CN101962824A - Method for preparing printed fibers for efficiently separating naringin in water phase based on electric spinning technology - Google Patents
Method for preparing printed fibers for efficiently separating naringin in water phase based on electric spinning technology Download PDFInfo
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Abstract
The invention relates to a preparation method of printed fibers, in particular to a method for preparing polymer printed fibers for efficiently separating naringin in a water phase based on an electric spinning technology, which is characterized by comprising the steps of: dissolving a high polymer matrix into an organic solvent to prepare high polymer-organic solvent gel; dissolving function body cyclodextrin and printed molecules into the organic solvent, mixing with the gel under room temperature to prepare high polymer-function body cyclodextrin-printed molecule electric spinning mixed gel; preparing a composite nano fiber by adopting the electric spinning technology; and soaking the composite fiber in a crosslinking agent for a crosslinking reaction, washing and drying in vacuum after the reaction is finished to obtain the one-dimensional nano printed cyclodextrin fiber. The fiber has the characteristics of high affinity and selectivity to the printed molecules, high elution efficiency, less soil loss tolerance, high repeatability ratio, and the like, and can be used for efficiently separating the naringin in the water phase.
Description
Technical field
The present invention relates to a kind of trace fiber preparation method, relate to a kind of method that preparation efficiently separates the high molecular polymer trace fiber of aurantiin at aqueous phase based on electrospinning silk technology specifically.
Background technology
Aurantiin (naringin, be called for short NG) be a kind of flavanone compounds, the active ingredient of multiple Chinese patent drug has non-oxidizability (inhibition oxidase active), anti-inflammatory and antalgic, antiviral, antibacterial and suppress various biological activity and pharmacological action such as eye aldose reductase.Aurantiin is one of the strongest material of accelerating oxidation effect in the flavone compound, and human body gene is had the toxic action of inducing.Therefore, preparation aurantiin imprinted polymer is significant to the separation and Extraction and the drug quality control of aurantiin.
Cyclodextrin molecular has " interior hydrophobic, outer hydrophilic " unique space structure, makes it to many molecules, and particularly drug molecule has clathration, is a kind of function monomer of very potential synthetic drug quasi-molecule imprinted polymer.Phenyl ring on the NG molecule helps forming bridge-type cyclodextrin polymer, simultaneously steric configuration is had control action, helps microsphere polymer stabilizing ground on every side in conjunction with microsphere, improves the selectivity recognition reaction of MIP.After removing microsphere NG, be left in the hole of cyclodextrin in size and the hole that is complementary in shape with microsphere.
Adopt the trace carrier of particle or nano-powder that though big specific surface is arranged, the wash-out of trace carrier and the complex process of regeneration, and number of dropouts is big.And adopt the thread or velutinate fibrous mass of spider of electrical spinning method preparation to have the one dimension line feature of quasi-nano, and having high specific surface, recovery, wash-out and regeneration are easy, have improved the trace speed and the transit dose of aurantiin molecule.
Summary of the invention
The object of the present invention is to provide a kind ofly be easy to reclaim, the one dimension quasi-nano of wash-out, regeneration, be microsphere with NG, cyclodextrin (CD) is a functive, can efficiently separate the imprinted polymer fiber preparation method of aurantiin at aqueous phase.The selective absorption of trace cyclodextrin nano fiber separates the process of aurantiin molecule.
It is the collection technique of the one dimension quasi-nano fiber of receiver with the rotating disk that another object of the present invention also is to provide a kind of.
The objective of the invention is to be achieved through the following technical solutions:
1, preparation electrospinning silk colloidal sol:
The high molecular polymer matrix is dissolved in is prepared into the high molecular polymer that concentration is 4.0～12% (W/V)-organic solvent colloidal sol in the organic solvent; Functive cyclodextrin and microsphere are dissolved in the organic solvent, at room temperature mix, stir 2～5h and carry out blend, make high molecular polymer-functive cyclodextrin-microsphere electrospinning silk mixed sols with high molecular polymer-organic solvent colloidal sol.
