CN105694071A - Molecular imprinting and preparation method thereof - Google Patents
Molecular imprinting and preparation method thereof Download PDFInfo
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- CN105694071A CN105694071A CN201610157326.4A CN201610157326A CN105694071A CN 105694071 A CN105694071 A CN 105694071A CN 201610157326 A CN201610157326 A CN 201610157326A CN 105694071 A CN105694071 A CN 105694071A
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/24—Crosslinking, e.g. vulcanising, of macromolecules
- C08J3/246—Intercrosslinking of at least two polymers
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L5/00—Compositions of polysaccharides or of their derivatives not provided for in groups C08L1/00 or C08L3/00
- C08L5/08—Chitin; Chondroitin sulfate; Hyaluronic acid; Derivatives thereof
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2305/00—Characterised by the use of polysaccharides or of their derivatives not provided for in groups C08J2301/00 or C08J2303/00
- C08J2305/08—Chitin; Chondroitin sulfate; Hyaluronic acid; Derivatives thereof
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2405/00—Characterised by the use of polysaccharides or of their derivatives not provided for in groups C08J2401/00 or C08J2403/00
- C08J2405/06—Pectin; Derivatives thereof
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2201/00—Properties
- C08L2201/06—Biodegradable
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Abstract
The invention provides molecular imprinting. The material of the molecular imprinting is prepared from chitosan and pectin, and one of 5-sulfosalicylic acid, L-tyrosine or R-tyrosine is used as a template molecule. The obtained molecular imprinting has good biocompatibility and biodegradability and low toxicity, is stable for hot solvent, organic solvent and strong acid and strong alkaline solvent, has the performance for resisting the adverse environment, has the advantage of being long in service life, and can meet requirements of the fields having high requirements for toxicity, degradability and the like of biological materials. The preparation process of the molecular imprinting is simple, the molecular imprinting is prepared only by conducting cross-linking reaction on chitosan and pectin in water without using modifier, cross-linking agents or other substances, the production cost is low, the process is safe, and the molecular imprinting is suitable for large-scale industrialized application.
Description
Technical field
The present invention relates to molecular imprinting field, particularly to a kind of molecular engram, meanwhile, the preparation method that the invention still further relates to this molecular engram。
Background technology
Molecular imprinting is the technology that synthesis has molecularly imprinted polymer (also referred to as the molecular engram) material of molecular recognition function, the principle of molecular engram is to form multiple action point with polymeric material monomer when template molecule (or microsphere) contacts, by polymerization process, this effect is memorized, after template molecule removes, polymeric material is the formation of the hole with multiple action point matched with template molecule steric configuration, template molecule and the like will be had selection evident characteristics by such hole, " manually the lock " identifying " molecule key " is manufactured by being depicted as visually, target molecule is had high affinity and selective function by the molecularly imprinted polymer (MIPs) therefore prepared, can be widely applied to chromatographic isolation, Solid-Phase Extraction, trace detection, the fields such as clinical medicine analysis。In prior art, the material for preparing molecularly imprinted polymer broadly falls into greatly chemical classes polymeric material, developmental research to biomaterials such as chitosans is also required for use chemical substance as modifying agent and cross-linking agent etc., therefore limits molecular imprinting in the high biological application requiring field。
Summary of the invention
For solving the deficiencies in the prior art, the invention provides a kind of molecular engram, prepare material with biodegradable innocuous substance, do not need to use the material such as modifying agent and cross-linking agent, while preparation process can be simplified, be also remarkably improved the biological of molecular engram。
For achieving the above object, the molecular engram of the present invention, prepare the material of described molecular engram with chitosan and pectin, using the one in 5-sulphosalicylic acid, TYR or R-tyrosine as template molecule。
