CN114029012A - Preparation method of microcapsule with metal organic coordination polymer as wall material - Google Patents

Preparation method of microcapsule with metal organic coordination polymer as wall material Download PDF

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CN114029012A
CN114029012A CN202110979623.8A CN202110979623A CN114029012A CN 114029012 A CN114029012 A CN 114029012A CN 202110979623 A CN202110979623 A CN 202110979623A CN 114029012 A CN114029012 A CN 114029012A
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anhydrous
sulfate
various types
oil
chloride
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徐宇曦
章昭
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Westlake University
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Westlake University
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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
    • B01J13/06—Making microcapsules or microballoons by phase separation
    • B01J13/14—Polymerisation; cross-linking
    • B01J13/16—Interfacial polymerisation
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/045—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates
    • A61K31/07—Retinol compounds, e.g. vitamin A
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
    • A61K38/16—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • A61K38/17—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
    • A61K38/22—Hormones
    • A61K38/28—Insulins
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
    • A61K9/5005—Wall or coating material
    • A61K9/5021—Organic macromolecular compounds
    • A61K9/5031—Organic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyethylene glycol, poly(lactide-co-glycolide)
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G83/00—Macromolecular compounds not provided for in groups C08G2/00 - C08G81/00
    • C08G83/008—Supramolecular polymers

Abstract

The invention discloses a microcapsule taking a metal organic coordination polymer as a wall material and a preparation method thereof. The preparation method of the microcapsule takes the microemulsion as a template, so that metal ions and phenolic organic ligands are subjected to coordination reaction at an oil-water interface to form a coordination polymer film, and then the microcapsule encapsulated with the medicine is obtained by washing, filtering and collecting. The invention adopts an emulsion interface reaction method to prepare the microcapsule, has simple process and strong universality, and can encapsulate both water-soluble drugs and oil-soluble drugs.