High molecular polymer 4～12 weight portions
Functive cyclodextrin 1～5 weight portion
Microsphere 0.10～0.5 weight portion
Organic solvent 15～25 parts by volume (ml).
2, electrospinning silk technology prepares composite nano fiber:
Utilize above-mentioned colloidal sol, carry out the electrospinning silk and make composite fibre.The electrospinning strand spare of electrospinning silk instrument: (1) voltage is 12～24V; (2) syringe needle and receiver spacing are 5～15cm; (3) electrospinning silk sol solutions rate of addition is 1～4ml/h; (4) the stainless pin bore dia is 0.2～0.8mm.Receiver is: plane aluminium foil or aluminium rotating disk.
3, the composite fibre of collecting is immersed in the crosslinking agent, carries out cross-linking reaction, soak 24～48h.After cross-linking reaction finishes, composite fibre filtered and be that 0.5～1% the NaOH aqueous solution fully washs, to remove impurity and microsphere with concentration.After washing finishes with composite fibre vacuumize to constant weight, obtain 1-dimention nano level trace cyclodextrin fiber (FMIP).At this moment, be left in the hole of trace cyclodextrin fiber in size and the hole that is complementary in shape with microsphere.
High molecular polymer matrix of the present invention is polyvinyl butyral resin (PVB), polystyrene (PS), polyacrylonitrile (PAN), polymethyl methacrylate (PMMA) or polyvinylpyrrolidone (PVP).
Cyclodextrin functive of the present invention is alpha-cyclodextrin, beta-schardinger dextrin-, gamma-cyclodextrin, hydroxypropyl cyclodextrin or carboxymethyl cyclodextrin.
Microsphere of the present invention is aurantiin, aurantiamarin, neohesperidin or aurantiin dihydrochalcone.
Organic solvent of the present invention is ethanol, acetone, N, dinethylformamide or N,N-dimethylacetamide.
Crosslinking agent of the present invention is hexamethylene diisocyanate (HMDI), toluene di-isocyanate(TDI) (TDI), XDI (XDI), lysinediisocyanate (LDI) or isocyanates (MDI).
The used high molecular polymer of the present invention plays the matrix supporting role, and functive and microsphere are evenly dispersed in the matrix; In addition, the present invention with HMDI etc. as crosslinking agent because the cyanate activity is very high, very easily with cyclodextrin on-the OH radical reaction forms polymer.In the presence of ad hoc structure molecule such as aurantiin (NG), phenyl ring on its molecule helps forming bridge-type CD polymer with CD, simultaneously steric configuration there is control action, helps microsphere polymer stabilizing ground on every side, improve the selectivity recognition reaction of trace fiber in conjunction with microsphere.After removing microsphere NG, be left in the hole of CD in size and the hole that is complementary in shape with microsphere.
In sum, the invention has the advantages that:
The method that the present invention adopts electrostatic spinning process and molecular imprinting to combine has prepared the one dimension trace cyclodextrin nano fiber that the aurantiin chromocor compound is had recognition capability.This fiber has that specific area is big, high adsorption capacity and being easy to reclaims, the characteristics of wash-out, regeneration.Simultaneously, can efficiently separate aurantiin at aqueous phase.
Description of drawings
Fig. 1 is the NG trace β-CD fiber Electronic Speculum figure of the embodiment of the invention 1 described method preparation.
Fig. 2 is the NG trace β-CD fiber Electronic Speculum figure of the embodiment of the invention 2 described method preparations.
Fig. 3 is the homemade electrostatic spinning machine structural representation of the present invention.
Fiber shown in Fig. 1, receiver are aluminium foil, and fibre diameter is quasi-nano less than 1 μ m.
Fiber shown in Fig. 2, receiver are the aluminium rotating disk, and fibre diameter is quasi-nano less than 1 μ m.
The specific embodiment
Below in conjunction with embodiment the present invention is described in more detail.
