CN113754828A - Method for preparing patterned gel material by polymerization of front end of micro-channel - Google Patents
Method for preparing patterned gel material by polymerization of front end of micro-channel Download PDFInfo
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- CN113754828A CN113754828A CN202110970508.4A CN202110970508A CN113754828A CN 113754828 A CN113754828 A CN 113754828A CN 202110970508 A CN202110970508 A CN 202110970508A CN 113754828 A CN113754828 A CN 113754828A
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- 238000006116 polymerization reaction Methods 0.000 title claims abstract description 37
- 238000000034 method Methods 0.000 title claims abstract description 28
- 239000000463 material Substances 0.000 title claims abstract description 22
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims abstract description 30
- 239000000178 monomer Substances 0.000 claims abstract description 19
- 229910052742 iron Inorganic materials 0.000 claims abstract description 15
- 238000005476 soldering Methods 0.000 claims abstract description 13
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims abstract description 11
- 230000000977 initiatory effect Effects 0.000 claims abstract description 10
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000010438 heat treatment Methods 0.000 claims abstract description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 7
- 239000003431 cross linking reagent Substances 0.000 claims abstract description 7
- 239000003999 initiator Substances 0.000 claims abstract description 7
- 239000003960 organic solvent Substances 0.000 claims abstract description 5
- 239000000243 solution Substances 0.000 claims description 31
- 239000004205 dimethyl polysiloxane Substances 0.000 claims description 18
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 claims description 18
- 239000002243 precursor Substances 0.000 claims description 18
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 15
- 238000003756 stirring Methods 0.000 claims description 13
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 claims description 12
- 239000003795 chemical substances by application Substances 0.000 claims description 11
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 10
- ZIUHHBKFKCYYJD-UHFFFAOYSA-N n,n'-methylenebisacrylamide Chemical group C=CC(=O)NCNC(=O)C=C ZIUHHBKFKCYYJD-UHFFFAOYSA-N 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- 238000005303 weighing Methods 0.000 claims description 8
- 239000011259 mixed solution Substances 0.000 claims description 7
- 229910001870 ammonium persulfate Inorganic materials 0.000 claims description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 5
- 229920002379 silicone rubber Polymers 0.000 claims description 5
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 claims description 4
- 239000004342 Benzoyl peroxide Substances 0.000 claims description 4
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 235000019400 benzoyl peroxide Nutrition 0.000 claims description 4
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims description 3
- CNCOEDDPFOAUMB-UHFFFAOYSA-N N-Methylolacrylamide Chemical compound OCNC(=O)C=C CNCOEDDPFOAUMB-UHFFFAOYSA-N 0.000 claims description 3
- 238000001035 drying Methods 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 239000002994 raw material Substances 0.000 claims description 2
- 238000004506 ultrasonic cleaning Methods 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- 235000013870 dimethyl polysiloxane Nutrition 0.000 claims 5
- CXQXSVUQTKDNFP-UHFFFAOYSA-N octamethyltrisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)O[Si](C)(C)C CXQXSVUQTKDNFP-UHFFFAOYSA-N 0.000 claims 5
- 238000004987 plasma desorption mass spectroscopy Methods 0.000 claims 5
- 238000002360 preparation method Methods 0.000 abstract description 5
- 238000006243 chemical reaction Methods 0.000 abstract description 3
- 230000035484 reaction time Effects 0.000 abstract 1
- 239000000499 gel Substances 0.000 description 39
- 238000002156 mixing Methods 0.000 description 6
- 230000008961 swelling Effects 0.000 description 4
- 239000011837 N,N-methylenebisacrylamide Substances 0.000 description 2
- WYTGDNHDOZPMIW-RCBQFDQVSA-N alstonine Natural products C1=CC2=C3C=CC=CC3=NC2=C2N1C[C@H]1[C@H](C)OC=C(C(=O)OC)[C@H]1C2 WYTGDNHDOZPMIW-RCBQFDQVSA-N 0.000 description 2
- 238000010276 construction Methods 0.000 description 2
- 238000000059 patterning Methods 0.000 description 2
- 206010024769 Local reaction Diseases 0.000 description 1
- -1 Polydimethylsiloxane Polymers 0.000 description 1
- 241000270295 Serpentes Species 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 229920001002 functional polymer Polymers 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 238000007348 radical reaction Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000007779 soft material Substances 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F226/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
- C08F226/06—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a heterocyclic ring containing nitrogen
- C08F226/10—N-Vinyl-pyrrolidone
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/04—Polymerisation in solution
- C08F2/06—Organic solvent
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/52—Amides or imides
- C08F220/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
- C08F220/56—Acrylamide; Methacrylamide
Abstract
The invention discloses a method for preparing a patterned gel material by polymerization of the front end of a micro-channel. The method is characterized in that: the acrylamide monomer, the acrylate monomer, the N-vinyl pyrrolidone, the initiator and the cross-linking agent are dissolved in an organic solvent to prepare a uniform solution, the uniform solution is transferred to an injector, and then the uniform solution is injected into the microchannel chip by the injector. And heating and initiating by using an electric soldering iron above one end of the micro-channel chip, wherein the solution can form a stable front end face and can move in the channel at a constant speed, and the patterned gel with a specific structure can be obtained after the reaction is finished. The invention does not need an external heating source to maintain the polymerization of the whole system in the polymerization reaction process, has controllability, short polymerization reaction time, energy saving and no pollution; the front-end polymerization is applied to the micro-channel chip with millimeter size, so that the pattern gel materials with different structures are quickly synthesized, a method is provided for the quick preparation of the pattern gel, and the method has high application value.
