CN110755305A - Nepeta cataria essential oil/naphthoylated β -cyclodextrin microcapsule and preparation method thereof - Google Patents
Nepeta cataria essential oil/naphthoylated β -cyclodextrin microcapsule and preparation method thereof Download PDFInfo
- Publication number
- CN110755305A CN110755305A CN201911235816.1A CN201911235816A CN110755305A CN 110755305 A CN110755305 A CN 110755305A CN 201911235816 A CN201911235816 A CN 201911235816A CN 110755305 A CN110755305 A CN 110755305A
- Authority
- CN
- China
- Prior art keywords
- cyclodextrin
- essential oil
- naphthoylated
- washing
- microcapsule
- Prior art date
- Legal status (The legal status 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 status listed.)
- Granted
Links
Images
Classifications
-
- 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
- A61K8/92—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
- A61K8/922—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof of vegetable origin
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/26—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests in coated particulate form
- A01N25/28—Microcapsules or nanocapsules
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N65/00—Biocides, pest repellants or attractants, or plant growth regulators containing material from algae, lichens, bryophyta, multi-cellular fungi or plants, or extracts thereof
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N65/00—Biocides, pest repellants or attractants, or plant growth regulators containing material from algae, lichens, bryophyta, multi-cellular fungi or plants, or extracts thereof
- A01N65/08—Magnoliopsida [dicotyledons]
- A01N65/22—Lamiaceae or Labiatae [Mint family], e.g. thyme, rosemary, skullcap, selfheal, lavender, perilla, pennyroyal, peppermint or spearmint
-
- 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
- A61K8/11—Encapsulated compositions
-
- 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
- A61K8/732—Starch; Amylose; Amylopectin; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
- A61Q17/02—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings containing insect repellants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
- A61K2800/805—Corresponding aspects not provided for by any of codes A61K2800/81 - A61K2800/95
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Plant Pathology (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Agronomy & Crop Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Birds (AREA)
- Biotechnology (AREA)
- Microbiology (AREA)
- Mycology (AREA)
- Natural Medicines & Medicinal Plants (AREA)
- Pest Control & Pesticides (AREA)
- Dermatology (AREA)
- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Toxicology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The invention relates to a catnip essential oil/naphthoyl β -cyclodextrin microcapsule and a preparation method thereof, belonging to the technical field of pesticides, wherein the microcapsule consists of a wall material and a core material wrapped in the wall material, wherein the wall material is the naphthoyl β -cyclodextrin, and the core material is the catnip essential oil, at a certain temperature, the microcapsule can control the release speed and uniformity of the catnip essential oil, so that the problem of controllable release rate of the embedded catnip essential oil is effectively solved.
Description
Technical Field
The invention belongs to the technical field of pesticides, and particularly relates to catnip essential oil/naphthoyl β -cyclodextrin microcapsules and a preparation method thereof.
Background
β -cyclodextrin (β -CD) has truncated cone shape, each glucose unit in the molecule adopts an untwisted chair type conformation as a glucopyranose unit, the 4C1 conformation structure β -cyclodextrin molecule has all primary hydroxyl groups located on one side of the ring, namely, 6-hydroxyl group of the glucose unit forms a main face (narrower end) of the truncated cone-shaped structure of cyclodextrin, and all secondary hydroxyl groups located on the other side of the ring, namely, 2-hydroxyl group and 3-hydroxyl group form a secondary face (broader face) of the truncated cone-shaped structure of cyclodextrin, the inner wall of cyclodextrin is composed of hydrogen atoms pointing to cavities C3 and C5 and glycosidic bond oxygen atoms, so that the inner part of the cavity has higher electron cloud density and shows certain hydrophobicity, the secondary hydroxyl group of cyclodextrin makes the large end and the outer wall of the cavity hydrophilic, in addition, because 6-methylene exists, the main face also shows certain hydrophobicity, therefore, the cyclodextrin molecule has a circular truncated cone-shaped molecular structure of 'external hydrophilic and internal hydrophobic', the β -cyclodextrin molecule has a plurality of shielding performance, and can form a plurality of organic and inorganic complexes, even can be used for a plurality of active food molecules, and can be used for mutual control, even for a plurality of organic and a plurality of active food.