Embodiment 1
PVB is that matrix, β-CD are that functive, NG are that microsphere, crosslinking agent are HMDI; Electrospinning silk instrument receiver is an aluminium foil
The PVB of 10g is dissolved in is prepared into the PVB-ethanol colloidal sol that concentration is 10% (W/V) in the alcohol solvent.The microsphere NG of the β-CD of 5g and 0.3g is dissolved in the N of 50ml, in dinethylformamide (DMF) solvent, is mixed with NG-β-CD-DMF solution, then it is slowly joined in the PVB-ethanol colloidal sol.At room temperature stir PVB-NG-DMF-β-CD colloidal sol 5h.
PVB-NG-β-CD the colloidal sol that stirs is injected in the syringe of 10ml electrospinning silk syringe and carries out the electrospinning silk, PVB-NG-β-CD one dimension quasi-nano composite fibre.Electrospinning strand spare: the stainless pin bore dia is 0.5mm, and links with DC high-voltage power supply; Receiver aluminium foil ground connection; Distance is 10cm between syringe needle and aluminium foil; Voltage is 18kV; Environment temperature is 25 ℃ during electrospinning.
PVB-NG-β-CD one dimension quasi-nano composite fibre of collecting is immersed in the crosslinking agent hexamethylene diisocyanate (HMDI) of 20ml, and normal temperature soaks 24h down, makes it full cross-linked.Composite fibre after crosslinked fully washs with 0.5～1%NaOH aqueous solution, to remove impurity and microsphere.After washing finishes with product vacuumize to constant weight, obtain 1-dimention nano level trace β-CD fiber, as shown in Figure 1.
Select for use NG and with the aurantiamarin of NG structural similarity, aurantiin dihydrochalcone as substrate, prepared trace β-CD fiber has been carried out the selectivity experiment.By the legal binding capacity of having measured MIP (trace β-CD fiber) and NIP (non-trace, promptly blank β-CD fiber) to above-mentioned substrate of junction at equilibrium.Specific as follows: as to take by weighing each 50mg of MIP and NIP and place 250mL tool plug conical flask, add each material mixed solution that 50mL concentration is 0.02mg/mL, put into the 48h that vibrates under the constant temperature shaking table room temperature.Adsorbed solution is moved in the centrifuge tube, take out supernatant behind the high speed centrifugation, with the content of each microsphere of high-performance liquid chromatogram determination.
Table 1: from aurantiin, aurantiamarin, aurantiin dihydrochalcone mixed solution, isolate aurantiin
Annotate: MIP (NIP): 50.0mg; Substrate initial concentration: 0.02mg/mL; Volume: 50mL; Adsorption time: 48h
Chromatographiccondition: (250 * 4.6mm), ultraviolet detects wavelength 283nm to Microsorb-MV 100-5C-18 post, is the phase that flows with acetonitrile: 2%HAc (25: 75), flow velocity: 1.0mL/min.Adopt the external standard calibration curve method.
The trace separating effect:
Aurantiin: aurantiamarin: aurantiin dihydrochalcone=18.3: 2.2: 1.7 ≈ 10.8: 1.3: 1.0
Embodiment 2
Polymethyl methacrylate (PMMA) is that matrix, β-CD are that functive, receiver are that aluminium rotating disk, crosslinking agent are toluene di-isocyanate(TDI) (TDI)
The polymethyl methacrylate (PMMA) of 4g is dissolved in is prepared into the PMMA-ethanol colloidal sol that concentration is 4% (W/V) in the alcohol solvent.β-the CD of 2g and the microsphere NG of 0.5g are dissolved in N,N-dimethylacetamide (DMF) solvent of 50ml, are mixed with NG-β-CD-DMF solution, then NG-β-CD-DMF solution is slowly joined in the PMMA-ethanol colloidal sol.At room temperature stir PMMA-NG-β-CD colloidal sol 2h.
