CN113519822B - Preparation method of temperature-responsive cyclodextrin nanoparticle pickering emulsion - Google Patents

Preparation method of temperature-responsive cyclodextrin nanoparticle pickering emulsion Download PDF

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CN113519822B
CN113519822B CN202110630419.5A CN202110630419A CN113519822B CN 113519822 B CN113519822 B CN 113519822B CN 202110630419 A CN202110630419 A CN 202110630419A CN 113519822 B CN113519822 B CN 113519822B
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cyclodextrin
functional active
emulsion
solution
active ingredient
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CN113519822A (en
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袁超
崔波
程彩云
郭丽
于滨
赵萌
陶海腾
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Qilu University of Technology
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    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
    • A23L29/10—Foods or foodstuffs containing additives; Preparation or treatment thereof containing emulsifiers
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
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    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
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    • A23L29/35—Degradation products of starch, e.g. hydrolysates, dextrins; Enzymatically modified starches
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    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
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    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
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    • A23L33/105—Plant extracts, their artificial duplicates or their derivatives
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    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
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    • A23L33/15—Vitamins
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    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • 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
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
    • A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline 
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    • 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
    • A61K47/44—Oils, fats or waxes according to two or more groups of A61K47/02-A61K47/42; Natural or modified natural oils, fats or waxes, e.g. castor oil, polyethoxylated castor oil, montan wax, lignite, shellac, rosin, beeswax or lanolin
    • 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
    • A61K47/6949—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 inclusion complexes, e.g. clathrates, cavitates or fullerenes
    • A61K47/6951—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 inclusion complexes, e.g. clathrates, cavitates or fullerenes using cyclodextrin
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Abstract

The invention relates to the technical field of emulsion innovation, and particularly discloses a preparation method of temperature-responsive cyclodextrin nanoparticle pickering emulsion. The invention takes cyclodextrin as a main body and functional active ingredients as objects, and the cyclodextrin and the functional active ingredients interact to form cyclodextrin composite nano particles, and the cyclodextrin composite nano particles are used as pickering particles and are matched with specific oil phase to form the temperature response pickering emulsion with special nutrition function. The preparation process is simple, the sources of raw materials are wide, the operation is convenient, and the obtained pickering emulsion has good functionality and temperature responsiveness and wide application range.

Description

Preparation method of temperature-responsive cyclodextrin nanoparticle pickering emulsion
Technical Field
The invention relates to the technical field of emulsion innovation, in particular to a preparation method of temperature response type cyclodextrin nanoparticle pickering emulsion.
Background
The Pickering emulsion is an emulsion system formed by using solid particles to replace a surfactant, and the fine solid particles can play the same emulsifying function as the molecular surfactant. The solid particles reduce the possibility of coalescence of the liquid drops, have higher deformation resistance, higher stability, lower toxicity and stimulus responsiveness, and have low toxicity of part of food-grade solid particles and high use safety in vivo. The change of temperature has obvious stimulus response to the stability of the emulsion, on one hand, the temperature rise enhances the mutual aggregation action among emulsion liquid drops, the thermal movement of water molecules is enhanced, the water phase and the oil phase of the emulsion are separated, and on the other hand, the temperature rise weakens the association action of cyclodextrin and functional active ingredients, so that the functional ingredients are released. In addition, the cocoa butter is used as the grease which has hardness and is easy to melt, is solid at the temperature of 4-25 ℃, can be quickly melted when the temperature is increased, can be completely melted at the temperature of 35 ℃, and can be used as part of oil phase for preparing the temperature response type Pickering emulsion.
The cyclodextrin is a cyclic oligosaccharide formed by connecting a plurality of glucose residues through alpha-1, 4 glycosidic bonds, the common parent cyclodextrin is alpha, beta and gamma-cyclodextrin formed by 6, 7 and 8 glucose residues, the cyclodextrin structure is cone-shaped, the hydroxyl faces the outer end of the molecule to show hydrophilicity, and a hydrophobic cavity is formed inside the cyclodextrin, so that a host-guest complex can be formed with a guest molecule, and the cyclodextrin has the functions of shielding, controlling release, protecting activity and the like for the guest molecule. The cyclodextrin is easy to form various stable hydrates, has good biodegradability and biocompatibility, and meets the requirement of consumers on cleaning labels. Because of the advantages of low cost, easy acquisition, good biocompatibility and the like, the molecular host is known as a green molecular host, and has wide research and application in the industries of foods, cosmetics and medicines in recent years. The cyclodextrin has special properties of internal hydrophobicity and external hydrophilicity, and has antioxidant protecting effect on easily-oxidizable substances, solubilization effect on insoluble substances, control effect on easily-volatile substances, masking effect on special odor substances, and slow release effect on the delivery carrier of flavor substances and medicinal components thereof.
