CN105906763B - A kind of preparation method of the phthalic acid ester molecular engram material based on titanium dioxide nano thread - Google Patents
A kind of preparation method of the phthalic acid ester molecular engram material based on titanium dioxide nano thread Download PDFInfo
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- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
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- C08F222/10—Esters
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Abstract
The preparation method of the invention discloses a kind of phthalic acid ester molecular engram material based on titanium dioxide nano thread, titanium dioxide nano thread and KH570 are added in DMF, and 12 ~ 24 h are stirred at 70 ~ 110 DEG C, obtain the titanium dioxide nano thread of surface silanization；Template molecule and function monomer are weighed, then the two is placed in tool plug bottle, and acetonitrile toluene mixture liquid is added and carries out vortex dissolving, the dissolving that is vortexed, which is placed in 4 DEG C of refrigerators, to be stood；It is then returned to room temperature, titanium dioxide nano thread, the crosslinking agent of 1.68 ~ 6.76g and the initiator of 90 ~ 150mg of surface silanization is added, uninterruptedly it is passed through nitrogen, cover bottle cap sealing, magnetic agitation reacts 12 ~ 24 h at 60 ~ 80 DEG C, molecularly imprinted polymer is made, pure product is obtained by filtration by washing.Titanium dioxide nano thread prepared by the present invention has operability strong, and nearly all binding site is distributed on the surface with good accessibility by surface molecule print.
Description
Technical field
The present invention relates to molecular engram material technical field, specifically a kind of O-phthalic based on titanium dioxide nano thread
The preparation method of acid ester molecules imprinted material.
Background technology
It is the technology being oriented to that molecular imprinting technology, which is with template molecule, designs and synthesizes to a certain or a kind of analyte tool
The cross-linked polymer for having specific recognition capability, due to molecularly imprinted polymer have to extraneous adverse circumstances (high temperature, high pressure,
Strong acid, highly basic, organic reagent etc.) tolerance is strong, and stability is good, and service life is long, and the outstanding spy such as have a wide range of application
Point so that molecular imprinting technology is gradually paid close attention to by people, and with development in science and technology, and performance is gradually developed, to be applied
In various fields, but the molecularly imprinted polymer for preparing of conventional bulk polymerization at present that there are binding sites is uneven, accessibility is poor,
The technical problems such as recognition speed is slow.
Invention content
The purpose of the present invention is to provide a kind of molecularly imprinted polymer knots for overcoming current conventional bulk polymerization and preparing
Close the phthalic acid ester molecule based on titanium dioxide nano thread for the problems such as site is uneven, accessibility is poor, recognition speed is slow
The preparation method of imprinted material, to solve the problems mentioned in the above background technology.
To achieve the above object, the present invention provides the following technical solutions：
A kind of preparation method of the phthalic acid ester molecular engram material based on titanium dioxide nano thread, including following step
Suddenly：
Step 1：Titanium dioxide nano thread and KH570 are added in DMF, and stirs 12 ~ 24 h at 70 ~ 110 DEG C, obtains
To the titanium dioxide nano thread of surface silanization；
Step 2：The repefral of 0.195g is weighed as template molecule, the function monomer of 0.25 ~ 1.0 g,
Then the two is placed in tool plug bottle, and the acetonitrile-methylbenzene mixed liquor that 70 ~ 150ml is added carries out vortex dissolving, is vortexed after dissolving
It is placed in 10 ~ 14h of standing in 4 DEG C of refrigerators；Be then returned to room temperature, be added 1 ~ 4g surface silanizations titanium dioxide nano thread,
The crosslinking agent of 1.68 ~ 6.76g and the initiator of 90 ~ 150mg cover bottle cap sealing after being uninterruptedly passed through 4 ~ 6 min of nitrogen,
Magnetic agitation reacts 12 ~ 24 h at 60 ~ 80 DEG C, and molecularly imprinted polymer is made；
Step 3：Molecularly imprinted polymer is poured into be lined in the Buchner funnel of two layers of filter paper and is filtered, is washed with 20mL acetonitriles
Tool plug bottle is washed, the liquid after washing is fallen on filter paper, in triplicate；Overlayer polymer 30mL volume ratios are 9:1 methanol-
Acetic acid mixture washs three times, then three times with 30mL distillations water washing, is finally washed twice with 20mL methanol, polymer is shifted
Into evaporating dish, in 60 DEG C of constant temperature dryings；
Step 4：The molecularly imprinted polymer of drying is ground, is fitted into filtration paper cylinder and is placed in Soxhlet extractor, use volume
Than being 9:1 methanol-acetic acid mixed liquor washs 12 ~ 36h to remove template molecule repeatedly；
Step 5：The molecularly imprinted polymer for removing template molecule taking-up is placed in Buchner funnel to filter, uses water
It is washed till after neutrality and is washed three times with 40mL methanol again, in 60 DEG C of constant temperature dryings to get to the surface molecular of titanium dioxide nano thread
Imprinted material.