Description

Preparation method of microcapsule with metal organic coordination polymer as wall material
Technical Field
The invention belongs to the technical field of biomedical engineering, medical carriers and membrane engineering, and relates to a microcapsule and a preparation method thereof, in particular to a microcapsule taking a metal organic coordination polymer as a wall material and a preparation method thereof.
Background
The microcapsule technology is a technology in which a solid, liquid or gas is embedded therein using a film-forming material to form a micro capsule having a diameter of several tens of nanometers to several thousands of micrometers, in which the encapsulated substance is referred to as a core material and the substance encapsulating the core material is referred to as a wall material. Because the microcapsule has good effects of protecting, slowly releasing, controlling release, changing form, covering bad smell and the like on the core material, the microcapsule technology is widely applied to a plurality of fields of food, medicine, dye, cosmetics, pesticide, chemical fertilizer and the like.
In recent years, the coordination supermolecule system based on metal ion-tannic acid is a very ideal microcapsule wall material due to the characteristics of rapid coordination reaction, pH responsiveness and the like, and attracts people's attention, for example, CN 110622965A. However, due to the water-soluble characteristics of metal ions and tannic acid, the interfacial polymerization method is difficult to prepare the microcapsule, and the application range of the microcapsule is greatly limited. Therefore, a new coordination system is still needed to be explored, and the preparation materials of the microcapsule are enriched.
Disclosure of Invention
In order to solve the technical problems in the background technology, the invention provides a preparation method of microcapsules taking metal organic coordination polymers as wall materials.
The invention is realized by the following technical scheme:
and taking the microemulsion as a template, and carrying out coordination reaction on metal ions and a phenolic organic ligand at an oil-water interface of the microemulsion to obtain the microcapsule.
The size of the microcapsule obtained by the method is about 10-300 mu m.
The microemulsions are oil-in-water emulsions, or water-in-oil emulsions.
The microemulsion is in a droplet wrapping form, and is an oil-in-water droplet or a water-in-oil droplet, so that an oil-water interface of the microemulsion is spherical.
The preparation method of the microcapsule is slightly different according to different modes of oil-in-water type and water-in-oil type needle micro-emulsion.
And aiming at the oil-in-water microemulsion, slowly adding an aqueous solution containing a metal salt with the concentration of 0.1-100 mM into the oil-in-water microemulsion, reacting at a spherical oil-water interface to form a metal ion-phenol coordination polymer film, and then washing, filtering and collecting to obtain the microcapsule encapsulated with the oil-soluble medicine.
The oil-in-water microemulsion is formed by stirring or swirling or ultrasonic treatment of an aqueous solution containing 0-10 wt% of a hydrophilic emulsifier and an oil phase solution containing 0.1-30 mM of a phenolic organic ligand, a specific drug and an organic solvent, wherein the volume of the aqueous phase is 1.5: 1-20: 1.
Adding an oil phase solution consisting of a phenolic organic ligand and an organic solvent with the concentration of 0.1-30 mM into the water-in-oil microemulsion, reacting at a spherical oil-water interface to form a metal ion-phenolic coordination polymer film, and then washing, filtering and collecting to obtain the microcapsule encapsulated with the water-soluble drug.
The water-in-oil microemulsion is formed by stirring or swirling or ultrasonic treatment of an oil phase solution containing a lipophilic emulsifier with a concentration of 0-10 wt% and an aqueous phase solution containing a metal salt with a concentration of 0.1-30 mM, a specific drug and water, wherein the volume of the aqueous phase to the volume of the oil phase is 1: 1.5-1: 20.
The hydrophilic emulsifier is one or more of polyvinyl alcohol (PVA), polyvinylpyrrolidone, sodium dodecyl sulfate, tween 20, tween 80 and triton 100.
Preferably, the lipophilic emulsifier is one or more of span 80 and span 20.
The phenolic organic ligand is one or two of the following molecular structures:
Figure BDA0003228556710000021
wherein A is one of-CHO, -CH ═ N-OH.
The metal salt is silver nitrate, anhydrous copper chloride, various hydrated copper chlorides, anhydrous copper sulfate, various hydrated copper sulfates, anhydrous copper nitrate, various hydrated copper nitrates, copper trifluoromethanesulfonate, anhydrous copper acetate, various hydrated copper acetates, copper bromide, anhydrous nickel chloride, various hydrated nickel chlorides, anhydrous nickel sulfate, various hydrated nickel sulfates, anhydrous nickel nitrate, various hydrated nickel nitrates, nickel trifluoromethanesulfonate, anhydrous nickel acetate, various hydrated nickel acetates, nickel bromide, anhydrous zinc chloride, various hydrated zinc chlorides, anhydrous zinc sulfate, various hydrated zinc sulfates, anhydrous zinc nitrate, various hydrated zinc nitrates, zinc trifluoromethanesulfonate, anhydrous zinc acetate, various hydrated zinc acetates, zinc bromide, anhydrous manganese chloride, anhydrous manganese sulfate, anhydrous manganese nitrate, various hydrated manganese nitrates, manganese trifluoromethanesulfonate, anhydrous zinc sulfate, anhydrous zinc acetate, anhydrous zinc bromide, anhydrous manganese chloride, various hydrated manganese chlorides, anhydrous manganese sulfate, anhydrous manganese nitrate, various hydrated manganese nitrate, manganese trifluoromethanesulfonate, anhydrous copper sulfate, anhydrous copper chloride, anhydrous copper sulfate, anhydrous nickel sulfate, anhydrous zinc nitrate, anhydrous zinc sulfate, anhydrous magnesium nitrate, anhydrous magnesium sulfate, anhydrous magnesium sulfate, magnesium sulfate, Anhydrous manganese acetate, hydrous manganese acetates of various types, manganese bromide, anhydrous cobalt chloride, hydrous cobalt chloride of various types, anhydrous cobalt sulfate, hydrous cobalt sulfate of various types, anhydrous cobalt nitrate, hydrous cobalt nitrate of various types, cobalt trifluoromethanesulfonate, anhydrous cobalt acetate, hydrous cobalt acetate of various types, cobalt bromide, anhydrous scandium