CN104310409A - Assembling and disassembling method of functional polymer on surface of nano mesoporous carbon dioxide - Google Patents
Assembling and disassembling method of functional polymer on surface of nano mesoporous carbon dioxide Download PDFInfo
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- CN104310409A CN104310409A CN201410538526.5A CN201410538526A CN104310409A CN 104310409 A CN104310409 A CN 104310409A CN 201410538526 A CN201410538526 A CN 201410538526A CN 104310409 A CN104310409 A CN 104310409A
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- silicon dioxide
- functionalized polymer
- nano silicon
- mesoporous nano
- pyrocatechol
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Abstract
The invention relates to an assembling and disassembling method of a functional polymer on the surface of nano mesoporous carbon dioxide and belongs to the field of nano materials. The method comprises the following steps: by using water as a solvent, preparing a nano mesoporous carbon dioxide aqueous solution, a catechol functional polymer aqueous solution and a metal ion aqueous solution; sequentially adding the catechol functional polymer aqueous solution and the metal ion aqueous solution into the nano mesoporous carbon dioxide aqueous solution, and after oscillation, coordinating the catechol functional polymer and the metal ions, and assembling on the surface of nano mesoporous carbon dioxide to obtain the nano mesoporous carbon dioxide aqueous solution wrapped by the catechol functional polymer; carrying out centrifugal separation, re-dispersing the nano mesoporous carbon dioxide wrapped by the catechol functional polymer in water; and adding an acid solution into the nano mesoporous carbon dioxide aqueous solution wrapped by the catechol functional polymer to adjust the pH to 5-6 so as to disassemble the catechol functional polymer on the surface of the nano mesoporous carbon dioxide.
Description
Technical field
The invention belongs to field of nanometer material technology, particularly the assembling of a kind of pyrocatechol functionalized polymer on silicon dioxide nanosphere surface and de-assembly behavior.
Background technology
From the people such as Kresge in 1992 the reported first ordered mesoporous silicon-dioxide material of a kind of MCM-41 by name on Nature magazine, the research of mesoporous silicon oxide becomes rapidly international focus.The appearance of ordered meso-porous silicon oxide is the once leap in molecular sieve and porous mass development history.
Meso-porous nano silicon-dioxide can form hybrid inorganic-organic materials with organic or macromolecular material, so both can play the small-size effect of himself, surface and interface effect, quantum size effect.Meanwhile, different modifying method can give again material other performances diversified.Thus have a wide range of applications in catalysis, drug delivery and Co ntrolled release, gene transfection, heavy metal ion and biomolecule detection etc.
In drug delivery and Co ntrolled release field, mesoporous silicon oxide has development space widely as drug molecule carrier, but how effectively encapsulates the duct of mesoporous silicon oxide and deblocking is the focus of research at present.And be mainly chemical modification for the method for mesoporous silicon oxide finishing at present, namely by chemical bond, some responsive polymer is modified mesoporous silicon surface.(the Chiyoung Park such as Chiyoung Park, Kyoungho Oh et al.Angew.Chem.Int.Ed.2007,46,1455 – 1457) utilize APTES first to carry out surface modification to mesoporous silicon dioxide nano particle, make its surface with amino, and then recycling contains the polymkeric substance of end carboxyl and amido modified meso-porous titanium dioxide pasc reaction, at mesoporous silicon oxide finishing one deck responsive polymer, the drug molecule in controllable release mesoporous silicon oxide duct.(the Huan Meng such as Zink, Min Xue, Tian Xia et al.J.Am.Chem.Soc.2010,132 (36), 12690 – 12697) first with the MBI finishing mesoporous silicon oxide containing arylamine, being nested in by cyclodextrin molecular on MBI adds a cover on mesoporous hole again, and encapsulated drug molecule forms the drug delivery system with pH responsiveness.
To sum up, the method at present for mesoporous silicon oxide finishing is all too loaded down with trivial details, and a kind of polymkeric substance that can realize quickly and easily has no report in the method for the assembling of mesoporous silicon dioxide nano microsphere surface and de-assembly.
Summary of the invention
The object of the present invention is to provide a kind of functionalized polymer in mesoporous nano silicon dioxide surface-assembled and de-assembly method.
