, but in the antibacterial test Among them, it can reduce the chance of bacterial survival by competing for food.
  • the above-mentioned three antibacterial agents namely inorganic antibacterial agents, organic antibacterial agents or natural antibacterial agents
  • various fillers will be used during processing, such as catalysts, accelerators, covering agents, whitening agents, pigments, thinners, thickeners, curing agents, etc., and some functions will also be used sexual fillers, etc., these should be regarded as extensions or deformations that do not deviate from the technical solutions of the present invention, and fall within the scope of protection determined by the claims of the present invention.
  • a biomimetic structure antibacterial microcapsule of the present invention is used in textile processing technology including at least one of finishing, coating, padding, printing or spinning, and the biomimetic structure antibacterial microcapsule can be mixed with additives In the form of finishing paste, or printing paste, padding bath, through further related processing, it is attached to the fabric or similar layered structure, thereby endowing the product with antibacterial properties, similar,
  • An antibacterial product claimed in the present invention includes textiles with antibacterial function prepared in the above process;
  • the antibacterial microcapsule with a bionic structure and its method described in the present invention can also be used in the fields of medical care, transportation or storage of food and medicine, cosmetics, and the like.
  • biomimetic structure antibacterial silicon dioxide-polystyrene microcapsule in this example, its preparation method comprises the following steps:
  • oil-in-water emulsion oil-in-water emulsion
  • the temperature of the emulsion is raised to 60-80°C, the initiator AIBN (azobisisobutyronitrile) is added, and the temperature is kept for 5h-12h to make it polymerize to form the second shell.
  • AIBN azobisisobutyronitrile
  • Figure 2 is a TEM photo of the obtained microcapsules.
  • the TEM photos show that the pores on the surface of the microcapsules penetrate the shell and form larger cavities inside the capsules.
  • the hole can be used to load functional substances such as essential oils.
  • the Zeta potential test showed that the Zeta potential of the microcapsules was -30.4mV, indicating that the surface of the microcapsules was negatively charged. This is because a kind of surfactant styrene-maleic anhydride hydrolyzed sodium salt used in this example is an anionic surfactant.
  • Figure 3 is the laser particle size analysis curve of the obtained microcapsules, it can be seen that the D50 diameter is 0.85 microns.
  • the microcapsules obtained in this example are used for the after-finishing of fabrics, and the treated fabrics are tested for antibacterial performance.
  • the test method refers to FZ/T 73023-2006 antibacterial knitwear, and the results in Table 1 are obtained: the antibacterial rate of Candida albicans is 86% , The antibacterial rate of Escherichia coli is 86%, and the antibacterial rate of Staphylococcus aureus is 88%.
  • n-octadecane and 8g tetraethyl silicate 0.6g aminopropyltrimethoxysilane coupling agent, 1.2g phenyltriethoxysilane coupling agent, 5g dimethacrylic acid 1,4 -butanediol ester, stirring for 20min, the process of uniformly forming an oil phase;
  • the temperature of the emulsion is raised to 50-80°C, the initiator APS (ammonium persulfate) is added, and the temperature is kept for 5h-12h, so that the organic monomers are polymerized to form the second shell.
  • APS ammonium persulfate
  • a kind of shell layer is a biomimetic structure antibacterial microcapsule of silicon dioxide-polyacrylate
  • Figure 5 is a TEM photo of the obtained microcapsules. TEM photos show that the pores on the surface of the microcapsules penetrate the shell;
  • the Zeta potential test showed that the Zeta potential of the microcapsules was -16.9mV, indicating that the surface of the microcapsules was negatively charged. This is because a kind of surfactant ethylene-maleic anhydride copolymer hydrolysis salt used in this example is a kind of anionic surfactant;
  • Figure 6 is the laser particle size analysis curve of the obtained microcapsules, it can be seen that the D50 diameter is 3.023 microns.
  • this example has obtained a biomimetic structure microcapsule with a negatively charged surface, a D50 of 3.023 microns, and several micropores on the surface. And did not introduce any aforementioned 3 kinds of antibacterial agents in this example;
  • the microcapsules obtained in this example are used for the finishing of fabrics, and the treated fabrics are tested for antibacterial properties.
  • the test method refers to GB/T20944.2 Appendix B, and the results in Table 2 are obtained as follows: 99.9% antibacterial rate against Candida albicans, washed with water The antibacterial rate after 50 times is 84.9%; the antibacterial rate against Escherichia coli is 99.9%, and the antibacterial rate after washing 50 times is 92.9%; the antibacterial rate against Staphylococcus aureus is 99.9%, and the antibacterial rate after washing 50 times is 96.4%;
  • each component in this example is analyzed, and each component is listed in the following table 3, and each comparative sample S2-0 etc. has expressed that only corresponding oil phase or water phase components are used, corresponding to other parts in this example 2 with etc. Measure water instead, and the operation steps are the same as in Example 2. After finishing the operation, carry out the antibacterial test respectively. The results showed that none of the formulations had antibacterial properties.
  • This example provides a kind of antibacterial silicon dioxide-polystyrene-polyacrylate composite microcapsule of bionic structure, and its preparation method comprises the following steps:
  • the temperature of the emulsion is raised to 60-80°C, benzoyl peroxide is added, and the temperature is kept for 5h-12h to allow it to polymerize to form a second shell.
  • the described shell layer is silicon dioxide-polystyrene-polyacrylate composite microcapsules
  • Accompanying drawing 8 and accompanying drawing 9 are the SEM photos of the obtained microcapsules of this example.
  • Accompanying drawing 9 is the partial enlargement of capsule shell, and it can be seen that there are some tiny holes therein;
  • the Zeta potential test showed that the Zeta potential of the microcapsules was -22.8mV, indicating that the surface of the microcapsules was negatively charged. This is due to the use of 2 anionic surfactants in this example;
  • the differential scanning calorimetry method obtained the phase change melting point of the phase change microcapsules in this example as 43.95°C, and the corresponding phase change enthalpy value was 140.1J/g;
  • the microcapsules obtained in this example are used for the finishing of fabrics, and the treated fabrics are tested for antibacterial performance.
  • the test method refers to FZ/T 73023-2006 antibacterial knitwear.
  • the test shows that the antibacterial rate of Candida albicans is 88%, and that of Escherichia coli The antibacterial rate is 85%, and the antibacterial rate for Staphylococcus aureus is 89%.
  • microcapsules in this example have good antibacterial effect.
  • This example provides a kind of biomimetic structure antibacterial silicon dioxide-polyurea composite microcapsule, and its preparation method comprises the following steps:
  • the temperature of the emulsion is raised to 50-80°C, and 1,6-hexanediamine is added dropwise, and kept for 2h-8h to make it polymerize to form a second shell.
  • the described shell layer is a silica-polyurea composite microcapsule
  • the Zeta potential test shows that the Zeta potential of the microcapsules is -31.5mV, indicating that the surface of the microcapsules is negatively charged;
  • the microcapsules obtained in this example are used for the finishing of fabrics, and the treated fabrics are tested for antibacterial properties.
  • the test method refers to FZ/T 73023-2006 antibacterial knitwear.
  • the test shows that the bacteriostatic rate of Candida albicans is 87%, and that of Escherichia coli The antibacterial rate is 85%, and the antibacterial rate for Staphylococcus aureus is 91%.
  • microcapsules in this example have good antibacterial effect.
  • the temperature of the emulsion is raised to 50-80°C, the initiator APS is added, and the temperature is kept for 5h-12h, so that the organic monomers are polymerized to form the second shell.
  • a kind of shell layer is a biomimetic structure antibacterial microcapsule of silicon dioxide-polyacrylate
  • the Zeta potential test shows that the Zeta potential of the microcapsules is -11.4mV, indicating that the surface of the microcapsules is negatively charged;
  • the microcapsules obtained in this example are used for fabric finishing, and the treated fabric is tested for antibacterial performance.
  • the test method refers to FZ/T 73023-2006 antibacterial knitwear.
  • the test shows that the antibacterial rate of Candida albicans is 85%, and that of Escherichia coli The antibacterial rate is 86%, and the antibacterial rate for Staphylococcus aureus is 94%.
  • microcapsules in this example have good antibacterial effect.