chloride of various types, hydrous scandium chloride of various types, anhydrous scandium sulfate, hydrous scandium sulfate of various types, scandium trifluoromethanesulfonate, anhydrous scandium nitrate, hydrous scandium nitrate of various types, anhydrous iron chloride of various types, hydrous iron chloride of various types, scandium bromide, anhydrous iron sulfate, iron sulfate of various types, anhydrous iron acetate, hydrous iron acetate of various types, iron bromide, anhydrous iron sulfate of various types, hydrous iron sulfate of various types, titanium tetrachloride, zirconium tetrachloride, platinum chloride, chromium chloride, hydrous chromium chloride of various types, chromium bromide, hydrous chromium bromide of various types, chromium sulfate of various types, anhydrous chromium nitrate of various types, One or more of various hydrated chromium nitrates, chromium chlorides, various hydrated chromium chlorides, chromium sulfates and various hydrated chromium sulfates.
The organic solvent is one or more of oleic acid, ethanol, ethyl acetate, methyl acetate, toluene, o-xylene, mesitylene, dichloromethane, chloroform, dimethyl carbonate, n-hexane, n-heptane, n-pentane, methyl tert-butyl ether, n-butyl ether, isobutyl ether, n-hexanol and ISOPAR series solvents.
The medicine comprises vitamin A, insulin, essence, nicotinamide and the like, but is not limited to the vitamin A, the insulin, the essence, the nicotinamide and the like.
The preparation method of the microcapsule takes the microemulsion as a template, so that metal ions and phenolic organic ligands are subjected to coordination reaction at an oil-water interface to form a coordination polymer film, and then the microcapsule encapsulated with the medicine is obtained by washing, filtering and collecting.
The invention has the beneficial effects that:
compared with the prior art, the separation membrane with high separation selectivity is prepared by an interface coordination self-assembly technology; the preparation method is simple, the operation is easy, and the industrial practicability is good.
The invention adopts an emulsion interface reaction method to prepare the microcapsule, has simple process and strong universality, can encapsulate both water-soluble drugs and oil-soluble drugs, realizes the slow release of the drugs and improves the utilization efficiency of the drugs; moreover, the metal-phenol microcapsule material is low in price and has no obvious toxic and side effects.
Drawings
FIG. 1 is a microscopic image of the microcapsule obtained in example 1.
Detailed Description
The invention is further described with reference to the accompanying drawings and the detailed description.
The examples of the invention are as follows:
example 1
Uniformly mixing 1 wt% PVA aqueous solution and 5mM o-xylene solution of trialdehyde phloroglucinol at a ratio of 5: 1 under stirring to form an oil-in-water emulsion, and slowly adding a certain amount of 5mM FeCl under the condition of continuous stirring3And (3) the solution initiates the oil-water interface of the microemulsion to perform coordination reaction to form a coordination polymer film, and after the solution is stabilized for 3min, the stirring is stopped, and the microcapsule is obtained by washing and filtering.
Example 2
A1 wt% span 80 solution in dichloromethane and 2mM FeCl3And (3) uniformly stirring and mixing the solution according to a ratio of 5: 1 by magnetic force to form a water-in-oil emulsion, slowly adding a certain amount of dichloromethane solution of 5mM trialdehyde phloroglucinol under the condition of continuous stirring to initiate the oil-water interface of the microemulsion to perform coordination reaction to form a coordination polymer film, stopping stirring after stabilizing for 3min, washing and filtering to obtain the microcapsule.
Example 3
Mixing 1 wt% Tween 20 water solution and 2mM trialdehyde phloroglucinol oleic acid solution at a ratio of 3: 1 under stirring to form oil-in-water emulsion, and slowly adding 1mM FeCl3And (3) the solution initiates the oil-water interface of the microemulsion to perform coordination reaction to form a coordination polymer film, and after the solution is stabilized for 3min, the stirring is stopped, and the microcapsule is obtained by washing and filtering.
Example 4
A0.5 wt% solution of span 80 in n-butyl ether and 2mM Fe (NO)3)3Stirring and mixing the solution uniformly according to the ratio of 10: 1 to form a water-in-oil emulsion, slowly adding a certain amount of n-butyl ether solution of 5mM2,4, 6-trihydroxybenzene-1, 3, 5-benzene trioxymethylene under the condition of continuously stirring to initiate the oil-water interface of the microemulsion to perform coordination reaction to form a coordination polymer film, stabilizing for 5min, stopping stirring, washing and filtering to obtain the microcapsule.
Example 5
Uniformly mixing 5 wt% PVA water solution and 2mM trialdehyde phloroglucinol oleic acid solution according to a ratio of 5: 1 under stirring to form an oil-in-water emulsion, and slowly adding a certain amount of 1mM CuCl under the condition of continuously stirring2And (3) the solution initiates the oil-water interface of the microemulsion to perform coordination reaction to form a coordination polymer film, and after the solution is stabilized for 3min, the stirring is stopped, and the microcapsule is obtained by washing and filtering.
Example 6
Mixing 2 wt% PVA water solution and oleic acid solution containing 3mM trialdehyde phloroglucinol and vitamin A medicine at a ratio of 4: 1 under stirring to form oil-in-water emulsion, and slowly adding a certain amount of 1mM CuCl under stirring2The solution initiates the oil-water interface of the microemulsion to generate coordination reaction to form a coordination polymer film, after the solution is stabilized for 3min, the stirring is stopped, and the microcapsule is obtained by washing and filtering, as shown in figure 1.
Example 7
0.5 wt% span 80 in oleic acid was mixed with 2mM FeCl3And uniformly mixing the micro-emulsion and an aqueous solution of an insulin medicament by magnetic stirring at a ratio of 5: 1 to form a water-in-oil emulsion, slowly adding a certain amount of dichloromethane solution of 5mM trialdehyde phloroglucinol under the condition of continuous stirring to initiate the oil-water interface of the micro-emulsion to perform coordination reaction to form a coordination polymer film, stopping stirring after stabilizing for 3min, washing and filtering to obtain the microcapsule, wherein the formula is shown in figure 1.