PMMA-NG-β-CD the colloidal sol that stirs is injected in the syringe of 10ml electrospinning silk syringe and carries out the electrospinning silk, PMMA-NG-β-CD one dimension quasi-nano composite fibre.Electrospinning strand spare: the stainless pin bore dia is 0.5mm, and links with DC high-voltage power supply; Aluminum rotary speed 800～2000r/min; Distance is 12cm between syringe needle and aluminium foil; Voltage is 20kV; Environment temperature is 45 ℃ during electrospinning.
PMMA-NG-β-CD one dimension quasi-nano composite fibre of collecting is immersed in the crosslinking agent toluene di-isocyanate(TDI) (TDI) of 20ml, and normal temperature soaks 36h down, makes it full cross-linked.Composite fibre after crosslinked fully washs with 0.5～1%NaOH aqueous solution, to remove impurity and microsphere.After washing finishes with product vacuumize to constant weight, obtain 1-dimention nano level NG trace β-CD fiber, as shown in Figure 2.Visible fibre diameter is quasi-nano less than 1 μ m among the figure, and fiber alignment is oriented and ordered basically.
Equally, select for use NG and with the aurantiamarin of NG structural similarity, aurantiin dihydrochalcone as substrate, prepared trace β-CD fiber has been carried out the selectivity experiment, the results are shown in Table 1.Trace separating effect: aurantiin: aurantiamarin: aurantiin dihydrochalcone=19.4: 1.8: 1.1 ≈ 17.6: 1.6: 1.0
By table 1 as seen, compare with other substrate, MIP (trace β-CD fiber) has shown strong selective binding ability to NG.This shows the size and the binding site (hole) that is shaped as the basis that has produced with NG in MIP (trace β-CD fiber) imprinted polymer, represented specific selectivity.And compare with the aluminium foil receiver, aluminium rotating disk receiver is orderly because of fiber architecture, is easy to wash-out, thereby has demonstrated more superior separation recognition performance.
Embodiment 3
PMMA is that matrix, α-CD are that functive, receiver are that aluminium rotating disk, crosslinking agent are XDI
The polymethyl methacrylate (PMMA) of 8g is dissolved in is prepared into the PMMA-ethanol colloidal sol that concentration is 4% (W/V) in the alcohol solvent.α-the CD of 2g and the microsphere NG of 0.5g are dissolved in the N,N-dimethylacetamide solvent (DMF) of 50ml, are mixed with NG-α-CD-DMF solution, then NG-α-CD-DMF solution is slowly joined in the PMMA-ethanol colloidal sol.At room temperature stir PMMA-NG-α-CD colloidal sol 2h.
PMMA-NG-α-CD the colloidal sol that stirs is injected in the syringe of 10ml electrospinning silk syringe and carries out the electrospinning silk, PMMA-NG-α-CD one dimension quasi-nano composite fibre.Electrospinning strand spare: the stainless pin bore dia is 0.5mm, and links with DC high-voltage power supply; Aluminum rotary speed 800～2000r/min; Distance is 12cm between syringe needle and aluminium foil; Voltage is 20kV; Environment temperature is 45 ℃ during electrospinning.
PMMA-NG-β-CD one dimension quasi-nano composite fibre of collecting is immersed in the crosslinking agent XDI (XDI) of 20ml, and normal temperature soaks 48h down, makes it full cross-linked.Composite fibre after crosslinked fully washs with 0.5～1%NaOH aqueous solution, to remove impurity and microsphere.After washing finishes with product vacuumize to constant weight, obtain 1-dimention nano level NG trace α-CD fiber (FMIP).FMIP behind the wash-out has big specific area and pore volume, helps contacting of substrate and binding site, improves load capacity.
Neohesperidin (NHD) is 950 times of dihydrochalcone sugariness, is a kind of sweetener of new generation of nontoxic, low-yield, high sugariness.But when preparation NHD sweetener, Chang Yin contains a spot of reactant NG, and sugariness descends.With the blotting membrane technology NG is isolated from NHD, have the practical application meaning.
Select for use NG and with neohesperidin (NHD) sweetener of NG structural similarity as substrate, prepared trace α-CD fiber has been carried out the selectivity experiment.The result is 17.2%: 1.7% ≈ 10.1 for aurantiin to the separation rate ratio of neohesperidin.
