CN107771790A - PH stimuli responsive types inorganic nano-particle/polymer combination drug carrier and its preparation method and application - Google Patents
PH stimuli responsive types inorganic nano-particle/polymer combination drug carrier and its preparation method and application Download PDFInfo
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- CN107771790A CN107771790A CN201710997405.0A CN201710997405A CN107771790A CN 107771790 A CN107771790 A CN 107771790A CN 201710997405 A CN201710997405 A CN 201710997405A CN 107771790 A CN107771790 A CN 107771790A
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- 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
- A01N25/08—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 containing solids as carriers or diluents
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- 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
- A01N25/08—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 containing solids as carriers or diluents
- A01N25/10—Macromolecular compounds
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- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/06—Unsaturated carboxylic acids or thio analogues thereof; Derivatives thereof
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- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
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- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
A kind of pH stimuli responsive types inorganic nano-particle/polymer combination drug carrier and its preparation method and application.Using surface modification C=C silica nanosphere as template, with alkylene function monomer, the crosslinking agent of pH stimuli responsives, initiator, in certain solvent, a kind of new inorganic/polymer composites for being obtained by distilling precipitation polymerization, and the composite is applied to farm chemical carrier.The new pH stimuli responsive types inorganic nano-particle/polymer combination drug carrier, the usage amount of agricultural chemicals can be substantially reduced, improve the utilization rate of medicine, it is not high to solve conventional carriers drugloading rate, the medicine of loading is difficult to controllably discharge, the polymer support of synthesis is difficult to decompose naturally, may cause the polymer support of residual for the secondary pollution problems of soil and water body.The invention has good application prospect in terms of agricultural insect pest's preventing and treating.
Description
Technical field
It is particularly multiple to a kind of pH stimuli responsive types inorganic nano-particle/polymer the invention belongs to pharmaceutical carrier field
The preparation method and agricultural of composite medicine carrier are applied.
Background technology
, it is necessary to which agricultural constantly provides enough food, this is the challenge that the whole mankind faces jointly for the sustainable growth of population.So
And insect, plant disease and weeds carry out the serious underproduction to agricultural belt.According to data statistics, there are about every year 9000 kinds of insects,
50000 kinds of phytopathogens and 8000 kinds of weeds damage to agricultural production.In order to control these pest and disease damages and weeds, largely
Agricultural chemicals and bioactivity medicine be widely used, and thereby result in environmental pollution, food security the problems such as, increasingly by
To the concern of people.Just as we know, the agricultural chemicals being sprayed directly on plant there are about 60~70% and not obtain effectively
Utilization, but be directly lost in soil, polluted underground water, or part is remained on the leaf and fruit of plant, is entered
The food chain of the mankind, it is food-safe to threaten.In addition, many insecticides and bioactivity medicine are all ester dissolubilities, need
First to be dissolved using a large amount of organic solvents (such as chloride polyaromatic, alkane, 1-METHYLPYRROLIDONE etc.), spray could be implemented
Spill, the use of these organic solvents can also cause to pollute again to environment, and the health to the mankind causes damage.
Agricultural chemicals control release technic can according to the requirement of prevention target, the rate of release of reasonable adjusting active component, from
And improve the utilization rate of agricultural chemicals, extend the lasting period.Because the farm chemical release amount in environment is controlled, it is possible to reduce agricultural chemicals is in ring
Migration in border, controls pollution by pesticides from source.Also contribute to reduce applications of pesticide total amount in addition, agricultural chemicals utilization rate improves,
Reduce agricultural production input.Therefore, contradiction of the agricultural chemicals control release technic between the volume increase of solution agricultural and pollution by pesticides control
Provide a feasible approach.The core of agricultural chemicals control release technic is carrier material, at present, has there is substantial amounts of related material
Material is reported.Mainly have：1) inorganic carrier material, including the inorganic porous oxidation such as silica, clay (bentonite), sepiolite
Thing.Using the big specific surface area of these materials and good absorption property, drug molecule can be loaded in its duct, recycled
These materials unique pore passage structure and its different active force between drug molecule, reach Drug controlled release speed
Purpose.2) natural macromolecular material, such as alginates, lignin, chitosan.This kind of carrier material has abundance, can be again
The advantages of raw, they mainly using the backbone of natural polymer and a variety of functional groups can be produced with pesticide activity component compared with
Strong adhesion, help to delay the release of active component.3) high polymer material is synthesized.Such as polyhydroxyalkanoate (PHA), gather
Butyric ester (PHB) and its with the copolymer of poly- hydroxyl valerate (PHV) etc..This kind of carrier material has structure diversity
Advantage, the load of different pesticide activity components and the application requirement of sustained release can be met.As fully visible, although three kinds of carrier materials
Respective advantage is respectively provided with terms of as farm chemical carrier, but has certain limitation.Such as inorganic carrier material and natural
High polymer material, do not have customization capability to the rate of release of different pesticide activity components, and synthesize high polymer material and then exist
Synthesis technique is more complicated, generally requires the tedious steps such as previously prepared polymer micelle, improves the cost of carrier.
CN201410258179.0 discloses a kind of dendroid nanometer macromolecule medicament carrier using imide derivative as fluorescent core,
Load hydrophobic drug Diacloden is applied to cotton bollworm control, and the carrier enhances the drug effect of insecticide, expands insecticidal range,
To avoid the excessive use of chemical insecticide from providing approach.But dendrimer building-up process is complicated, cost is high, it is more difficult to real
Existing large-scale application.
The content of the invention
Drugloading rate is not high existing for current farm chemical carrier the present invention seeks to solving, and the medicine of loading is difficult to controllably release
Put, the problems such as polymer support of synthesis is difficult natural degradation, there is provided a kind of pH stimuli responsive types inorganic nano-particle/polymer
Combination drug carrier and its preparation method and application.
The present invention is directed to the function and feature of Typical Agricultural bio-pharmaceutical, to reduce medication, extends drug effect, avoids organic molten
The use of agent, toxicity is reduced, it is target to facilitate dispenser, is prepared for a kind of intelligent inorganic nano-particle/polymer combination drug
Carrier, the synthetic method is simple, and cost is low, and 2- hexenoic acids (HE) drug model trans- to insect pheromone has efficient control
Release performance.
Technical solution of the present invention
A kind of pH stimuli responsive types inorganic nano-particle/polymer combination drug carrier, the combination drug carrier is by nothing
Machine nano-particle, function monomer, the crosslinking agent of pH stimuli responsives and initiator are dissolved in solvent, by distilling precipitation polymerization
Obtained from compound.
Described function monomer is the highly polar group with amido, amide groups, hydroxyl or carboxyl, or the weak pole of ester group
Single vinyl compound of property group.
The crosslinking agent of described pH stimuli responsives is the one or more in the molecule containing full reduced aldehyde or full ketal structure,
Concrete structure formula is as follows：
Described solvent is the one or more in nitrile, alcohol, aromatic hydrocarbon, aliphatic hydrocarbon, ester or ketone.
Described initiator is the one or more in peroxide, persulfide or azo-compound.Preferably over cure
Sour sodium, potassium peroxydisulfate, ammonium persulfate, hydrogen peroxide, benzoyl peroxide, lauroyl peroxide, cumene hydroperoxide, idol
- 2- methyl propanamides the hydrochloride of nitrogen two, 2,2 '-azo two (2- methyl propanamides oxime) salt, azodiisobutyronitrile or azo two
One or more in NSC 18620 hydrochloride.
, should invention also provides the preparation method of pH stimuli responsive types nano-particle/polymer combination drug carrier
Method is by SiO2Nano-particle, function monomer, the crosslinking agent of pH stimuli responsives and initiator according to calculate dosage in solvent,
Above-mentioned raw materials are reacted into 1~5h, centrifugation under 70~130 DEG C of stirrings, drying obtains pH stimuli responsive types inorganic nano-particle/poly-
Compound combination drug support products.The mass ratio of crosslinking agent and function monomer is 10%~90% in the raw material.Initiator
Measure as the 1%~5% of function monomer quality, the dosage of inorganic nano-particle is 0.1~1 times of function monomer dosage.
Concrete operation step is as follows：
According toMethod synthesizes SiO2, and double bond modification is carried out to it.The anhydrous second of 400mL is added in 1L four-hole bottles
Alcohol, 44mL distilled water, 7.5mL 25% concentrated ammonia liquor are configured to mixed solution, mechanical agitation 1h, rotating speed 500r/min.Add
9mL tetraethyl orthosilicates (TEOS), at room temperature with 400r/min rotating speed stirring reaction 24h.Colourless transparent solution viscosity gradually increases
Greatly, transparent colloidal solution is formed.6mL methacryloxypropyl trimethoxy silicon is added into the solution after stirring 24h
Alkane (MPS), continue to stir 24h, rotating speed 400r/min.Stop reaction, centrifugation, and washed with absolute ethyl alcohol at 3 times, 40 DEG C very
Sky is dried, and obtains the MPS-SiO of surface double-bond2Nanoparticle.Nano particles of silicon dioxide is added to ultrasonic disperse in solvent
30min, it is completely dispersed it.Then the function monomer of the group containing difference in functionality, the crosslinking agent of pH stimuli responsives are added thereto
And initiator, reaction system is reacted into 1~5h, centrifugation under 70~130 DEG C of stirrings, precipitating solvent is washed 3 times, and drying obtains pH
Stimuli responsive type inorganic nano-particle/polymer combination drug support products.
The advantages of the present invention：
1) raw material for synthetic vectors is easy to get, and synthetic method is simple, mild condition；
2) medicine loaded can carry out controlled release according to environmental pH；
3) carrier can avoid secondary pollution of the polymer support to soil and water body with natural decomposition.
Brief description of the drawings
Fig. 1 is preparation and drug loading and the control release process schematic of combination drug carrier of the present invention.
Fig. 2 is the change of size figure under combination drug carrier DC-1 acid conditions in the present invention.
Fig. 3 is combination drug carrier DC-1-HE releasing curve diagrams in the present invention.
Fig. 4 is compound pharmaceutical carrier structural representation.
Embodiment
The invention will be further described with reference to the accompanying drawings and detailed description, it will help to the reason of the present invention
Solution.But it can not be limited the scope of the invention with this, and what the interest field of the present invention should be illustrated with claims
It is defined.The synthesis schematic diagram of the present invention is as shown in Figure 1.
Embodiment 1：
1)SiO2The synthesis of nano-particle and surface modification
400mL absolute ethyl alcohols, 44mL distilled water are added in 1L four-hole bottles, 7.5mL 25% concentrated ammonia liquor is configured to mix
Solution, mechanical agitation 1h, rotating speed 500r/min.9mL tetraethyl orthosilicates (TEOS) are added, are stirred at room temperature with 400r/min rotating speed
Mix reaction 24h.Colourless transparent solution viscosity gradually increases, and forms transparent colloidal solution.Added into the solution after stirring 24h
6mL methacryloxypropyl trimethoxy silanes (MPS), continue to stir 24h, rotating speed 400r/min.Stop reaction, from
The heart, and washed 3 times with absolute ethyl alcohol, it is dried in vacuo at 40 DEG C, obtains the MPS-SiO of surface double-bond2Nanoparticle.
2) synthesis of pH stimuli responsives crosslinking agent (DMOEM)
In reaction bulb, 3g paraformaldehydes are added in 60mL toluene, sequentially add 7.32mL hydroxyethyl methacrylates
Ethyl ester (HEMA), 30mg p-methyl benzenesulfonic acid (pTSA), 3.2mg phenthazine, 3h is reacted under 100 DEG C of reflux states.By reactant mistake
Filter, removes unreacted solid-state paraformaldehyde, and solution is spin-dried for obtaining crude product, then purifies that (column chromatography eluant, eluent is through column chromatography
N-hexane：Ethyl acetate=8:1) DMOEM, is made.Its architectural feature：1H NMR(400MHz,CDCl3)δ6.10(s,2H),
5.59-5.53 (m, 2H), 4.79-4.70 (m, 2H), 4.30 (t, J=6.1Hz, 4H), 3.80 (dd, J=9.6,3.4Hz, 4H),
1.98-1.87(m,6H).
3) preparation of pH stimuli responsive types pharmaceutical carrier DC-1 microballoons
By 0.10g MPS-SiO obtained by step 1)2Nanoparticle is dispersed in 40mL acetonitriles, and ultrasonic disperse is uniform, will be walked
Rapid 2) gained crosslinking agent DMOEM 0.1g, monomeric acrylamide (AM) 0.15g, azodiisobutyronitrile (AIBN) 6mg are added thereto,
70 DEG C are heated to, half acetonitrile is steamed after 5h, stops heating.Reaction solution centrifuges, and is washed 3 times with ethanol, 40 DEG C of vacuum drying chamber
Drying, obtains pH stimuli responsive type pharmaceutical carrier DC-1 microballoons.
Embodiment 2：
1) synthesis of pH stimuli responsives crosslinking agent (CL2m)
By methoxybenzaldehyde (1g), hydroxyethyl methacrylate (HEMA, 3.82g) is added in 100mL round-bottomed flasks,
It is placed in ice-water bath, adds p-methyl benzenesulfonic acid (pTSA, 98mg) and molecular sieve, N26h is reacted under atmosphere.Reaction adds about
Reaction is quenched in 0.2mL triethylamines (TEA).Solution adds tetrahydrofuran (THF) dilution.Crude product silicagel column (n-hexane：Dichloromethane
Alkane：TEA=85:5:10) purify.Obtain pH stimuli responsive crosslinking agents CL2m..
The preparation of pH stimuli responsive type pharmaceutical carrier DC-2 microballoons
2) MPS-SiO for synthesizing step 1) in embodiment 12Nanoparticle is dispersed in 40mL acetonitriles, and ultrasonic disperse is equal
It is even, by crosslinking agent CL2m 0.1g obtained by the present embodiment step 1), monomers hydroxy ethyl ester (HEMA) 0.15g, azo two
Isobutyronitrile (AIBN) 6mg is added thereto, and is heated to 70 DEG C, and half acetonitrile is steamed after 5h, stops heating.Reaction solution centrifuges, and uses second
Alcohol washs 3 times, 40 DEG C of drying of vacuum drying chamber, obtains pH stimuli responsive type pharmaceutical carrier DC-2 microballoons.
Embodiment 3：
The MPS-SiO that step 1) in embodiment 1 is synthesized2Nanoparticle is dispersed in 40mL acetonitriles, and ultrasonic disperse is uniform,
By crosslinking agent CL2m 0.1g obtained by the step 1) of embodiment 2, monomer methacrylic acid (MAA) 0.15g, benzoyl peroxide (BPO)
6mg is added thereto, and is heated to 70 DEG C, and half acetonitrile is steamed after 5h, stops heating.Reaction solution centrifuges, and washs 3 times with ethanol, very
Empty 40 DEG C of drying of drying box, obtain pH stimuli responsive type pharmaceutical carrier DC-3 microballoons.
Embodiment 4:
The MPS-SiO that step 1) in embodiment 1 is synthesized2Nanoparticle is dispersed in 40mL acetonitriles, and ultrasonic disperse is uniform,
By crosslinking agent DMOEM 0.1g obtained by the step 2) of embodiment 1, monomer propylene acetoacetic ester (EA) 0.15g, benzoyl peroxide (BPO)
6mg is added thereto, and is heated to 70 DEG C, and half acetonitrile is steamed after 5h, stops heating.Reaction solution centrifuges, and washs 3 times with ethanol, very
Empty 40 DEG C of drying of drying box, obtain pH stimuli responsive type pharmaceutical carrier DC-4 microballoons.
The load medicine and insoluble drug release of pH stimuli responsive types inorganic nano-particle/polymer combination drug carrier, using DC-1 as
Example, pharmaceutical carrier DC-2, DC-3, DC-4 still can reach effect same, will not enumerate herein.
1) degraded under combination drug carrier DC-1 acid conditions
Combination drug carrier DC-1 microballoons obtained by the step 3) of embodiment 1 are scattered in the pH=2 aqueous solution, are respectively separated
0.5h, 1h, 2h ... timing its dynamic particle size change, its change schematic diagram is as shown in Figure 2.
2) the load medicine of pH stimuli responsive types inorganic nano-particle/polymer combination drug carrier
Take combination drug carrier DC-1 microballoons 300mg, trans- 2- hexenoic acids (HE) 300mg obtained by the step 3) of embodiment 1,
It is added in 150mL ethanol, stirs 48h at room temperature.Reaction solution centrifuges, and must carry the combination drug carrier DC-1-HE of medicine.
3) release of pH stimuli responsive types inorganic nano-particle/polymer combination drug carrier medicament
Weigh 10mg DC-1-HE and be placed in 50mL difference pH value and obtain in the aqueous solution, under the conditions of being stirred at room temperature, be respectively separated
0.5h, 1h, 2h ... determine the ultra-violet absorption spectrum of solution.Spectrogram can be seen that the accumulative release of the medicine under the conditions of pH=2
Amount reaches 50%, realizes effective release of medicine, combination drug carrier DC-1-HE release profiles are referring to accompanying drawing 3.
Product of the present invention is used for the loading of the trans- 2- hexenoic acids (HE) of insect pheromone, can realize the controlled release of medicine.
Simultaneously synthesizing polymer support can decompose naturally, will not cause the polymer support of residual for the two of soil and water body
Secondary pollution, there is good application prospect.
From the foregoing it is appreciated that although describing specific embodiments of the present invention for the purpose of exemplary illustration,
But under condit without departing from the spirit and scope of the present invention, technical staff described in this area can make various modifications or change
Enter.These deformations or modification should all fall into the application scope of the following claims.
Claims (9)
1. a kind of pH stimuli responsive types inorganic nano-particle/polymer combination drug carrier, it is characterized in that：The combination drug carrier
It is to be dissolved in by inorganic nano-particle, function monomer, the crosslinking agent of pH stimuli responsives and initiator in solvent, it is heavy by distilling
Formed sediment compound obtained from polymerization, and compound is carried out to carry medicine and insoluble drug release.
2. pH stimuli responsive types inorganic nano-particle according to claim 1/polymer combination drug carrier, its feature exist
In：Described function monomer is the highly polar group with amido, amide groups, hydroxyl or carboxyl, or the low pole base of ester group
Single vinyl compound of group.
3. pH stimuli responsive types inorganic nano-particle according to claim 1/polymer combination drug carrier, its feature exist
In：The crosslinking agent of described pH stimuli responsives is the one or more in the molecule containing full reduced aldehyde or full ketal structure, specifically
Structural formula difference is as follows：
4. pH stimuli responsive types inorganic nano-particle according to claim 1/polymer combination drug carrier, its feature exist
In：Described solvent is the one or more in nitrile, alcohol, aromatic hydrocarbon, aliphatic hydrocarbon, ester or ketone.
5. pH stimuli responsive types inorganic nano-particle according to claim 1/polymer combination drug carrier, its feature exist
In：Described initiator is the one or more in peroxide, persulfide or azo-compound.
6. pH stimuli responsive types inorganic nano-particle according to claim 5/polymer combination drug carrier, its feature exist
In：Described initiator is preferably sodium peroxydisulfate, potassium peroxydisulfate, ammonium persulfate, hydrogen peroxide, benzoyl peroxide, lauroyl
Peroxide, the cumene hydroperoxide, -2- methyl propanamides hydrochloride of azo two, 2, (the 2- methyl propanamides of 2 '-azo two
Oxime) one or more in salt, azodiisobutyronitrile or azo-bis-isobutyrate hydrochloride.
7. the preparation method of pH stimuli responsive types inorganic nano-particle/polymer combination drug carrier described in claim 1, its
It is characterised by：Inorganic nano-particle, function monomer, the crosslinking agent of pH stimuli responsives and initiator are dissolved according to dosage is calculated
In solvent, 1~5h is reacted under 70~130 DEG C of stirrings, is centrifuged, drying, obtains pH stimuli responsive types inorganic nano-particle/polymerization
Thing combination drug carrier, the mass ratio of the crosslinking agent of pH stimuli responsives and function monomer is 10%~90% in the raw material, is drawn
The amount for sending out agent is the 1%~5% of function monomer quality, and the dosage of inorganic nano-particle is 0.1~1 times of function monomer dosage.
8. the application of pH stimuli responsive types inorganic nano-particle described in claim 1/polymer combination drug carrier, its feature
It is：For the pharmaceutical carrier in control of agricultural pest.
9. application according to claim 8, it is characterized in that：The drug molecule that can be loaded in the pharmaceutical carrier is organic
Phosphorus, carbamates, organic nitrogen, pyrethroid, organochlorine class, organic fluoride class, botanical pesticide, microorganism
One or more in insecticide, insect growth regulator, IGR, insect behaviour regulator, plant hormone, particularly trans- 2- hexenoic acids
(HE), heteroauxin (IAA), d ichlorbenzuron, the one or more in tebufenozide medicine.
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| CN109316606A (en) * | 2018-10-25 | 2019-02-12 | 华南理工大学 | A kind of preparation method of multistage pH response mesoporous silicon oxide composite nanoparticle |
| CN109805021A (en) * | 2019-02-11 | 2019-05-28 | 中南大学 | A kind of nano pesticide and its preparation method and application of pH regulation |
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