CN104987513A - Preparing method for sugar responsive magnetic hybridization nano particles - Google Patents
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Abstract
The invention relates to a preparing method for sugar responsive magnetic hybridization nano particles. Surface amino-functionalization ferroferric oxide nano particles are obtained through the reaction of ferroferric oxide nano particles and 3-aminopropyl trimethoxysilane; the surface amino-functionalization ferroferric oxide nano particles are made to react with 2-bromopropionyl bromide, and bromo-functionalization ferroferric oxide nano particles are obtained. The bromo-functionalization ferroferric oxide nano particles are used for initiating the atom transfer radical polymerization of monomer (2-phenylboronic acid ester-1,3-dioxane-5-ethyl) acrylic ester, and ferroferric oxide nano hybridization particles with the surfaces grafted with poly-(2-phenylboronic acid ester-1,3-dioxane-5-ethyl) acrylic ester are obtained. The ferroferric oxide nano hybridization particles are made to react with sodium azide, azide-functionalization ferroferric oxide nano hybridization particles are obtained, the click reaction with alkynyl-terminated methoxy polyethylene glycol is further carried out, and the magnetic hybridization nano particles with the surfaces grafted with PPBDEMA and polyethylene glycol monomethyl ether segmented copolymers are obtained. According to the preparing method, sugar responsiveness is achieved, the sugar responsive magnetic hybridization nano particles can be stably dispersed in water, and wide application in the fields of intelligent sensors, insulin controlled release carriers and the like is achieved.
Description
Technical field
The invention belongs to intelligent material and field of nanometer material technology, be specifically related to a kind of preparation method of magnetic hybrid nanoparticle of sugar response.
Background technology
Ferriferrous oxide nano-particle is owing to having the features such as nontoxic, stable, superparamagnetic and being subject to extensive concern.They can by finishing and modification, be endowed the multiple reactive functional group in surface, as hydroxyl, carboxyl, amino, aldehyde radical etc., thus improve dispersiveness or the consistency of nanoparticle, be combined with enzyme, cell, medicine isoreactivity material by the mode of absorption or covalent bonding.In addition, due to the superparamagnetism of ferriferrous oxide nano-particle, can carry out leading or being separated under the effect of externally-applied magnetic field.Thus at biotechnology, catalysis, separation and medical field, as immunoassay, immobilized enzyme, DNA fix, target administration, cell/albumen sepn, tumor thermotherapy, magnetic resonance radiography etc.As at its surface grafting functional polymer, and during for pharmaceutical carrier, medicine-feeding part can be controlled easily, be that medicine concentrates on targeting moiety, improve drug availability and reduce the damage and fracture of medicine normal tissue.And after carrier completes drug release, can be separated by externally-applied magnetic field, excrete fast.
Intelligence organic materials obtains extensive concern in recent years, these materials can stimulate to external world, as temperature, pH value, light, sugar, ionic strength, carbonic acid gas, the change such as ultrasonic respond, be all widely used in nanosecond science and technology, biomedicine, intelligent material field.Wherein, sugar response type polymer be recently grow up and obtain pay attention to smart material, they can combine with glycan molecule (as glucose), realize the conversion of polymer segment from hydrophobic to hydrophilic, are conducive to the insulin molecule of load to carry out Co ntrolled release, (the Yuan Yao such as effective treatment diabetes, Liyuan Zhao, Junjiao Yang and Jing Yang, Biomacromolecules 2012,13,1837-1844).Therefore, the copolymer material containing sugared responsive polymer is incorporated into ferroferric oxide magnetic nano-particles surface by in-situ polymerization, the magnetic hybrid nanoparticle of sugar response can be prepared.In the present invention, we are by in-situ polymerization and click chemistry method, prepare the amphipathic magnetic hybrid nanoparticle of sugared responsiveness.They can stable dispersion in aqueous, can to the Regular Insulin Co ntrolled release of load.
Summary of the invention
The object of the present invention is to provide a kind of preparation method of magnetic hybrid nanoparticle of sugar response.