Described functionalized polymer is pyrocatechol functionalized polymer, described pyrocatechol functionalized polymer is the polymkeric substance containing two hydroxyl phenol structure, be designated as PEGMA-co-PMAAPHBA, obtain by modifying through 3,4-Dihydroxy benzaldehyde after N-(4 aminophenyl)-Methacrylamide and polyethylene glycol methacrylate-styrene polymer random copolymerization.
The preparation method of described functionalized polymer is with reference to Chinese patent 201410032517.9, and concrete steps are as follows:
(1) suitable solvent is selected, preparation monomer solution, by metering than adding initiator, the solution of N-(4 aminophenyl)-Methacrylamide and polyethylene glycol methacrylate-styrene polymer and initiator is placed in freezing degassed and lower 65 ~ 80 DEG C of reaction 24h of sealing after being filled with argon gas of reaction vessel, liquid nitrogen freezing 2min stopped reaction after polymerization;
(2) dissolving precipitated method is adopted to remove unreacted monomer, by precipitation agent precipitation after solubilizing agent dilution, dry.
(3) polymkeric substance obtained in step (2) is got 0.2 ~ 1g to be dissolved in 2 ~ 6ml methylene dichloride and to be made into solution A, 0.1 ~ 1g3,4-Dihydroxy benzaldehyde is dissolved in 0.5 ~ 2mL methanol solution and is made into B solution;
(4) by A, B two solution N
2after bubbling 15min, B solution is injected solution A and reacts 12h, reaction terminates rear washed with dichloromethane, suction filtration, drying, obtains target substance.
In step (1), described solvent can be tetrahydrofuran (THF), Isosorbide-5-Nitrae-dioxane etc., preferred tetrahydrofuran (THF) (THF); Described monomer concentration scope is 0.3 ~ 1.0mol/L; The scope of the mol ratio of described monomer polyethylene glycol methacrylate-styrene polymer and N-(4 aminophenyl)-Methacrylamide is 1 ~ 4; Described initiator is the compound that can add thermogenesis free radical and cause polyethylene glycol methacrylate-styrene polymer and the polymerization of N-(4 aminophenyl)-Methacrylamide, preferred Diisopropyl azodicarboxylate (AIBN); The scope of the mol ratio of described monomer and initiator is 50 ~ 100.
In step (2), described precipitation agent can be selected from the one in normal hexane, sherwood oil, methyl alcohol etc., preferred normal hexane.
Described functionalized polymer, in mesoporous nano silicon dioxide surface-assembled and de-assembly method, comprises the following steps:
(1) select water as solvent, the preparation of nano mesoporous silicon oxide aqueous solution, the pyrocatechol functionalized polymer aqueous solution, aqueous metallic ions;
(2) the pyrocatechol functionalized polymer aqueous solution, aqueous metallic ions are added in the mesoporous nano silicon dioxide aqueous solution successively, pyrocatechol functionalized polymer and metallic ion coordination after concussion, realize assembling on mesoporous nano silicon dioxide surface, obtain the mesoporous nano silicon dioxide aqueous solution of coated pyrocatechol functionalized polymer;
(3) the mesoporous nano silicon dioxide aqueous solution centrifugation of coated pyrocatechol functionalized polymer step (2) obtained, the mesoporous nano silicon dioxide of coated pyrocatechol functionalized polymer is dispersed in water again, in the mesoporous nano silicon dioxide aqueous solution of coated pyrocatechol functionalized polymer, add acidic solution regulates pH to 5 ~ 6, and pyrocatechol functionalized polymer can be made in meso-porous titanium dioxide silicon face generation de-assembly.
In step (1), described mesoporous nano silicon dioxide can be prepared as follows:
A. the cats product of 0.3 ~ 0.9g is joined in 40 ~ 60mL PBS buffered soln, at 95 DEG C, stir 30min;
B. 0.5 ~ 1.0g tetraethyl orthosilicate (TEOS) is added drop-wise to the solution in step a, stirring reaction 6 ~ 10h at 95 DEG C;
C. end is reacted, centrifugal, by throw out drying treatment 1.5h under the condition of 50 DEG C, be then calcination processing 6h under the condition of 550 DEG C in temperature, obtain mesoporous nano silicon dioxide;
In step (1), the mass concentration of described mesoporous nano silicon dioxide solution can be 2 ~ 10mg/mL, and the mass concentration of polymers soln can be 2 ~ 10mg/mL, and the mass concentration of metal ion solution can be 10 ~ 20mg/mL; Described metal ion can be containing Fe
3+, Zn
2+compound, described containing Fe
3+compound can be selected from FeCl
3or Fe
2(SO
4)
3deng; Described containing Zn
2+compound can be selected from ZnCl
2or Zn (SO
4)
2deng; Preferred FeCl
3.