As a further solution of the present invention：Titanium dioxide nano thread in the step 1 replaces with nano titania
Stick or titanium dioxide granule.
As a further solution of the present invention：Crosslinking agent is ethylene glycol dimethacrylate or three hydroxyls in the step 2
Trimethacrylate.
As a further solution of the present invention：Initiator is two different heptan of azodiisobutyronitrile or azo in the step 2
Nitrile.
As a further solution of the present invention：The volume ratio of solvent acetonitrile-toluene in the step 2 is 2：1~4：1.
As a further solution of the present invention：Function monomer is methacrylic acid or trifluoromethyl propylene in the step 2
Ester.
As a further solution of the present invention：The molecularly imprinted material on surface of titanium dioxide nano thread in the step 5
After removing molecule using acetone sedimentation, it is filled into nanowire surface molecularly imprinted solid phase extraction column.
Compared with prior art, the beneficial effects of the invention are as follows：Nano-titanium dioxide is a kind of cheap, nontoxic, light
Stablize, there is better optical and photocatalysis property, due to special skin effect, Small-scale fading, quantum effect and macroscopic view
Quantum tunneling effect and with of increasing concern different from the characteristic of conventional material, but main zero-dimension nano particle of concentrating
Research, and the research of titanium dioxide nano thread is still in infancy.Titanium dioxide nano thread prepared by the present invention has
Operability is strong, and nearly all binding site is distributed on the surface with good accessibility by surface molecule print, is overcome
Molecularly imprinted polymer binding site prepared by current conventional bulk polymerization is uneven, accessibility is poor, recognition speed is slow etc. asks
Topic is conducive to the elution of template molecule and with target molecule in conjunction with raising target molecule selectivity.This method is based on calculating
Machine is simulated and molecular engram is theoretical, using silanization titanium dioxide nano thread as carrier, is prepared by surface molecule print technology
Molecular engram material has wide and application prospect in fields such as food security, environmental protection, the energy.
Description of the drawings
Fig. 1 is the infrared figure of molecularly imprinted polymer.
Specific implementation mode
Following will be combined with the drawings in the embodiments of the present invention, and technical solution in the embodiment of the present invention carries out clear, complete
Site preparation describes, it is clear that described embodiments are only a part of the embodiments of the present invention, instead of all the embodiments.It is based on
Embodiment in the present invention, it is obtained by those of ordinary skill in the art without making creative efforts every other
Embodiment shall fall within the protection scope of the present invention.
