Startseite Preparation and adsorption properties of Ni(ii) ion-imprinted polymers based on synthesized novel functional monomer
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Preparation and adsorption properties of Ni(ii) ion-imprinted polymers based on synthesized novel functional monomer

  • Li Zhao , Xianzhi Hu , Futing Zi , Yingmei Liu , Deqiong Hu , Peng Li und Huiling Cheng EMAIL logo
Veröffentlicht/Copyright: 11. August 2021
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e-Polymers
Aus der Zeitschrift e-Polymers Band 21 Heft 1

Abstract

In this study, a novel functional monomer N-(1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethyl)acrylamide (NDTEA) was designed and synthesized, and was used to prepare Ni(ii) ion-imprinted polymers (Ni(ii)-IIPs). Sixteen kinds of Ni(ii)-IIP (Ni(ii)-IIP1–16) and corresponding non-imprinted polymers (NIP1–16) were prepared by precipitation polymerization method. After optimized condition experiment, Ni(ii)-IIP5 possessed maximum adsorption capacity and better imprinting factor under optimal experimental conditions which indicated by equilibrium adsorption experiments. The morphology and structural characteristics of Ni(ii)-IIP5 were characterized by scanning electron microscopy (SEM) and Brunauer–Emmett–Teller (BET). The adsorption selectivity of Ni(ii)-IIP5 was analyzed by ICP-OES, and the results showed that Ni(ii)-IIP5 had favorable selectivity recognition ability for Ni(ii) when Cu(ii), Co(ii), and Cd(ii) are used as competitive ions. The kinetic experiment indicated that the performance of Ni(ii) adsorption on the surface of Ni(ii)-IIP5 obeyed the pseudo-first-order model, and adsorption equilibrium was attained after 15 min. Isothermal adsorption process fitted to Langmuir and Freundlich isothermal adsorption models, simultaneously. The results showed that Ni(ii)-IIP5 prepared by using a new functional monomer had better permeation selectivity and higher affinity for Ni(ii), which also verified the rationality of the functional monomer design. At the same time, it also provided a broad application prospect for removal of Ni(ii) in complex samples.

Keywords: Ni(ii) ion; novel functional monomer; NDTEA; Ni(ii) ion-imprinted polymer; selectivity

1 Introduction

Nickel (Ni) is a heavy metal material closely associated with human life, which possesses favorable characteristics of corrosion resistance and ductility, and has been widely used in steel, alloy manufacturing, electroplating, and batteries. Meanwhile, Ni is one of the trace elements necessary for organisms, but its availability is not up to the demand. Due to the serious problem of Ni pollution (1,2), it can damage kidney organs and cause irreparable harms to the physical health (3,4). Therefore, it is particularly important to develop a method for rapid and effective removal of Ni. In order to alleviate Ni ion pollution, many researchers have conducted a lot of explorations and experiments (5,6,7). The current conventional methods for treating Ni-containing wastewater are as follows: chemical precipitation (8,9,10), ion exchange (11,12), electrolysis (13,14), membrane separation (15,16), adsorption (17,18), etc. For example, Anna Wołowicz published an article in which they described an effective removal of Ni(ii) from aqueous solutions with ion exchange resins (19).

Foong et al. demonstrated that heavy metal ion can be detected and separated by nanofiber membranes (20). Salama and co-workers proved that algae can remove heavy metal ions from various wastewater by adsorption process (21). The method of adsorption is effective and environmentally friendly, which has been widely used in the field of Ni-containing wastewater treatment in recent years (22,23). However, most adsorption processes are non-specific and have low selectivity for target ions. In view of the serious environmental pollution caused by Ni ion, there is an urgent need to find an adsorption separation material with high selectivity for Ni(ii).

As an important developmental direction of molecular imprinting technology (24,25,26), metal ion imprinting technology (27) has vital academic and application value in various fields of environment and material science (28,29,30,31,32), for instance, solid phase extraction (33), sensor (34,35,36), membrane separation (37), etc. The concept of ion imprinting technology is that metal ion is used as template to form a chelate by combining with monomer through electrostatic and coordination actions. After polymerization, the template ions are eluted with acidic reagents. Finally, the imprinted material with three-dimensional pore structure corresponding to the target metal ion is prepared.

In this work, novel functional monomers are designed and synthesized to be used as monomers for preparing Ni ion polymers (Ni(ii)-IIPs/NIPs). In the previous study of our research group (38), a novel functional monomer N,N′-(ethane-1,2-diyl)bis(2-methylacrylamide) (EBMA) was successfully prepared and applied to prepare ion-imprinted membranes of Cr(vi). In this study, a novel functional monomer N-(1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethyl)acrylamide (NDTEA) was designed and synthesized for recognizing Ni(ii) ion in aqueous solution, using ethylene glycol dimethacrylate (EDMA) as cross-linker and 2,2′-azobis(2-methylpropionitrile) (AIBN) as initiator. Diverse parameters affecting the adsorbing capacity of polymers were optimized, such as the type and dosage of solvent, the dosage of functional monomer, cross-linker, etc.

The preparation of polymers with optimal conditions was characterized by scanning electron microscopy (SEM), thermogravimetric analysis (TGA), and Brunauer–Emmett–Teller (BET), and the selectivity of Ni(ii)-IIP5 was conducted by choosing Cd2+, Co2+, Cu2+ as competing ions. The polymer of Ni(ii)-IIP5 possesses positive specific selective recognition performance for Ni(ii), and, therefore, it is expected to be used for separation and enrichment of Ni(ii) in actual samples.

2 Experimental methods

2.1 Apparatus

A UV-2500 ultraviolet-visible (UV-Vis) spectrophotometer (Shimadzu, Japan) was used to detect metal ion concentration. The pH value was measured with a PHS-3C pH meter. XL 30esem-tm phenom electron microscope-energy spectrometer (Funer Scientific Instrument) was used to identify the surface morphologies of Ni(ii)-IIP and NIP. The selectivity of polymer was validated by plasma emission spectrometer (ICAP 6000 series). The specific surface area of polymers were determined using NOVA2000e BET surface area analyzer (Quantachrome Instruments, USA). And the other apparatuses used were AS-series ultrasonic cleaning instrument (Tianjin, China); SHZ-82 Bath constant temperature oscillator (Changzhou, China); DZKW S 4 electric-heated thermostatic water bath (Beijing, China); and analytical balance (Shanghai, China).

2.2 Materials

Nickel(ii) chloride hexahydrate (98%, NiCl2·6H2O), chloride hexahydrate (99%, CoCl2·6H2O), copper chloride (99%, CuCl2), cadmium chloride (99%, CdCl2), AIBN (99%) and EDMA (98%) were purchased from Aladdin Bio-Chem Technology Co., Ltd, Shanghai. Methanol, ethanol absolute, isopropyl alcohol, acetonitrile, N,N-dimethylformamide, and acetic acid glacial were obtained from Tianjin Sailboat Chemical Reagent Technology Co., Ltd. All reagents were of analytical grade. The laboratory water was deionized water.

2.3 Preparation of Ni(ii) ion-imprinted polymer

2.3.1 Synthesis of novel functional monomer N-(1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethyl)acrylamide (NDTEA)

The synthesizing process of NDTEA is conducted according to the following steps:

2.3.1.1 Synthesis of compound 1

The process of synthesis can be seen from Scheme 1. The 2′-chloro-2,4-difluoroacetophenone and 1,2,4-triazole weighing 10 mmoL and 30 mmoL, respectively, were taken in a 50 mL round-bottom flask, added with 30 mL of anhydrous acetonitrile, and stirred overnight at room temperature. After the reaction was completed, the reactant was poured into 100 mL of cold water and stirred until solids precipitated. Afterwards filtration was performed with suction and the filter cake was washed three times with water and dried. A light yellow solid of 1.87 g was obtained with yield up to 84%.

Scheme 1 Synthesis of compound 1.
Scheme 1

Synthesis of compound 1.

2.3.1.2 Synthesis of compound 2

The process of synthesis as can be seen from Scheme 2.

Scheme 2 Synthesis of compound 2.
Scheme 2

Synthesis of compound 2.

The prepared compound 1, ammonium chloride, and sodium cyanoborohydride were separately weighed for 10, 50, and 20 mmoL, respectively, and taken in a 100 mL round-bottom flask, to which 50 mL of methanol was added later. The reaction was carried out at room temperature for 2 h and then heated to reflux for 12 h. After the reaction finished, the reactant was poured into 100 mL of cold water and stirred, and extracted with ethyl acetate. After the organic phase was dried over anhydrous sodium sulfate, it was filtered and concentrated to obtain 1.81 g of white solid with a yield of 81%.