In step (2), the volume ratio of the described pyrocatechol functionalized polymer aqueous solution, aqueous metallic ions, the mesoporous nano silicon dioxide aqueous solution can be (0.5 ~ 2): (0.1 ~ 1): (1 ~ 2).
In step (3), described acidic solution can be selected from the one in hydrochloric acid soln, acetum, phosphoric acid solution etc.
The present invention utilizes a kind of polymkeric substance (PEGMA-co-PMAAPHBA) containing pyrocatechol structure to be coated on meso-porous titanium dioxide silicon face with metal ion-chelant self-assembly, forms effective encapsulation to mesoporous silicon oxide; And the two hydroxyl on pyrocatechol and the interaction of meso-porous titanium dioxide silicon face have pH responsiveness, de-assembly can be there is in lower pH (about 5.6) environment, be convenient to mesoporous silicon oxide release guest molecule.
Accompanying drawing explanation
Fig. 1 is the Flied emission transmission electron microscope (TEM) of the mesoporous nano silicon dioxide of not coated pyrocatechol functionalized polymer in embodiment 1;
Fig. 2 is the Flied emission transmission electron microscope (TEM) of pyrocatechol functionalized polymer after mesoporous nano silicon dioxide surface-assembled in embodiment 1;
Fig. 3 is the Flied emission transmission electron microscope (TEM) of pyrocatechol functionalized polymer after the de-assembly of mesoporous nano silicon dioxide surface in embodiment 1;
Fig. 4 is the change of size figure of pyrocatechol functionalized polymer after mesoporous nano silicon dioxide surface-assembled and de-assembly in embodiment 1.
Embodiment
Embodiment will the invention will be further described by reference to the accompanying drawings below.
Embodiment 1
The preparation of PEGMA-co-PMAAPHBA:
(1) taking N-(4 aminophenyl)-Methacrylamide 0.176g and polyethylene glycol methacrylate-styrene polymer 0.475g and initiator 10mg is dissolved in 1.5mL THF, solution is placed in freezing degassed and lower 65 ~ 80 DEG C of reaction 24h of sealing after being filled with argon gas of reaction vessel, liquid nitrogen freezing 2min stopped reaction after polymerization;
(2) by reacted solution 100mL normal hexane precipitation twice, drying.
(3) polymkeric substance obtained in step (2) is got 0.4g and be dissolved in wiring solution-forming A in 5mL methylene dichloride, 0.15g3,4-Dihydroxy benzaldehyde is dissolved in wiring solution-forming B in 1mL methanol solution;
(4) by A, B two solution N
2after bubbling 15min, B solution is injected solution A and reacts 12h, reaction terminates rear washed with dichloromethane, suction filtration, drying, obtains target substance.
The assembling of pyrocatechol functionalized polymer on mesoporous nano silicon dioxide surface and de-assembly:
1. prepare mesoporous nano silicon dioxide
(1) cats product of 0.5g is joined in 50mL PBS buffered soln, at 95 DEG C, stir 30min;
(2) 0.8g tetraethyl orthosilicate (TEOS) is slowly added drop-wise to the solution in step (1), stirring reaction 8h at 95 DEG C;
(3) reaction terminates, centrifugal, by throw out drying treatment 1.5h under the condition of 50 DEG C, is then calcination processing 6h under the condition of 550 DEG C in temperature, obtains mesoporous nano silicon dioxide.
2. prepare the mesoporous nano silicon dioxide aqueous solution, the pyrocatechol functionalized polymer aqueous solution of 5g/L, the FeCl of 20g/L of 5g/L
3the aqueous solution; By pyrocatechol functionalized polymer aqueous solution 2mL, aqueous metallic ions 1mL adds in the mesoporous nano silicon dioxide aqueous solution of 2mL successively, pyrocatechol functionalized polymer and metallic ion coordination after concussion, realize assembling on mesoporous nano silicon dioxide surface, obtain the mesoporous nano silicon dioxide aqueous solution of coated pyrocatechol functionalized polymer.