Claims (10)

1. A method for preparing microcapsules by taking metal organic coordination polymers as wall materials is characterized in that: and taking the microemulsion as a template, and carrying out coordination reaction on metal ions and a phenolic organic ligand at an oil-water interface of the microemulsion to obtain the microcapsule.
2. The method for preparing microcapsules using metal-organic coordination polymers as wall materials according to claim 1, wherein the method comprises the following steps: the microemulsions are oil-in-water emulsions, or water-in-oil emulsions.
3. The method for preparing microcapsules using metal-organic coordination polymers as wall materials according to claim 1 or 2, wherein: and adding an aqueous solution containing metal salt with the concentration of 0.1-100 mM into the oil-in-water microemulsion aiming at the oil-in-water microemulsion, reacting at an oil-water interface to form a metal ion-phenol coordination polymer film, and then washing, filtering and collecting to obtain the microcapsule encapsulated with the oil-soluble medicine.
4. The method for preparing microcapsules using metal-organic coordination polymers as wall materials according to claim 3, wherein the method comprises the following steps: the oil-in-water microemulsion is formed by stirring or swirling or ultrasonic treatment of an aqueous solution containing 0-10 wt% of a hydrophilic emulsifier and an oil phase solution containing 0.1-30 mM of a phenolic organic ligand, a drug and an organic solvent, wherein the volume of the aqueous phase to the volume of the oil phase is 1.5: 1-20: 1.
5. The method for preparing microcapsules using metal-organic coordination polymers as wall materials according to claim 1 or 2, wherein: adding an oil phase solution consisting of a phenol organic ligand and an organic solvent with the concentration of 0.1-30 mM into the water-in-oil microemulsion, reacting at an oil-water interface to form a metal ion-phenol coordination polymer film, and then washing, filtering and collecting to obtain the microcapsule encapsulated with the water-soluble medicine.
6. The method for preparing microcapsules using metal-organic coordination polymers as wall materials according to claim 5, wherein the method comprises the following steps: the water-in-oil microemulsion is formed by stirring or swirling or ultrasonic treatment of an oil phase solution containing a lipophilic emulsifier with a concentration of 0-10 wt% and an aqueous phase solution containing a metal salt with a concentration of 0.1-30 mM, a drug and water, wherein the volume of the aqueous phase to the volume of the oil phase is 1: 1.5-1: 20.
7. The method for preparing microcapsules using metal-organic coordination polymers as wall materials according to claim 4, wherein the method comprises the following steps: the hydrophilic emulsifier is one or more of polyvinyl alcohol (PVA), polyvinylpyrrolidone, sodium dodecyl sulfate, tween 20, tween 80 and triton 100.
8. The method for preparing microcapsules using metal-organic coordination polymers as wall materials according to claim 4 or 5, wherein: the phenolic organic ligand is one or two of the following molecular structures:
Figure FDA0003228556700000011
wherein A is one of-CHO, -CH ═ N-OH.
9. The method for preparing microcapsules using metal-organic coordination polymers as wall materials according to claim 3 or 6, wherein: the metal salt is silver nitrate, anhydrous copper chloride, various hydrated copper chlorides, anhydrous copper sulfate, various hydrated copper sulfates, anhydrous copper nitrate, various hydrated copper nitrates, copper trifluoromethanesulfonate, anhydrous copper acetate, various hydrated copper acetates, copper bromide, anhydrous nickel chloride, various hydrated nickel chlorides, anhydrous nickel sulfate, various hydrated nickel sulfates, anhydrous nickel nitrate, various hydrated nickel nitrates, nickel trifluoromethanesulfonate, anhydrous nickel acetate, various hydrated nickel acetates, nickel bromide, anhydrous zinc chloride, various hydrated zinc chlorides, anhydrous zinc sulfate, various hydrated zinc sulfates, anhydrous zinc nitrate, various hydrated zinc nitrates, zinc