Since it was reported in 1954 that DEET (N, N-diethyl-l, 3-methylbenzamide, DEET) has a mosquito repellent activity, it has been widely used as the most effective repellent, however, many years of research on toxicity and safety have been paid attention to, various countries in the world have been intensified to search for safer and more effective repellents, many plants and artificially synthesized compounds have been studied extensively, but no alternatives have been found to be superior to DEET, Peterson's research in 2001 found that pseudonepetalactone (nepetalactone), an active ingredient present in Nepetatacia cata, has a very high mosquito repellent activity 10 times that of DEET, has a repellent effect on mosquitoes, cockroaches, and termites, but catmint essential oils, which have a prolonged action duration after being spread or sprayed, cannot be directly used in applications requiring a product with a long-lasting uniform release, have not been reported for the controlled release rate of cat essential oils, but there have been no patent on the application of catmint essential oils, including natural cat oils β -cyclodextrin, and the release rate of volatile peppermint essential oils has been controlled.
Disclosure of Invention
In view of the above, the present invention provides a method for preparing catnip essential oil/naphthoyl β -cyclodextrin microcapsule, and provides a catnip essential oil/naphthoyl β -cyclodextrin microcapsule.
In order to achieve the purpose, the invention provides the following technical scheme:
1. the catnip essential oil/naphthoyl β -cyclodextrin microcapsule consists of a wall material and a core material wrapped in the wall material, wherein the wall material is naphthoyl β -cyclodextrin, and the core material is catnip essential oil.
2. The preparation method of the catnip essential oil/naphthoyl β -cyclodextrin microcapsule comprises the following steps:
(1) adding 1-naphthoic acid and dicyclohexylcarbodiimide into β -cyclodextrin, carrying out reflux stirring reaction at 65-85 ℃ for 2.5-3.5h, adding water, continuing stirring reaction until the dicyclohexylcarbodiimide is decomposed, cooling to room temperature, standing until a solid is precipitated, carrying out suction filtration washing on the solid, and drying to obtain naphthoyl β -cyclodextrin;
(2) dissolving the naphthoyl β -cyclodextrin prepared in the step (1) in water to form saturated solution of the naphthoyl β -cyclodextrin, adding ethanol solution of catmint essential oil into the saturated solution, stirring and reacting until white solid is separated out, cooling to room temperature, standing until the white solid is not separated out, carrying out suction filtration, washing and drying on the white solid, and thus obtaining the catmint essential oil/naphthoyl β -cyclodextrin microcapsule.
Preferably, in the step (1), the molar ratio of the β -cyclodextrin to the 1-naphthoic acid is 1:2-5, and the mass ratio of the 1-naphthoic acid to the dicyclohexylcarbodiimide is 1: 1.
Preferably, in the step (1), the mass ratio of the dicyclohexylcarbodiimide to the water is 1: 100-150.
Preferably, in the step (1), the standing is performed at 0-5 ℃, and ice water is used as a washing liquid for washing 3-5 times during suction filtration washing.
Preferably, in step (1), the drying is performed at 100-105 ℃ for 1-1.5 h.
Preferably, in the step (2), the molar ratio of the naphthoylated β -cyclodextrin to the catmint essential oil is 1.9280-1.9970: 1.
Preferably, in the step (2), the standing is performed at 0-5 ℃, ice water is firstly used as a washing solution for washing 3-5 times during suction filtration washing, and then absolute ethyl alcohol is used as a washing solution for washing 3-5 times.
Preferably, in the step (2), the drying is carried out for 4-5h under vacuum at 25-30 ℃.