Most of the functional active ingredients have biological activities such as anti-inflammation, anti-cancer, antioxidation and the like, and are widely distributed in various animals, plants, marine organisms and microorganisms. For example, the main bioactive substances in vegetables include carotene, organic sulfur compounds, polysaccharides, lycopene and anthocyanin in flavonoids, etc., which can remarkably promote human health and prevent diseases. For example, quercetin is used as a very potential flavonoid compound, contains various bioactive components, is widely applied to the food and medicine industries, and can be used as an antioxidant and an anti-inflammatory analgesic auxiliary agent. Retinol is a fat-soluble antioxidant and has the medicinal effects of effectively treating night blindness, inhibiting tumor growth and enhancing immunity. With the health and safety concerns, the development of functional foods is a hot spot in the food field, and most of the functional active ingredients are fat-soluble. The problems of solubility and stability limit the scope of application of the functional active substances. Therefore, the cyclodextrin molecular inclusion technology can effectively improve the solubility and stability of the functional active ingredient, and is expected to expand the application of the active ingredient in functional foods. The cyclodextrin nano particles are taken as green bio-based solid particles, and the prepared food-grade pickering emulsion has good biocompatibility and environmental friendliness, so that the oxidation rate of grease can be reduced, and the coating and conveying of functional active ingredients can be realized. The Pickering emulsion at different temperatures shows different properties, and the emulsion with different properties can be obtained through temperature regulation, so that a new research idea is provided for the practical production and application of the Pickering emulsion.
Disclosure of Invention
The invention provides a preparation method of a temperature response type cyclodextrin nanoparticle pickering emulsion with high biocompatibility, good water solubility and strong stability, in order to make up the defects of the prior art.
The invention is realized by the following technical scheme:
the preparation method of the pickering emulsion with the temperature-responsive cyclodextrin nano particles comprises the following steps:
(1) Preparation of functional active ingredient/cyclodextrin composite nano-particles: adding cyclodextrin into deionized water, dissolving under ultrasonic condition, adding functional active ingredient into cyclodextrin solution, sealing, and performing ultrasonic treatment under dark condition to obtain mixed solution, stirring, clathrating, filtering to obtain clathrate solution, and vacuum freeze drying to obtain functional active ingredient/cyclodextrin composite nanoparticle;
(2) Adding the functional active ingredient/cyclodextrin composite nano particles obtained in the step (1) into deionized water, stirring and dissolving to obtain cyclodextrin nano particle stock solution; adding an oil phase into the cyclodextrin nanoparticle stock solution, and carrying out homogeneous mixing and cooling to obtain a product.
The invention takes cyclodextrin as a main body and functional active ingredients as objects, and the cyclodextrin and the functional active ingredients interact to form cyclodextrin composite nano particles, and the cyclodextrin composite nano particles are used as pickering particles and are matched with specific oil phase to form the temperature response pickering emulsion with special nutrition function. Under different temperature regulation and control, the Pickering emulsion is converted from stable to demulsification, so that effective transportation and stable release of functional active ingredients are realized.
The more preferable technical scheme of the application is as follows:
in the step (1), the cyclodextrin is one of alpha-cyclodextrin, beta-cyclodextrin, gamma-cyclodextrin and cyclodextrin derivatives thereof.
Preferably, 1-5g of cyclodextrin is added into 100ml of deionized water, and the cyclodextrin solution is obtained by ultrasonic treatment for 10-30min at 25 ℃ and 100 Hz.
Preferably, the molar ratio of cyclodextrin to functional active ingredient is 1:1-1:2, and the functional active ingredient is one or more of quercetin, retinol and lycopene.
Preferably, adding functional active ingredient into cyclodextrin solution, immediately sealing, keeping away from light, and performing ultrasonic treatment for 15min to obtain mixed solution, magnetically stirring at 50deg.C and 200rpm for 12-72 hr, immediately filtering with 0.45 μm filter membrane after inclusion, and removing undissolved cyclodextrin to obtain pure clathrate solution.
Preferably, the inclusion compound solution after filtration is frozen and dried for 72 hours under the conditions of-60 ℃ and 100Pa to obtain the functional active ingredient/cyclodextrin composite nano-particles.
In the step (2), 1-5g of the functional active ingredient/cyclodextrin composite nano particles are added into 30-80ml of deionized water, magnetically stirred for 10-30min at 50 ℃ and 200rpm, and fully dissolved to obtain cyclodextrin nano particle stock solution.
Preferably, the oil phase comprises cocoa butter 10-20% and other oil phase 80-90% by volume, wherein the other oil phase is one of soybean oil, olive oil and maize germ oil.
Preferably, adding an oil phase into 30-80ml of cyclodextrin nanoparticle stock solution, fixing the volume to 100ml, keeping the temperature at 50 ℃, and uniformly mixing the water phase and the oil phase by using a high-pressure homogenizer at 5000-25000rpm for 1-5min to obtain an emulsion, and rapidly cooling the emulsion to below 20 ℃ by a heat exchanger to obtain the product.
In the invention, the cyclodextrin is a nano-scale solid particle with high biocompatibility, good water solubility and no toxicity, and has a cavity structure with hydrophobic inside and hydrophilic outside. The functional active ingredient is compounded with cyclodextrin to form cyclodextrin composite nano particles through a cyclodextrin molecular inclusion technology, so that the solubility of the functional ingredient is improved, and meanwhile, the stability is improved; in addition, the cyclodextrin composite nano particles have special microstructure and functional characteristics, and can be used as proper Pickering particles to form temperature response type Pickering emulsion with special nutrition function by being matched with specific oil phase.
The temperature-responsive pickering emulsion of the invention has the advantages that: the response characteristics of emulsion droplets formed by the functional active ingredient/cyclodextrin composite nano particles and the oil phase mainly comprising cocoa butter at different temperatures lead to the change of the nutrition properties of the prepared pickering emulsion, and the particle sizes of pickering emulsion droplets stabilized by the cyclodextrin nano particles are different at different storage temperatures, so that the stability of the emulsion shows different change trends. At 4 ℃, the oil phase and the water phase are partially separated along with the extension of the storage time of the emulsion, and the total is kept in a metastable range; at 25 ℃, the particle size shows a stable trend, cyclodextrin nano particles are tightly adsorbed on a water-oil interface, collision fusion between liquid drops is greatly reduced, an internal oil phase is also in a stable state, and the stable Pickering emulsion state is still maintained after long-time storage; at 37 ℃, the particle size of the emulsion has a remarkable tendency to increase in the storage process, cyclodextrin nano particles cannot be tightly distributed on an oil-water interface, the fluidity of an oil phase is enhanced, the Pickering emulsion has a demulsification phenomenon, and the oil phase and the water phase are separated to form a layered structure. As the temperature of 37 ℃ is close to the body temperature of a human body, the emulsion is favorable for the application of the emulsion in foods and medicines, and has good application value.
The preparation process is simple, the sources of raw materials are wide, the operation is convenient, and the obtained pickering emulsion has good functionality and temperature responsiveness and wide application range.
Drawings
The invention is further described below with reference to the accompanying drawings.
FIG. 1 is a schematic illustration of a preparation process flow of the present invention;
FIG. 2 is a graph showing macroscopic and microscopic characterization of the Pickering emulsion of α -cyclodextrin nanoparticles of the present invention at various temperatures;
FIG. 3 is a graph showing the apparent viscosity and shear rate change of an alpha-cyclodextrin nanoparticle pickering emulsion of the present invention at various temperatures;
FIG. 4 is a graph showing dynamic oscillation frequency scan of a Pickering emulsion of an α -cyclodextrin nanoparticle at various temperatures according to the present invention.
Detailed Description
The preparation process and operation steps of the cyclodextrin nanoparticle pickering emulsion with temperature response performance obtained by the invention will be described in detail below with reference to the accompanying drawings in the embodiment of the invention. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
Example 1:
(1) Alpha-cyclodextrin complex nanoparticle preparation: weighing 0.973g of alpha-cyclodextrin, adding 100mL of deionized water, carrying out ultrasonic treatment at 25 ℃ and 100Hz for 10min to promote dissolution, adding quercetin according to a molar ratio of 1:1, immediately sealing, avoiding light, and carrying out ultrasonic treatment for 15min to obtain a mixed solution of cyclodextrin and quercetin, and carrying out magnetic stirring at 50 ℃ and 200rpm for 24h. And immediately filtering the mixture through a 0.45um filter membrane after the inclusion is finished, removing undissolved cyclodextrin to obtain a pure inclusion compound solution, and placing the filtered sample in-60 ℃/100Pa vacuum freeze drying for 72 hours to obtain alpha-cyclodextrin compound nano particles.
(2) Preparation of an alpha-cyclodextrin complex pickering emulsion: weighing 3g of the alpha-cyclodextrin composite nano particles prepared in the first step, adding 50mL of deionized water, magnetically stirring for 20min at 50 ℃ and 200rpm to uniformly disperse the cyclodextrin nano particles in an aqueous solution to obtain quercetin/alpha-cyclodextrin composite nano particle stock solution, adding 50mL of an oil phase (20% of cocoa butter and 80% of soybean oil) into the solution, keeping the temperature at 50 ℃, and uniformly mixing the aqueous phase and the oil phase at 25000rpm and 2min by using a high-pressure homogenizer. The obtained emulsion is rapidly cooled to below 20 ℃ through a heat exchanger, and the temperature-sensitive alpha-cyclodextrin nanoparticle pickering emulsion is obtained.
As shown in fig. 2, macroscopic and microscopic characterization graphs of the α -cyclodextrin nanoparticle pickering emulsion at different temperatures in this example are shown; as shown in fig. 3, the apparent viscosity and shear rate change curves of the α -cyclodextrin nanoparticle pickering emulsion at different temperatures in this example are shown; as shown in fig. 4, the dynamic oscillation frequency scan curve of the α -cyclodextrin nanoparticle pickering emulsion at different temperatures in this example is shown.
Apparent stability: 15mL of temperature response type alpha-cyclodextrin nanoparticle pickering emulsion is taken and placed in a transparent glass bottle, the transparent glass bottle is sealed, the transparent glass bottle is stored at the temperature of 4 ℃, the temperature of 25 ℃ and the temperature of 37 ℃, and the apparent stability of the alpha-cyclodextrin nanoparticle pickering emulsion at different storage temperatures is visually observed;
droplet distribution: observing the distribution state of the droplets of the alpha-cyclodextrin nanoparticle pickering emulsion at the temperature of 4 ℃,25 ℃ and 37 ℃ by an optical microscope; observing the microstructure of stable and demulsification transition of the liquid drops of the alpha-cyclodextrin nanoparticle Pickering emulsion at the temperature of 4 ℃,25 ℃ and 37 ℃ through a scanning electron microscope;
viscoelasticity: the rheological properties of the α -cyclodextrin nanoparticulate pickering emulsion were analyzed by rheometer at 4 ℃,25 ℃ and 37 ℃.
It was found that at 4 ℃ the oil phase and the water phase are partly separated, but the population remains within the metastable range. At 25 ℃, the particle size shows the most stable trend, cyclodextrin nano particles are tightly adsorbed on a water-oil interface, collision fusion between liquid drops is greatly reduced, an internal oil phase is in a stable state, and the alpha-cyclodextrin nano particles are uniformly adsorbed on the surface of the oil drops under a scanning electron microscope to form a compact interface layer, so that the surface is rough, and the appearance is hard and still keeps a stable Pickering emulsion state after long-time storage. At 37 ℃, the particle size of emulsion has a remarkable tendency to increase in the storage process, cyclodextrin nano particles cannot be tightly distributed on an oil-water interface, the fluidity of an oil phase is enhanced, the apparent emulsion is layered, relative migration and coalescence of emulsion droplets occur, the interface layer of Pickering emulsion is broken under a scanning electron microscope, and the oil phase and the water phase are in a layered structure.