Embodiment 1
A kind of preparation method of the phthalic acid ester molecular engram material based on titanium dioxide nano thread, including following step
Suddenly：
Step 1：Titanium dioxide nano thread and KH570 are added in DMF, and stirs 12 h at 70 DEG C, obtains surface silicon
The titanium dioxide nano thread of alkanisation, titanium dioxide nano thread could alternatively be titanium dioxide nano-rod or titanium dioxide granule；
Step 2：The repefral of 0.195g is weighed as template molecule, the function monomer of 0.25g（Methyl
Acrylic acid or trifluoromethyl acrylic ester）, then the two is placed in tool plug bottle, and the acetonitrile-methylbenzene of 70ml is added（Acetonitrile-first
The volume ratio of benzene is 2：1）Mixed liquor carries out vortex dissolving, and the dissolving that is vortexed, which is placed in 4 DEG C of refrigerators, stands 10h；It is then returned to
The titanium dioxide nano thread of 1g surface silanizations, the crosslinking agent of 1.68g is added in room temperature（Ethylene glycol dimethacrylate or three
Methylolpropane trimethacrylate）With the initiator of 90mg（Azodiisobutyronitrile or azobisisoheptonitrile）, uninterrupted logical
After entering 4 min of nitrogen, bottle cap sealing is covered, magnetic agitation reacts 12 h at 60 DEG C, and molecularly imprinted polymer is made；
Step 3：Molecularly imprinted polymer is poured into be lined in the Buchner funnel of two layers of filter paper and is filtered, is washed with 20mL acetonitriles
Tool plug bottle is washed, the liquid after washing is fallen on filter paper, in triplicate；Overlayer polymer 30mL volume ratios are 9:1 methanol-
Acetic acid mixture washs three times, then three times with 30mL distillations water washing, is finally washed twice with 20mL methanol, polymer is shifted
Into evaporating dish, in 60 DEG C of constant temperature dryings；
Step 4：The molecularly imprinted polymer of drying is ground, is fitted into filtration paper cylinder and is placed in Soxhlet extractor, use volume
Than being 9:1 methanol-acetic acid mixed liquor washs 12h to remove template molecule repeatedly；
Step 5：The molecularly imprinted polymer for removing template molecule taking-up is placed in Buchner funnel to filter, uses water
It is washed till after neutrality and is washed three times with 40mL methanol again, in 60 DEG C of constant temperature dryings to get to the surface molecular of titanium dioxide nano thread
Imprinted material.
Step 6：After the molecularly imprinted material on surface of titanium dioxide nano thread is using acetone sedimentation removal molecule,
It is filled into nanowire surface molecularly imprinted solid phase extraction column.
Embodiment 2
A kind of preparation method of the phthalic acid ester molecular engram material based on titanium dioxide nano thread, including following step
Suddenly：
Step 1：Titanium dioxide nano thread and KH570 are added in DMF, and stirs 18 h at 90 DEG C, obtains surface silicon
The titanium dioxide nano thread of alkanisation, titanium dioxide nano thread could alternatively be titanium dioxide nano-rod or titanium dioxide granule；
Step 2：The repefral of 0.195g is weighed as template molecule, the function monomer of 0.625 g（First
Base acrylic acid or trifluoromethyl acrylic ester）, then the two is placed in tool plug bottle, and the acetonitrile-methylbenzene of 110ml is added（Acetonitrile-
The volume ratio of toluene is 3：1）Mixed liquor carries out vortex dissolving, and the dissolving that is vortexed, which is placed in 4 DEG C of refrigerators, stands 12h；Then restore
To room temperature, the titanium dioxide nano thread of 2.5g surface silanizations, the crosslinking agent of 4.22g is added（Ethylene glycol dimethacrylate
Or trimethylol-propane trimethacrylate）With the initiator of 120mg（Azodiisobutyronitrile or azobisisoheptonitrile）, not between
It is open close enter nitrogen 5min after, cover bottle cap sealing, at 70 DEG C magnetic agitation react 18 Mei h, be made molecularly imprinted polymer；
Step 3：Molecularly imprinted polymer is poured into be lined in the Buchner funnel of two layers of filter paper and is filtered, is washed with 20mL acetonitriles
Tool plug bottle is washed, the liquid after washing is fallen on filter paper, in triplicate；Overlayer polymer 30mL volume ratios are 9:1 methanol-
Acetic acid mixture washs three times, then three times with 30mL distillations water washing, is finally washed twice with 20mL methanol, polymer is shifted
Into evaporating dish, in 60 DEG C of constant temperature dryings；
Step 4：The molecularly imprinted polymer of drying is ground, is fitted into filtration paper cylinder and is placed in Soxhlet extractor, use volume
Than being 9:1 methanol-acetic acid mixed liquor is washed for 24 hours repeatedly to remove template molecule；
Step 5：The molecularly imprinted polymer for removing template molecule taking-up is placed in Buchner funnel to filter, uses water
It is washed till after neutrality and is washed three times with 40mL methanol again, in 60 DEG C of constant temperature dryings to get to the surface molecular of titanium dioxide nano thread
Imprinted material.