Preferably, in the step (1) and the step (2), the stirring speed is 300-600 r/min.
The catnip essential oil/naphthoyl β -cyclodextrin microcapsule and the preparation method thereof have the advantages that the catnip essential oil is taken as a core material, the naphthoyl β -cyclodextrin is taken as a wall material, and the microcapsule can control the release speed and uniformity of the catnip essential oil at a certain temperature, so that the problem of controllable release speed of the embedded catnip essential oil is effectively solved.
Additional advantages, objects, and features of the invention will be set forth in part in the description which follows and in part will become apparent to those having ordinary skill in the art upon examination of the following or may be learned from practice of the invention. The objectives and other advantages of the invention may be realized and attained by the means of the instrumentalities and combinations particularly pointed out hereinafter.
Drawings
For the purposes of promoting a better understanding of the objects, aspects and advantages of the invention, reference will now be made to the following detailed description taken in conjunction with the accompanying drawings in which:
FIG. 1 is a graph showing the results of a test of the release rate of Nepeta cataria essential oil from microcapsules in comparative example and examples 1 to 4 at 40 deg.C, respectively;
FIG. 2 is a graph showing the results of a test of the release rate of the catnip essential oil from the microcapsules in comparative example and examples 1 to 4 at 60 deg.C, respectively;
fig. 3 is a graph showing the results of the release rate test of the catnip essential oil from the microcapsules of comparative example and examples 1 to 4 at 80 c, respectively.
Detailed Description
The embodiments of the present invention are described below with reference to specific embodiments, and other advantages and effects of the present invention will be easily understood by those skilled in the art from the disclosure of the present specification. The invention is capable of other and different embodiments and of being practiced or of being carried out in various ways, and its several details are capable of modification in various respects, all without departing from the spirit and scope of the present invention.
Example 1
Preparation of Nepeta Catariae essential oil/Naphthylated β -Cyclodextrin microcapsules
(1) Adding 2.270g of β -cyclodextrin into a round-bottom flask, then adding 0.4080g of 1-naphthoic acid and 0.4080g of dicyclohexylcarbodiimide, installing a reflux device, heating in an oil bath at 80 ℃, carrying out reflux stirring reaction at the rotating speed of 450r/min for 3 hours, then adding 45g of distilled water, continuing stirring reaction at the rotating speed of 450r/min until the dicyclohexylcarbodiimide is decomposed, cooling to room temperature, then standing at 4 ℃ until a solid is separated out, carrying out suction filtration washing on the solid for 5 times by using ice water, and then drying at 100 ℃ for 1 hour to obtain the naphthoyl β -cyclodextrin;
(2) adding 1.0025g of the naphthoylated β -cyclodextrin prepared in the step (1) into distilled water, heating and stirring in a water bath at 85 ℃ until the naphthoylated β -cyclodextrin is dissolved to form a saturated solution of the naphthoylated β -cyclodextrin, then adding a catnip essential oil ethanol solution (containing 0.5020g of catnip essential oil) into the saturated solution, stirring and reacting at the rotating speed of 450r/min until a white solid is separated out, then cooling to room temperature, standing at 4 ℃ until no white solid is separated out, firstly washing the white solid by suction filtration with ice water for 3 times, then washing the white solid by suction filtration with absolute ethanol for 4 times, and then drying at 30 ℃ for 4.5 hours in vacuum to obtain the catnip essential oil/naphthoylated β -cyclodextrin microcapsule.