As the restriction to aforesaid way, described template molecule is 5-sulphosalicylic acid。
As the restriction to aforesaid way, the pectin of materials'use preparing described molecular engram is (1～4) with the weight ratio of chitosan: 6。
As the restriction to aforesaid way, increasing, when preparing the material of described molecular engram, the weight ratio using porogen polyethylene glycol 6000, described polyethylene glycol 6000 addition and chitosan is (1～4): 10。
Natural polymer chitosan is a kind of cationic polysaccharide, natural polymer pectin is a kind of anion polysaccharide, the ions binding effect that chitosan and pectin can pass through between material forms electrostatic cross linked polymer, utilize this polymer can be swelling and keep large quantity of moisture and undissolved character in water, wrap hydrophilic template molecule, then soak in water, make template molecule be dissolved in water at polymer swelling process, wash away template molecule, obtain molecular engram。For improving material porosity and the aperture of molecular engram, thus improving the absorption property to template molecule, on the one hand by being limited in material preparation process the reasonable volume of template molecule, on the other hand by increasing use porogen and porogen kind, consumption, the comprehensive of these two aspects factor limits the molecular engram with excellent。The molecular engram of the present invention is using chitosan and pectin as material body, it is thus achieved that material there is good biocompatibility, degradability and hypotoxicity, it is possible to meet the domain requirement that the toxicity of biomaterial, degradability etc. are had high request。
Meanwhile, the preparation method that present invention also offers a kind of molecular engram, this preparation method comprises the following steps:
A, add chitosan in the acetic acid solution that mass content is 2%, be stirred well to after being completely dissolved, add pectin and template molecule, continue stirring, be fully obtained by reacting viscous solution；The weight ratio of described pectin and chitosan is (1～4): 6, and the weight ratio of described template molecule and chitosan is (1～3): 60。
B, the viscous solution obtained by step a prolong stream film forming, fully dry at 40～45 DEG C, then soak eluted template molecule in water, obtain molecular engram。
The preparation of molecular engram of the present invention, is at normal temperatures and pressures pectin, chitosan are dissolved in water so as to there is cross-linking reaction, produces cross linked polymer, forms the material of molecular engram。Course of reaction first dissolves chitosan in the acetic acid solution of 2%, because Viscosity of Chitosan is big, not readily dissolves, utilizes acetic acid solution dissolution, add pectin and template molecule, make pectin and chitosan carry out cross-linking reaction, wrap template molecule。Preparation process does not need to use the material such as modifying agent, cross-linking agent, and only by the chemical reaction between chitosan and pectin, the molecular engram therefore prepared has better biocompatibility, degradability and hypotoxicity。
Proportioning as the restriction to aforesaid way, described chitosan and acetic acid solution is 6g:200ml。
As the restriction to aforesaid way, template molecule described in step a makes the form addition of solution to be dissolved in water, and described template molecule solution concentration is 10mg/mL。
Template molecule joins in preparation process all as an aqueous solution, is more conducive to the dispersion between material, and the molecular engram performance making acquisition is more excellent。
As the restriction to aforesaid way, before adding pectin and template molecule operation described in step a, increasing the weight ratio adding porogen polyethylene glycol 6000, described polyethylene glycol 6000 addition and chitosan is (1～4): 10。
As the restriction to aforesaid way, described polyethylene glycol 6000 makes the form addition of solution to be dissolved in water, and the mass percent of described polyethylene glycol 6000 solution is 3%。
Preparation process increases use porogen polyethylene glycol 6000, porosity and the aperture of material can be improved on the one hand, polyethylene glycol 6000 is alternatively arranged as dispersant on the other hand, promote the dispersion of chitosan, pectin and template molecule, promote the polyreaction of chitosan and pectin, be more conducive to optimize the performance of molecular engram。