Step 6：After the molecularly imprinted material on surface of titanium dioxide nano thread is using acetone sedimentation removal molecule,
It is filled into nanowire surface molecularly imprinted solid phase extraction column.
Embodiment 3
A kind of preparation method of the phthalic acid ester molecular engram material based on titanium dioxide nano thread, including following step
Suddenly：
Step 1：Titanium dioxide nano thread and KH570 are added in DMF, and stirs 24 h at 110 DEG C, obtains surface
The titanium dioxide nano thread of silanization, titanium dioxide nano thread could alternatively be titanium dioxide nano-rod or titanium dioxide granule；
Step 2：The repefral of 0.195g is weighed as template molecule, the function monomer of 1.0 g（Methyl
Acrylic acid or trifluoromethyl acrylic ester）, then the two is placed in tool plug bottle, and the acetonitrile-methylbenzene of 150ml is added（Acetonitrile-first
The volume ratio of benzene is 4：1）Mixed liquor carries out vortex dissolving, and the dissolving that is vortexed, which is placed in 4 DEG C of refrigerators, stands 14h；It is then returned to
The titanium dioxide nano thread of 4g surface silanizations, the crosslinking agent of 6.76g is added in room temperature（Ethylene glycol dimethacrylate or three
Methylolpropane trimethacrylate）With the initiator of 150mg（Azodiisobutyronitrile or azobisisoheptonitrile）, uninterrupted logical
After entering 6 min of nitrogen, bottle cap sealing is covered, magnetic agitation reacts 24 h at 80 DEG C, and molecularly imprinted polymer is made；
Step 3：Molecularly imprinted polymer is poured into be lined in the Buchner funnel of two layers of filter paper and is filtered, is washed with 20mL acetonitriles
Tool plug bottle is washed, the liquid after washing is fallen on filter paper, in triplicate；Overlayer polymer 30mL volume ratios are 9:1 methanol-
Acetic acid mixture washs three times, then three times with 30mL distillations water washing, is finally washed twice with 20mL methanol, polymer is shifted
Into evaporating dish, in 60 DEG C of constant temperature dryings；
Step 4：The molecularly imprinted polymer of drying is ground, is fitted into filtration paper cylinder and is placed in Soxhlet extractor, use volume
Than being 9:1 methanol-acetic acid mixed liquor washs 36h to remove template molecule repeatedly；
Step 5：The molecularly imprinted polymer for removing template molecule taking-up is placed in Buchner funnel to filter, uses water
It is washed till after neutrality and is washed three times with 40mL methanol again, in 60 DEG C of constant temperature dryings to get to the surface molecular of titanium dioxide nano thread
Imprinted material.
Step 6：After the molecularly imprinted material on surface of titanium dioxide nano thread is using acetone sedimentation removal molecule,
It is filled into nanowire surface molecularly imprinted solid phase extraction column.
It is obvious to a person skilled in the art that invention is not limited to the details of the above exemplary embodiments, Er Qie
In the case of without departing substantially from spirit or essential attributes of the invention, the present invention can be realized in other specific forms.Therefore, no matter
From the point of view of which point, the present embodiments are to be considered as illustrative and not restrictive, and the scope of the present invention is by appended power
Profit requires rather than above description limits, it is intended that all by what is fallen within the meaning and scope of the equivalent requirements of the claims
Variation is included within the present invention.Any reference signs in the claims should not be construed as limiting the involved claims.
In addition, it should be understood that although this specification is described in terms of embodiments, but not each embodiment is only wrapped
Containing an independent technical solution, this description of the specification is merely for the sake of clarity, and those skilled in the art should
It considers the specification as a whole, the technical solutions in the various embodiments may also be suitably combined, forms those skilled in the art
The other embodiment being appreciated that.