The object of the invention is ferriferrous oxide nano-particle and 3-TSL 8330 to react, obtain the ferriferrous oxide nano-particle of surface amino groups functionalization; Again with amino functional ferriferrous oxide nano-particle and 2-bromine isobutyryl bromine reaction, obtain the ferriferrous oxide nano-particle of bromo functionalization.With the ferriferrous oxide nano-particle of bromo functionalization for initiator trigger monomer (2-borate ester-1,3-dioxane-5-ethyl) atom transfer radical polymerization of acrylate (PBDEMA), obtain the ferriferrous oxide nano hybrid particle that surface grafting has poly-(2-borate ester-1,3-dioxane-5-ethyl) acrylate (PPBDEMA).By ferriferrous oxide nano hybrid particle and reaction of sodium azide, obtain the ferriferrous oxide nano hybrid particle of azide functionalization.Carry out click-reaction with the poly glycol monomethyl ether of alkynyl end-blocking further again, obtain the magnetic hybrid nanoparticle of surface grafting PPBDEMA and poly glycol monomethyl ether (mPEG) segmented copolymer.
Magnetic hybrid nanoparticle of the sugar response that the present invention proposes and preparation method thereof, concrete steps are as follows:
(1) ferriferrous oxide nano-particle is scattered in solvent orange 2 A, add the coupling agent 3-TSL 8330 of ferriferrous oxide nano-particle quality 0.5 ~ 3 times, react 12 ~ 48 hours 40 ~ 80 DEG C time, centrifugal, washing, dry, obtain the ferriferrous oxide nano-particle of surface amino groups functionalization;
(2) ferriferrous oxide nano-particle of surface amino groups functionalization step (1) obtained is dispersed in solvent B, add the acid binding agent C of the ferriferrous oxide nano-particle quality 1 ~ 4 times of amino functional, the 2-bromine isobutyl acylbromide of the ferriferrous oxide nano-particle quality 1 ~ 4 times of amino functional is instilled at 0 ~ 5 DEG C, then react 24 ~ 48 hours under 10 ~ 30 DEG C and argon shield, obtain the ferriferrous oxide nano-particle of surperficial bromo functionalization;
(3) ferriferrous oxide nano-particle of the bromo functionalization obtained with step (2) is for initiator, add solvent D and catalyst system E, (the 2-borate ester-1 of the ferriferrous oxide nano-particle quality 5 ~ 20 times of bromo functionalization is caused 70 ~ 120 DEG C time, 3-dioxane-5-ethyl) atom transfer radical polymerization (ATRP) of acrylate (PBDEMA) reacts 30 ~ 60 hours, precipitate further by precipitation agent F, obtain poly-(the 2-borate ester-1 of surface grafting, 3-dioxane-5-ethyl) ferriferrous oxide nano-particle of acrylate,
(4) surface grafting step (3) obtained gathers (2-borate ester-1,3-dioxane-5-ethyl) ferriferrous oxide nano-particle of acrylate is scattered in solvent G, add poly-(the 2-borate ester-1 of surface grafting, 3-dioxane-5-ethyl) sodiumazide of ferriferrous oxide nano-particle quality 10 ~ 50 times of acrylate, react 24 ~ 72 hours 10 ~ 30 DEG C time, further filtration, centrifugal, washing, dry, obtain the Z 250 hybridized nanometer particle of azide functionalization;
(5) azide functionalization Z 250 hybridized nanometer particle dispersion step (4) obtained is in solvent H, and add the alkynyl poly glycol monomethyl ether of azide functionalization Z 250 hybridized nanometer particle mass 1 ~ 5 times, react 24 ~ 72 hours 50 ~ 80 DEG C time, further by dialysis, lyophilize, obtain the magnetic hybrid nanoparticle of sugar response.
In the present invention, described solvent orange 2 A is one or more in toluene, DMF or N, N-diethylformamide.
In the present invention, described solvent B is one or more in methylene dichloride, chloroform, tetrahydrofuran (THF) or toluene.