In sum, adopt technical scheme, the molecular engram obtained, using chitosan and pectin as material body, there is good biocompatibility, degradability and hypotoxicity, to hot solvent, organic solvent and strong acid and strong base solvent-stable, the advantage with the performance and used life length of anti-adverse environment, present good application prospect in a lot of fields, it is possible to meet the domain requirement that the toxicity of biomaterial, degradability etc. are had high request。The preparation process of this molecular engram is simple, carries out cross-linking reaction merely with pectin and chitosan, prepare molecular engram in water, does not need to use the material such as modifying agent, cross-linking agent, low production cost, process safety, is suitable to heavy industrialization application。
Accompanying drawing explanation
The accompanying drawing constituting the present invention is used for providing a further understanding of the present invention, and the schematic description and description of the present invention is used for explaining the present invention, is not intended that inappropriate limitation of the present invention。In the accompanying drawings:
Fig. 1 is the 5-sulphosalicylic acid absorption curve described in the embodiment of the present invention；
Fig. 2 is the working curve of the 5-sulphosalicylic acid described in the embodiment of the present invention；
Fig. 3 is the influence curve to adsorbance of the PEG6000 consumption described in the embodiment of the present invention；
Fig. 4 is the influence curve to adsorbance of the 5-sulphosalicylic acid consumption described in the embodiment of the present invention；
Fig. 5 is MIP, NIP, the MIP described in the embodiment of the present invention0、NIP0Adsorption isotherm；
Fig. 6 is the TYR standard curve described in the embodiment of the present invention。
Fig. 7 is the SEM figure of the MIP described in the embodiment of the present invention；
Fig. 8 is the SEM figure of the NIP described in the embodiment of the present invention；
Fig. 9 is the infrared detection spectrogram of the MIP described in the embodiment of the present invention, NIP and CS。
Detailed description of the invention
Embodiment one
The present embodiment relates to one group of molecular engram and preparation thereof。
The preparation of molecular engram adopts following steps:
A, at 25 DEG C, 1 standard atmosphere pressure, chitosan (CS) is joined in the acetic acid solution that 20mL mass content is 2%, it is stirred well to after being completely dissolved, add the polyethylene glycol 6000 (PEG6000) that mass fraction is 3%, be stirred continuously 30min and make its mix homogeneously, add pectin (PT) and template molecule, continue stirring 20min, be fully obtained by reacting viscous solution；
B, the viscous solution obtained by step a are placed on surface plate to prolong and flow to flat, are placed in 42 ± 1 DEG C of air dry ovens and make it fully dry, are soaked in deionized water 12 hours by the polymer of drying, and eluted template molecule obtains molecular engram。
Each material (including PT, CS, PEG6000,5-sulphosalicylic acid) consumption shown according to the form below prepares molecular engram。
The various embodiments described above obtain molecular engram for follow-up performance verification experiment, and wherein molecular engram is adsorbed the impact of template molecule performance by embodiment 1.1～1.3 for measuring the chitosan consumption proportion with pectin；Molecular engram is adsorbed the impact of template molecule performance by embodiment 1.4～1.8 for measuring porogen PEG6000；Embodiment 1.9～1.13 is used for the consumption measuring template molecule 5-sulphosalicylic acid and molecular engram adsorbs the impact of template molecule performance。
Embodiment two
The present embodiment relates to the molecular engram of the present invention absorption property to template molecule and verifies。
In the present embodiment, the absorption property of template molecule being embodied by adsorbance Q, the assay method of Q-value is:
Determinand is placed in template molecule solution, after reaching adsorption equilibrium, utilize centrifugal separator that solution is easily separated, take supernatant, by UV spectrophotometer measuring absorbance, calculated its concentration and C1 by the standard curve of template molecule, the molecular weight M according to template molecule, by following formula calculating formula adsorbance Q。