Example 2
(1) Adding 2.270g of β -cyclodextrin into a round-bottom flask, then adding 0.6120g of 1-naphthoic acid and 0.6120g of dicyclohexylcarbodiimide, installing a reflux device, heating in an oil bath at 65 ℃, carrying out reflux stirring reaction at the rotating speed of 300r/min for 3.5 hours, then adding 80g of distilled water, continuing stirring reaction at the rotating speed of 300r/min until the dicyclohexylcarbodiimide is decomposed, cooling to room temperature, then standing at 5 ℃ until a solid is separated out, washing the solid for 4 times by using ice water through suction filtration, and then drying at 105 ℃ for 1 hour to obtain the naphthoylated β -cyclodextrin;
(2) 1.0117g of naphthoylated β -cyclodextrin prepared in the step (1) is added into distilled water, the mixture is heated and stirred in a water bath at 85 ℃ until the naphthoylated β -cyclodextrin is dissolved to form a saturated solution of the naphthoylated β -cyclodextrin, then a catnip essential oil ethanol solution (0.5120 g of catnip essential oil is contained in the saturated solution) is added into the saturated solution, the mixture is stirred and reacted at the rotating speed of 300r/min until white solid is separated out, then the mixture is cooled to the room temperature, the mixture is stood at 5 ℃ until no white solid is separated out, the white solid is washed by ice water in a suction filtration mode for 4 times, the white solid is washed by absolute ethanol in a suction filtration mode for 5 times, and then the white solid is dried in vacuum at 25 ℃ for 5 hours to obtain the catnip essential oil/naphthoylated β -cyclodextrin microcapsule.
Example 3
(1) Adding 2.270g of β -cyclodextrin into a round-bottom flask, then adding 0.8160g of 1-naphthoic acid and 0.8160g of dicyclohexylcarbodiimide, installing a reflux device, heating in an oil bath at 85 ℃, carrying out reflux stirring reaction at the rotating speed of 600r/min for 2.5 hours, then adding 120g of distilled water, continuing stirring reaction at the rotating speed of 600r/min until the dicyclohexylcarbodiimide is decomposed, cooling to room temperature, then standing at 0 ℃ until a solid is separated out, washing the solid for 3 times by using ice water through suction filtration, and then drying at 100 ℃ for 1.5 hours to obtain the naphthoylated β -cyclodextrin;
(2) 1.0122g of naphthoylated β -cyclodextrin prepared in the step (1) is added into distilled water, the mixture is heated and stirred in a water bath at 85 ℃ until the naphthoylated β -cyclodextrin is dissolved to form a saturated solution of the naphthoylated β -cyclodextrin, then a catnip essential oil ethanol solution (0.5250 g of catnip essential oil is contained in the saturated solution) is added into the saturated solution, the mixture is stirred and reacted at the rotating speed of 600r/min until white solid is separated out, then the mixture is cooled to room temperature, the mixture is stood at 0 ℃ until no white solid is separated out, the white solid is washed by ice water in a suction filtration mode for 5 times, the white solid is washed by absolute ethanol in a suction filtration mode for 3 times, and then the mixture is dried in vacuum at 30 ℃ for 4 hours to obtain the catnip essential oil/naphthoylated β -cyclodextrin microcapsule.
Example 4
(1) Adding 2.270g of β -cyclodextrin into a round-bottom flask, then adding 1.0200g of 1-naphthoic acid and 1.0200g of dicyclohexylcarbodiimide, installing a reflux device, heating in an oil bath at 80 ℃, carrying out reflux stirring reaction at the rotating speed of 500r/min for 3 hours, then adding 102g of distilled water, continuing stirring reaction at the rotating speed of 500r/min until the dicyclohexylcarbodiimide is decomposed, cooling to room temperature, then standing at 3 ℃ until a solid is separated out, washing the solid for 5 times by ice water suction filtration, and then drying at 105 ℃ for 1 hour to obtain the naphthoylated β -cyclodextrin;
(2) 1.0105g of naphthoylated β -cyclodextrin prepared in the step (1) is added into distilled water, the mixture is heated and stirred in a water bath at 85 ℃ until the naphthoylated β -cyclodextrin is dissolved to form a saturated solution of the naphthoylated β -cyclodextrin, then a catnip essential oil ethanol solution (0.5070 g of catnip essential oil is contained in the saturated solution) is added into the saturated solution, the mixture is stirred and reacted at the rotating speed of 500r/min until white solid is separated out, then the mixture is cooled to the room temperature, the mixture is stood at 3 ℃ until no white solid is separated out, the white solid is washed by ice water in a suction filtration mode for 4 times, the white solid is washed by absolute ethanol in a suction filtration mode for 5 times, and then the white solid is dried in vacuum at 30 ℃ for 5 hours to obtain the catnip essential oil/naphthoylated β -cyclodextrin microcapsule.