trifluoromethanesulfonate, anhydrous zinc acetate, various hydrated zinc acetates, zinc bromide, anhydrous manganese chloride, anhydrous manganese sulfate, anhydrous manganese nitrate, various hydrated manganese nitrates, manganese trifluoromethanesulfonate, anhydrous zinc sulfate, anhydrous zinc acetate, anhydrous zinc bromide, anhydrous manganese chloride, various hydrated manganese chlorides, anhydrous manganese sulfate, anhydrous manganese nitrate, various hydrated manganese nitrate, manganese trifluoromethanesulfonate, anhydrous copper sulfate, anhydrous copper chloride, anhydrous copper sulfate, anhydrous nickel sulfate, anhydrous zinc nitrate, anhydrous zinc sulfate, anhydrous magnesium nitrate, anhydrous magnesium sulfate, anhydrous magnesium sulfate, magnesium sulfate, Anhydrous manganese acetate, hydrous manganese acetates of various types, manganese bromide, anhydrous cobalt chloride, hydrous cobalt chloride of various types, anhydrous cobalt sulfate, hydrous cobalt sulfate of various types, anhydrous cobalt nitrate, hydrous cobalt nitrate of various types, cobalt trifluoromethanesulfonate, anhydrous cobalt acetate, hydrous cobalt acetate of various types, cobalt bromide, anhydrous scandium chloride of various types, hydrous scandium chloride of various types, anhydrous scandium sulfate, hydrous scandium sulfate of various types, scandium trifluoromethanesulfonate, anhydrous scandium nitrate, hydrous scandium nitrate of various types, anhydrous iron chloride of various types, hydrous iron chloride of various types, scandium bromide, anhydrous iron sulfate, iron sulfate of various types, anhydrous iron acetate, hydrous iron acetate of various types, iron bromide, anhydrous iron sulfate of various types, hydrous iron sulfate of various types, titanium tetrachloride, zirconium tetrachloride, platinum chloride, chromium chloride, hydrous chromium chloride of various types, chromium bromide, hydrous chromium bromide of various types, chromium sulfate of various types, anhydrous chromium nitrate of various types, One or more of various hydrated chromium nitrates, chromium chlorides, various hydrated chromium chlorides, chromium sulfates and various hydrated chromium sulfates.
10. The method for preparing microcapsules using metal-organic coordination polymers as wall materials according to claim 4 or 5, wherein: the organic solvent is one or more of oleic acid, ethanol, ethyl acetate, methyl acetate, toluene, o-xylene, mesitylene, dichloromethane, chloroform, dimethyl carbonate, n-hexane, n-heptane, n-pentane, methyl tert-butyl ether, n-butyl ether, isobutyl ether, n-hexanol and ISOPAR series solvents.
CN202110979623.8A 2021-08-25 2021-08-25 Preparation method of microcapsule with metal organic coordination polymer as wall material Pending CN114029012A (en)

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Cited By (2)

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CN115404048A (en) * 2022-09-21 2022-11-29 东南大学 Composite phase change energy storage material and preparation method thereof
CN115418503A (en) * 2022-08-23 2022-12-02 成都先进金属材料产业技术研究院股份有限公司 Method for selectively extracting scandium from leachate based on microemulsion

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CN105080445A (en) * 2015-09-14 2015-11-25 哈尔滨工业大学 Method for preparing microcapsule with tannic acid-ferric ion polymer serving as wall material by taking micro emulsion as template by interface reaction
CN106221674A (en) * 2016-07-14 2016-12-14 中国矿业大学 A kind of inorganic hydrous salt phase transition microcapsule energy storage material and preparation method
CN110721644A (en) * 2019-10-22 2020-01-24 北京理工大学 Radiation preparation method of vinyl polymer microcapsule

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CN105080445A (en) * 2015-09-14 2015-11-25 哈尔滨工业大学 Method for preparing microcapsule with tannic acid-ferric ion polymer serving as wall material by taking micro emulsion as template by interface reaction
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CN115404048A (en) * 2022-09-21 2022-11-29 东南大学 Composite phase change energy storage material and preparation method thereof

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