CN108484900B - A kind of poly ion liquid gel and method with nanometer hole - Google Patents
A kind of poly ion liquid gel and method with nanometer hole Download PDFInfo
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
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- B01J20/22—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material
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- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
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- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
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- C02F2101/00—Nature of the contaminant
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Abstract
The invention discloses a kind of poly ion liquid gel and method with nanometer hole, which has the monomer structure such as formula (1)；In formula (1), R is N heterocycle, it includes:In any one, X includes: Br‑、Cl‑OrN is 6~30.Poly ion liquid gel of the invention has nanometer hole, include three-dimensional hyperbranched topological structure, excellent adsorption capacity is shown, the application range in fields such as dyestuff, heavy metal ion adsorbed, medicine controlled releasing, molecular engram and protein identifications has huge potentiality.
Description
Technical field
The invention belongs to synthetic material fields, and in particular to a kind of with the poly ion liquid gel in nanometer hole and side
Method.
Background technique
It is various big that Cr VI (Cr (VI)) pollutant is widely present in metallurgy, machinery, tanning, plating, leather and printing and dyeing etc.
In type industrial wastewater.As a kind of acute carcinogen, Cr (VI) is solvable within the scope of almost entire pH, and is easy by human body
It absorbs, can cause to damage by digestion, breathing, skin and transmucosal human body, and to these organs.Therefore, Cong Shuizhong has
Effect removal Cr (VI) is of great significance for protection public health and ecological environment.
So far, many methods have been developed to handle containing Cr (VI) waste water, such as precipitating, electrocoagulation, bioelectrochemical
System, photocatalytic degradation, biological prosthetic, UF membrane and absorption.In these methods, due to its economic feasibility, high efficiency
With property easy to operate, absorption method is considered as handling one of the maximally efficient method of heavy metal ions in wastewater.Therefore, how
Design and synthesis have important theoretical and practical significance with the adsorbent of high-adsorption-capacity.
Hydrogel be it is a kind of can water-soluble swelling but not dissolution three-dimensional network material, due to setting for its molecular level
Meter property, swelling network are conducive to guest molecule and spread and facilitate operation, and hydrogel is considered as effective adsorbent material.
However, conventional hydrogels (the i.e. free radical of vinyl monomer and cross-linking monomer prepared by typical polymerization methods
Copolymerization) network structure that usually shows random crosslinking, it will lead to the entanglement of its strand and lead to the embedding of adsorption site,
Therefore the absorption property of hydrogel is limited.In order to improve adsorption capacity, the research of hydrogel adsorbent has been concentrated on recently
In design and building conducive to the new network structure of internal adsorption site exposure.Based on three-dimensional hyperbranched structure and numerous
Molecule inner cavity, hyperbranched topological structure be promote internal functionality exposure and increase guest molecule internal functionality utilize it is effective
Topological structure.In addition, increase the interaction between functional group and adsorbate be improve hydrogel absorption property another is heavy
Want direction.
A kind of functional material that ionic liquid (ILs) is made of organic cation and inorganic anion.Since it is good
Adjustability of structure and and the strong interaction with pollutant, a large number of studies show that, based on ionic liquid functional groups as absorption
The utilization of agent adsorption site can significant its absorption property of raising.
Summary of the invention
The object of the present invention is to provide a kind of poly ion liquid gel and method with nanometer hole, which is solved
Conventional gel can be formed in the interior thereof three-dimensional highly branched structure, have without network cross-linked structure, the problem of adsorption capacity difference
Excellent adsorption capacity.
In order to achieve the above object, the present invention provides a kind of poly ion liquid gel with nanometer hole, this gather from
Sub- liquid gel has the polymer constitutional repeating unit such as formula (1):
In formula (1), R is N heterocycle, it includes:In any one, wherein X includes:
Br-、Cl-OrIn formula (1), n is 6~30.
Preferably, the poly ion liquid gel by the compound A with such as formula (2) structure and has such as formula (3)
The compound B of structure is prepared through N- alkylated reaction:
In formula (2), R ' includes:In any one；
In formula (3), R1、R2、R3It is each independently Cl or Br；N is 6~30, the molecular weight of compound B is 1000~
5000。
Preferably, the poly ion liquid gel has several nanometers of holes, and the diameter in the hole is nanoscale.
The present invention also provides a kind of preparation methods of poly ion liquid gel with nanometer hole, and this method includes:
To there is the compound A such as formula (2) structure and have as the compound B of formula (3) structure is prepared through N- alkylated reaction:
In formula (2), R ' includes:In any one；In formula (3), R1、R2、R3It is respectively independent
Ground is Cl, Br；N is 6~30；The total concentration of the compound A and compound B are 200~1000mg/mL.
Preferably, the poly ion liquid gel of this method preparation has the structure such as formula (1):
In formula (1), R is N heterocycle, it includes:In any one, wherein X includes:
Br-、Cl-OrIn formula (1), n is 6~30.
Preferably, the R ' isThe preparation method of the compound A includes: by tri- acryloyl of 1,3,5-
Base hexahydro -1,3,5-triazines and imidazoles obtain compound A through Michael addition reaction.
Preferably, 1,3, the 5- triacryl hexahydros -1,3,5-triazines and imidazoles flow back in anhydrous methanol, instead
It answers liquid precipitate in ethyl acetate/tetrahydrofuran mixed solvent, washs, filter, it is dry, to obtain the compound A.
Preferably, the preparation method of the compound B includes: will have compound C and alpha-halogenate such as formula (4) structure
Acetic acid carries out esterification, obtains compound B；
In formula (4), n is 6~30.
Preferably, the compound C, alpha-halogenate acetic acid and p-methyl benzenesulfonic acid are heated to reflux in toluene, are removed molten
Agent obtains crude product, and purifying obtains compound B；The n is 6~7.
The present invention also provides a kind of processing method of processing waste water containing chrome, there is nanometer hole described in this method use
Poly ion liquid gel with Adsorption of Chromium or anionic heavy metal, further includes:With
Poly ion liquid gel and method with nanometer hole of the invention, solves conventional gel without network cross-linked knot
Structure, the problem of adsorption capacity difference, has the advantage that
Poly ion liquid gel of the invention contains hyperbranched topological structure, has three-dimensional highly branched structure, realizes in it
The exposure of the numerous ionic liquid functional groups in portion is improved with achieving the purpose that increase guest molecule contact and functional group's utilization rate, and
Excellent adsorption capacity is shown to heavy metal ion (such as hexavalent chromium), in dyestuff, heavy metal ion adsorbed, drug control
It releases, the application range in the fields such as molecular engram and protein identification has huge potentiality.
Detailed description of the invention
Fig. 1 is the preparation route figure of the poly ion liquid gel with nanometer hole of the invention.
Fig. 2 is the synthetic route chart of the A monomer of experimental example 1 of the present invention.
Fig. 3 is the nuclear magnetic spectrogram of the A monomer of experimental example 1 of the present invention preparation.
Fig. 4 is the synthetic route chart of the B monomer of experimental example 2 of the present invention.
Fig. 5 is the nuclear magnetic spectrogram of the B monomer of experimental example 2 of the present invention preparation.
Fig. 6 is the infrared spectrogram of the ATR-FTIR of poly ion liquid gel of the present invention.
Fig. 7 is the SEM image of poly ion liquid gel of the present invention.
Specific embodiment
Below in conjunction with drawings and examples, the following further describes the technical solution of the present invention.
A kind of poly ion liquid gel with nanometer hole, the poly ion liquid gel have the polymer such as formula (1)
Constitutional repeating unit:
In formula (1), R is N heterocycle, it includes:In any one, wherein X includes:
Br-、Cl-OrIn formula (1), n is 6~30.The gel of different X, the absorption of gel can be obtained by anion exchange
Ability is also different.
Above-mentioned poly ion liquid gel is mainly used for adsorbing metal chromium, to handle wastewater with chromium etc..
A kind of preparation method of the above-mentioned poly ion liquid gel with nanometer hole, as shown in Figure 1, being tool of the invention
There is the preparation route figure of the poly ion liquid gel in nanometer hole, prepare new oligo tribromo monomer first (as B monomer)
With three imidazoles monomers (as A monomer), then by one kettle way, B monomer and A monomer are subjected to N- alkane through step growth polymerization mechanism
Glycosylation reaction can be formed in situ the IL functional group of hyperbranched topological structure and imidazole radicals, polyion of the invention is prepared
Liquid gel, specific as follows:
The synthetic method of A monomer of 1 end group of experimental example with imidazoles
As shown in Fig. 2, the synthetic route chart of the A monomer for experimental example 1 of the present invention, passes through 1,3,5- triacryl six
Hydrogen -1,3,5-triazines (TT) is prepared with imidazoles (Im) Michael addition reaction, and specific technical solution is as follows:
TT (5g, 20mmol) and Im (10g, 106mmol) are added in 30mL anhydrous methanol, reflux is for 24 hours.Reaction terminates
Afterwards, reaction system is deposited in ethyl acetate/tetrahydrofuran (volume ratio 1:1) in the mixed solvent.Using dissolution-precipitating
(methanol-ethyl acetate/tetrahydrofuran) washes twice, filtering, and gained precipitating is dried under vacuum to constant weight at room temperature, obtains A
Monomer (TT Im), as shown in figure 3, the nuclear magnetic spectrogram of the A monomer for experimental example 1 of the present invention preparation.
2 end group of experimental example has the synthetic method of chlorine or bromine B monomer
As shown in figure 3, the synthetic route chart of the B monomer for experimental example 2 of the present invention, with polyoxyethylene groups glycerin ether (B-
PEG-OH, i.e. compound C) and monoxone (CAA) or bromoacetic acid (BAA) be typical reaction, technical solution is as follows:
By B-PEG-OH (10g, 10mmol), CAA (4.25g, 45mmol) or BAA (6.25g, 45mmol), p-TSA
(0.11g, 0.6mmol) (p-TSA, i.e. p-methyl benzenesulfonic acid) and 200mL toluene are added to Dean-Stark device, are heated to
120 DEG C, flow back 12h.After reaction, toluene is evaporated off, in methylene chloride by crude product dissolution, successively uses 2%Na2CO3Washing
3 times, 5%NaCl wash 2 times and pure water to water layer pH be neutrality.With anhydrous MgSO4Dry organic layer, is filtered, decompression
Solvent is removed, 40 DEG C are dried under vacuum to constant weight, the B monomer that end group has chlorine or bromine are obtained, as shown in figure 5, for present invention experiment
The nuclear magnetic spectrogram of B monomer prepared by example 2.
The preparation method of 3 imidazoles salt form hyperbranched poly ionic liquid of experimental example
660mgA monomer and 660mg B monomer (functional group's equimolar ratio of A and B reaction) and different volumes is dry
DMF is added in reagent bottle (A monomer obtains sample 1#~6# with the B monomer of bromine with end group), after stirring and dissolving, takes out rotor.
Reaction flask sealing is placed in 60~80 DEG C of oil baths, standing 14~for 24 hours.After reaction, reaction flask is taken out from oil bath,
It is cooled to room temperature to system, takes out sample, slice.The gel of taking-up is placed in deionized water and impregnates that (period changes water daily 2 days
3 times), to wash away unreacted monomer and DMF.Then, gel film is pulled out, is placed in ethanol solution and impregnates that (period is daily one day
Change ethyl alcohol 3 times), to replace the water in gel network, gel film is pulled out, after 25 DEG C are dried under vacuum to constant weight, obtains imidazole salts
Type hyperbranched poly ionic liquid (i.e. poly ion liquid gel).
Since poly ion liquid gel of the invention is obtained by the N- alkylated reaction between monomer, A and B monomer
Between alkylated reaction efficiency be control gel-forming key factor.In addition, reaction efficiency is mainly by total monomer concentration
Influence, as shown in table 1 below, for various concentration monomer preparation poly ion liquid gel gel fraction and swelling ratio:
The gel fraction and swelling ratio of the poly ion liquid gel of 1 various concentration monomer of table preparation
Note: C(A+B)And, Gel fraction is gel fraction for the concentration of A monomer and B monomer, and ESR is total for electron spin
Vibration, DZFor the diameter of gel.
As shown in Table 1, when the total concentration of A and B monomer are about 100mgmL-1When, only diameter is obtained about by dialysing
The microgel (sample 1#) of 300nm.However, when total monomer concentration is greater than 200mgmL-1When, it can be formed a series of with difference
The macroscopic hydrogel (sample 2#~6#) of gel fraction.With the increase of total monomer, gel fraction increases.When total monomer is dense
Degree is higher than 600mgmL-1When, the gel fraction of hydrogel is up to 80% or more.
The poly ion liquid gel of above-mentioned preparation is detected using ATR-FTIR (Attenuated Total Reflect ion Infrared Spectroscopy),
The result shows that poly ion liquid gel synthesizes successfully.As shown in fig. 6, being the red of the ATR-FTIR of poly ion liquid gel of the present invention
External spectrum figure, it can be seen from the figure that in 1569cm-1And 1653cm-1The characteristic peak at place belongs to the miaow of B constitutional repeating unit
Azoles ring, and in 1746cm-1Adsorption peak be respectively belonging to O-C=O key, in 1100cm-1The adsorption peak at place belongs to A and repeats to tie
The C-O-C key of structure unit.
The SEM image of the poly ion liquid gel of above-mentioned preparation is observed, as shown in fig. 7, solidifying for poly ion liquid of the present invention
The SEM image of glue, it can be seen from the figure that the structure of poly ion liquid gel of the invention shows porous network structure, often
The diameter in a hole is about 10 μm, which can promote quick adsorption of the adsorption molecule inside the poly ion liquid gel flat
Weighing apparatus and transmitting.
The absorption property of above-mentioned sample 2#~6# is measured, is adsorbed using the simulated wastewater containing hexavalent chromium
Test: waste water 50mL, Cr6+Concentration is 500mg/L, amount of samples 0.5mg, Cr6+Removal rate is respectively 30.5%, 60.1%,
87.1%, 94.6%, 98.1%.
In conclusion the poly ion liquid gel with nanometer hole of the invention contains hyperbranched topological structure, have three
Tie up highly branched structure, show excellent adsorption capacity, dyestuff, heavy metal ion adsorbed, medicine controlled releasing, molecular engram and
The application range in the fields such as protein identification has huge potentiality.
It is discussed in detail although the contents of the present invention have passed through above preferred embodiment, but it should be appreciated that above-mentioned
Description is not considered as limitation of the present invention.After those skilled in the art have read above content, for of the invention
A variety of modifications and substitutions all will be apparent.Therefore, protection scope of the present invention should be limited to the appended claims.
Claims (10)
1. a kind of poly ion liquid gel with nanometer hole, which is characterized in that the poly ion liquid gel has such as formula (1)
Polymer constitutional repeating unit:
In formula (1), R is N heterocycle, it includes:In any one, wherein X includes: Br-、
Cl-Or
In formula (1), n is 6~30.
2. the poly ion liquid gel according to claim 1 with nanometer hole, which is characterized in that the polyion
Liquid gel is by the compound A with such as formula (2) structure and has if the compound B of formula (3) structure is through N- alkylated reaction
It prepares:
In formula (2), R ' includes:With in any one；
In formula (3), R1、R2、R3It is each independently Cl or Br；N is 6~30.
3. the poly ion liquid gel according to claim 1 or 2 with nanometer hole, which is characterized in that described is poly-
Ionic liquid gel has several nanometers of holes, and the diameter in the hole is nanoscale.
4. a kind of preparation method of the poly ion liquid gel with nanometer hole, which is characterized in that this method includes:
To there is the compound A such as formula (2) structure and there is the compound B such as formula (3) structure to obtain through the preparation of N- alkylated reaction
:
In formula (2), R ' includes:In any one；
In formula (3), R1、R2、R3It is each independently Cl, Br；N is 6~30；
The total concentration of the compound A and compound B are 200~1000mg/mL.
5. the preparation method of the poly ion liquid gel according to claim 4 with nanometer hole, which is characterized in that should
The poly ion liquid gel of method preparation has the structure such as formula (1):
In formula (1), R is N heterocycle, it includes:In any one, wherein X includes: Br-、
Cl-Or
In formula (1), n is 6~30.
6. the preparation method of the poly ion liquid gel according to claim 4 with nanometer hole, which is characterized in that institute
The R ' stated is
The preparation method of the compound A includes:
By 1,3,5- triacryl hexahydro -1,3,5-triazines and imidazoles through Michael addition reaction, compound A is obtained.
7. the preparation method of the poly ion liquid gel according to claim 6 with nanometer hole, which is characterized in that institute
1 stated, 3,5- triacryl hexahydros -1,3,5-triazines and imidazoles flow back in anhydrous methanol, and reaction solution is deposited in acetic acid second
Ester/tetrahydrofuran mixed solvent washs, and filters, dry, to obtain the compound A.
8. the preparation method of the poly ion liquid gel according to any one of claim 4-7 with nanometer hole,
It is characterized in that, the preparation method of the compound B includes:
To have compound C and alpha-halogenate acetic acid such as formula (4) structure to carry out esterification, and obtain compound B；
In formula (4), n is 6~30.
9. the preparation method of the poly ion liquid gel according to claim 8 with nanometer hole, which is characterized in that institute
Compound C, alpha-halogenate acetic acid and the p-methyl benzenesulfonic acid stated are heated to reflux in toluene, are removed solvent, are obtained crude product, pure
Change, obtains compound B；The n is 6~7.
10. a kind of processing method of processing waste water containing chrome, which is characterized in that this method using according to claim 1 in -3 it is any
Poly ion liquid gel described in one with nanometer hole is with Adsorption of Chromium or anionic heavy metal, comprising:With
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