The NMR data of the compound 2 are shown:

1H NMR (400 MHz, CDCl3) δ: 8.02(s, 1H), 8.20(d, J = 5.4 Hz, 2H), 7.82(s, 1H), 7.43–7.49(m, 1H), 6.86–6.91(m, 1H), 6.79–6.84(m, 1H), 5.34(d, J = 7.5 Hz, 1H), 4.85(br, 2H), 4.43–4.47(dd, J = 2.6 Hz, 2.6 Hz, 1H), 4.22–4.28(dd, J = 8.2 Hz, 8.2 Hz, 1H).

13C NMR (100 MHz, CDCl3) δ: 164.2(d, J C–F = 12.1 Hz), 161.7(d, J C–F = 11.8 Hz), 160.9(d, J C–F = 11.7 Hz), 158.4(d, J C–F = 11.7 Hz), 151.8, 144.0, 128.7(q, J C–F = 5.8 Hz), 123.5(d, J C–F = 13.7 Hz), 112.0(q, J C–F = 3.4 Hz), 104.3(t, J C–F = 25.3 Hz), 66.6, 55.5.

2.3.1.3 Synthesis of compound 3

The process of synthesis as can be seen from Scheme 3.

Scheme 3 Synthesis of compound 3.
Scheme 3

Synthesis of compound 3.

The prepared compound 2 and potassium carbonate were weighed for 5 mmoL and 10 mmoL, respectively and taken in a 50 mL round-bottom flask, and was added with 30 mL of anhydrous dichloromethane and 7.5 mmoL of acrylic acid chloride under ice water slowly, and raised to room temperature for 5 h. After the reaction was detected by thin-layer chromatography, the reactant was poured into 100 mL of cold water and stirred for half an hour and dichloromethane (20 mL × 3) was extracted. The organic phase was dried over anhydrous sodium sulfate. It was then filtered and concentrated, and the residue was separated by column chromatography to obtain 1.21 g of red solid with 87% yield. The compound 3 is the new functional monomer synthesized for the preparation of polymers.

The NMR data of the compound 3 are shown:

1H NMR (400 MHz, DMSO-d6) δ: 8.43(s, 1H), 8.20(d, J = 5.4 Hz, 2H), 7.95(s, 1H), 7.73(s, 1H), 7.50–7.56(m, 1H), 7.18–7.23(m, 1H), 7.08–7.13(m, 1H), 5.93–6.02(dd, J = 7.5 Hz, 15.2 Hz, 1H), 5.71(d, J = 15.3 Hz, 1H), 5.34(d, J = 10.6 Hz, 1H), 5.16(s, 1H), 4.20(s, 1H), 4.16(s, 1H).

13C NMR (100 MHz, DMSO-d6) δ: 163.5(d, J C–F = 12.4 Hz), 161.0(q, J C–F = 8.7 Hz), 158.5, 158.4(d, J C–F = 12.1 Hz), 151.7, 145.2, 129.8(q, J C–F = 6.2 Hz), 128.8, 125.7(d, J C–F = 3.7 Hz), 113.9, 112.1(t, J C–F = 3.6 Hz), 104.3(t, J C–F = 25.7 Hz), 65.3, 55.1, 51.9.

2.3.2 Preparation of Ni(ii) ion-imprinted polymers

The major optimization of the preparation process can be seen in Table 1. Detailed procedure: 0.1 mmoL of NiCl2·6H2O (template ion) was weighed in a stoppering triangular conical flask and 0.4 mmoL of novel functional monomer was added to it. After dissolving with different solvents and then shaking at ambient temperature for 3 h, the Ni(ii) ion and functional monomer were made to react completely; then 2 mmoL of cross-linker EDMA and 15 mg of initiator AIBN were added to form a pre-polymerization solution which was transferred to an ampule and degassed for 5–10 min with ultrasonic. The solution was then placed in a constant temperature shaker at 60°C for 24 h. Finally, a 9:1 (v/v) methanol and acetic acid mixed solution was used to remove the template ions, eluted with methanol to neutral, and vacuum dried for 24 h and Ni(ii)-IIPs were prepared. NIPs were also obtained under the same conditions, but without adding template ion. The process is shown in Scheme 4.

Table 1

Preparation of Ni(ii)-IIP and NIP

Polymers Types of solvent (v/v) Ratio of solvent (v/v) Dosage of functional monomer (mmoL) Dosage of cross-linker (mmoL)
Ni(ii)-IIP1 MeOH:H2O 1:1 4 20
Ni(ii)-IIP2 EtOH:H2O — — —
Ni(ii)-IIP3 IPA:H2O — — —
Ni(ii)-IIP4 DMF:H2O — — —
Ni(ii)-IIP5 MeOH:H2O 1:2 — —
Ni(ii)-IIP6 — 2:1 — —
Ni(ii)-IIP7 — 1:3 — —
Ni(ii)-IIP8 — 3:1 — —
Ni(ii)-IIP9 — 1:2 2 —
Ni(ii)-IIP11 — — 6 —
Ni(ii)-IIP12 — — 8 —
Ni(ii)-IIP13 — — 4 10
Ni(ii)-IIP14 — — — 30
Ni(ii)-IIP15 — — — 40
Ni(ii)-IIP16 — — — 50
Scheme 4 Preparation of Ni(ii)-IIP and NIP.
Scheme 4

Preparation of Ni(ii)-IIP and NIP.

2.4 Adsorption experiments

The adsorption performance of Ni(ii)-IIP5 was assessed by a series of triplicate equilibrium adsorption experiments. Accurately weighed 0.0200 g of Ni(ii)-IIP5 and the corresponding NIP5 were placed in a 25 mL stoppered conical flask, and 10 mL of the prepared Ni(ii) solution was added. The reaction was placed in a thermostatic air bath shaker (at ambient temperature) for 12 h and filtered in a colorimetric tube. The concentration of Ni(ii) was determined with an UV-Vis spectrophotometer which proceeded under corresponding wavelength conditions. Finally, the equilibrium adsorption capacity Q e (mg/g) and the imprinting factor (α) were calculated according to Eqs. 1 and 2:

(1) Q e = ( C 0 − C e ) V M

(2) α = Q IIP Q NIP

where Q e (mg/g) is the equilibrium adsorption capacity, C 0 (mg/L) and C e (mg/L) are the initial and equilibrium concentrations of Ni(ii) in solution, respectively, V (mL) is the volume of the solution, and M (g) is the mass of Ni(ii)-IIP5 and NIP5.

2.5 Selectivity experiments

In order to obtain the selectivity of Ni(ii)-IIP5 for Ni(ii) adsorption, Cu(ii), Co(ii), and Cd(ii) were selected as competitive ions with the valence and ionic radius similar to that of the template ion Ni(ii), and a mixed solution with an initial concentration of 100.00 mg/L was prepared. Twenty milligram of Ni(ii)-IIP5 were added to 10 mL of the above mixed solution and shaken at room temperature for 12 h. In addition, the adsorption capacity of each ion was measured, and the selective parameters, such as the distribution coefficient (K d), selection factor (K), and relative selection factor (K′), of Ni(ii) ions were calculated by the following Eqs. 3–5:

(3) K d = ( C 0 − C e ) V w C e

(4) K = K d ( Ni ( II ) ) K d ( M )

(5) K ′ = K Ni(IIP)/M K Ni(NIP)/M

where K d, K, and K′ are the distribution coefficient, selectivity coefficient, and relative selectivity coefficient, respectively; C 0 and C e are the initial and equilibrium concentrations of metal ions (mg/L); V is the volume of the solution (mL); w is the mass of Ni(ii)-IIP5; and M is the mass of each metal ion.

3 Results and discussions

3.1 The effect of polymer preparation conditions

3.1.1 The effect of solvent types

The purpose of solvent is to provide chemical environment for polymerization process, it not only influences the morphology of polymers but also impacts the chelating of functional monomers with the template before polymerization (39,40). Metal ions are soluble in water easily and difficult to dissolve in organic solvents, but functional monomers, cross-linker, and initiator are hardly soluble in water. However, the experiments required that the prepolymer which is formed by the template ion Ni(ii) and the functional monomer and cross-linker coexisted homogeneously, so that the polymer can be maintained in binding sites during the polymerization process. Hence, the solvent must be a mixed solution which is composed of water and organic solvents. In this experiment, a mixed solvent of organic solvents (MeOH, EtOH, IPA, and DMF) and H2O were used as the solvent in the volume ratio of 1:1. The experimental results are shown in Figure 1. The polymer with the best adsorption capacity and imprinting effect were prepared using MeOH/H2O (v/v, 1:1) as the solvent, and the imprinting factor reached 1.27.

Figure 1 Effect of the types of solvent on adsorption properties.
Figure 1

Effect of the types of solvent on adsorption properties.

3.1.2 The effect of solvent ratio

The difference of solvent ratio mainly affected the tightness of the binding of the template ion and functional monomer. When the dosage of solvent was more or less in the preparation process, the texture of the prepared imprinted polymer would be hard and dense or loose (40). Therefore, in this study, the polymer was prepared by changing the solvent ratio (methanol:water, v:v = 1:1, 1:2, 2:1, 1:3, 3:1). As shown in Figure 2, the solvent ratio of 1:2 (methanol:water, v/v) was the best preparation condition.