Description
Technical Field
The invention relates to the technical field of functional polymer material preparation, in particular to a method for preparing patterned gel by adopting front-end polymerization.
Background
Front-end polymerization is a novel free radical reaction mode for converting gel monomers into gels by the movement of local reaction zones in the gel monomers. After the heat source is removed, the heat generated by the polymerization reaction is diffused to the unreacted area, and the polymerization is continuously initiated until the monomer in the container is completely polymerized. The method is simple to operate, does not need stirring in polymerization, saves energy and time, and is an ideal polymerization mode. However, the current research on front-end polymerization is mainly focused on the centimeter scale (in test tubes), because at the millimeter/micrometer scale, the heat released by the reaction is rapidly dissipated and the polymerization cannot be continuously initiated. Thus, achieving front-end polymerization at the millimeter/micrometer scale is still currently a difficult problem. The gel is a soft material, can generate structural change under the stimulation of environmental signals, is expected to be applied to the fields of micro soft robots and biomedical equipment, however, the structural diversity and the lack of patterning limit the wide application. Although the document reports that the patterned gel is prepared by front-end polymerization (adv. mater.2015,27, 6118-. The micro-channel chip provides an ideal reaction platform for the patterning construction of the gel material, so that the one-step rapid preparation of the patterned gel can be realized by carrying out front-end polymerization reaction in the micro-channel chip with the millimeter scale, and the micro-channel chip has innovative significance and creativity and has greater popularization and application values.
Disclosure of Invention
The invention aims to improve the defects of the prior art and provides a method for preparing a patterned gel material by microchannel front-end polymerization; the method has the advantages of high speed, high efficiency, low cost, high molding speed and the like, provides a path for realizing the rapid preparation of the patterned gel, and has higher application value in industrial production.
The technical scheme of the invention is as follows: method for preparing patterned gel material by microchannel front-end polymerization
(1) Engraving a transparent acrylic plate in a real object by using a numerical control engraving machine, respectively carrying out ultrasonic cleaning and drying on a template by using ethanol and pure water after engraving, and preparing a Polydimethylsiloxane (PDMS) micro-channel chip by using a reverse template method; the method comprises the following specific steps: uniformly stirring and defoaming the mixed solution of PDMS and a curing agent, pouring the mixed solution into a template, and curing to obtain a millimeter-scale PDMS microchannel chip;
(2) weighing a certain amount of acrylamide monomer, acrylate monomer, N-vinyl pyrrolidone and solvent, putting into a container, and stirring at room temperature until the solution is clear and transparent;
(3) dissolving an initiator and a cross-linking agent in the solution, stirring and dissolving to prepare a precursor solution of gel, and ultrasonically removing bubbles in the precursor solution;
(4) transferring the prepared gel precursor solution into an injector, and then injecting the gel precursor solution into a millimeter-scale PDMS microchannel chip by using the injector;
(5) and heating the upper part of one end of the PDMS microchannel chip by using an electric soldering iron to initiate polymerization reaction, then removing the electric soldering iron, and diffusing the heat released by the polymerization reaction to an unreacted area until all the raw materials in the whole reactor are converted into gel, thereby finally obtaining the patterned gel material.
Preferably, the curing agent is 184 silicone elastomer curing agent; the mass ratio of the PDMS to the curing agent is 10 (1-1.5); the curing temperature is 45-60 ℃, and the curing time is 3-4 hours.
The micro-channel chip can be any shape structure, the inner diameter size is preferably 1-3mm, and the length is preferably 6-12 cm.
Preferably, the acrylamide monomer is at least one of acrylamide and hydroxymethyl acrylamide; the acrylate monomer is at least one of hydroxyethyl acrylate and hydroxypropyl acrylate; the organic solvent is one of dimethyl sulfoxide and glycerol; the cross-linking agent is N, N' -methylene bisacrylamide; the initiator is one of ammonium persulfate and benzoyl peroxide.
Preferably, the mass percent of the acrylamide monomer, the mass percent of the acrylate monomer, the mass percent of the N-vinyl pyrrolidone, the mass percent of the organic solvent, the mass percent of the cross-linking agent and the mass percent of the initiator in the precursor solution of the gel are respectively 20-30%, 8-25%, 25-35%, 0.19-0.4% and 0.09-0.3%, respectively.
The polymerization reaction described above is a front-end polymerization method. The temperature of the electric soldering iron for initiating polymerization reaction is 80-120 ℃, and the distance between the electric soldering iron and the liquid level is 0.8-1.2 mm; the polymerization time of the electric iron is 20-40 s.
Heating one end of the micro-channel chip, forming the end face without any external energy, finishing polymerization by the heat released by the polymerization reaction, placing an electric soldering iron above one end of the micro-channel chip before initiating polymerization, and obtaining the patterned gel material within 5-10min preferably.
Has the advantages that:
the invention combines the front-end polymerization with the micro-channel chip, realizes the front-end polymerization reaction with millimeter size, can complete the preparation of the patterned gel material within 5-10min, has simple method and low energy consumption, and provides a new method for the multi-structural construction of the gel material. In addition, the aperture of the patterned gel material prepared by the method is 70-120 microns, the range of the equilibrium swelling ratio is 300-400%, the tensile strength is 0.7-1.0 MPa, and the elongation at break is 320-400%.
Drawings
FIG. 1 is a schematic representation of a patterned gel prepared in example 1.
Detailed Description
The present invention will be described below with reference to specific examples, but the present invention is not limited to these examples.
Example 1
The transparent acrylic plate is carved by a numerical control carving machine in a real object, and the PDMS micro-channel chip is prepared by a reverse template method and comprises a linear channel, a parallel channel, a divergent channel, a snake channel, a circular channel and a concentric circular channel. The mass ratio of PDMS to 184 silicone elastomer curing agent is 10:1.5, the curing temperature is 60 ℃, and the curing time is 3 hours. The length of the microchannel chip obtained in the above microchannel chip (linear, parallel, divergent, serpentine, circular and concentric circular channels) was 6cm, with an inner diameter of 2 mm. Weighing 2.6g of acrylamide, 0.9g of hydroxypropyl acrylate, 3.5g of N-vinyl pyrrolidone and 3g of solvent glycerol, putting the materials into a container together, stirring at room temperature, completely mixing the mixed solution, completely dissolving a monomer in the glycerol until the solution is clear and transparent, weighing 0.02g of ammonium persulfate and 0.03g of N, N-methylene bisacrylamide, dissolving the ammonium persulfate and the N, N-methylene bisacrylamide in the monomer solvent, stirring and dissolving to prepare a precursor solution of gel, and ultrasonically removing bubbles in the solution after uniformly mixing. The prepared gel precursor solution was transferred to an injector, and then injected into the above microchannel chips (linear, parallel, divergent, serpentine, circular, and concentric circular channels) having an inner diameter of 2mm, respectively, using the injector, and the length of the microchannel chip was 6 cm. After heating and initiating for 40s at a position 1mm above one end of the microchannel chip by using an electric soldering iron, the initiation temperature is 100 ℃, the solution can form a stable front end face and move in the channel at a constant speed, and the monomers in the microchannel chip are polymerized for 5min, so that the patterned gel with structural diversity can be obtained, as shown in fig. 1. The aperture of the gel material is 70 μm, the equilibrium swelling ratio range is 300%, the tensile strength is 0.88MPa, the elongation at break is 340%, and the gel material has excellent performance.
Example 2
The transparent acrylic plate is physically carved by a numerical control carving machine, and the divergent PDMS micro-channel chip is prepared by a reverse template method, wherein the mass ratio of PDMS to 184 organic silicon elastomer curing agent is 10:1.2, the curing temperature is 50 ℃, and the curing time is 3.5 hours. Weighing 3g of acrylamide, 2g of hydroxyethyl acrylate, 3g N-vinyl pyrrolidone and 2g of solvent glycerol, putting the mixture into a container, stirring at room temperature, completely mixing the mixed solution, completely dissolving a monomer in dimethyl sulfoxide until the solution is clear and transparent, weighing 0.03g of ammonium persulfate and 0.02g N of N-methylene bisacrylamide, dissolving the ammonium persulfate and the N-methylene bisacrylamide in the monomer solvent, stirring and dissolving to prepare a precursor solution of gel, and ultrasonically removing bubbles in the solution after uniformly mixing. Transferring the prepared gel precursor solution into an injector, and injecting the gel precursor solution into the divergent microchannel chip with the inner diameter of 1mm by using the injector, wherein the length of the microchannel chip is 8 cm. Heating and initiating for 30s at a position 1.2mm above one end of the microchannel chip by using an electric soldering iron, wherein the initiating temperature is 120 ℃, the solution can form a stable front end face and move in the channel at a constant speed, and all monomers in the microchannel chip are polymerized for 7min to obtain the patterned gel with a divergent structure. The gel material has the aperture of 106 mu m, the equilibrium swelling ratio range of 375 percent, the tensile strength of 1.0MPa and the elongation at break of 320 percent, and has excellent performance.
Example 3
The transparent acrylic plate is physically carved by a numerical control carving machine, a concentric circular PDMS micro-channel chip is prepared by a reverse template method, the mass ratio of PDMS to 184 organic silicon elastomer curing agent is 10:1, the curing temperature is 45 ℃, and the curing time is 4 hours. Weighing 2.1g of hydroxymethyl acrylamide, 2.1g of hydroxypropyl acrylate, 2.8g of N-vinyl pyrrolidone and 3g of dimethyl sulfoxide solvent, putting the materials into a container, stirring at room temperature, completely mixing the mixed solution, completely dissolving a monomer in the dimethyl sulfoxide until the solution is clear and transparent, weighing 0.01g of benzoyl peroxide and 0.04g N of N-methylene bisacrylamide, dissolving the benzoyl peroxide and the N-methylene bisacrylamide in the monomer solvent, stirring and dissolving to prepare a precursor solution of gel, and ultrasonically removing bubbles in the solution after uniform mixing. Transferring the prepared gel precursor solution into an injector, and injecting the gel precursor solution into the concentric circular microchannel chip with the inner diameter of 3mm by using the injector, wherein the length of the microchannel chip is 12 cm. Heating and initiating for 20s at a position 0.8mm above one end of the microchannel chip by using an electric soldering iron, wherein the initiating temperature is 80 ℃, the solution can form a stable front end face and move in the channel at a constant speed, and all monomers in the microchannel chip are polymerized for 10min to obtain the concentric patterned gel. The aperture of the gel material is 120 mu m, the equilibrium swelling ratio range is 400 percent, the tensile strength is 0.7MPa, the elongation at break is 400 percent, and the gel material has excellent performance.
Claims (7)
1. Method for preparing patterned gel material by microchannel front-end polymerization
(1) Physically carving the transparent acrylic plate by using a numerical control carving machine, respectively carrying out ultrasonic cleaning and drying on the template by using ethanol and pure water after carving, uniformly stirring and defoaming a mixed solution of PDMS and a curing agent, pouring the mixed solution into the template, and curing to obtain a millimeter-scale PDMS microchannel chip;
(2) weighing a certain amount of acrylamide monomer, acrylate monomer, N-vinyl pyrrolidone and solvent, putting into a container, and stirring until the solution is clear and transparent;
(3) dissolving an initiator and a cross-linking agent in the solution, stirring and dissolving to prepare a precursor solution of gel, and ultrasonically removing bubbles in the precursor solution;
(4) transferring the prepared gel precursor solution into an injector, and then injecting the gel precursor solution into a millimeter-scale PDMS microchannel chip by using the injector;
(5) and heating the upper part of one end of the PDMS microchannel chip by using an electric soldering iron to initiate polymerization reaction, then removing the electric soldering iron, and diffusing the heat released by the polymerization reaction to an unreacted area until all the raw materials in the whole reactor are converted into gel, thereby finally obtaining the patterned gel material.
2. The method of claim 1, wherein: the curing agent is 184 organic silicon elastomer curing agent; the mass ratio of the PDMS to the curing agent is 10 (1-1.5); the curing temperature is 45-60 ℃, and the curing time is 3-4 hours.
3. The method of claim 1, wherein: the micro-channel chip has an inner diameter of 1-3mm and a length of 6-12 cm.
4. The method of claim 1, wherein: the acrylamide monomer is at least one of acrylamide or hydroxymethyl acrylamide; the acrylate monomer is at least one of hydroxyethyl acrylate or hydroxypropyl acrylate; the organic solvent is one of dimethyl sulfoxide or glycerol; the cross-linking agent is N, N' -methylene bisacrylamide; the initiator is one of ammonium persulfate or benzoyl peroxide.
5. The method of claim 1, wherein: the mass percent of the acrylamide monomer, the mass percent of the acrylate monomer, the mass percent of the N-vinyl pyrrolidone, the mass percent of the organic solvent, the mass percent of the cross-linking agent and the mass percent of the initiator in the precursor solution of the gel are respectively 20-30%, 8-25%, 25-35%, 0.19-0.4% and 0.09-0.3%, respectively.
6. The method of claim 1, wherein: the polymerization reaction is carried out within 5-10min to obtain the patterned gel material.
7. The method of claim 1, wherein: the temperature of the electric soldering iron for initiating polymerization reaction is 80-120 ℃, and the distance between the electric soldering iron and the liquid level is 0.8-1.2 mm; the polymerization time of the electric iron is 20-40 s.
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