Embodiment 4
PVP is that matrix, hydroxypropyl-CD are that functive, receiver are that aluminium rotating disk, crosslinking agent are MDI
It is the PVP-ethanol colloidal sol of 6% (W/V) that PVP is dissolved in the alcohol solvent preparation concentration.The microsphere NG of 1g hydroxypropyl-CD and 0.5g is dissolved in N, in the dinethylformamide solvent, then NG-hydroxypropyl-CD-DMF solution is slowly joined in the PVP-ethanol colloidal sol.In the PVP-NG-hydroxypropyl-CD colloidal sol of preparation.At room temperature stir PVP-NG-hydroxypropyl-CD colloidal sol 4h fast.PVP-NG-hydroxypropyl-CD the colloidal sol that stirs is carried out the electrospinning silk, and device for spinning and condition are with embodiment 2.
PVP-NG-hydroxypropyl-CD one dimension quasi-nano composite fibre of collecting is immersed among the crosslinking agent MDI, and 30 ℃ are soaked 28h down, make it full cross-linked.Composite fibre after crosslinked fully washs with the 0.8%NaOH aqueous solution, to remove impurity and microsphere.After washing finishes with product vacuumize to constant weight, obtain 1-dimention nano level trace hydroxypropyl-CD fiber.
Select for use NG and with neohesperidin (NHD) sweetener of NG structural similarity as substrate, prepared trace hydroxypropyl-CD fiber has been carried out the selectivity experiment.The result is 15.2%: 2.4% ≈ 6.3 for aurantiin to the separation rate ratio of neohesperidin.
Embodiment 5
PS is that matrix, γ-CD are that functive, receiver are that aluminium rotating disk, crosslinking agent are LDI
The microsphere NG of the PS of 10g, the functive γ of 5g-CD and 0.2g is dissolved in an amount of N, in the dinethylformamide, stirs 5h under the room temperature, make PS-NG-γ-CD colloidal sol.This colloidal sol is carried out the electrospinning silk, and device for spinning and condition are with embodiment 2.
PS-NG-γ-CD composite fibre of collecting is immersed among the crosslinking agent LDI, and 35 ℃ are soaked 24h down, make it full cross-linked.Composite fibre after crosslinked fully washs with 0.5～1%NaOH aqueous solution, to remove impurity and microsphere.After washing finishes with product vacuumize to constant weight, obtain molecular engram γ-CD polymer fiber.
Select for use NG and with the aurantiamarin of NG structural similarity, aurantiin dihydrochalcone as substrate, prepared trace γ-CD fiber has been carried out the selectivity experiment.The trace separating effect is:
Aurantiin: aurantiamarin: aurantiin dihydrochalcone=16.6: 1.9: 1.4 ≈ 11.9: 1.4: 1.0
Embodiment 6
PAN is that matrix, carboxymethyl-CD are that functive, receiver are that aluminium rotating disk, crosslinking agent are TDI
Functive carboxymethyl-the CD of PAN, the 4g of 8g and the microsphere NG of 0.2g are dissolved in an amount of N, in the dinethylformamide, stir 4h under the room temperature, make PAN-NG-carboxymethyl-CD colloidal sol.This colloidal sol is carried out the electrospinning silk, and device for spinning and condition are with embodiment 2.
PAN-NG-carboxymethyl-CD composite fibre of collecting is immersed among the crosslinking agent TDI, and 30 ℃ are soaked 36h down, make it full cross-linked.Composite fibre after crosslinked fully washs with 0.5～1%NaOH aqueous solution, to remove impurity and microsphere.After washing finishes with product vacuumize to constant weight, obtain molecular engram carboxymethyl-CD polymer fiber.
Select for use NG and with neohesperidin (NHD) sweetener of NG structural similarity as substrate, prepared trace carboxymethyl-CD fiber has been carried out the selectivity experiment.The result is 15.7%: 1.6% ≈ 9.8 for aurantiin to the separation rate ratio of neohesperidin.