In the present invention, described acid binding agent C is one or more in diethylamine, triethylamine, pyridine or sodium acetate.
In the present invention, described solvent D is one or more in tetrahydrofuran (THF), methyl-phenoxide, DMF or N, N-diethylformamide.
In the present invention, described catalyst system E is one or more in cuprous chloride/dipyridyl, cuprous bromide/dipyridyl, cuprous chloride/pentamethyl-diethylenetriamine, cuprous bromide/pentamethyl-diethylenetriamine, cuprous chloride/hexamethyl Triethylenetetramine (TETA) or cuprous bromide/hexamethyl Triethylenetetramine (TETA).
In the present invention, described precipitation agent F is one or more of normal hexane, hexanaphthene, sherwood oil or ether.
In the present invention, described solvent G is one or both in DMF or N, N-diethylformamide.
In the present invention, described solvent H is one or more in toluene, methyl-phenoxide, DMF or N, N-diethylformamide
Beneficial effect of the present invention is: raw material sources are extensive, and monomer used, ferriferrous oxide nano-particle, poly glycol monomethyl ether, solvent, catalyzer, precipitation agent etc. all can suitability for industrialized production, and synthetic method is simple.The surface grafting PPBDEMA of preparation and the ferriferrous oxide nano-particle of poly glycol monomethyl ether segmented copolymer have superparamagnetism, sugared responsiveness and amphipathic.This hybridized nanometer particle has a wide range of applications in fields such as nano-medicament carrier, Magneto separate system, biological intelligence switch, biosensors.
Accompanying drawing explanation
Fig. 1 is that the structure of the surface grafting PPBDEMA of embodiment 1 preparation and the ferriferrous oxide nano-particle of poly glycol monomethyl ether segmented copolymer responds schematic diagram with sugar.
Embodiment
Following examples further illustrate of the present invention, instead of limit the scope of the invention.
Embodiment 1
(1) 0.5 gram of ferriferrous oxide nano-particle is scattered in toluene (100 milliliters), add 0.25 gram of 3-TSL 8330,48 hours are reacted 40 DEG C time, centrifugal, washing, dry, obtain the ferriferrous oxide nano-particle of surface amino groups functionalization.
(2) ferriferrous oxide nano-particle (0.4 gram) of surface amino groups functionalization step (1) obtained is dispersed in 20 milliliters of methylene dichloride; add 0.4 gram of triethylamine; 0.4 gram of 2-bromine isobutyl acylbromide is instilled at 0 DEG C; then react 48 hours under 10 DEG C and argon shield, obtain the ferriferrous oxide nano-particle of surperficial bromo functionalization.
(3) the bromo functionalization ferriferrous oxide nano-particle (0.3 gram) step (2) obtained is initiator, methyl-phenoxide is solvent, cuprous chloride/dipyridyl is catalyst system, 1.5 grams of (2-borate esters-1 are caused 70 DEG C time, 3-dioxane-5-ethyl) atom transfer radical polymerization (ATRP) of acrylate (PBDEMA) reacts 30 hours, precipitate further by normal hexane, obtain the ferriferrous oxide nano-particle of poly-(2-borate ester-1, the 3-dioxane-5-ethyl) acrylate of surface grafting
(4) surface grafting step (3) obtained gathers (2-borate ester-1,3-dioxane-5-ethyl) ferriferrous oxide nano-particle (0.7 gram) of acrylate is scattered in N, in dinethylformamide, add 7 grams of sodiumazide, 72 hours are reacted 10 DEG C time, further filtration, centrifugal, washing, dry, obtain the Z 250 hybridized nanometer particle of azide functionalization.
(5) the azide functionalization Z 250 hybridized nanometer particle (0.5 gram) step (4) obtained is scattered in toluene, and add 0.5 gram of alkynyl poly glycol monomethyl ether, 72 hours are reacted 50 DEG C time, further by dialysis, lyophilize, obtain the magnetic hybrid nanoparticle of sugar response.