Wherein Q: the unit determinand adsorbance (μm ol/g) to template molecule；
C0: original template molecular solution concentration (μ g/mL)；
C1: template molecule concentration (μ g/mL) in supernatant；
M: determinand quality (g)；
M: the relative molecular mass of template molecule。
For 5-sulphosalicylic acid as template molecule, the assay method of its standard curve is as follows:
Weighing 0.2500g5-sulfosalicylic acid preparation 250mL concentration is the solution of 1g/L, then pipettes in 25mL to 250mL volumetric flask, is diluted to 250mL, obtains the solution of 0.1g/L。Again with the solution of 0.1g/L prepare 0.5 respectively, 1.0,1.5,2.0,2.5,3.0,3.5,4.0,4.5,5.0,5.5,6.0,6.5,7.0,7.5, the solution of 8.0ug/L, each solution is surveyed from the absorbance within the scope of 200nm-400nm by ultraviolet spectrophotometer, 5-sulphosalicylic acid absorption curve as shown in Figure 1 is drawn, as seen from Figure 1 at 207.5 and 235 place two place's crests by determination data。
Take its summit, be in the solution to its variable concentrations at 207.5nm and carry out quantitative analysis, survey its absorbance, the working curve of 5-sulphosalicylic acid as shown in Figure 2 can be prepared by the absorbance recorded: y=-0.01508+0.1553x；R2=99964。The concentration of unknown 5-sulphosalicylic acid is calculated by this working curve。
Embodiment 2.1
The present embodiment relates to the chitosan consumption proportion with pectin and molecular engram adsorbs the impact of template molecule performance。The molecular engram that detection embodiment 1.1～1.3 the obtains adsorbance Q to 5-sulphosalicylic acid, as shown in the table:
In table, in embodiment 2.1.1, embodiment 1.1 (0) represents the molecular engram material of embodiment 1.1, namely material, material consumption and the preparation method that employing is essentially identical with embodiment 1.1, only difference is that preparation process is added without template molecule 5-sulphosalicylic acid；Selective factor B a is the ratio of embodiment 1.1 and embodiment 1.1 (0) adsorbance, is used for characterizing selective absorption performance。In like manner, embodiment 1.2 (0), 1.3 (0) represents the material of embodiment 1.2,1.3 respectively。
From upper table result, in embodiment 2.1.2, the adsorbance of template molecule is significantly greater than the adsorbance of all the other embodiments by the molecular engram of embodiment 1.2, and selective factor B a value is also significantly greater than the selective factor B of other two groups of embodiments, illustrate that its absorption template molecule effect is better when chitosan and pectin quality proportioning are 3:1, now chitosan is better with the polymerization effect of pectin, provide good molecular engram for template molecule, be more conducive to the absorption to 5-sulphosalicylic acid。
Embodiment 2.2
The present embodiment relates to the consumption of porogen PEG6000 and molecular engram adsorbs the impact of template molecule performance。The molecular engram that detection embodiment 1.4～1.8 the obtains adsorbance Q to 5-sulphosalicylic acid, draws the PEG6000 consumption influence curve to adsorbance, as shown in Figure 3。
From the influence curve of Fig. 3, when PEG6000 consumption is 6mL, prepared molecular engram (embodiment 1.7) is maximum to the adsorbance of template molecule 5-sulphosalicylic acid。And more than or less than this consumption, adsorbance all presents the state of minimizing, and the speed reduced is very fast, illustrates that porogen PEG6000 serves important function, but consumption is wanted suitably, otherwise to cause counter productive。
Embodiment 2.3
The present embodiment relates to the consumption of template molecule 5-sulphosalicylic acid and molecular engram adsorbs the impact of template molecule performance。The molecular engram that detection embodiment 1.9～1.13 the obtains adsorbance Q to 5-sulphosalicylic acid, draws the 5-sulphosalicylic acid consumption influence curve to adsorbance, as shown in Figure 4。
From the influence curve of Fig. 4,5-sulphosalicylic acid is along with consumption increases within the scope of consumption 0-20mg, and adsorbance significantly increases therewith, and after 20mg, adsorbance tends towards stability, without significantly increasing trend。Therefore chitosan is 0.6g, pectin is 0.2g, and 5-sulphosalicylic acid consumption has reached optimal conditions when being 20mg, makes 5-sulphosalicylic acid be fully utilized。
Embodiment three