Figure 2 Effect of the ratio of solvent on adsorption properties.
Figure 2

Effect of the ratio of solvent on adsorption properties.

3.1.3 The effect of functional monomer dosage

The dosage of functional monomers had a crucial effect on the adsorption performance of the ion-imprinted polymers. When the dosage of the added functional monomers was too little, the degree of coordination between monomers and template ions would be insufficient, resulting in the reduction of the polymer recognition sites and selectivity; when the amount of functional monomer was too high, the prepared polymer was not conducive to specific recognition (41). Therefore, the polymer was prepared by changing the molar ratio of template ions to functional monomers (1:2, 1:4, 1:6, and 1:8), and the experimental results can be seen from Figure 3. The imprinting factors are 1.22, 1.96, 1.08, and 1.24 for molar ratios of 1:2, 1:4, 1:6, and 1:8, respectively, and the Ni(ii)-IIP prepared with a molar ratio of 1:4 had preferable recognition performance. As a consequence, in the subsequent optimized experimental conditions, the molar ratio between the template ion and the functional monomer was 1:4 for synthesizing the polymer.

Figure 3 Effect of the dosage of functional monomer on adsorption properties.
Figure 3

Effect of the dosage of functional monomer on adsorption properties.

3.1.4 The effect of cross-linker dosage

One of the significant factors influencing the preparation of ion-imprinted polymers was the dosage of cross-linker. Its role was to fix the prepolymer formed by the template and monomer, by not only making the polymer to have a rigid structure and maintaining the recognition site after the template was eluted but also possessing certain chemical stability. The mass of cross-linker would slow the diffusion rate of the substrate into the polymer, which was not conducive for template mass transfer; nevertheless, a handful of cross-linker would cause the polymer to swell in the solution excessively, and reduce the selectivity of polymer to template ion (42). As shown in Figure 4, the imprinting factor reached 1.96 when the molar ratio of template ion and cross-linker was 1:20, and the recognition performance and adsorption capacity were favorable.

Figure 4 Effect of the dosage of cross-linker on adsorption properties.
Figure 4

Effect of the dosage of cross-linker on adsorption properties.

3.2 Equilibrium adsorption

3.2.1 Adsorption isotherm

Accurately weighed 20.00 mg of Ni(ii)-IIP5 and NIP5 were taken in a series of triangular conical flasks, added Ni(ii) solutions in a concentration range of 10.00–60.00 mg/mL, and the amount of imprinted polymer Ni(ii)-IIP5 and the corresponding NIP5 were investigated for template ion Ni(ii) in the solution with various concentrations, and the adsorption isotherm was drawn based on the experimental data (as shown in Figure 5).

Figure 5 The adsorption isotherm of Ni(ii)-IIP5 and NIP5.
Figure 5

The adsorption isotherm of Ni(ii)-IIP5 and NIP5.

It can be observed from the adsorption isotherm that the absorption capacity of Ni(ii)-IIP5 and NIP5 strengthened with the increase in the concentration, and the adsorption amount of Ni(ii)-IIP5 in the range of 10.00–60.00 mg/mL of Ni(ii) solution concentration was higher than the corresponding NIP5 adsorption amount. This is because the adsorption of NIP5 with template ions was non-specific mainly and there was no binding site, so the selectivity and adsorption capacity were weak. However, Ni(ii)-IIP5 contained holes that matched the size and configuration of the template ion, so it had better specific selective recognition performance.

In order to prove the adsorption performance of Ni(ii) ion on the surface of Ni(ii)-IIP5, the experimental data were analyzed and they fitted the adsorption isotherm models of Langmuir, Freundlich, and Scatchard models. Its related linear fitting equation was expressed as follows:

Langmuir isotherm:

(6) C e Q e = 1 Q m K L + C e Q m

Freundlich isotherm:

(7) ln Q e = ln K F + 1 n ln C e

where C e is the concentration of Ni(ii) ion at adsorption equilibrium, (mg/mL); Q e and Q m are the equilibrium adsorption capacity and maximum adsorption capacity of Ni(ii) ions by imprinted polymer, respectively (mg/g); K L is the Langmuir constant; and n and K F are the constants of Freundlich model.

The Langmuir and Freundlich isothermal adsorption models represented the monomolecular adsorption on heterogeneous surfaces and multimolecular adsorption on heterogeneous surfaces, respectively. The fitted curves are shown in Figure 6a and b. The relevant parameters of the fitted equation were calculated. It could be seen that the correlation coefficient obtained through the Langmuir and Freundlich adsorption isotherm models were both 1, indicating that Ni(ii)-IIP adsorbed Ni(ii) ions fitting the Langmuir and Freundlich isothermal adsorption models. Simultaneously, the result showed that monolayer adsorption and multimolecular layer adsorption were coexistent.

Figure 6 (a) Langmuir fitting isotherm of Ni(ii)-IIP5 and (b) Freundlich fitting isotherm of NIP5.
Figure 6

(a) Langmuir fitting isotherm of Ni(ii)-IIP5 and (b) Freundlich fitting isotherm of NIP5.

In addition, for demonstrating the binding properties of Ni(ii)-IIP for Ni(ii), the Scatchard isotherm adsorption model was proposed, and is expressed as Eq. 8.

Scatchard isotherm:

(8) Q e C = Q e − Q m K d

where Q e and Q m are the equilibrium adsorption capacity and maximum adsorption capacity of Ni(ii) ions by imprinted polymer (mg/g), respectively; C is the initial concentration (mg/mL) and K d is the Scatchard constant.

The fitting plot of the Scatchard adsorption model is shown in Figure 7. The Scatchard curve of the Ni(ii)-IIP was composed of two straight lines with a positive correlation. This showed that within the concentration range of this experiment, there were two different affinity binding sites in the adsorption process of Ni(ii)-IIP5. Among them, the K d value of high affinity binding site was 79.30 mg/mL, and the K d value of low affinity binding site was 305.26 mg/mL, the maximum apparent adsorption was due to the combined action of variety of sites.

Figure 7 Scatchard fitting isotherm of Ni(ii)-IIP5.
Figure 7

Scatchard fitting isotherm of Ni(ii)-IIP5.

3.2.2 Adsorption kinetics

Twenty milligram of Ni(ii)-IIP5 and NIP5 were dropped into stoppered conical flask, to which 10.00 mL of 50.00 mg/mL Ni(ii) solution was added with shaking at room temperature to measure the amount of change in substrate adsorption at different times. The kinetic adsorption curves of Ni(ii)-IIP5 and NIP5 are shown in Figure 8. Ni(ii)-IIP5 adsorbed for Ni(ii) in the first 5 min rapidly, and the adsorption speed of inter-ion slowed down significantly within 5–15 min, subsequently, it reached the adsorption equilibrium after 15 min. The reason of vast adsorption rate was because the surface of Ni(ii)-IIP5 had enough imprinting cavities to match Ni(ii) at the initial stage, and the adsorption site had strong coordination with Ni(ii) so that the diffusion resistance was small and mass transfer rate of Ni(ii) ions was fast; whereas when the adsorption of the imprinted sites on polymer surface reached saturation, the resistance of the imprinted ions to the internal transfer of Ni(ii)-IIP5 increased, causing adsorption rate of Ni(ii)-IIP5 for Ni(ii) to decrease.

Figure 8 The kinetic adsorption curves of Ni(ii)-IIP5 and NIP5.
Figure 8

The kinetic adsorption curves of Ni(ii)-IIP5 and NIP5.

In order to investigate the adsorption kinetics of ion-imprinted polymers, pseudo-first-order kinetic model, pseudo-second-order kinetic model, and ion diffusion models were used to fit experimental data to determine the kinetic process of adsorption. Its linear fitting Eqs. 9–11 are as follows:

Pseudo-first-order kinetic model:

(9) log ( Q e − Q t )=log Q e − k 1 t 2 .303

Pseudo-second-order kinetic model:

(10) t Q t = 1 k 2 Q e 2 + t Q e

Ion diffusion model:

(11) Q t = K p t 1 / 2 + C

where Q e and Q t are the equilibrium adsorption capacity and adsorption capacity at time t of Ni(ii) ions by imprinted polymer (mg/g), respectively; k 1 and k 2 are the rate constants of the pseudo-first-order and pseudo-second-order of these equations; K p is the rate constant of ion diffusion model.

The fitting models of Ni(ii)-IIP for Ni(ii) adsorption is shown in Figure 9a–c, and the kinetic parameters were calculated from the equations fitted by the three models as shown in Table 2. It can be seen that k 1 is equal to 0.0046, correlation coefficient R 2 is 0.99962, and Q e is 5248.10 mg/g. The pseudo-second-order kinetics model showed that k 2 is equal to 0.012, correlation coefficient R 2 is 0.99011, and Q e is 76.90 mg/g; The ion diffusion model showed that K p is equal to 72.86 and the correlation coefficient R 2 is 0.88817. The linear correlation coefficient of the curve fitted by the pseudo-first-order kinetic model was more than the others, which indicated that the process of adsorption was more consistent with the pseudo-first-order kinetic model.

Figure 9 (a) Pseudo-first-order model, (b) Pseudo-second-order model, and (c) Ion diffusion model.
Figure 9

(a) Pseudo-first-order model, (b) Pseudo-second-order model, and (c) Ion diffusion model.

Table 2

Linear fitting parameters of adsorption kinetics of Ni(ii)-IIP5

Pseudo-first-order Pseudo-second-order Ion diffusion model
Q e (mg/g) K 1 R 2 Q e (mg/g) K 2 R 2 K p C R 2
5248.1 0.0046 0.99962 76.9 0.012 0.99011 72.86 368.32 0.88817

3.2.3 Selectivity experiments

To evaluate the selectivity of Ni(ii)-IIP5 and NIP5, Cu(ii), Co(ii), and Cd(ii) ions which had similar charge numbers and ionic radius as that of the template ion were chosen as the competitive ions for the selective experiments. The data of K d, K, and K′ for Ni(ii) ions as contrasted with other competing ions are shown in Table 3. Under the same experimental conditions, K d values of Ni(ii)-IIP5 for Ni(ii) ions were greater than that of NIP5, while the K value of Ni(ii)-IIP5 was much greater than that of other competitive ions. The K′ values of Ni2+/Cd2+, Ni2+/Co2+, and Ni2+/Cu2+ were 1.1, 1.07, and 1.08, respectively, which were more than 1. The results indicated that Ni(ii)-IIP5 had strong specific recognition for target ions Ni(ii) as compared to other interfering ions, that is these data revealed that Ni(ii)-IIP5 had specific binding sites, which possessed favorable selectivity for Ni(ii).

Table 3

Parameters of ion competitive adsorption study for Ni(ii)-IIP5 and NIP5

Metal ions Ni(ii)-IIP5 NIP5 K′
K d K Ni/M K d K Ni/M
Ni(ii) 2.076 1.918
Cd(ii) 0.532 3.902 0.540 3.549 1.100
Co(ii) 1.623 1.279 1.618 1.186 1.079
Cu(ii) 1.268 1.637 1.274 1.505 1.088

3.2.4 Effect of pH on adsorption of Ni(ii)

The influence of pH is of vital importance for containing maximum adsorption with polymers (43,44). Hence, 20.00 mg of Ni(ii)-IIP5 and NIP5 were immersed in 10 mL of 50.00 mg/L solution of Ni(ii) under different pH conditions from 1–10 for 12 h. As can be seen from Figure 10, the curves of Ni(ii)-IIP5 and NIP5 have similar trend. The adsorption capacity of Ni(ii)-IIP5 for Ni(ii) decreased between the pH values of 1–3, it may ascribe to the higher concentration of H+ which produces competitive adsorption of Ni(ii) and occupies the adsorption sites of Ni(ii). The competitive ability of Ni(ii) was reduced as the acidity of the solution decreased and the adsorption effect of Ni(ii)-IIP5 was obviously enhanced, maximum absorption capacity was obtained at pH = 4. This study also demonstrated that the adsorption amount would not have noticeable change with the increase in pH at 5–10; this range of pH has little impact on the adsorption process, and the Ni(ii)-IIP5 represents stable property. This research also illustrates that the preparation of Ni(ii)-IIP5 under optimal conditions has favorable stability with the range of alkaline, so it will be used in a wider application domain.

Figure 10 Effect of pH on adsorption properties.
Figure 10

Effect of pH on adsorption properties.

3.3 Characterization

3.3.1 SEM analysis

The morphological images of the Ni(ii)-IIP5, NIP5, Ni(ii)-IIP5 after adsorption, and EDS analysis of loaded Ni(ii) of Ni(ii)-IIP5 were characterized by SEM as shown in Figure 11a–d. There was significant difference in the surface morphology between Ni(ii)-IIP5 and NIP5, wherein Ni(ii)-IIP5 exhibited porous and rough surface on account of imprinting of Ni(ii) ion above polymer as shown in Figure 11a. Figure 11b shows an obvious relative flat surface and compact texture with less porous surface; however, an apparent increase in roughness and porous surface were observed after adsorption of Ni(ii) as shown in Figure 11c. Figure 11d expresses the EDS analysis of image (c). This indicates that the Ni ions were successfully adsorbed by Ni(ii)-IIP5.

Figure 11 (a) SEM images of Ni(ii)-IIP5, (b) NIP5, (c) Ni(ii)-IIP5 after adsorption, and (d) EDS analysis of image (c).
Figure 11

(a) SEM images of Ni(ii)-IIP5, (b) NIP5, (c) Ni(ii)-IIP5 after adsorption, and (d) EDS analysis of image (c).

3.3.2 BET analysis

The adsorption–desorption isotherms and surface properties which contained surface area (m2/g), average pore diameter (nm), and pore volume (cm3/g) of Ni(ii)-IIP5 and NIP5 are shown in Figure 12a and b and Table 4, respectively. They were obtained by BET theory and Barrett–Joyner–Halenda (BJH) theory. It can be seen from the figure that the shapes of the adsorption/desorption isotherms of Ni(ii)-IIP5 and NIP5 were fitted to the classic IV isotherms in the IUPAC classification method, which were typical characteristics of mesoporous materials. The pore size in Table 4 also proved that it was a mesoporous material. It could be seen that the BET surface area of Ni(ii)-IIP5 and NIP5 were 89.04 and 67.36 m2/g and pore volumes were 0.28 and 0.14 cm3/g, respectively. The parameters of Ni(ii)-IIP5 were all less than that of NIP5. The results indicated that there was highly porous structure with imprinted material. After adsorption, the obvious changes in BET surface area, total pore volume, and average pore diameter were observed on Ni(ii)-IIP5 and NIP5, indicating that Ni(ii)-IIP5 possessed the active sites which had identical shape and size of imprinting ion Ni(ii) on adsorbent.

Figure 12 Nitrogen adsorption and desorption isotherm of Ni(ii)-IIP5 (a) and NIP5 (b).
Figure 12

Nitrogen adsorption and desorption isotherm of Ni(ii)-IIP5 (a) and NIP5 (b).

Table 4

Nitrogen adsorption data of Ni(ii)-IIP5 and NIP5

Polymer Surface area (m2/g) Average pore diameter (nm) Pore volume (cm3/g)
Ni(ii)-IIP5 89.04 12.4 0.28
NIP5 67.36 8.18 0.14

3.3.3 TGA analysis

Thermogravimetric analysis (TGA) is a thermal analysis technique applied to material analysis extensively. In this experiment, the method of thermogravimetric was used to investigate the thermal stability of Ni(ii)-IIP5 and NIP5 by the TGA curves. The analysis is carried out under conditions, such as temperature in the range of 40–600°C, nitrogen atmosphere, and the heating rate of 20°C/min.

The curve of TGA is shown in Figure 13. Ni(ii)-IIP5 and NIP5 have similar linear trends, all of them have preferable stability in the range of 40–270°C which without apparent mass loss, it may cause by evaporation of water, both of them with roughly trend weight loss from 270°C to 420°C. In this condition, it is possible that the framework of polymers was damaged at high degradation temperature and some organic components decomposed following the increase in the temperature. Calculated from the curve data that Ni(II)-IIP5 and NIP5 with total mass loss of 93% and 81% at the temperature of 420°C, respectively. The result indicated that both of them have a good thermal stability and these polymers will probably evaporate completely at temperature above 600°C. This provides a new mind for the preparation of a highly efficient and environmentally friendly adsorbent material that can be recovered at high temperature after repeated usage, which hardly causes secondary pollution.

Figure 13 TGA curve of Ni(ii)-IIP5 and NIP5.
Figure 13

TGA curve of Ni(ii)-IIP5 and NIP5.

3.4 Regeneration and reusability

Regeneration and recyclability of adsorption material are often used to evaluate its properties. Excellent imprinted materials should not only have superior adsorption capacity but also have good regeneration performance, which is of great significance to reduce the cost of water treatment in actual production. In this study, the method of desorption and regeneration of adsorbent is carried out as follows: Ni(ii)-IIP5 after adsorption was dried and ground, and then reflux-extracted at a temperature of 70°C for 24 h, the mixed ratio of methanol and acetic acid with 9:1, after extraction and dried, and the regenerated adsorbent was obtained. As shown in Figure 14, the adsorption and desorption rates of Ni(ii)-IIP5 were 90% and 85% after first usage, respectively. And after using it a few times, Ni(ii)-IIP5 still maintained good adsorption performance, and the removal rate was still about 80%. It is shown that the number of regeneration did not affect the adsorption process, and the prepared Ni(ii)-IIP5 had a higher adsorption rate and stability for Ni ions.

Figure 14 Regeneration and reusability of Ni(ii)-IIP5.
Figure 14

Regeneration and reusability of Ni(ii)-IIP5.

3.5 Comparison with other methods

To attest the advantages of Ni-IIP5, it was compared with other recent studies (45,46,47,48,49,50) with regard to maximum adsorption for recovery of Ni(ii) as shown in Table 5. It can be seen that there exists difference in the adsorption capacity of Ni(ii) wherein the adsorption materials were prepared by various methods. This study revealed that the prepared Ni(ii)-IIP has a large amount of adsorption capacity by contrast, and the results indicated that Ni-IIP5 can be a great potential adsorbent for heavy metal ion adsorption.

Table 5

Comparison of adsorption capacity of nickel ion using different adsorbents

Adsorbents Q e (mg/g) References
Magnetic imprinted polymer 158.73 (45)
Multi-wall carbon nanotube 115.8 (46)
Bentonite/GO composite 402.5 (47)
Clay 2,590 (48)
ZIF-8/Fly ash composite 93 (49)
Paper-based adsorbent 317.5 (50)
Ni(ii) ionimprinted polymer 5,387 This work

4 Conclusion

In this study, a favorable performance of Ni(ii)-IIP (Ni-IIP5) by using a novel functional monomer NDTEA had been prepared by precipitation polymerization method. The Ni-IIP5 was adsorbed for Ni(ii) in the solution containing Ni(ii) which was obtained through optimizing various affecting parameters. It exhibited satisfactory adsorption ability, the high adsorption capacity and imprinting factor were 5387.00 mg/g and 1.96, respectively. The morphological structure and properties were characterized by SEM, BET, and TGA, and the result showed a series of excellent properties including thermal stability, porous structure, and specific selectivity identity with the performance of Ni-IIP5 for Ni(ii). The result simultaneously indicated that Ni-IIP5 was a typical mesoporous material. The adsorption process of Ni-IIP5 for Ni(ii) was fitted with Pseudo-first-order adsorption models, and Ni-IIP5 performed better selectivity with competing ions in the solution. These preferable properties would lead this imprinted polymer to have a potential application for separating and gathering Ni(ii) in wastewater, and this novel functional monomer NDTEA exhibited an attractive application prospect in the functional adsorption material fields.

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Acknowledgements

The authors acknowledge the financial support provided by the National Natural Science Foundation of China, also express sincere gratitude to co-authors who have made invaluable contributions, both directly and indirectly to my research.

  1. Funding information: This work was supported by the National Natural Science Foundation of China (No. 21764008).

  2. Author contributions: Li Zhao: methodology, writing – original draft, data curation; Xianzhi Hu: supervision, validation; Futing Zi: supervision; Yingmei Liu: software; Deqiong Hu: investigation, data analysis; Peng Li: investigation; Huiling Cheng: project administration, funding acquisition, writing – review and editing.

  3. Conflict of interest: Authors state no conflict of interest.

Appendix

Compound 2: 1H NMR (400 MHz, CDCl3) δ: 8.02(s, 1H), 8.20(d, J = 5.4 Hz, 2H), 7.82(s, 1H), 7.43–7.49(m, 1H), 6.86–6.91(m, 1H), 6.79–6.84(m, 1H), 5.34(d, J = 7.5 Hz, 1H), 4.85(br, 2H), 4.43–4.47(dd, J = 2.6 Hz, 2.6 Hz, 1H), 4.22–4.28(dd, J = 8.2 Hz, 8.2 Hz, 1H); 13C NMR (100 MHz, CDCl3) δ: 164.2(d, J C–F = 12.1 Hz), 161.7(d, J C–F = 11.8 Hz), 160.9(d, J C–F = 11.7 Hz), 158.4(d, J C–F = 11.7 Hz), 151.8, 144.0, 128.7(q, J C–F = 5.8 Hz), 123.5(d, J C–F = 13.7 Hz), 112.0(q, J C–F = 3.4 Hz), 104.3(t, J C–F = 25.3 Hz), 66.6, 55.5.

Compound 3: 1H NMR (400 MHz, DMSO-d6) δ: 8.43(s, 1H), 8.20(d, J = 5.4 Hz, 2H), 7.95(s, 1H), 7.73(s, 1H), 7.50–7.56(m, 1H), 7.18–7.23(m, 1H), 7.08–7.13(m, 1H), 5.93–6.02(dd, J = 7.5 Hz, 15.2 Hz, 1H), 5.71(d, J = 15.3 Hz, 1H), 5.34(d, J = 10.6 Hz, 1H), 5.16(s, 1H), 4.20(s, 1H), 4.16(s, 1H); 13C NMR (100 MHz, DMSO-d6) δ: 163.5(d, J C–F = 12.4 Hz), 161.0(q, J C–F = 8.7 Hz), 158.5, 158.4(d, J C–F = 12.1 Hz), 151.7, 145.2, 129.8(q, J C–F = 6.2 Hz), 128.8, 125.7(d, J C–F = 3.7 Hz), 113.9, 112.1(t, J C–F = 3.6 Hz), 104.3(t, J C–F = 25.7 Hz), 65.3, 55.1, 51.9.

Figure A1 1H NMR spectra of compound 2.
Figure A1

1H NMR spectra of compound 2.

Figure A2 13C NMR spectra of compound 2.
Figure A2

13C NMR spectra of compound 2.

Figure A3 1H NMR spectra of compound 3.
Figure A3

1H NMR spectra of compound 3.

Figure A4 13C NMR spectra of compound 3.
Figure A4

13C NMR spectra of compound 3.

References

(1) Wang L, Yang X, Liu W, Liu M, Chen H. Nickel contamination of laterite soil by hydraulic fracturing flowback water: Geochemical behaviour and policy implications. Soil Use Manag. 2020;37(2):330–41. 10.1111/sum.12620.Suche in Google Scholar

(2) Chen X, Yu J, Chen Z, Zhang H, Cheng W, Bai F, et al. Acetotrophic methanogens are sensitive to long-term nickel contamination in paddy soil. Env Sci Process Impacts. 2020;22(4):1014–25. 10.1039/d0em00029a.Suche in Google Scholar PubMed

(3) Genchi G, Carocci A, Lauria G, Stefania Sinicropi M, Catalano A. Nickel: human health and environmental toxicology. Int J Env Res Public Health. 2020;17(3):679–700. 10.3390/ijerph17030679.Suche in Google Scholar PubMed PubMed Central

(4) Proshad R, Abdullah Al M, Islam MS, Khadka S, Kormoker T, Uddin M, et al. Investigation of trace metals in riverine waterways of Bangladesh using multivariate analyses: spatial toxicity variation and potential health risk assessment. Env Sci Pollut Res Int. 2021;28:31872–84. 10.1007/s11356-021-13077-4.Suche in Google Scholar PubMed

(5) Nazaripour M, Reshadi MAM, Mirbagheri SA, Nazaripour M, Bazargan A. Research trends of heavy metal removal from aqueous environments. J Env Manage. 2021;287:112322. 10.1016/j.jenvman.2021.112322.Suche in Google Scholar PubMed

(6) Rafiee Z, Golriz L, Karimipour G, Kowkabi S. Preparation and properties of polyimides having porphyrin moieties for heavy metals removal. Polym Bull. 2020;78(1):481–92. 10.1007/s00289-020-03118-2.Suche in Google Scholar

(7) Gao J, Yuan Y, Yu Q, Yan B, Qian Y, Wen J, et al. Bio-inspired antibacterial cellulose paper-poly(amidoxime) composite hydrogel for highly efficient uranium(vi) capture from seawater. Chem Commun (Camb). 2020;56(28):3935–8. 10.1039/c9cc09936k.Suche in Google Scholar PubMed

(8) Zhang Y, Duan X. Chemical precipitation of heavy metals from wastewater by using the synthetical magnesium hydroxy carbonate. Water Sci Technol. 2020;81(6):1130–6. 10.2166/wst.2020.208.Suche in Google Scholar PubMed

(9) Pohl A. Removal of heavy metal ions from water and wastewaters by sulfur-containing precipitation agents. Water, Air, Soil Pollut. 2020;231(10):503. 10.1007/s11270-020-04863-w.Suche in Google Scholar

(10) Hu H, Zhang Q, Li X, Wu L, Liu Y. Efficient heterogeneous precipitation and separation of iron in copper-containing solution using dolomite. Sep Purif Technol. 2020;248:248. 10.1016/j.seppur.2020.117021.Suche in Google Scholar

(11) Ibrahim Y, Naddeo V, Banat F, Hasan SW. Preparation of novel polyvinylidene fluoride (PVDF)-Tin(iv) oxide (SnO2) ion exchange mixed matrix membranes for the removal of heavy metals from aqueous solutions. Sep Purif Technol. 2020;250:250. 10.1016/j.seppur.2020.117250.Suche in Google Scholar

(12) Laatikainen M, Sainio T. Ion exchange in complexing media – Nickel removal from ammoniacal ammonium sulfate solutions. Chem Eng J. 2019;373:831–9. 10.1016/j.cej.2019.05.128.Suche in Google Scholar

(13) Krstić V, Pešovski B. Novel multifunctional two layer catalytic activated titanium electrodes for various technological and environmental processes. Arab J Chem. 2021;14(4):103101. 10.1016/j.arabjc.2021.103101.Suche in Google Scholar

(14) Li T, Duan Z, Qin R, Xu X, Li B, Liu Y, et al. Enhanced characteristics and mechanism of Cu(ii) removal from aqueous solutions in electrocatalytic internal micro-electrolysis fluidized-bed. Chemosphere. 2020;250:126225. 10.1016/j.chemosphere.2020.126225.Suche in Google Scholar PubMed

(15) Bandehali S, Parvizian F, Moghadassi A, Shen J, Hossein SM. Improvement in separation performance of PEI-based nanofiltration membranes by using L-cysteine functionalized POSS-TiO2 composite nanoparticles for removal of heavy metal ion. Korean J Chem Eng. 2020;37(9):1552–64. 10.1007/s11814-020-0535-0.Suche in Google Scholar

(16) Modi A, Bellare J. Zeolitic imidazolate framework-67/carboxylated graphene oxide nanosheets incorporated polyethersulfone hollow fiber membranes for removal of toxic heavy metals from contaminated water. Sep Purif Technol. 2020;249:249. 10.1016/j.seppur.2020.117160.Suche in Google Scholar

(17) Pei X, Gan L, Tong Z, Gao H, Meng S, Zhang W, et al. Robust cellulose-based composite adsorption membrane for heavy metal removal. J Hazard Mater. 2021;406:124746. 10.1016/j.jhazmat.2020.124746.Suche in Google Scholar PubMed

(18) Godwin PM, Pan Y, Xiao H, Afzal MT. Progress in preparation and application of modified biochar for improving heavy metal ion removal from wastewater. J Bioresour Bioprod. 2019;4(1):31–42. 10.21967/jbb.v4i1.180.Suche in Google Scholar

(19) Wołowicz A, Wawrzkiewicz M. Screening of ion exchange resins for hazardous Ni(ii) removal from aqueous solutions: kinetic and equilibrium batch adsorption method. Processes. 2021;9(2):285. 10.3390/pr9020285.Suche in Google Scholar

(20) Foong CY, Wirzal MDH, Bustam MA. A review on nanofibers membrane with amino-based ionic liquid for heavy metal removal. J Mol Liq. 2020;297:297. 10.1016/j.molliq.2019.111793.Suche in Google Scholar

(21) Salama ES, Roh HS, Dev S, Khan MA, Abou-Shanab R, Chang SW, et al. Algae as a green technology for heavy metals removal from various wastewater. World J Microbiol Biotechnol. 2019;35(5):75. 10.1007/s11274-019-2648-3.Suche in Google Scholar PubMed

(22) Lim ZE, Thai QB, Le DK, Luu TP, Nguyen PTT, Do NHN, et al. Functionalized pineapple aerogels for ethylene gas adsorption and nickel(ii) ion removal applications. J Environ Chem Eng. 2020;8(6):104524. 10.1016/j.jece.2020.104524.Suche in Google Scholar

(23) Aijaz MO, Karim MR, Alharbi HF, Alharthi NH, Al-Mubaddel FS, Abdo HS. Magnetic/polyetherimide-acrylonitrile composite nanofibers for nickel ion removal from aqueous solution. Membr (Basel). 2021;11(1):E50–62. 10.3390/membranes11010050.Suche in Google Scholar PubMed PubMed Central

(24) Dong C, Shi H, Han Y, Yang Y, Wang R, Men J. Molecularly imprinted polymers by the surface imprinting technique. Eur Polym J. 2021;145:145. 10.1016/j.eurpolymj.2020.110231.Suche in Google Scholar

(25) Sarpong KA, Xu W, Huang W, Yang W. The development of molecularly imprinted polymers in the clean-up of water pollutants: a review. Am J Anal Chem. 2019;10(05):202–26. 10.4236/ajac.2019.105017.Suche in Google Scholar

(26) Ding X, Heiden PA. Recent developments in molecularly imprinted nanoparticles by surface imprinting techniques. Macromol Mater Eng. 2014;299(3):268–82. 10.1002/mame.201300160.Suche in Google Scholar

(27) Dobrzyńska J, Dąbrowska M, Olchowski R, Zieba E, Dobrowolski R. Development of a method for removal of platinum from hospital wastewater by novel ion-imprinted mesoporous organosilica. J Environ Chem Eng. 2021;9(4):105302. 10.1016/j.jece.2021.105302.Suche in Google Scholar

(28) Chen L, Lu Y, Qin M, Liu F, Huang L, Wang J, et al. Preparation of “ion-imprinting” difunctional magnetic fluorescent nanohybrid and its application to detect cadmium ions. Sens (Basel). 2020;20(4):995–1005. 10.3390/s20040995.Suche in Google Scholar PubMed PubMed Central

(29) Nchoe OB, Klink MJ, Mtunzi FM, Pakade VE. Synthesis, characterization, and application of β-cyclodextrin-based ion-imprinted polymer for selective sequestration of Cr(vi) ions from aqueous media: Kinetics and isotherm studies. J Mol Liq. 2020;298:298. 10.1016/j.molliq.2019.111991.Suche in Google Scholar

(30) Karrat A, Lamaoui A, Amine A, Palacios-Santander JM, Cubillana-Aguilera L. Applications of chitosan in molecularly and ion imprinted polymers. Chem Afr. 2020;3(3):513–33. 10.1007/s42250-020-00177-w.Suche in Google Scholar

(31) Mesa RLM, Villa JEL, Khan S, Peixoto RRA, Morgano MA, Concalves LM, et al. Rational design of an ion-imprinted polymer for aqueous methylmercury sorption. Nanomaterials (Basel). 2020;10(12):2541–55. 10.3390/nano10122541.Suche in Google Scholar PubMed PubMed Central

(32) Jalilian R, Taheri A. Synthesis and application of a novel core-shell-shell magnetic ion imprinted polymer as a selective adsorbent of trace amounts of silver ions. e-Polymers. 2018;18(2):123–34. 10.1515/epoly-2017-0108.Suche in Google Scholar

(33) Yang P, Cao H, Mai D, Ye T, Wu X, Yuan M, et al. A novel morphological ion imprinted polymers for selective solid phase extraction of Cd(ii): Preparation, adsorption properties and binding mechanism to Cd(ii). Reactive Funct Polym. 2020;151:104569. 151.10.1016/j.reactfunctpolym.2020.104569.Suche in Google Scholar

(34) Diouf A, El Bari N, Bouchikhi B. A novel electrochemical sensor based on ion imprinted polymer and gold nanomaterials for nitrite ion analysis in exhaled breath condensate. Talanta. 2020;209:120577. 10.1016/j.talanta.2019.120577.Suche in Google Scholar PubMed

(35) Wang Z, Zhang D, Xiao X, Su C, Li Z, Xue J, et al. A highly sensitive and selective sensor for trace uranyl (vi) ion based on a graphene-coated carbon paste electrode modified with ion imprinted polymer. Microchem J. 2020;155:104767. 10.1016/j.microc.2020.104767.Suche in Google Scholar

(36) Dahaghin Z, Kilmartin PA, Mousavi HZ. Novel ion imprinted polymer electrochemical sensor for the selective detection of lead(ii). Food Chem. 2020;303:125374. 125374.10.1016/j.foodchem.2019.125374.Suche in Google Scholar

(37) Xi Y, Shi H, Liu R, Yin X, Yang L, Huang M, et al. Insights into ion imprinted membrane with a delayed permeation mechanism for enhancing Cd(2+) selective separation. J Hazard Mater. 2021;416:125772. 10.1016/j.jhazmat.2021.125772.Suche in Google Scholar PubMed

(38) Liu Y, Hu D, Hu X, Chen S, Zhao L, Chen Y, et al. Preparation and characterization of chromium(vi) ion-imprinted composite membranes with a specifically designed functional monomer. Anal Lett. 2019;53(7):1113–39. 10.1080/00032719.2019.1698589.Suche in Google Scholar

(39) Venkata Jagadeesh R, Lakshminarayanan V. Electrochemical investigation on adsorption kinetics of long chain alkylsilanes and influence of solvents on their self-assembly and electron transfer behavior on indium tin oxide. J Appl Electrochem. 2020;50(11):1129–38. 10.1007/s10800-020-01467-4.Suche in Google Scholar

(40) Shatla AS, Bawol PP, Baltruschat H. Adsorption of iodide and bromide on Au(111) electrodes from aprotic electrolytes: role of the solvent. ChemElectroChem. 2020;7(23):4782–93. 10.1002/celc.202001296.Suche in Google Scholar

(41) Zhao G, Liu J, Liu M, Han X, Peng Y, Tian X, et al. Synthesis of molecularly imprinted polymer via emulsion polymerization for application in solanesol separation. Appl Sci. 2020;10(8):2868. 10.3390/app10082868.Suche in Google Scholar

(42) Liu Y, Wu Y, Lin H, Xiao Y, Zhu X, Zhang K, et al. Study on an injectable biomedical paste using cross-linked sodium hyaluronate as a carrier of hydroxyapatite particles. Carbohydr Polym. 2018;195:378–86. 10.1016/j.carbpol.2018.04.093.Suche in Google Scholar PubMed

(43) Zhang M, Zhang Z, Peng Y, Feng L, Li X, Zhao C, et al. Novel cationic polymer modified magnetic chitosan beads for efficient adsorption of heavy metals and dyes over a wide pH range. Int J Biol Macromol. 2020;156:289–301. 10.1016/j.ijbiomac.2020.04.020.Suche in Google Scholar PubMed

(44) Yang W, Wang Y, Wang Q, Wu J, Jian S. Magnetically separable and recyclable Fe3O4@PDA covalent grafted by L-cysteine core-shell nanoparticles toward efficient removal of Pb2+. Vacuum. 2021;189:189. 10.1016/j.vacuum.2021.110229.Suche in Google Scholar

(45) Kumar S, Balouch A, Alveroglu E, Jagirani MS, AbdullahMughal MA. Fabrication of nickel-tagged magnetic imprinted polymeric network for the selective extraction of Ni(ii) from the real aqueous samples. Env Sci Pollut Res Int. 2021;28:40022–34. 10.1007/s11356-021-13375-x.Suche in Google Scholar PubMed

(46) Rahmati N, Rahimnejad M, Pourali M, Muallah SK. Effective removal of nickel ions from aqueous solution using multi-wall carbon nanotube functionalized by glycerol-based deep eutectic solvent. Colloid Interface Sci Commun. 2021;40:40. 10.1016/j.colcom.2020.100347.Suche in Google Scholar

(47) Chang YS, Au PI, Mubarak NM, Khalid M, Jagadish P, Walvekar R, et al. Adsorption of Cu(ii) and Ni(ii) ions from wastewater onto bentonite and bentonite/GO composite. Env Sci Pollut Res Int. 2020;27(26):33270–96. 10.1007/s11356-020-09423-7.Suche in Google Scholar PubMed

(48) Dammak N, Bel Hadjltaief H, Hamza W, Benzina M. Sonosynthesis of iron-supported clay for heavy metal removal via sonoassisted adsorption process. Arab J Sci Eng. 2020;45(9):7645–54. 10.1007/s13369-020-04754-6.Suche in Google Scholar

(49) Wang C, Yang R, Wang H. Synthesis of ZIF-8/fly ash composite for adsorption of CU(2+), ZN(2+) and NI(2+) from aqueous solutions. Mater (Basel). 2020;13(1):214–28. 10.3390/ma13010214.Suche in Google Scholar PubMed PubMed Central

(50) Awang NA, Salleh WNW, Hasbullah H, Ahmad SZN, Ismail NH, Rosman N, et al. Modified recycled paper-based adsorbent for nickel removal. IOP Conf Series: Mater Sci Eng. 2020;736:736. 10.1088/1757-899x/736/7/072001.Suche in Google Scholar
Received: 2021-04-27
Revised: 2021-06-21
Accepted: 2021-06-22
Published Online: 2021-08-11

© 2021 Li Zhao et al., published by De Gruyter

This work is licensed under the Creative Commons Attribution 4.0 International License.

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  45. Study on controlling nicotine release from snus by the SIPN membranes
  46. Catalase biosensor based on the PAni/cMWCNT support for peroxide sensing
  47. Synthesis and characterization of different soybean oil-based polyols with fatty alcohol and aromatic alcohol
  48. Molecularly imprinted electrospun fiber membrane for colorimetric detection of hexanoic acid
  49. Poly(propylene carbonate) networks with excellent properties: Terpolymerization of carbon dioxide, propylene oxide, and 4,4ʹ-(hexafluoroisopropylidene) diphthalic anhydride
  50. Polypropylene/graphene nanoplatelets nanocomposites with high conductivity via solid-state shear mixing
  51. Mechanical properties of fiber-reinforced asphalt concrete: Finite element simulation and experimental study
  52. Applying design of experiments (DoE) on the properties of buccal film for nicotine delivery
  53. Preparation and characterizations of antibacterial–antioxidant film from soy protein isolate incorporated with mangosteen peel extract
  54. Preparation and adsorption properties of Ni(ii) ion-imprinted polymers based on synthesized novel functional monomer
  55. Rare-earth doped radioluminescent hydrogel as a potential phantom material for 3D gel dosimeter
  56. Effects of cryogenic treatment and interface modifications of basalt fibre on the mechanical properties of hybrid fibre-reinforced composites
  57. Stable super-hydrophobic and comfort PDMS-coated polyester fabric
  58. Impact of a nanomixture of carbon black and clay on the mechanical properties of a series of irradiated natural rubber/butyl rubber blend
  59. Preparation and characterization of a novel composite membrane of natural silk fiber/nano-hydroxyapatite/chitosan for guided bone tissue regeneration
  60. Study on the thermal properties and insulation resistance of epoxy resin modified by hexagonal boron nitride
  61. A new method for plugging the dominant seepage channel after polymer flooding and its mechanism: Fracturing–seepage–plugging
  62. Analysis of the rheological property and crystallization behavior of polylactic acid (Ingeo™ Biopolymer 4032D) at different process temperatures
  63. Hybrid green organic/inorganic filler polypropylene composites: Morphological study and mechanical performance investigations
  64. In situ polymerization of PEDOT:PSS films based on EMI-TFSI and the analysis of electrochromic performance
  65. Effect of laser irradiation on morphology and dielectric properties of quartz fiber reinforced epoxy resin composite
  66. The optimization of Carreau model and rheological behavior of alumina/linear low-density polyethylene composites with different alumina content and diameter
  67. Properties of polyurethane foam with fourth-generation blowing agent
  68. Hydrophobicity and corrosion resistance of waterborne fluorinated acrylate/silica nanocomposite coatings
  69. Investigation on in situ silica dispersed in natural rubber latex matrix combined with spray sputtering technology
  70. The degradable time evaluation of degradable polymer film in agriculture based on polyethylene film experiments
  71. Improving mechanical and water vapor barrier properties of the parylene C film by UV-curable polyurethane acrylate coating
  72. Thermal conductivity of silicone elastomer with a porous alumina continuum
  73. Copolymerization of CO2, propylene oxide, and itaconic anhydride with double metal cyanide complex catalyst to form crosslinked polypropylene carbonate
  74. Combining good dispersion with tailored charge trapping in nanodielectrics by hybrid functionalization of silica
  75. Thermosensitive hydrogel for in situ-controlled methotrexate delivery
  76. Analysis of the aging mechanism and life evaluation of elastomers in simulated proton exchange membrane fuel cell environments
  77. The crystallization and mechanical properties of poly(4-methyl-1-pentene) hard elastic film with different melt draw ratios
  78. Review Articles
  79. Aromatic polyamide nonporous membranes for gas separation application
  80. Optical elements from 3D printed polymers
  81. Evidence for bicomponent fibers: A review
  82. Mapping the scientific research on the ionizing radiation impacts on polymers (1975–2019)
  83. Recent advances in compatibility and toughness of poly(lactic acid)/poly(butylene succinate) blends
  84. Topical Issue: (Micro)plastics pollution - Knowns and unknows (Guest Editor: João Pinto da Costa)
  85. Simple pyrolysis of polystyrene into valuable chemicals
  86. Topical Issue: Recent advances of chitosan- and cellulose-based materials: From production to application (Guest Editor: Marc Delgado-Aguilar)
  87. In situ photo-crosslinking hydrogel with rapid healing, antibacterial, and hemostatic activities
  88. A novel CT contrast agent for intestinal-targeted imaging through rectal administration
  89. Properties and applications of cellulose regenerated from cellulose/imidazolium-based ionic liquid/co-solvent solutions: A short review
  90. Towards the use of acrylic acid graft-copolymerized plant biofiber in sustainable fortified composites: Manufacturing and characterization
https://doi.org/10.1515/epoly-2021-0055
Schlagwörter für diesen Artikel
Ni(ii) ion; novel functional monomer; NDTEA; Ni(ii) ion-imprinted polymer; selectivity
Creative Commons
BY 4.0

Artikel in diesem Heft

  1. Research Articles
  2. Research on the mechanism of gel accelerator on gel transition of PAN solution by rheology and dynamic light scattering
  3. Gel point determination of gellan biopolymer gel from DC electrical conductivity
  4. Composite of polylactic acid and microcellulose from kombucha membranes
  5. Synthesis of highly branched water-soluble polyester and its surface sizing agent strengthening mechanism
  6. Fabrication and characterization of poly(3-hydroxybutyrate-co-3-hydroxyhexanoate) modified with nano-montmorillonite biocomposite
  7. Fabrication of N-halamine polyurethane films with excellent antibacterial properties
  8. Formulation and optimization of gastroretentive bilayer tablets of calcium carbonate using D-optimal mixture design
  9. Sustainable nanocomposite films based on SiO2 and biodegradable poly(3-hydroxybutyrate-co-3-hydroxyhexanoate) (PHBH) for food packaging
  10. Evaluation of physicochemical properties of film-based alginate for food packing applications
  11. Electrically conductive and light-weight branched polylactic acid-based carbon nanotube foams
  12. Structuring of hydroxy-terminated polydimethylsiloxane filled by fumed silica
  13. Surface functionalization of nanostructured Cu/Ag-deposited polypropylene fiber by magnetron sputtering
  14. Influence of composite structure design on the ablation performance of ethylene propylene diene monomer composites
  15. MOFs/PVA hybrid membranes with enhanced mechanical and ion-conductive properties
  16. Improvement of the electromechanical properties of thermoplastic polyurethane composite by ionic liquid modified multiwall carbon nanotubes
  17. Natural rubber latex/MXene foam with robust and multifunctional properties
  18. Rheological properties of two high polymers suspended in an abrasive slurry jet
  19. Two-step polyaniline loading in polyelectrolyte complex membranes for improved pseudo-capacitor electrodes
  20. Preparation and application of carbon and hollow TiO2 microspheres by microwave heating at a low temperature
  21. Properties of a bovine collagen type I membrane for guided bone regeneration applications
  22. Fabrication and characterization of thermoresponsive composite carriers: PNIPAAm-grafted glass spheres
  23. Effect of talc and diatomite on compatible, morphological, and mechanical behavior of PLA/PBAT blends
  24. Multifunctional graphene nanofiller in flame retarded polybutadiene/chloroprene/carbon black composites
  25. Strain-dependent wicking behavior of cotton/lycra elastic woven fabric for sportswear
  26. Enhanced dielectric properties and breakdown strength of polymer/carbon nanotube composites by coating an SrTiO3 layer
  27. Analysis of effect of modification of silica and carbon black co-filled rubber composite on mechanical properties
  28. Polytriazole resins toughened by an azide-terminated polyhedral oligomeric silsesquioxane (OADTP)
  29. Phosphine oxide for reducing flammability of ethylene-vinyl-acetate copolymer
  30. Study on preparation and properties of bentonite-modified epoxy sheet molding compound
  31. Polyhedral oligomeric silsesquioxane (POSS)-modified phenolic resin: Synthesis and anti-oxidation properties
  32. Study on structure and properties of natural indigo spun-dyed viscose fiber
  33. Biodegradable thermoplastic copolyester elastomers: Methyl branched PBAmT
  34. Investigations of polyethylene of raised temperature resistance service performance using autoclave test under sour medium conditions
  35. Investigation of corrosion and thermal behavior of PU–PDMS-coated AISI 316L
  36. Modification of sodium bicarbonate and its effect on foaming behavior of polypropylene
  37. Effect of coupling agents on the olive pomace-filled polypropylene composite
  38. High strength and conductive hydrogel with fully interpenetrated structure from alginate and acrylamide
  39. Removal of methylene blue in water by electrospun PAN/β-CD nanofibre membrane
  40. Theoretical and experimental studies on the fabrication of cylindrical-electrode-assisted solution blowing spinning nanofibers
  41. Influence of l-quebrachitol on the properties of centrifuged natural rubber
  42. Ultrasonic-modified montmorillonite uniting ethylene glycol diglycidyl ether to reinforce protein-based composite films
  43. Experimental study on the dissolution of supercritical CO2 in PS under different agitators
  44. Experimental research on the performance of the thermal-reflective coatings with liquid silicone rubber for pavement applications
  45. Study on controlling nicotine release from snus by the SIPN membranes
  46. Catalase biosensor based on the PAni/cMWCNT support for peroxide sensing
  47. Synthesis and characterization of different soybean oil-based polyols with fatty alcohol and aromatic alcohol
  48. Molecularly imprinted electrospun fiber membrane for colorimetric detection of hexanoic acid
  49. Poly(propylene carbonate) networks with excellent properties: Terpolymerization of carbon dioxide, propylene oxide, and 4,4ʹ-(hexafluoroisopropylidene) diphthalic anhydride
  50. Polypropylene/graphene nanoplatelets nanocomposites with high conductivity via solid-state shear mixing
  51. Mechanical properties of fiber-reinforced asphalt concrete: Finite element simulation and experimental study
  52. Applying design of experiments (DoE) on the properties of buccal film for nicotine delivery
  53. Preparation and characterizations of antibacterial–antioxidant film from soy protein isolate incorporated with mangosteen peel extract
  54. Preparation and adsorption properties of Ni(ii) ion-imprinted polymers based on synthesized novel functional monomer
  55. Rare-earth doped radioluminescent hydrogel as a potential phantom material for 3D gel dosimeter
  56. Effects of cryogenic treatment and interface modifications of basalt fibre on the mechanical properties of hybrid fibre-reinforced composites
  57. Stable super-hydrophobic and comfort PDMS-coated polyester fabric
  58. Impact of a nanomixture of carbon black and clay on the mechanical properties of a series of irradiated natural rubber/butyl rubber blend
  59. Preparation and characterization of a novel composite membrane of natural silk fiber/nano-hydroxyapatite/chitosan for guided bone tissue regeneration
  60. Study on the thermal properties and insulation resistance of epoxy resin modified by hexagonal boron nitride
  61. A new method for plugging the dominant seepage channel after polymer flooding and its mechanism: Fracturing–seepage–plugging
  62. Analysis of the rheological property and crystallization behavior of polylactic acid (Ingeo™ Biopolymer 4032D) at different process temperatures
  63. Hybrid green organic/inorganic filler polypropylene composites: Morphological study and mechanical performance investigations
  64. In situ polymerization of PEDOT:PSS films based on EMI-TFSI and the analysis of electrochromic performance
  65. Effect of laser irradiation on morphology and dielectric properties of quartz fiber reinforced epoxy resin composite
  66. The optimization of Carreau model and rheological behavior of alumina/linear low-density polyethylene composites with different alumina content and diameter
  67. Properties of polyurethane foam with fourth-generation blowing agent
  68. Hydrophobicity and corrosion resistance of waterborne fluorinated acrylate/silica nanocomposite coatings
  69. Investigation on in situ silica dispersed in natural rubber latex matrix combined with spray sputtering technology
  70. The degradable time evaluation of degradable polymer film in agriculture based on polyethylene film experiments
  71. Improving mechanical and water vapor barrier properties of the parylene C film by UV-curable polyurethane acrylate coating
  72. Thermal conductivity of silicone elastomer with a porous alumina continuum
  73. Copolymerization of CO2, propylene oxide, and itaconic anhydride with double metal cyanide complex catalyst to form crosslinked polypropylene carbonate
  74. Combining good dispersion with tailored charge trapping in nanodielectrics by hybrid functionalization of silica
  75. Thermosensitive hydrogel for in situ-controlled methotrexate delivery
  76. Analysis of the aging mechanism and life evaluation of elastomers in simulated proton exchange membrane fuel cell environments
  77. The crystallization and mechanical properties of poly(4-methyl-1-pentene) hard elastic film with different melt draw ratios
  78. Review Articles
  79. Aromatic polyamide nonporous membranes for gas separation application
  80. Optical elements from 3D printed polymers
  81. Evidence for bicomponent fibers: A review
  82. Mapping the scientific research on the ionizing radiation impacts on polymers (1975–2019)
  83. Recent advances in compatibility and toughness of poly(lactic acid)/poly(butylene succinate) blends
  84. Topical Issue: (Micro)plastics pollution - Knowns and unknows (Guest Editor: João Pinto da Costa)
  85. Simple pyrolysis of polystyrene into valuable chemicals
  86. Topical Issue: Recent advances of chitosan- and cellulose-based materials: From production to application (Guest Editor: Marc Delgado-Aguilar)
  87. In situ photo-crosslinking hydrogel with rapid healing, antibacterial, and hemostatic activities
  88. A novel CT contrast agent for intestinal-targeted imaging through rectal administration
  89. Properties and applications of cellulose regenerated from cellulose/imidazolium-based ionic liquid/co-solvent solutions: A short review
  90. Towards the use of acrylic acid graft-copolymerized plant biofiber in sustainable fortified composites: Manufacturing and characterization
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