3. by the mesoporous nano silicon dioxide aqueous solution centrifugation of the coated pyrocatechol functionalized polymer in 2, the mesoporous nano silicon dioxide of the coated pyrocatechol functionalized polymer obtained is dispersed in water again, in the mesoporous nano silicon dioxide aqueous solution of the coated pyrocatechol functionalized polymer of 1mL, adds hydrochloric acid soln regulate pH can realize the de-assembly of pyrocatechol functionalized polymer on mesoporous nano silicon dioxide surface to 5.0.
In embodiment 1, the Flied emission transmission electron microscope (TEM) of the mesoporous nano silicon dioxide of not coated pyrocatechol functionalized polymer is see Fig. 1, the Flied emission transmission electron microscope (TEM) of pyrocatechol functionalized polymer after mesoporous nano silicon dioxide surface-assembled is see Fig. 2, the Flied emission transmission electron microscope (TEM) of pyrocatechol functionalized polymer after the de-assembly of mesoporous nano silicon dioxide surface is see Fig. 3, and the change of size figure of pyrocatechol functionalized polymer after mesoporous nano silicon dioxide surface-assembled and de-assembly is see Fig. 4.
Embodiment 2
1. with reference to polymer P EGMA-co-PMAAPHBA and the mesoporous nano silicon dioxide of embodiment 1 preparation.
2. prepare the mesoporous nano silicon dioxide aqueous solution, the pyrocatechol functionalized polymer aqueous solution of 5g/L, the FeCl of 20g/L of 5g/L
3the aqueous solution; By pyrocatechol functionalized polymer aqueous solution 1.5mL, aqueous metallic ions 0.5mL adds in the mesoporous nano silicon dioxide aqueous solution of 2mL successively, pyrocatechol functionalized polymer and metallic ion coordination after concussion, realize assembling on mesoporous nano silicon dioxide surface, obtain the mesoporous nano silicon dioxide aqueous solution of coated pyrocatechol functionalized polymer.
3. by the mesoporous nano silicon dioxide aqueous solution centrifugation of the coated pyrocatechol functionalized polymer in 2, the mesoporous nano silicon dioxide of the coated pyrocatechol functionalized polymer obtained is dispersed in water again, in the mesoporous nano silicon dioxide aqueous solution of the coated pyrocatechol functionalized polymer of 1mL, adds acetum regulate pH can realize the de-assembly of pyrocatechol functionalized polymer on mesoporous nano silicon dioxide surface to 5.5.
Embodiment 3
1. with reference to polymer P EGMA-co-PMAAPHBA and the mesoporous silicon oxide of embodiment 1 preparation.
2. prepare the mesoporous nano silicon dioxide aqueous solution, the pyrocatechol functionalized polymer aqueous solution of 5g/L, the FeCl of 20g/L of 5g/L
3the aqueous solution; By pyrocatechol functionalized polymer aqueous solution 1.5mL, aqueous metallic ions 0.4mL adds in the mesoporous nano silicon dioxide aqueous solution of 1.5mL successively, pyrocatechol functionalized polymer and metallic ion coordination after concussion, realize assembling on mesoporous nano silicon dioxide surface, obtain the mesoporous nano silicon dioxide aqueous solution of coated pyrocatechol functionalized polymer.
3. by the mesoporous nano silicon dioxide aqueous solution centrifugation of the coated pyrocatechol functionalized polymer in 2, the mesoporous nano silicon dioxide of the coated pyrocatechol functionalized polymer obtained is dispersed in water again, in the mesoporous nano silicon dioxide aqueous solution of the coated pyrocatechol functionalized polymer of 1mL, adds acetum regulate pH can realize the de-assembly of pyrocatechol functionalized polymer on mesoporous nano silicon dioxide surface to 6.0.