Comparative examples
The difference from example 1 is that instead of step (1), the naphthoylated β -cyclodextrin in step (2) was replaced by β -cyclodextrin.
Example 5
The yields of naphthoylated β -cyclodextrin in examples 1-4 were tested and calculated as follows:
naphthoylation β -Cyclodextrin yield (%) β -Cyclodextrin Mass/(β -Cyclodextrin Mass + 1-Naphthoic acid Mass). times.100%
The results are shown in Table 1.
TABLE 1 yield of naphthoylated β -cyclodextrin in examples 1 to 4
As can be seen from Table 1, the yield of the product gradually decreases with the increase of the proportion of 1-naphthoic acid, β -cyclodextrin has 7 primary hydroxyl groups and 14 secondary hydroxyl groups, and the reactivity of 1-naphthoic acid with these hydroxyl groups gradually decreases with the increase of naphthoyl group introduced on β -cyclodextrin molecule, because the difficulty of the subsequent naphthoylation reaction is increased by the steric hindrance of naphthoyl group.
Example 6
The yields of catnip essential oil/naphthoylated β -cyclodextrin microcapsules in examples 1 to 4 were tested and calculated as catnip essential oil/naphthoylated β -cyclodextrin microcapsule yield (%) -catnip essential oil/naphthoylated β -cyclodextrin microcapsule mass/(naphthoylated β -cyclodextrin mass + catnip essential oil mass) × 100%
The results are shown in Table 2.
Table 2 yield of catnip essential oil/naphthoylated β -cyclodextrin microcapsules in examples 1 to 4
From table 2, the obtained catnip essential oil/naphthoyl β -cyclodextrin microcapsule is white powder and has no catnip odor basically, under the condition of basically consistent material ratio, the more naphthoyl modified on β -cyclodextrin, the lower the yield of the catnip essential oil/naphthoyl β -cyclodextrin microcapsule is formed, which shows that the naphthoyl introduced on β -cyclodextrin increases the steric hindrance around the inner cavity of the catnip essential oil/naphthoyl β -cyclodextrin, so that the more steric hindrance needs to be overcome to enable the catnip essential oil to enter the inner cavity of β -cyclodextrin, and the yield of the catnip essential oil/naphthoyl β -cyclodextrin microcapsule is reduced.
Example 7
Testing of the Release Performance of Nepeta Catariae essential oil in the comparative example and Nepeta Catariae essential oil/Naphthylated β -Cyclodextrin microcapsules in examples 1 to 4
Accurately weighed amounts of catmint essential oil/naphthoylated β -cyclodextrin microcapsules (noted as m) in each example0) Placing into a constant temperature oven (40 deg.C, 60 deg.C, 80 deg.C respectively) at certain temperature, and weighing at certain intervals (respectively recorded as m)1，m2，m3。。。。。mt) Finally, the temperature of the oven is raised to 120 ℃, the drying is continued for 6 hours, at the moment, the catnip essential oil in the microcapsule is completely released, and the residual mass is recorded as mf。
Catnip essential oil inclusion rate (%) (m)0—mf)/m0×100％
Catnip essential oil release rate (%) (m)0—mt)/(m0—mf)×100％
The test results are shown in table 3 and fig. 1 to 3, wherein fig. 1 to 3 are graphs sequentially showing the test results of the release rate of the catnip essential oil from the microcapsules in comparative example and examples 1 to 4 at 40 ℃, 60 ℃ and 80 ℃, respectively.