Claims (8)
1. method of efficiently separating the trace fiber based on the aurantiin water of electrical spinning method preparation, with the high molecular polymer matrix is electrospinning silk colloidal sol base material, and preparation electrospinning silk colloidal sol utilizes electrospinning silk instrument to prepare composite nano fiber, utilize crosslinking agent to carry out cross-linking reaction at last, it is characterized in that:
1) preparation electrospinning silk colloidal sol:
The high molecular polymer matrix is dissolved in is prepared into high molecular polymer-organic solvent colloidal sol in the organic solvent; Functive cyclodextrin and microsphere are dissolved in the organic solvent, at room temperature mix, stir 2～5h and carry out blend, make high molecular polymer-functive cyclodextrin-microsphere electrospinning silk mixed sols with high molecular polymer-organic solvent colloidal sol;
2) electrospinning silk technology prepares composite nano fiber;
3) composite fibre is immersed in the crosslinking agent, carries out cross-linking reaction, soak 24～48h; Reaction finishes the back, and fully washing, vacuumize obtain 1-dimention nano level trace cyclodextrin fiber to constant weight.
2. method of efficiently separating aurantiin trace fiber based on the aurantiin water of electrical spinning method preparation according to claim 1 is characterized in that described high molecular polymer is polyvinyl butyral resin, polystyrene, polyacrylonitrile, polymethyl methacrylate or polyvinylpyrrolidone.
3. according to claim 1, the 2 described methods that preparation efficiently separates aurantiin trace cyclodextrin polymer nanofiber at aqueous phase based on electrical spinning method, it is characterized in that describedly with high molecular polymer-organic solvent colloidal sol, its concentration is 4.0～12% (W/V).
4. method of efficiently separating aurantiin trace fiber based on the aurantiin water of electrical spinning method preparation according to claim 1 is characterized in that described organic solvent is ethanol, acetone, N, dinethylformamide or N,N-dimethylacetamide.
5. method of efficiently separating aurantiin trace fiber based on the aurantiin water of electrical spinning method preparation according to claim 1 is characterized in that microsphere is aurantiin, aurantiamarin, neohesperidin or aurantiin dihydrochalcone.
6. method of efficiently separating aurantiin trace fiber based on the aurantiin water of electrical spinning method preparation according to claim 1 is characterized in that described cyclodextrin functive is alpha-cyclodextrin, beta-schardinger dextrin-, gamma-cyclodextrin, hydroxypropyl cyclodextrin or carboxymethyl cyclodextrin.
7. method of efficiently separating aurantiin trace fiber based on the aurantiin water of electrical spinning method preparation according to claim 1 is characterized in that described crosslinking agent is hexamethylene diisocyanate, toluene di-isocyanate(TDI), XDI, lysinediisocyanate or isocyanates.
8. method of efficiently separating aurantiin trace fiber according to claim 1 based on the aurantiin water of electrical spinning method preparation, it is characterized in that high molecular polymer accounts for 4～12 weight portions in described high molecular polymer-functive cyclodextrin-microsphere electrospinning silk mixed sols, the functive cyclodextrin accounts for 1～5 weight portion, microsphere accounts for 0.10～0.5 weight portion, and organic solvent accounts for 15～25 parts by volume (ml).
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| CN104704162A (en) * | 2012-08-24 | 2015-06-10 | 奇特罗克斯生物科学有限公司 | Bioflavonoid impregnated materials |
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| WO2021114459A1 (en) * | 2019-12-13 | 2021-06-17 | 江苏集萃先进高分子材料研究所有限公司 | Halogen-free flame-retardant and smoke-suppressant fiber, and preparation method therefor |
| CN113062003A (en) * | 2021-04-13 | 2021-07-02 | 浙江理工大学 | Method for preparing high latent heat nanometer intelligent fiber through crosslinking |
| CN113308877A (en) * | 2021-06-18 | 2021-08-27 | 广州绿徽新材料研究院有限公司 | Preparation method of high-performance flame-retardant fiber |
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