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Abstract

La présente invention se rapporte au domaine technique des produits antibactériens, et en particulier à une microcapsule antibactérienne d'une structure bionique, son procédé de préparation et son utilisation. La solution comprend un matériau de noyau et un matériau de paroi de capsule enveloppant la surface du matériau de noyau. Le matériau de paroi de capsule est pourvu d'une structure de trou traversant. La surface du matériau de paroi de capsule est chargée négativement. La microcapsule antibactérienne est sphérique ou de type sphère et présente un diamètre de 0,8 à 10 micromètres. Le procédé de préparation comprend les étapes suivantes : mélange du matériau de noyau, d'un agent de couplage au silane et d'un monomère pour former un premier mélange ; mélange d'un émulsifiant composite d'une phase aqueuse avec le premier mélange pour former une émulsion H/E ; ajustement de la valeur de pH de l'émulsion H/E à 2 à 4 ; et ajout d'un initiateur dans l'émulsion h/e, et formation de la microcapsule antibactérienne au moyen d'un chauffage et d'une polymérisation. La microcapsule antibactérienne préparée à partir du procédé peut fournir une microcapsule fonctionnelle composite ayant au moins deux fonctions, c'est-à-dire que le matériau de noyau de microcapsule fournit une fonction, tandis que la propriété propre du matériau de noyau peut être libérée par l'intermédiaire des trous traversants sur la surface de la microcapsule. Pendant ce temps, la microcapsule présente une performance antibactérienne efficace.
PCT/CN2022/117969 2021-12-15 2022-09-09 Microcapsule antibactérienne de structure bionique, son procédé de préparation, et son utilisation WO2023109209A1 (fr)

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