Claims (9)
1. functionalized polymer is in mesoporous nano silicon dioxide surface-assembled and de-assembly method, it is characterized in that described functionalized polymer is pyrocatechol functionalized polymer, described pyrocatechol functionalized polymer is the polymkeric substance containing two hydroxyl phenol structure, be designated as PEGMA ?co ?PMAAPHBA, be by after N ?(4 aminophenyl) ?Methacrylamide and polyethylene glycol methacrylate-styrene polymer random copolymerization through 3,4 ?Dihydroxy benzaldehydes modify obtain;
Described functionalized polymer, in mesoporous nano silicon dioxide surface-assembled and de-assembly method, comprises the following steps:
(1) select water as solvent, the preparation of nano mesoporous silicon oxide aqueous solution, the pyrocatechol functionalized polymer aqueous solution, aqueous metallic ions;
(2) the pyrocatechol functionalized polymer aqueous solution, aqueous metallic ions are added in the mesoporous nano silicon dioxide aqueous solution successively, pyrocatechol functionalized polymer and metallic ion coordination after concussion, realize assembling on mesoporous nano silicon dioxide surface, obtain the mesoporous nano silicon dioxide aqueous solution of coated pyrocatechol functionalized polymer;
(3) the mesoporous nano silicon dioxide aqueous solution centrifugation of coated pyrocatechol functionalized polymer step (2) obtained, the mesoporous nano silicon dioxide of coated pyrocatechol functionalized polymer is dispersed in water again, in the mesoporous nano silicon dioxide aqueous solution of coated pyrocatechol functionalized polymer, add acidic solution regulates pH to 5 ~ 6, and pyrocatechol functionalized polymer can be made in meso-porous titanium dioxide silicon face generation de-assembly.
2. functionalized polymer, in mesoporous nano silicon dioxide surface-assembled and de-assembly method, is characterized in that described mesoporous nano silicon dioxide is prepared as follows in step (1) as claimed in claim 1:
A. the cats product of 0.3 ~ 0.9g is joined in 40 ~ 60mL PBS buffered soln, at 95 DEG C, stir 30min;
B. 0.5 ~ 1.0g tetraethyl orthosilicate (TEOS) is added drop-wise to the solution in step a, stirring reaction 6 ~ 10h at 95 DEG C;
C. end is reacted, centrifugal, by throw out drying treatment 1.5h under the condition of 50 DEG C, be then calcination processing 6h under the condition of 550 DEG C in temperature, obtain mesoporous nano silicon dioxide.
3. as claimed in claim 1 functionalized polymer in mesoporous nano silicon dioxide surface-assembled and de-assembly method, it is characterized in that in step (1), the mass concentration of described mesoporous nano silicon dioxide solution is 2 ~ 10mg/mL, the mass concentration of polymers soln is 2 ~ 10mg/mL, and the mass concentration of metal ion solution is 10 ~ 20mg/mL.
4. functionalized polymer, in mesoporous nano silicon dioxide surface-assembled and de-assembly method, is characterized in that in step (1) as claimed in claim 1, and described metal ion is for containing Fe
3+, Zn
2+compound.
5. functionalized polymer, in mesoporous nano silicon dioxide surface-assembled and de-assembly method, is characterized in that described containing Fe as claimed in claim 4
3+compound be selected from FeCl
3or Fe
2(SO
4)
3.
6. functionalized polymer, in mesoporous nano silicon dioxide surface-assembled and de-assembly method, is characterized in that described containing Fe as claimed in claim 5
3+compound be FeCl
3.
7. functionalized polymer, in mesoporous nano silicon dioxide surface-assembled and de-assembly method, is characterized in that described containing Zn as claimed in claim 4
2+compound be selected from ZnCl
2or Zn (SO
4)
2.
8. as claimed in claim 1 functionalized polymer in mesoporous nano silicon dioxide surface-assembled and de-assembly method, it is characterized in that in step (2), the volume ratio of the described pyrocatechol functionalized polymer aqueous solution, aqueous metallic ions, the mesoporous nano silicon dioxide aqueous solution is (0.5 ~ 2): (0.1 ~ 1): (1 ~ 2).
9. functionalized polymer, in mesoporous nano silicon dioxide surface-assembled and de-assembly method, is characterized in that described acidic solution is selected from the one in hydrochloric acid soln, acetum, phosphoric acid solution in step (3) as claimed in claim 1.
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| CN111557306A (en) * | 2020-05-21 | 2020-08-21 | 中国热带农业科学院南亚热带作物研究所 | Nano-drug preparation and application thereof in prevention and control of banana vascular wilt |
| CN113387365A (en) * | 2021-07-19 | 2021-09-14 | 安徽瑞联节能科技股份有限公司 | Method for organically modifying nano silicon dioxide aerogel |
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| CN113387365A (en) * | 2021-07-19 | 2021-09-14 | 安徽瑞联节能科技股份有限公司 | Method for organically modifying nano silicon dioxide aerogel |
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