TABLE 3 Release Rate of Nepeta Catariae essential oil from microcapsules of various examples
As can be seen from table 3 and fig. 1 to 3:
(1) in a 40 ℃ constant temperature oven, the catnip essential oil/β -cyclodextrin microcapsule without naphthoylation in the comparative example releases the catnip essential oil most rapidly, and has been released basically completely in about 5 h. the catnip essential oil/naphthoylated β -cyclodextrin microcapsule in example 1 and example 2 has a significantly slower release rate under the same conditions, and the catnip essential oil/naphthoylated β -cyclodextrin microcapsule in example 3 and example 4 has no obvious release of the catnip essential oil.
(2) When the temperature is increased to 60 ℃, the release rate of the catnip essential oil in each microcapsule is improved, wherein the release rate of the catnip essential oil/naphthoyl β -cyclodextrin microcapsule in example 4 is uniform, the uniform release is complete within 10 hours, and the catnip essential oil/naphthoyl β -cyclodextrin microcapsule is suitable for development and application of the electrothermal mosquito-repellent tablet.
(3) When the temperature is increased to 80 ℃, the release rate of the mint essential oil in each microcapsule is further accelerated, but the release rate of the catnip essential oil/naphthoyl β -cyclodextrin microcapsule in example 4 is still uniform, and the release time is still about 9h, so that the application requirement of uniform and continuous release can be met.
Compared with the catnip essential oil/naphthaloyl β -cyclodextrin microcapsule with non-naphthaloyzed catnip essential oil/β -cyclodextrin microcapsule, the release speed of the catnip essential oil at the measured temperature is in sequence as comparison example > example 1> example 2> example 3> example 4, namely, the higher the thermal stability of the microcapsule is, the slower the catnip essential oil is released and the better the uniformity is along with the increase of the naphthoyl on β -cyclodextrin, therefore, through the naphthaloylation degree on β -cyclodextrin, the introduction of the steric hindrance group can effectively control the speed and the uniformity of the catnip essential oil released from the microcapsule, and a feasible method is provided for developing a mosquito repellent product with sustained and controlled release.
Finally, the above embodiments are only intended to illustrate the technical solutions of the present invention and not to limit the present invention, and although the present invention has been described in detail with reference to the preferred embodiments, it will be understood by those skilled in the art that modifications or equivalent substitutions may be made on the technical solutions of the present invention without departing from the spirit and scope of the technical solutions, and all of them should be covered by the claims of the present invention.
Claims (10)
1. The catnip essential oil/naphthoylated β -cyclodextrin microcapsule is characterized by comprising a wall material and a core material wrapped in the wall material, wherein the wall material is naphthoylated β -cyclodextrin, and the core material is catnip essential oil.
2. The method for preparing the catnip essential oil/naphthoylated β -cyclodextrin microcapsule as claimed in claim 1, wherein the method comprises the following steps:
(1) adding 1-naphthoic acid and dicyclohexylcarbodiimide into β -cyclodextrin, carrying out reflux stirring reaction at 65-85 ℃ for 2.5-3.5h, adding water, continuing stirring reaction until the dicyclohexylcarbodiimide is decomposed, cooling to room temperature, standing until a solid is precipitated, carrying out suction filtration washing on the solid, and drying to obtain naphthoyl β -cyclodextrin;
(2) dissolving the naphthoyl β -cyclodextrin prepared in the step (1) in water to form saturated solution of the naphthoyl β -cyclodextrin, adding ethanol solution of catmint essential oil into the saturated solution, stirring and reacting until white solid is separated out, cooling to room temperature, standing until the white solid is not separated out, carrying out suction filtration, washing and drying on the white solid, and thus obtaining the catmint essential oil/naphthoyl β -cyclodextrin microcapsule.
3. The method of claim 2, wherein in step (1), the molar ratio of β -cyclodextrin to 1-naphthoic acid is 1:2-5, and the mass ratio of 1-naphthoic acid to dicyclohexylcarbodiimide is 1: 1.