The rheological result shows that the pickering emulsion with alpha-cyclodextrin nano particles is in a typical gel structure, shows a shearing thinning phenomenon, and has the maximum apparent viscosity, storage modulus and loss modulus under the condition of 25 ℃, and the viscosity of the emulsion obtained under the condition of 37 ℃ is lower because the emulsion undergoes phase change, so that the unstable pickering emulsion is formed.
Example 2:
(1) Beta-cyclodextrin complex nanoparticle preparation: 1.135g of beta-cyclodextrin is weighed, 100mL of deionized water is added, ultrasonic treatment is carried out for 30min at 25 ℃ and 100Hz, dissolution is promoted, retinol is added according to the molar ratio of host to guest of 1:1, immediate sealing, light shielding and ultrasonic treatment are carried out for 15min, and the mixed solution of cyclodextrin and retinol is obtained, and magnetic stirring is carried out for 48h at 50 ℃ and 200 rpm. And immediately filtering the mixture through a 0.45um filter membrane after the inclusion is finished, removing undissolved cyclodextrin to obtain a pure inclusion compound solution, and placing the filtered sample in-60 ℃/100Pa vacuum freeze drying for 72 hours to obtain the beta-cyclodextrin compound nano particles.
(2) Preparation of beta-cyclodextrin nanoparticle pickering emulsion: weighing 3g of cyclodextrin composite nano particles prepared in the first step, adding 100mL of deionized water, magnetically stirring for 20min at 50 ℃ and 200rpm to uniformly disperse the cyclodextrin nano particles in an aqueous solution to obtain a 3% cyclodextrin nano particle stock solution, adding 60mL of oil phase (15% of cocoa butter and 85% of olive oil) into the solution, keeping the temperature at 50 ℃, and uniformly mixing the aqueous phase and the oil phase at 25000rpm for 3min by using a high-pressure homogenizer. The obtained emulsion is rapidly cooled to below 20 ℃ through a heat exchanger, and the temperature-sensitive beta-cyclodextrin nanoparticle pickering emulsion is obtained.
Example 3:
(1) Gamma-cyclodextrin complex nanoparticle preparation: weighing 1.297g of gamma-cyclodextrin, adding 100mL of deionized water, carrying out ultrasonic treatment at 25 ℃ and 100Hz for 10min to promote dissolution, adding lycopene according to a molar ratio of 1:1, immediately sealing, avoiding light, carrying out ultrasonic treatment for 15min to obtain a mixed solution of the cyclodextrin and the lycopene, and carrying out magnetic stirring for 12h at 50 ℃ and 200 rpm. And immediately filtering the mixture through a 0.45um filter membrane after the inclusion is finished, removing undissolved cyclodextrin to obtain a pure inclusion compound solution, and placing the filtered sample in-60 ℃/100Pa vacuum freeze drying for 72 hours to obtain gamma-cyclodextrin compound nano particles.
(2) Preparation of gamma-cyclodextrin nanoparticle pickering emulsion: weighing 3g of gamma-cyclodextrin composite nano particles prepared in the first step, adding 100mL of deionized water, magnetically stirring for 20min at 50 ℃ and 200rpm to uniformly disperse the cyclodextrin nano particles in an aqueous solution to obtain a 3% cyclodextrin nano particle stock solution, adding 60mL of oil phase (20% of cocoa butter and 80% of corn germ oil) into the solution, keeping the temperature at 50 ℃, and uniformly mixing the water phase and the oil phase at 25000rpm and 5min by using a high-pressure homogenizer. The obtained emulsion is rapidly cooled to below 20 ℃ through a heat exchanger, and the temperature-sensitive gamma-cyclodextrin nanoparticle pickering emulsion is obtained.
Example 4:
(1) Beta-cyclodextrin complex nanoparticle preparation: 1.135g of beta-cyclodextrin is weighed, 100mL of deionized water is added, ultrasonic treatment is carried out for 20min at 25 ℃ and 100Hz, dissolution is promoted, 50% of retinol and 50% of quercetin are added according to a molar ratio of 1:1, immediately sealing, light shielding and ultrasonic treatment are carried out for 15min, and a mixed solution of cyclodextrin and retinol is obtained, and magnetic stirring is carried out for 72h at 50 ℃ and 200 rpm. And immediately filtering the mixture through a 0.45um filter membrane after the inclusion is finished, removing undissolved cyclodextrin to obtain a pure inclusion compound solution, and placing the filtered sample in-60 ℃/100Pa vacuum freeze drying for 72 hours to obtain the beta-cyclodextrin compound nano particles.
(2) Preparation of beta-cyclodextrin nanoparticle pickering emulsion: weighing 3g of cyclodextrin composite nano particles prepared in the first step, adding 100mL of deionized water, magnetically stirring for 20min at 50 ℃ and 200rpm to uniformly disperse the cyclodextrin nano particles in an aqueous solution to obtain a 3% cyclodextrin nano particle stock solution, adding 70mL of oil phase (20% of cocoa butter and 80% of olive oil) into the solution, keeping the temperature at 50 ℃, and uniformly mixing the aqueous phase and the oil phase at 25000rpm and 4min by using a high-pressure homogenizer. The obtained emulsion is rapidly cooled to below 20 ℃ through a heat exchanger, and the temperature-sensitive beta-cyclodextrin nanoparticle pickering emulsion is obtained.
In the above embodiments, the best mode of the present invention has been described, it is apparent that many variations are possible within the inventive concept of the present invention. It should be noted here that any changes made under the inventive concept of the present invention will fall within the scope of the present invention.

Claims (7)

1. The preparation method of the pickering emulsion with the temperature-responsive cyclodextrin nano particles is characterized by comprising the following steps of: (1) Preparation of functional active ingredient/cyclodextrin composite nano-particles: adding cyclodextrin into deionized water, dissolving under ultrasonic condition, adding functional active ingredient into cyclodextrin solution, sealing, and performing ultrasonic treatment under dark condition to obtain mixed solution, stirring, clathrating, filtering to obtain clathrate solution, and vacuum freeze drying to obtain functional active ingredient/cyclodextrin composite nanoparticle;
the cyclodextrin is one of alpha-cyclodextrin, beta-cyclodextrin, gamma-cyclodextrin and cyclodextrin derivatives thereof;
(2) Adding the functional active ingredient/cyclodextrin composite nano particles obtained in the step (1) into deionized water, stirring and dissolving to obtain cyclodextrin nano particle stock solution; adding an oil phase into the cyclodextrin nanoparticle stock solution, and carrying out homogeneous mixing and cooling to obtain a product;
the oil phase comprises cocoa butter 10-20% and other oil phases 80-90%, wherein the other oil phases are one of soybean oil, olive oil and maize germ oil.
2. The method of manufacturing according to claim 1, wherein: in the step (1), 1-5g of cyclodextrin is added into 100ml of deionized water, and is subjected to ultrasonic treatment at 25 ℃ and 100Hz for 10-30min, so that a cyclodextrin solution is obtained by dissolution.
3. The method of manufacturing according to claim 1, wherein: in the step (1), the molar ratio of the cyclodextrin to the functional active ingredient is 1:1-1:2, and the functional active ingredient is one or more of quercetin, retinol and lycopene.
4. The method of manufacturing according to claim 1, wherein: in the step (1), adding functional active ingredients into cyclodextrin solution, immediately sealing, avoiding light, and performing ultrasonic treatment for 15min to obtain mixed solution, magnetically stirring at 50 ℃ and 200rpm for 12-72h, immediately filtering with a 0.45 μm filter membrane after inclusion, and removing undissolved cyclodextrin to obtain pure inclusion compound solution.
5. The method of claim 1 or 4, wherein: in the step (1), the filtered inclusion compound solution is freeze-dried for 72 hours under the conditions of-60 ℃ and 100Pa, and the functional active ingredient/cyclodextrin composite nano particles are obtained.
6. The method of manufacturing according to claim 1, wherein: in the step (2), 1-5g of the functional active ingredient/cyclodextrin composite nano particles are added into 30-80ml of deionized water, magnetically stirred for 10-30min at 50 ℃ and 200rpm, and fully dissolved to obtain cyclodextrin nano particle stock solution.
7. The method of claim 1 or 6, wherein: in the step (2), adding an oil phase into 30-80ml of cyclodextrin nanoparticle stock solution, fixing the volume to 100ml, keeping the temperature at 50 ℃, and uniformly mixing the water phase and the oil phase by using a high-pressure homogenizer at 5000-25000rpm for 1-5min to obtain an emulsion, and rapidly cooling the emulsion to below 20 ℃ by using a heat exchanger to obtain the product.
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