The present embodiment relates to the molecular engram of the present invention specific adsorption to template molecule and verifies。
Embodiment 3.1
The present embodiment relates to the contrast to the specific adsorption performance of template molecule of one group of material, adopts the preparation method described in embodiment one, prepares material as shown in the table:
Embodiment 3.1.1～3.1.4 is obtained material and is designated as MIP, NIP, MIP respectively0、NIP0MIP adopt Equilibrium Adsorption Method (method is with embodiment two) measure the adsorbance to 5-sulphosalicylic acid in the 5-sulphosalicylic acid solution that concentration is 4ug/mL, 6ug/mL, 8ug/mL, 10ug/mL, 12ug/mL, 14ug/mL, draw adsorption isotherm, be measured in the same method NIP, MIP0And NIP0Adsorption isotherm, four adsorption isotherms are plotted in same coordinate diagram, as shown in Figure 5。
From figure 5 it can be seen that along with the increase of 5-sulphosalicylic acid initial concentration, MIP, NIP, MIP in solution0And NIP0The adsorbance of template molecule 5-sulphosalicylic acid is all being gradually increased, and is finally tending to balance。Relatively four curves, the adsorption effect obtaining MIP is best, and adsorbance MIP > NIP > MIP0>NIP0, template molecule is had higher absorption property by the specificity solid hole illustrated in MIP structure。
Embodiment 3.2
The present embodiment relates to the molecular engram of the present invention contrast to template molecule and non-template Molecular Adsorption performance, Equilibrium Adsorption Method (method is with embodiment two) is adopted to detect molecular engram of the present invention (for material MIP) to the adsorbance of 5-sulphosalicylic acid, selective factor B, to the adsorbance of TYR, selective factor B, contrasting, result is as shown in the table:
From upper table result, with 5-sulphosalicylic acid be template molecule MIP to the adsorbance of 5-sulphosalicylic acid apparently higher than NIP, the binding capacity of TYR is also higher than NIP by MIP, but the selective factor B value of 5-sulphosalicylic acid far above the MIP selective factor B value to TYR, to be illustrated that 5-sulphosalicylic acid is had specific adsorption ability by MIP by MIP。
For obtaining the adsorbance of TYR in the present embodiment, it is necessary to measuring the standard curve of TYR, concrete operations are as follows:
Take a certain amount of TYR to insert baking oven at 105 DEG C, toast 3h, the tyrosine that will dry, first it is configured to the TYR solution of 500ug/mL, dilute 10 times and obtain 50ug/mL solution, then done mother solution by the tyrosine solution of 50ug/mL, make 1ug/mL respectively, 5ug/mL, the TYR solution of 10ug/mL, 15ug/mL, 20ug/mL。
Measure the absorbance of the solution of configuration as above with ultraviolet spectrophotometer, draw TYR standard curve as shown in Figure 6。By the concentration of standard curve determination the unknown tyrosine solution, obtain standard curve equation: y=0.00518+0.0359x, R2=0.99914。
Embodiment four
The present embodiment relates to the structural characterization of molecular engram of the present invention。
Embodiment 4.1
The present embodiment relates to the surface texture of molecular engram of the present invention and characterizes, and is respectively placed under scanning electron microscope by material MIP sample, material NIP sample, observes its surface topography, obtains the SEM figure of SEM figure, the NIP shown in Fig. 8 of the MIP shown in Fig. 7。
Comparison diagram 7, Fig. 8 are visible, and MIP surface is uniform-distribution with a lot of small holes, and rough surface is uneven, wherein substantially has the marking that template molecule stays；NIP surface uniformly and is compared smooth, it does not have hole。Therefore the absorption of template molecule is served important function by the branding on MIP surface, and template molecule has good absorbability。
Embodiment 4.2
The present embodiment relates to the infrared structure of molecular engram of the present invention and characterizes, respectively chitosan CS sample, material MIP sample, material NIP sample KBr are carried out tabletting, adopt Fourier infrared spectrograph to detect the infrared detection of these three samples, obtain the infrared detection spectrogram of material MIP as shown in Figure 9, material NIP and CS。