4. The method as claimed in claim 2, wherein the mass ratio of dicyclohexylcarbodiimide to water in step (1) is 1: 100-150.
5. The method of claim 2, wherein in the step (1), the standing is performed at 0-5 ℃, and the washing with suction filtration is performed 3-5 times by using ice water as a washing solution.
6. The method as claimed in claim 2, wherein in the step (1), the drying is performed at 100-105 ℃ for 1-1.5 h.
7. The method of claim 2, wherein in step (2), the molar ratio of naphthoylated β -cyclodextrin to catmint essential oil is 1.9280-1.9970: 1.
8. The method of claim 2, wherein in the step (2), the standing is performed at 0-5 ℃, and ice water is used as a washing solution for washing 3-5 times, and then absolute ethyl alcohol is used as a washing solution for washing 3-5 times during the suction filtration washing.
9. The method of claim 2, wherein in the step (2), the drying is performed at 25-30 ℃ for 4-5h under vacuum.
10. The method as claimed in claim 2, wherein the stirring speed in step (1) and step (2) is 300-600 r/min.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201911235816.1A CN110755305B (en) | 2019-12-05 | 2019-12-05 | Nepeta cataria essential oil/naphthacylation beta-cyclodextrin microcapsule and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201911235816.1A CN110755305B (en) | 2019-12-05 | 2019-12-05 | Nepeta cataria essential oil/naphthacylation beta-cyclodextrin microcapsule and preparation method thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN110755305A true CN110755305A (en) | 2020-02-07 |
| CN110755305B CN110755305B (en) | 2022-07-29 |
Family
ID=69341047
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201911235816.1A Active CN110755305B (en) | 2019-12-05 | 2019-12-05 | Nepeta cataria essential oil/naphthacylation beta-cyclodextrin microcapsule and preparation method thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN110755305B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113754796A (en) * | 2021-10-18 | 2021-12-07 | 中国石油大学(华东) | Naphthalene-modified crosslinked beta-cyclodextrin gel, preparation method and application |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101048705A (en) * | 2004-11-01 | 2007-10-03 | 日产化学工业株式会社 | Lower layer film-forming composition for lithography containing cyclodextrin compound |
| US20120094954A1 (en) * | 2009-04-09 | 2012-04-19 | Emmanuelle At | Compositions comprising at least one complex composed of a derivative of naphthoic acid and of at least one cyclodextrin and uses thereof |
| CN103651589A (en) * | 2013-09-26 | 2014-03-26 | 信阳农林学院 | Chenopodium ambrosioides volatile oil microcapsule and preparation method thereof |
| US20140220112A1 (en) * | 2013-02-01 | 2014-08-07 | Zoneone Pharma, Inc. | Transformation of drug cyclodextrin complex compositions into compositions of mixtures of lipid vesicle encapsulated drug and cyclodextrin drug complexes |
| CN109651533A (en) * | 2018-12-27 | 2019-04-19 | 浙江外国语学院 | A kind of the beta-cyclodextrin fluorescent optical sensor and its synthetic method of naphthylamino modification |
-
2019
- 2019-12-05 CN CN201911235816.1A patent/CN110755305B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101048705A (en) * | 2004-11-01 | 2007-10-03 | 日产化学工业株式会社 | Lower layer film-forming composition for lithography containing cyclodextrin compound |
| US20120094954A1 (en) * | 2009-04-09 | 2012-04-19 | Emmanuelle At | Compositions comprising at least one complex composed of a derivative of naphthoic acid and of at least one cyclodextrin and uses thereof |
| US20140220112A1 (en) * | 2013-02-01 | 2014-08-07 | Zoneone Pharma, Inc. | Transformation of drug cyclodextrin complex compositions into compositions of mixtures of lipid vesicle encapsulated drug and cyclodextrin drug complexes |