The structure of the ferriferrous oxide nano-particle of surface grafting PPBDEMA and poly glycol monomethyl ether segmented copolymer responds schematic diagram as shown in Figure 1 with sugar.
Embodiment 2
(1) 0.5 gram of ferriferrous oxide nano-particle is scattered in N, in dinethylformamide (70 milliliters), add 0.5 gram of 3-TSL 8330,60 DEG C time, react 30 hours, centrifugal, washing, dry, obtain the ferriferrous oxide nano-particle of surface amino groups functionalization.
(2) ferriferrous oxide nano-particle (0.4 gram) of surface amino groups functionalization step (1) obtained is dispersed in 20 milliliters of chloroforms; add 0.8 gram of diethylamine; 0.8 gram of 2-bromine isobutyl acylbromide is instilled at 5 DEG C; then react 40 hours under 15 DEG C and argon shield, obtain the ferriferrous oxide nano-particle of surperficial bromo functionalization.
(3) the bromo functionalization ferriferrous oxide nano-particle (0.3 gram) step (2) obtained is initiator, N, dinethylformamide is solvent, cuprous bromide/dipyridyl is catalyst system, 2 grams of (2-borate esters-1 are caused 90 DEG C time, 3-dioxane-5-ethyl) atom transfer radical polymerization (ATRP) of acrylate (PBDEMA) reacts 40 hours, precipitate further by hexanaphthene, obtain the ferriferrous oxide nano-particle of poly-(2-borate ester-1, the 3-dioxane-5-ethyl) acrylate of surface grafting
(4) surface grafting step (3) obtained gathers (2-borate ester-1,3-dioxane-5-ethyl) ferriferrous oxide nano-particle (0.7 gram) of acrylate is scattered in N, in N-diethylformamide, add 14 grams of sodiumazide, 60 hours are reacted 20 DEG C time, further filtration, centrifugal, washing, dry, obtain the Z 250 hybridized nanometer particle of azide functionalization.
(5) the azide functionalization Z 250 hybridized nanometer particle (0.5 gram) step (4) obtained is scattered in toluene, and add 1 gram of alkynyl poly glycol monomethyl ether, 60 hours are reacted 60 DEG C time, further by dialysis, lyophilize, obtain the magnetic hybrid nanoparticle of sugar response.
Embodiment 3
(1) 0.5 gram of ferriferrous oxide nano-particle is scattered in N, in N-diethylformamide (60 milliliters), add 1.5 grams of 3-TSL 8330,60 DEG C time, react 30 hours, centrifugal, washing, dry, obtain the ferriferrous oxide nano-particle of surface amino groups functionalization.
(2) ferriferrous oxide nano-particle (0.4 gram) of surface amino groups functionalization step (1) obtained is dispersed in 15 milliliters of tetrahydrofuran (THF)s, adds 1.2 grams of pyridines, 2
dEG Clower instillation 1.6 grams of 2-bromine isobutyl acylbromides, then react 24 hours, obtain the ferriferrous oxide nano-particle of surperficial bromo functionalization under 30 DEG C and argon shield.
(3) the bromo functionalization ferriferrous oxide nano-particle (0.3 gram) step (2) obtained is initiator, N, dinethylformamide is solvent, cuprous chloride/pentamethyl-diethylenetriamine is catalyst system, 4.5 grams of (2-borate esters-1 are caused 100 DEG C time, 3-dioxane-5-ethyl) atom transfer radical polymerization (ATRP) of acrylate (PBDEMA) reacts 45 hours, precipitate further by sherwood oil, obtain poly-(the 2-borate ester-1 of surface grafting, 3-dioxane-5-ethyl) ferriferrous oxide nano-particle of acrylate
(4) surface grafting step (3) obtained gathers (2-borate ester-1,3-dioxane-5-ethyl) ferriferrous oxide nano-particle (0.5 gram) of acrylate is scattered in N, in dinethylformamide, add 15 grams of sodiumazide, 40 hours are reacted 10 DEG C time, further filtration, centrifugal, washing, dry, obtain the Z 250 hybridized nanometer particle of azide functionalization.
(5) the azide functionalization Z 250 hybridized nanometer particle (0.3 gram) step (4) obtained is scattered in N, in dinethylformamide, and add 1.3 grams of alkynyl poly glycol monomethyl ethers, 60 hours are reacted 70 DEG C time, further by dialysis, lyophilize, obtain the magnetic hybrid nanoparticle of sugar response.
Embodiment 4
(1) 0.5 gram of ferriferrous oxide nano-particle is scattered in toluene (50 milliliters), add 1.5 grams of 3-TSL 8330,12 hours are reacted 80 DEG C time, centrifugal, washing, dry, obtain the ferriferrous oxide nano-particle of surface amino groups functionalization.
(2) ferriferrous oxide nano-particle (0.4 gram) of surface amino groups functionalization step (1) obtained is dispersed in toluene (30 milliliters); add 1.6 grams of triethylamines; 1.2 grams of 2-bromine isobutyl acylbromides are instilled at 0 DEG C; then react 48 hours under 30 DEG C and argon shield, obtain the ferriferrous oxide nano-particle of surperficial bromo functionalization.
(3) the bromo functionalization ferriferrous oxide nano-particle (0.3 gram) step (2) obtained is initiator, N, dinethylformamide is solvent, cuprous bromide/pentamethyl-diethylenetriamine is catalyst system, 6 grams of (2-borate esters-1 are caused 120 DEG C time, 3-dioxane-5-ethyl) atom transfer radical polymerization (ATRP) of acrylate (PBDEMA) reacts 60 hours, precipitate further by normal hexane, obtain poly-(the 2-borate ester-1 of surface grafting, 3-dioxane-5-ethyl) ferriferrous oxide nano-particle of acrylate
(4) surface grafting step (3) obtained gathers (2-borate ester-1,3-dioxane-5-ethyl) ferriferrous oxide nano-particle (0.5 gram) of acrylate is scattered in N, in dinethylformamide, add 25 grams, 24 hours are reacted 10 DEG C time, further filtration, centrifugal, washing, dry, obtain the Z 250 hybridized nanometer particle of azide functionalization.
(5) the azide functionalization Z 250 hybridized nanometer particle (0.4 gram) step (4) obtained is scattered in N, in dinethylformamide, and add 2 grams of alkynyl poly glycol monomethyl ethers, 24 hours are reacted 80 DEG C time, further by dialysis, lyophilize, obtain the magnetic hybrid nanoparticle of sugar response.
Embodiment 5
(1) 0.5 gram of ferriferrous oxide nano-particle is scattered in N, in dinethylformamide (60 milliliters), add 1.5 grams of 3-TSL 8330,40 DEG C time, react 48 hours, centrifugal, washing, dry, obtain the ferriferrous oxide nano-particle of surface amino groups functionalization.
(2) ferriferrous oxide nano-particle (0.4 gram) of surface amino groups functionalization step (1) obtained is dispersed in N; in dinethylformamide (30 milliliters); add 1.6 grams of triethylamines; 0.4 gram of 2-bromine isobutyl acylbromide is instilled at 5 DEG C; then react 48 hours under 10 DEG C and argon shield, obtain the ferriferrous oxide nano-particle of surperficial bromo functionalization.
(3) the bromo functionalization ferriferrous oxide nano-particle (0.3 gram) step (2) obtained is initiator, tetrahydrofuran (THF) is solvent, cuprous bromide/hexamethyl Triethylenetetramine (TETA) is catalyst system, 6 grams of (2-borate esters-1 are caused 120 DEG C time, 3-dioxane-5-ethyl) atom transfer radical polymerization (ATRP) of acrylate (PBDEMA) reacts 60 hours, precipitate further by hexanaphthene, obtain the ferriferrous oxide nano-particle of poly-(2-borate ester-1, the 3-dioxane-5-ethyl) acrylate of surface grafting
(4) surface grafting step (3) obtained gathers (2-borate ester-1,3-dioxane-5-ethyl) ferriferrous oxide nano-particle (0.5 gram) of acrylate is scattered in N, in dinethylformamide, add 20 grams of sodiumazide, 40 hours are reacted 30 DEG C time, further filtration, centrifugal, washing, dry, obtain the Z 250 hybridized nanometer particle of azide functionalization.
(5) the azide functionalization Z 250 hybridized nanometer particle (0.4 gram) step (4) obtained is scattered in N, in dinethylformamide, and add 1.6 grams of alkynyl poly glycol monomethyl ethers, 30 hours are reacted 80 DEG C time, further by dialysis, lyophilize, obtain the magnetic hybrid nanoparticle of sugar response.
Claims (9)
1. a preparation method for the magnetic hybrid nanoparticle of sugar response, is characterized in that concrete steps are as follows:
(1) ferriferrous oxide nano-particle is scattered in solvent orange 2 A, add the coupling agent 3-TSL 8330 of ferriferrous oxide nano-particle quality 0.5 ~ 3 times, react 12 ~ 48 hours 40 ~ 80 DEG C time, centrifugal, washing, dry, obtain the ferriferrous oxide nano-particle of surface amino groups functionalization;
(2) ferriferrous oxide nano-particle of surface amino groups functionalization step (1) obtained is dispersed in solvent B, add the acid binding agent C of the ferriferrous oxide nano-particle quality 1 ~ 4 times of amino functional, the 2-bromine isobutyl acylbromide of the ferriferrous oxide nano-particle quality 1 ~ 4 times of amino functional is instilled at 0 ~ 5 DEG C, then react 24 ~ 48 hours under 10 ~ 30 DEG C and argon shield, obtain the ferriferrous oxide nano-particle of surperficial bromo functionalization;
(3) ferriferrous oxide nano-particle of the bromo functionalization obtained with step (2) is for initiator, add solvent D and catalyst system E, (the 2-borate ester-1 of the ferriferrous oxide nano-particle quality 5 ~ 20 times of bromo functionalization is caused 70 ~ 120 DEG C time, 3-dioxane-5-ethyl) atom transfer radical polymerization (ATRP) of acrylate (PBDEMA) reacts 30 ~ 60 hours, precipitate further by precipitation agent F, obtain poly-(the 2-borate ester-1 of surface grafting, 3-dioxane-5-ethyl) ferriferrous oxide nano-particle of acrylate,
(4) surface grafting step (3) obtained gathers (2-borate ester-1,3-dioxane-5-ethyl) ferriferrous oxide nano-particle of acrylate is scattered in solvent G, add poly-(the 2-borate ester-1 of surface grafting, 3-dioxane-5-ethyl) sodiumazide of ferriferrous oxide nano-particle quality 10 ~ 50 times of acrylate, react 24 ~ 72 hours 10 ~ 30 DEG C time, further filtration, centrifugal, washing, dry, obtain the Z 250 hybridized nanometer particle of azide functionalization;
(5) azide functionalization Z 250 hybridized nanometer particle dispersion step (4) obtained is in solvent H, and add the alkynyl poly glycol monomethyl ether of azide functionalization Z 250 hybridized nanometer particle mass 1 ~ 5 times, react 24 ~ 72 hours 50 ~ 80 DEG C time, further by dialysis, lyophilize, obtain the magnetic hybrid nanoparticle of sugar response.
2. the preparation method of magnetic hybrid nanoparticle of sugar response according to claim 1, is characterized in that described solvent orange 2 A is one or more in toluene, DMF or N, N-diethylformamide.
3. the preparation method of magnetic hybrid nanoparticle of sugar response according to claim 1, is characterized in that described solvent B is one or more in methylene dichloride, chloroform, tetrahydrofuran (THF) or toluene.
4. the preparation method of magnetic hybrid nanoparticle of sugar response according to claim 1, is characterized in that described acid binding agent C is one or more in diethylamine, triethylamine, pyridine or sodium acetate.
5. the preparation method of magnetic hybrid nanoparticle of sugar response according to claim 1, is characterized in that described solvent D is one or more in tetrahydrofuran (THF), methyl-phenoxide, DMF or N, N-diethylformamide.
6. the preparation method of magnetic hybrid nanoparticle of sugar response according to claim 1, is characterized in that described catalyst system E is one or more in cuprous chloride/dipyridyl, cuprous bromide/dipyridyl, cuprous chloride/pentamethyl-diethylenetriamine, cuprous bromide/pentamethyl-diethylenetriamine, cuprous chloride/hexamethyl Triethylenetetramine (TETA) or cuprous bromide/hexamethyl Triethylenetetramine (TETA).
7. the preparation method of magnetic hybrid nanoparticle of sugar response according to claim 1, is characterized in that described precipitation agent F is one or more of normal hexane, hexanaphthene, sherwood oil or ether.
8. the preparation method of magnetic hybrid nanoparticle of sugar response according to claim 1, is characterized in that described solvent G is one or both in DMF or N, N-diethylformamide.
9. the preparation method of magnetic hybrid nanoparticle of sugar response according to claim 1, is characterized in that described solvent H is one or more in toluene, methyl-phenoxide, DMF or N, N-diethylformamide.
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| CN105713134A (en) * | 2016-04-21 | 2016-06-29 | 同济大学 | Preparation method of acylhydrazone-bond-based dynamic reversible self-repair magnetic field/temperature-responsive intelligent hydrogel |
| CN106832245A (en) * | 2017-01-23 | 2017-06-13 | 同济大学 | A kind of preparation method of the degradable films of sugared response |
| CN106832158A (en) * | 2017-02-18 | 2017-06-13 | 湖南工业大学 | A kind of pH responses dynamic shell crosslinked polymers nano-particle and preparation method thereof |
| CN110614011A (en) * | 2019-09-25 | 2019-12-27 | 湖北大学 | Functional carbon dioxide adsorbent with temperature and magnetic response and preparation method thereof |
| CN113092784A (en) * | 2021-04-06 | 2021-07-09 | 中国科学院深圳先进技术研究院 | Functionalized magnetic bead and bioorthogonal chemistry macromolecule one-step capturing method adopting same |
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| CN105713134A (en) * | 2016-04-21 | 2016-06-29 | 同济大学 | Preparation method of acylhydrazone-bond-based dynamic reversible self-repair magnetic field/temperature-responsive intelligent hydrogel |
| CN105713134B (en) * | 2016-04-21 | 2017-07-07 | 同济大学 | A kind of magnetic field based on acylhydrazone key dynamic reversible selfreparing, the preparation method of the double response type intelligent aqueous gels of temperature |
| CN106832245A (en) * | 2017-01-23 | 2017-06-13 | 同济大学 | A kind of preparation method of the degradable films of sugared response |
| CN106832245B (en) * | 2017-01-23 | 2018-11-13 | 同济大学 | A kind of preparation method of the degradable films of sugar response |
| CN106832158A (en) * | 2017-02-18 | 2017-06-13 | 湖南工业大学 | A kind of pH responses dynamic shell crosslinked polymers nano-particle and preparation method thereof |
| CN106832158B (en) * | 2017-02-18 | 2021-06-08 | 湖南工业大学 | PH-responsive dynamic shell cross-linked polymer nano-particle and preparation method thereof |
| CN110614011A (en) * | 2019-09-25 | 2019-12-27 | 湖北大学 | Functional carbon dioxide adsorbent with temperature and magnetic response and preparation method thereof |
| CN113092784A (en) * | 2021-04-06 | 2021-07-09 | 中国科学院深圳先进技术研究院 | Functionalized magnetic bead and bioorthogonal chemistry macromolecule one-step capturing method adopting same |
| CN113092784B (en) * | 2021-04-06 | 2023-09-08 | 中国科学院深圳先进技术研究院 | One-step capturing method and application of macromolecules by adopting functionalized magnetic beads to carry out bio-orthogonal chemistry |
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