As seen from Figure 9, in the infrared figure of CS, at 1600cm-1There is-NH2Characteristic peak；In the infrared figure of MIP and NIP, at 1600cm-1-NH2Peak disappears, 1734cm-1-COOH peak significantly weaken, and at 1620cm-1Neighbouring appearance-NH1-OOC the strong characteristic absorption peak of valency, 1530cm-1-NH-symmetric curvature vibration absorption peak occurs；1421cm-1-COO-symmetrical stretching vibration absworption peak occurs；MIP is relative to NIP, 1749cm-1-COOH the peak at place weakens significantly, and at 1624cm-1There is-NH.COO-secondary bond characteristic absorption peak in place。Can being obtained by infrared spectrum map analysis, Chitosan/Pectin-PEC structure is significant for forming porous three dimensional network structure。
Claims (9)
1. a molecular engram, it is characterised in that: prepare the material of described molecular engram with chitosan and pectin, using the one in 5-sulphosalicylic acid, TYR or R-tyrosine as template molecule。
2. molecular engram according to claim 1, it is characterised in that: described template molecule is 5-sulphosalicylic acid。
3. molecular engram according to claim 1, it is characterised in that: the pectin of materials'use preparing described molecular engram is (1～4) with the weight ratio of chitosan: 6。
4. molecular engram according to any one of claim 1 to 3, it is characterized in that: increasing, when preparing the material of described molecular engram, the weight ratio using porogen polyethylene glycol 6000, described polyethylene glycol 6000 addition and chitosan is (1～4): 10。
5. the preparation method of a molecular engram, it is characterised in that this preparation method comprises the following steps:
A, add chitosan in the acetic acid solution that mass content is 2%, be stirred well to after being completely dissolved, add pectin and template molecule, continue stirring, be fully obtained by reacting viscous solution；The weight ratio of described pectin and chitosan is (1～4): 6, and the weight ratio of described template molecule and chitosan is (1～3): 60。
B, the viscous solution obtained by step a prolong stream film forming, fully dry at 40～45 DEG C, then soak eluted template molecule in water, obtain molecular engram。
6. the preparation method of molecular engram according to claim 5, it is characterised in that: the proportioning of described chitosan and acetic acid solution is 6g:200ml。
7. the preparation method of molecular engram according to claim 5, it is characterised in that: template molecule described in step a makes the form addition of solution to be dissolved in water, and described template molecule solution concentration is 10mg/mL。
8. the preparation method of molecular engram according to claim 5, it is characterized in that: before adding pectin and template molecule operation described in step a, increasing the weight ratio adding porogen polyethylene glycol 6000, described polyethylene glycol 6000 addition and chitosan is (1～4): 10。
9. the preparation method of molecular engram according to claim 8, it is characterised in that: described polyethylene glycol 6000 makes the form addition of solution to be dissolved in water, and the mass percent of described polyethylene glycol 6000 solution is 3%。
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108970593A (en) * | 2018-07-28 | 2018-12-11 | 西京学院 | A kind of phenolic aldehyde trace resin particle preparation method |
| CN110698591A (en) * | 2019-09-05 | 2020-01-17 | 东南大学 | 5-sulfosalicylic acid imprinted polymer and preparation method thereof |
| CN111592670A (en) * | 2020-06-24 | 2020-08-28 | 上海应用技术大学 | Preparation method of gamma-polyglutamic acid molecularly imprinted polymer membrane |
-
2016
- 2016-03-18 CN CN201610157326.4A patent/CN105694071B/en not_active Expired - Fee Related
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| P.BERNABÉ ET AL.: ""Swelling behavior of chitosan/pectin polyelectrolyte complex membranes. Effect of thermal cross-linking"", 《POLYMER BULLETIN》 * |
| XUE-FANG ZHENG ET AL.: ""Molecularly Imprinted Polymer for L-Tyrosine Recognition and Controlled Release"", 《RUSSIAN JOURNAL OF APPLIED CHEMISTRY》 * |
| 王筱平等: ""壳聚糖/果胶聚电解质配合物的制备及其性能研究"", 《化学世界》 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108970593A (en) * | 2018-07-28 | 2018-12-11 | 西京学院 | A kind of phenolic aldehyde trace resin particle preparation method |
| CN110698591A (en) * | 2019-09-05 | 2020-01-17 | 东南大学 | 5-sulfosalicylic acid imprinted polymer and preparation method thereof |
| CN110698591B (en) * | 2019-09-05 | 2021-06-11 | 东南大学 | 5-sulfosalicylic acid imprinted polymer and preparation method thereof |
| CN111592670A (en) * | 2020-06-24 | 2020-08-28 | 上海应用技术大学 | Preparation method of gamma-polyglutamic acid molecularly imprinted polymer membrane |
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