| CN103651589A (en) * | 2013-09-26 | 2014-03-26 | 信阳农林学院 | Chenopodium ambrosioides volatile oil microcapsule and preparation method thereof |
| CN109651533A (en) * | 2018-12-27 | 2019-04-19 | 浙江外国语学院 | A kind of the beta-cyclodextrin fluorescent optical sensor and its synthetic method of naphthylamino modification |
Non-Patent Citations (1)
| Title |
|---|
| YU LIU等: ""Synthesis of Novel β-cyclodextrin Derivatives Bearing a 1-naphthyloxamino-oligo(ethyleneamino) Moiety and their Inclusion Complexation with some Fluorescent Dyes"", 《SUPRAMOLECULAR CHEMISTRY》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113754796A (en) * | 2021-10-18 | 2021-12-07 | 中国石油大学(华东) | Naphthalene-modified crosslinked beta-cyclodextrin gel, preparation method and application |
Also Published As
| Publication number | Publication date |
|---|---|
| CN110755305B (en) | 2022-07-29 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN108739807B (en) | Vegetable oleic acid-chitosan-based nano microcapsule pesticide, and preparation method and application thereof | |
| DK165361B (en) | PREPARATIONS WITH WRAPPED PARTICULARS AND PROCEDURES FOR PRODUCING THEREOF | |
| CN111620964A (en) | Compound essential oil microcapsule preparation for preventing and treating banana wilt and preparation method thereof | |
| CN111533848B (en) | Photothermal dual-responsive chitosan derivative, and preparation method and application thereof | |
| CN110622965B (en) | Preparation method of leaf surface affinity type pesticide nano microcapsule based on tannic acid modification | |
| CN106831905A (en) | The preparation of pH responses adriamycin dopamine conjugate and its prodrug nano-particle | |
| CN110755305A (en) | Nepeta cataria essential oil/naphthoylated β -cyclodextrin microcapsule and preparation method thereof | |
| WO2006042078A2 (en) | A system and method for a fragant polymer configured for use in a growing medium | |
| Lipaikin et al. | Development of biodegradable delivery systems containing novel 1, 2, 4‐trioxolane based on bacterial polyhydroxyalkanoates | |
| CN113603874B (en) | Polyester based on vanillyl alcohol derivatives, preparation and use as pesticide slow-release agents | |
| Li et al. | Pheromone enclosed in halloysite with n-octadecane releases rhythmically under simulated diurnal temperature | |
| CN109260029A (en) | A kind of water-soluble nano essential oil micellar solution and preparation method thereof | |
| JP6296381B2 (en) | Disulfur 5-membered ring functional group-containing cyclic carbonate monomer and method for preparing the same | |
| CN108904474A (en) | Degradable curcumin derivate-polylactic acid-polyglycolic acid composite membrane and preparation method thereof | |
| CN111011370B (en) | High-retention pesticide microsphere with special topological morphology modified by polymer and preparation method thereof | |
| US20090022764A1 (en) | Organic compounds | |
| CN107159069A (en) | A kind of leather osmanthus flower fragrance capsule | |
| Qian et al. | Preparation of long-lasting releasing methyl eugenol fiber membrane and its trapping analysis on Bactrocera dorsalis | |
| RU2494621C1 (en) | Herbicidal long-acting composition for use in soil | |
| Wang et al. | Nanocapsule-based reactive nano-fragrances with slow-release and antibacterial performances for applications of commodities | |
| CN114144394A (en) | Calcium phosphate coated with humic acid or phenolic polymer and use thereof | |
| CN110452368A (en) | A kind of star-shaped comb type fluorescence polylactic acid and preparation method thereof | |
| RU2724887C1 (en) | Method of producing iron (iii) sulphate nanocapsules | |
| RU2736053C1 (en) | Method for producing chloramphenicol nanocapsules (levomycetin) | |
| RU2731854C1 (en) | Method for producing chloramphenicol (levomycetin) nanocapsules |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |