CN101507909A - Molecular engram microspheres preparation method using micro-fluidic reactor - Google Patents
Molecular engram microspheres preparation method using micro-fluidic reactor Download PDFInfo
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Abstract
The invention relates to a method for combined synthesis of molecular engram microspheres through a micro-fluidic reactor, which is characterized in that a micro-fluidic reactor system comprises a fluid drive unit (an injection pump group), a liquid droplet or milk droplet forming unit and an ultraviolet illumination and polymerization unit, wherein the micro-fluidic reactor comprises n groups of '*'-shaped microchannels with the same structure, and can simultaneously prepare the molecular engram microspheres under n conditions or prepare the molecular engram microspheres of n template molecules; and dispersed phases and continuous phases are driven by injection pumps to enter respective microchannels and form milk droplets when encountering each other on crossings of the microchannels, and the prepared milk droplets arrive at the ultraviolet illumination unit for polymerization reaction.
Description
[technical field]:
The invention belongs to technical field of chemical engineering, relate to the method for utilizing the micro-fluidic reactor molecular engram microspheres preparation.
[background technology]:
Molecular imprinting is a kind of emerging, separate analytical technique efficiently, it can prepare the polymer that target molecule is had predetermined selectivity, prepared polymer is called as molecularly imprinted polymer (Molecularly ImprintedPolymers is abbreviated as MIPs usually).Concern to have the advantage of high selectivity and high strength (promptly heat-resisting, organic solvent-resistant, acid and alkali-resistance) because MIPs and target molecule have " lock-key ", be rapidly developed in recent years.Molecularly imprinted polymer has been widely used in Pharmaceutical Analysis, detection of veterinary drugs in food, Detecting Pesticide, antibody or has been subjected to numerous areas such as n-body simulation n, sensor, has demonstrated good prospects for application.
It is block that the molecularly imprinted polymer of early stage report is generally, and resolution ratio is low, and cause chromatographic peak broadening, hangover easily seriously.In recent years, the technology of preparing of molecular blotting polymer microsphere has become the research focus of this area.The preparation method of molecular blotting polymer microsphere mainly contains that dispersin polymerization, precipitation polymerization, seed swelling suspend and the suspension polymerisation of multistep swelling, surperficial matrix polymerization, surface imprinted etc., the most good molecular engram microspheres of preparation monodispersities that are difficult to of said method.
Adopting micro fluidic device (Microfluidic Device also can be called micro-fluidic chip) or micro-fluidic reactor (Microfluidic Reactor) preparation microballoon is a kind of preparation size homogeneous that just occurs recent years, the effective ways of controlled microballoon.At present existing with this technology be used to prepare molecular engram microsphere report, it has designed a spiral microfluidic channel device, the micro fluidic device for preparing other microballoon with great majority is the same, has only an oil phase/water crossing, promptly have only one to form emulsion droplet (drop) crossing, the micro fluidic device of this " single cross prong (or being single channel) " prepare microballoon speed slow, measure less, time-consuming.
In addition, in molecular blotting polymer microsphere synthetic, the factor that influences the molecular engram effect has a lot, comprise: the selection of function monomer, crosslinking agent kind, the selection of template molecule and function monomer and crosslinking agent ratio, polymerization reaction time, pore-foaming agent kind and consumption etc., and when utilizing suspension polymerisation or inverse suspension polymerization, also need to consider the selection of dispersant kind and consumption.Therefore, in order to obtain a kind of molecular engram microsphere of optimum efficiency, often need to screen various conditions through a large amount of experiments.And during some detect, often there are a variety of material demands to detect, need set up the molecular engram storehouse,, when these molecularly imprinted polymers of preparation, need the cost plenty of time as the molecular engram storehouse of detection of veterinary drugs in food.
[summary of the invention]:
The objective of the invention is to utilize micro-fluidic reactor, adopt the combination synthetic method, realize the synthetic and screening of combination of molecular engram microsphere, can be used in the screening of molecular engram compound microballoon synthesis condition, also can be used for the foundation in molecular engram microsphere storehouse, and when n group "
" when the type microchannel was used for a kind of molecular engram microsphere simultaneously and prepares, its preparation speed " single cross prong " micro fluidic device was fast.
The method of utilizing the micro-fluidic reactor molecular engram microspheres preparation of the present invention is characterized in that, the micro-fluidic reactor system comprises that fluid driver element (syringe pump group or constant-flux pump group), drop or emulsion droplet form unit, ultraviolet lighting polymerized unit.
Above-mentioned micro-fluidic reactor comprises n group same structure
The type microchannel, every group
The type microchannel comprises 2 microchannels, a microchannel operation continuous phase solution, another microchannel operation decentralized photo solution; Decentralized photo and continuous phase enter microchannel separately respectively under the driving of syringe pump, when decentralized photo enters continuous phase in the passage crossing, form emulsion droplet or drop, and drop that makes or emulsion droplet arrive the ultraviolet lighting unit and carry out polymerisation.
Above-mentioned fluid driver element comprises a plurality of syringe pumps or constant-flux pump, wherein syringe pump is the syringe pump of single channel, binary channels, six passages or 10 passages, and the syringe pump of the single channel here, binary channels, six passages or 10 passages refers to drive simultaneously the syringe pump of 1,2,6 or 10 syringe respectively.
Utilize micro-fluidic reactor every group
The type microchannel prepares the method for molecular engram microsphere, may further comprise the steps:
1. prepare decentralized photo solution, the mixed solution of forming by function monomer, template molecule, pore-foaming agent, crosslinking agent, initator, ultrasonic degas 3～12min, feed nitrogen 10～60min, then this solution is changed in the syringe of syringe pump, and be connected with decentralized photo inlet in the micro-fluidic reactor;
2. prepare continuous phase solution, it is in the continuous phase that dispersant is added decentralized medium, and ultrasonic degas 3～12min feeds nitrogen 15～60min, then this solution is changed in the syringe of syringe pump, and is connected with continuous phase inlet in the micro-fluidic reactor;
3. under the driving of syringe pump, when decentralized photo solution and continuous phase solution exist
When meet in the crossing of type microchannel, form drop or emulsion droplet;
4. drop that generates in 3. or emulsion droplet flow to micro-fluidic reactor the ultraviolet lighting unit time, under the ultraviolet lighting about 365nm, carry out polymerisation and obtain microballoon, the ultraviolet source here is that (centre wavelength of its emission wavelength is 365nm ± 10nm) or mercury lamp to ultraviolet lamp tube, preferred ultraviolet lamp tube;
5. the microballoon that will 4. obtain washs, washes, and to remove template molecule and the unreacted function monomer in the microballoon, just obtains having the molecular engram microsphere with template molecule complementary hole in solid space or functional group.
When n group "
" during (or parallel) operation simultaneously of type microchannel; the just molecular engram microsphere of (or parallel) preparation n kind template molecule simultaneously; perhaps can under n kind condition, carry out molecular engram microsphere preparation; perhaps under a certain optimal conditions, carry out the molecular engram microsphere of a certain template molecule with a kind of template molecule, can productivity gain.
Said method, utilize micro-fluidic reactor and carry out the synthesis condition screening and optimization of molecular engram microsphere in conjunction with the method for combinatorial chemistry, and can be under optimal conditions separately, carry out the molecular engram microsphere preparation of different templates molecule, provide quick, high-throughout synthetic method for setting up the molecular engram storehouse; And compare with traditional stirring suspension polymerization, the molecular engram microsphere narrow diameter distribution of this method preparation, coefficient of variation CV value is little.
The method of above-mentioned micro-fluidic reactor molecular engram microspheres preparation can be used in the combination of multiclass molecular engram microsphere synthesizes, as being the molecular engram microsphere of template molecule with the veterinary drug, being the molecular engram microsphere of template molecule with the agricultural chemicals, being the preparation of the molecular engram microsphere of template with the natural activity molecule.
The method of above-mentioned micro-fluidic reactor molecular engram microspheres preparation, the mol ratio of described template molecule, function monomer, crosslinking agent is 1:4～8:15～40, the pore-foaming agent consumption is 0.5～3 times of crosslinking agent quality, and initator is 0.1%～20% of crosslinking agent and a pore-foaming agent quality summation.
In the method for above-mentioned micro-fluidic reactor molecular engram microspheres preparation, template molecule is drug molecule chloramphenicol, erythromycin, rifampin, fortimicin, terramycin, Cimetidine, Ciprofloxacin or tetracycline;
In the method for above-mentioned micro-fluidic reactor molecular engram microspheres preparation, template molecule is agricultural chemicals Quizalotop-ethyl, triazolone, metrifonate, parathion, Azodrin, maleic acid hydrazide, daminozide or malachite green.
In the method for above-mentioned micro-fluidic reactor molecular engram microspheres preparation, template molecule be Quercetin, kudzuvine root isoflavone,
Beta carotene, GINKGO BILOBA EXTRACT or isoflavones.
Above-mentioned micro-fluidic reactor comprises the n group
The type microchannel, 2≤n 〉=30 wherein, and be integer.
In the method for above-mentioned micro-fluidic reactor molecular engram microspheres preparation, function monomer is a kind or 2 kinds in methacrylic acid, acrylamide, 4-vinylpridine, 2-vinylpyridine, styrene, cyclodextrin or the methyl methacrylate.
In the method for above-mentioned micro-fluidic reactor molecular engram microspheres preparation, crosslinking agent is ethylene glycol dimethacrylate (EDMA), divinylbenzene, Toluene-2,4-diisocyanate, 4-vulcabond or 2,2-methylol butanols trimethyl propylene ester.
In the method for above-mentioned micro-fluidic reactor molecular engram microspheres preparation, pore-foaming agent is a kind, 2 kinds or 3 kinds in chloroform, cyclohexane, toluene, oxolane, second eyeball, methyl alcohol, ethyl acetate, cyclohexanol or the lauryl alcohol.
In the method for above-mentioned micro-fluidic reactor molecular engram microspheres preparation, described decentralized medium (being continuous phase) is silicone oil, atoleine or water.
In the method for above-mentioned micro-fluidic reactor molecular engram microspheres preparation, when decentralized photo contains nonpolar stronger pore-foaming agent (as chloroform, cyclohexane), its continuous phase is water, and in water, add a certain amount of suitable dispersant, as PVAC polyvinylalcohol, the amount of PVA is 0.2%～8% of a water quality; When decentralized photo contained polarity pore-foaming agent such as second eyeball, its continuous phase was silicone oil or atoleine, and added surfactant in silicone oil or atoleine, and as polysorbas20, polysorbate40, Tween 80, the amount of surfactant is 0.5%～8% of a continuous phase.
In the method for above-mentioned micro-fluidic reactor molecular engram microspheres preparation, decentralized photo is 200:1～1:500 with the volume flow rate ratio of continuous phase.
[description of drawings]:
Fig. 1 is for having 6 groups
The structural representation of the micro-fluidic reactor of type microchannel, wherein the fluid driver element is 26 passage syringe pumps, 1,2,3,4,5,6 is 6
The type microchannel, a, b, c, d, e and f are the ultraviolet lighting unit.Under driving at syringe pump, when decentralized photo enters continuous phase in the crossing, microchannel, form drop or emulsion droplet, drop continues to flow forward to arrive the ultraviolet lighting unit, and polymerization reaction take place under the 365nm ultraviolet lighting enters receiving flask at last.
[specific embodiment]:
Embodiment 1.
The screening of chloramphenicol molecular imprinting microballoon synthesis condition.
Contain 4 groups at one
In the micro-fluidic reactor of type microchannel, every group
The type microchannel is synthetic microballoon under different condition respectively, can obtain 4 kinds of molecular engram microspheres under the different condition simultaneously.
At first prepare decentralized photo solution, with template molecule chloramphenicol ultrasonic dissolution in pore-foaming agent or solvent chloroform, add function monomer methacrylic acid or 4-vinylpridine, crosslinking agent EDMA 60mmol, initator azodiisobutyronitrile AIBN 0.24g, solution is through ultrasonic degas 5min, logical nitrogen deoxygenation 15min is then with in the syringe of this solution immigration syringe pump (avoiding air to enter syringe) as far as possible; The preparation continuous phase solution adds dispersant PVA in the entry, stirring and dissolving, and ultrasonic degas 5min feeds nitrogen deoxygenation 20min.4 kinds of conditions of chloramphenicol molecular imprinting microballoon preparation see Table 1.
4 kinds of conditions of table 1. chloramphenicol molecular imprinting microballoon preparation
The microballoon that makes under above-mentioned 4 kinds of conditions is washed with chloroform with elder generation, use ethyl acetate rinse then, use methyl alcohol-acetate (9:1 again, v/v) solution flushing, use washed with methanol at last, obtain 4 kinds of molecular engram microspheres, respectively with the analysis of 4 kinds of molecular engram microsphere vibration absorption methods, be about to the 100mg molecular engram microsphere and insert in the centrifuge tube of 5ml, add chloramphenicol methanol-water (5:5, v/v) solution of 3ml, 0.06mmol/L again, vibration absorption is after 2 hours, centrifugal, measure the chloramphenicol concentration of supernatant, just can calculate the adsorption rate of molecular engram microsphere.The result shows that the molecular engram microsphere effect of No.2 gained is better, is 92% to the adsorption rate of chloramphenicol.
Embodiment 2.
The screening of triazolone molecular engram microsphere synthesis condition.
Contain 6 groups at one
In the micro-fluidic reactor of type microchannel, every group
The type microchannel is synthetic microballoon under different condition respectively, can obtain 6 kinds of molecular engram microspheres under the different condition simultaneously.
At first prepare decentralized photo solution, with template molecule triazolone ultrasonic dissolution in pore-foaming agent or solvent toluene, add function monomer methacrylic acid or 4-vinylpridine, crosslinking agent EDMA 60mmol, initator azodiisobutyronitrile AIBN 0.20g, solution is through ultrasonic degas 6min, logical nitrogen deoxygenation 20min is then with in the syringe of this solution immigration syringe pump (avoiding air to enter syringe) as far as possible; The preparation continuous phase solution adds dispersant PVA in the entry, stirring and dissolving, and ultrasonic degas 5min feeds nitrogen deoxygenation 25min.6 kinds of conditions of triazolone molecular engram microsphere preparation see Table 2.
6 kinds of conditions of table 2. triazolone molecular engram microsphere preparation
With the microballoon vacuum drying that makes under above-mentioned 6 kinds of conditions, with the water flushing microballoon that contains acetate, with the flushing of second eyeball, obtain 6 kinds of molecular engram microspheres again, respectively with the analysis of 6 kinds of molecular engram microsphere vibration absorption methods, being about to the 120mg molecular engram microsphere inserts in the centrifuge tube of 5ml, the second eyeball solution that adds the triazolone of 3ml, 0.08mmol/L again, vibration absorption is after 2 hours, and is centrifugal, measure the triazolone concentration of supernatant, just can calculate the adsorption rate of molecular engram microsphere.The result shows that the molecular engram microsphere effect of No.3 gained is better, is 86% to the adsorption rate of triazolone.
Embodiment 3.
The screening of terramycin molecular engram microsphere synthesis condition.
Contain 8 groups at one
In the micro-fluidic reactor of type microchannel, every group
The type microchannel is synthetic microballoon under different condition respectively, can obtain 8 kinds of molecular engram microspheres under the different condition simultaneously.
At first prepare decentralized photo solution, with template molecule terramycin ultrasonic dissolution in pore-foaming agent or solvent second eyeball, add function monomer methacrylic acid or 4-vinylpridine, crosslinking agent EDMA 60mmol, initator azodiisobutyronitrile AIBN 0.20g, solution is through ultrasonic degas 6min, logical nitrogen deoxygenation 20min is then with in the syringe of this solution immigration syringe pump (avoiding air to enter syringe) as far as possible; The preparation continuous phase solution joins the surfactant Tween 80 in the atoleine, stirring and dissolving, and ultrasonic degas 5min feeds nitrogen deoxygenation 25min.8 kinds of conditions of terramycin molecular engram microsphere preparation see Table 3.
8 kinds of conditions of table 3. terramycin molecular engram microsphere preparation
The microsphere suspension liquid that makes under above-mentioned 8 kinds of conditions is centrifugal, use acetone rinsing, with the second eyeball solution flushing that contains acetate, obtain 8 kinds of molecular engram microspheres under the condition again, respectively with the analysis of 8 kinds of molecular engram microsphere vibration absorption methods, being about to the 100mg molecular engram microsphere inserts in the centrifuge tube of 5ml, the second eyeball solution that adds the terramycin of 3ml, 0.08mmol/L again, vibration absorption is after 2 hours, and is centrifugal, measure the terramycin concentration of supernatant, just can calculate the adsorption rate of molecular engram microsphere.The result shows that the molecular engram microsphere effect of No.7 gained is better, is 87% to the adsorption rate of terramycin.
Claims (11)
1, a kind of method of utilizing the micro-fluidic reactor molecular engram microspheres preparation, it is characterized in that, micro-fluidic reactor comprises n group microchannel, n group microchannel is moved simultaneously, the molecular engram microsphere that can prepare n kind template molecule simultaneously perhaps can carry out the molecular engram microsphere preparation with a kind of template molecule under n kind condition.
2, method according to claim 1 is characterized in that, in micro-fluidic reactor, utilizes the microchannel to prepare drop, and the drop that makes passes through the ultraviolet lighting polymerisation in microchannel subsequently; Utilize every group of microchannel of micro-fluidic reactor to prepare the method for molecular engram microsphere, may further comprise the steps:
1. prepare decentralized photo solution, by the mixed solution that function monomer, a kind of template molecule, pore-foaming agent, crosslinking agent, initator are formed, ultrasonic degas 5～10min feeds nitrogen 15min, then decentralized photo solution is changed in the syringe of syringe pump;
2. prepare continuous phase solution, it is in the continuous phase that dispersant is added decentralized medium, and ultrasonic degas 5～10min feeds nitrogen 20min, then continuous phase solution is changed in the syringe of syringe pump;
3. start syringe pump, when 1. described solution when 2. described solution meets in the crossing of type microchannel, just form drop;
4. when the droplet flow that 3. forms arrives the ultraviolet lighting polymeric part of micro-fluidic reactor, under ultraviolet lighting, carry out polymerisation and obtain microballoon;
5. the microballoon that will 4. obtain washes, and to remove template molecule and the unreacted function monomer in the microballoon, just obtains molecular blotting polymer microsphere.
3, method according to claim 1 is characterized in that, micro-fluidic reactor comprises n group microchannel, 2≤n 〉=30 wherein, and n is an integer.
4, the preparation method of molecular engram microsphere according to claim 1 is characterized in that, the mol ratio of described template molecule, function monomer, crosslinking agent is 1:4～8:15～40.
According to claim 1 and 2 described methods, it is characterized in that 5, template molecule is drug molecule chloramphenicol, erythromycin, rifampin, fortimicin, terramycin, Cimetidine, Ciprofloxacin or tetracycline.
According to claim 1 and 2 described methods, it is characterized in that 6, template molecule is agricultural chemicals Quizalotop-ethyl, triazolone, metrifonate, parathion, Azodrin, maleic acid hydrazide, daminozide or malachite green.
According to claim 1 and 2 described methods, it is characterized in that 7, template molecule is Quercetin, kudzuvine root isoflavone or isoflavones.
According to claim 1 and 2 described methods, it is characterized in that 8, function monomer is methacrylic acid, acrylamide, 4-vinylpridine, 2-vinylpyridine, styrene, cyclodextrin or methyl methacrylate.
According to claim 1 and 2 described methods, it is characterized in that 9, crosslinking agent is ethylene glycol dimethacrylate, divinylbenzene, Toluene-2,4-diisocyanate, 4-vulcabond or 2,2-methylol butanols trimethyl propylene ester.
According to claim 1 and 2 described methods, it is characterized in that 10, pore-foaming agent is chloroform, cyclohexane, toluene, oxolane, second eyeball, methyl alcohol, ethyl acetate or cyclohexanol.
According to claim 1 and 2 described methods, it is characterized in that 11, decentralized medium is silicone oil, atoleine or water.
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