Claims (2)
1. a kind of preparation method of the phthalic acid ester molecular engram material based on titanium dioxide nano thread,
It is characterized by comprising the following steps：
Step 1：It is added titanium dioxide nano thread and KH570 in DMF, and the stirring 12~for 24 hours at 70~110 DEG C, obtains table
The titanium dioxide nano thread of face silanization；
Step 2：The repefral of 0.195g is weighed as template molecule, the function monomer of 0.25~1.0g, then
The two is placed in tool plug bottle, and the acetonitrile-methylbenzene mixed liquor that 70~150ml is added carries out vortex dissolving, the body of acetonitrile-methylbenzene
Product is than being 2：1~4：1, the dissolving that is vortexed is placed on 10~14h of standing in 4 DEG C of refrigerators；It is then returned to room temperature, 1~4g tables are added
The initiator of the titanium dioxide nano thread of face silanization, the crosslinking agent of 1.68~6.76g and 90~150mg, is uninterruptedly passed through nitrogen
After 4~6min of gas, cover bottle cap sealing, at 60~80 DEG C magnetic agitation reaction 12~for 24 hours, be made molecularly imprinted polymer；
Step 3：Molecularly imprinted polymer is poured into be lined in the Buchner funnel of two layers of filter paper and is filtered, tool is washed with 20mL acetonitriles
Bottle is filled in, the liquid after washing is fallen on filter paper, in triplicate；Overlayer polymer 30mL volume ratios are 9:1 methanol-acetic acid
Mixed liquor washs three times, then three times with 30mL distillations water washing, is finally washed twice with 20mL methanol, polymer is transferred to steaming
It sends out in ware, in 60 DEG C of constant temperature dryings；
Step 4：The molecularly imprinted polymer of drying is ground, is fitted into filtration paper cylinder and is placed in Soxhlet extractor, be with volume ratio
9:1 methanol-acetic acid mixed liquor washs 12~36h to remove template molecule repeatedly；
Step 5：The molecularly imprinted polymer for removing template molecule taking-up is placed in Buchner funnel and filters, be washed with water to
It is washed three times with 40mL methanol again after neutrality, in 60 DEG C of constant temperature dryings to get to the surface molecule print of titanium dioxide nano thread
Material；After the molecularly imprinted material on surface of titanium dioxide nano thread is using acetone sedimentation removal molecule, it is filled into nanometer
Line surface molecule print solid phase extraction column；
Crosslinking agent is ethylene glycol dimethacrylate or trimethylol-propane trimethacrylate in the step 2；It is described
Function monomer is methacrylic acid or trifluoromethyl acrylic ester in step 2.
2. a kind of system of phthalic acid ester molecular engram material based on titanium dioxide nano thread according to claim 1
Preparation Method, which is characterized in that initiator is azodiisobutyronitrile or azobisisoheptonitrile in the step 2.
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| CN110327662B (en) * | 2019-04-30 | 2021-08-27 | 云南警官学院 | Molecularly imprinted solid-phase extraction column for amphetamine drugs and preparation method thereof |
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| CN104610548A (en) * | 2015-01-06 | 2015-05-13 | 江西出入境检验检疫局检验检疫综合技术中心 | Method for preparing surface molecularly imprinted material based on titania nanowires |
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| CN104610548A (en) * | 2015-01-06 | 2015-05-13 | 江西出入境检验检疫局检验检疫综合技术中心 | Method for preparing surface molecularly imprinted material based on titania nanowires |
Non-Patent Citations (3)
| Title |
|---|
| Inorganic molecular imprinted titanium dioxide photocatalyst:synthesis,characterization and its application for efficient and selective degradation of phthalate esters;Xiantao Shen等;《Journal of Materials Chemistry》;20090604(第19期);第4843-4851页 * |
| 纳米TiO2基绿原酸印迹聚合物的制备及其吸附研究;谭先周等;《化工进展》;20130205;第32卷(第2期);第389页第1.3.1节、图2 * |
| 邻苯二甲酸二甲酯印迹聚合物的制备及其在固相萃取中的应用;杨顺香等;《云南大学学报（自然科学版）》;20130110;第35卷(第1期);第81页第3节 * |
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