CN110938173A - Hydrogel with interpenetrating network structure and preparation method thereof - Google Patents
Hydrogel with interpenetrating network structure and preparation method thereof Download PDFInfo
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- 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
- C08F265/00—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00
- C08F265/10—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00 on to polymers of amides or imides
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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
- C08F120/00—Homopolymers 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
- C08F120/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F120/52—Amides or imides
- C08F120/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
- C08F120/58—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide containing oxygen in addition to the carbonamido oxygen, e.g. N-methylolacrylamide, N-acryloyl morpholine
Abstract
The invention provides an interpenetrating network structure hydrogel and a preparation method thereof, wherein N-acryloyl glycine (ACG) is firstly used as a comonomer, and is subjected to free radical polymerization to prepare N-acryloyl glycine (PACG) by initiating carbon-carbon double bonds on the N-acryloyl glycine (ACG) monomer, and then N-acryloyl glycinamide (NAGA) monomer is added into the poly N-acryloyl glycine (PACG) to initiate carbon-carbon double bonds on the N-acryloyl glycinamide (NAGA) to be subjected to free radical polymerization to prepare the interpenetrating network structure hydrogel. The method adopts a two-step method, uses poly N-acryloyl glycine (PACG) as a first heavy network and poly N-acryloyl glycinamide (PNAGA) as a second heavy network, and initiates monomers to carry out free radical polymerization under the action of an initiator to form the interpenetrating network structure hydrogel of poly N-acryloyl glycine (PACG) and poly N-acryloyl glycinamide (PNAGA).
Description
Technical Field
The invention relates to the technical field of high polymer materials, in particular to an interpenetrating network structure hydrogel and a preparation method thereof.
Background
Since the report entitled "hydrophilic gels for biological applications" published by Wichterl and Lim in 1960, the scientific community opened up a new area of scientific research. Hydrogel refers to a three-dimensional network of polymer materials containing a large amount of water formed by crosslinking polymer molecular chains together through physical, ionic, or covalent interactions. The special material composition and structure of the hydrogel are different from those of the traditional materials, so that the unique performance of the hydrogel is determined, the hydrogel has attracted extensive attention in the scientific research field at present, and certain research results are obtained.
Interpenetrating polymer networks refer to three-dimensional network structures formed by interpenetration of two or more crosslinked polymer networks, and similarly, interpenetrating polymer network hydrogels refer to hydrogel materials formed by interpenetration of two or more polymer networks in a network structure. Compared with a single network, the interpenetrating network hydrogel not only can enhance the gel strength, but also can properly combine the properties of the two networks and endow the two networks into a gel system without damaging the properties of the respective networks, thereby having considerable advantages.
Disclosure of Invention
The invention overcomes the defects in the prior art and provides an interpenetrating network structure hydrogel and a preparation method thereof, wherein N-acryloyl glycine (ACG) and N-acryloyl glycinamide (NAGA) are used as raw materials, a two-step method is adopted, poly N-acryloyl glycine (PACG) is used as a first heavy network, poly N-acryloyl glycinamide (PNAGA) is used as a second heavy network, and a monomer is initiated to carry out free radical polymerization under the action of an initiator to form the interpenetrating network structure hydrogel.
The purpose of the invention is realized by the following technical scheme.
An interpenetrating network structure hydrogel and a preparation method thereof, firstly, N-acryloyl glycine (ACG) is used as a comonomer, N-acryloyl glycine (PACG) is prepared by initiating carbon-carbon double bond on the N-acryloyl glycine (ACG) monomer to carry out free radical polymerization, secondly, N-acryloyl glycinamide (NAGA) monomer is added into the poly N-acryloyl glycine (PACG) to initiate carbon-carbon double bond on the N-acryloyl glycinamide (NAGA) to carry out free radical polymerization to prepare the interpenetrating network structure hydrogel, the molecules of the interpenetrating network structure hydrogel are mutually interpenetrated by the carbon-carbon main chain of the poly N-acryloyl glycine (PACG) and the carbon-carbon main chain of the poly N-acryloyl glycinamide (PNAGA) to form a three-dimensional crosslinking network structure, and the side chains are an amide group and a carboxyl group, wherein the mass ratio of N-acryloyl glycine (ACG) to N-acryloyl glycine amide (NAGA) is 1: (8-22), preferably 1: (9-20) a solid content of 20-30%, preferably 20-25%, (the solid content being the sum of the masses of N-Acryloylglycine (ACG) and N-acryloylglycinamide (NAGA)/the sum of the masses of both monomers and the solvent).
The chemical formulae of N-acryloyl glycine (ACG) and N-acryloyl glycine amide (NAGA) are as follows:
poly-N-acryloylglycine (PACG) contains a large number of carboxyl groups in its molecular structure, and if it is in a neutral to alkaline condition, the carboxyl groups are ionized in a large number to be in an ionic state and intermolecular hydrogen bonds are broken, a network structure stabilized by the intermolecular hydrogen bonds is broken and the stability of the whole is lost; the poly N-acryloyl glycinamide (PNAGA) gel has a double hydrogen bond structure, and internal hydrogen bonds are compact and are orderly arranged. If a certain amount of carboxyl groups are introduced into a poly N-acryloyl glycinamide (PNAGA) gel system to be used as functional modification, and carboxyl groups are introduced into the poly N-acryloyl glycinamide (PNAGA) gel system to be used as functional modification in a copolymerization mode, the originally regular double hydrogen bond arrangement in the poly N-acryloyl glycinamide (PNAGA) can be damaged, and the mechanical property and the stability of the whole gel are influenced. The method of adopting the interpenetrating polymer network is expected to perform functional modification, namely, introduce carboxyl groups, on the poly-N-acryloyl glycinamide (PNAGA) under the condition of not reducing the original gel performance of the poly-N-acryloyl glycinamide (PNAGA).
The solvent adopts deionized water, and N-acryloyl glycine (ACG) is dissolved in the deionized water to initiate free radical polymerization.
The amount of initiator used is 1-5%, preferably 2-3% of N-acryloyl glycine (ACG) and N-acryloyl glycine amide (NAGA).
The preparation method utilizes free radicals provided by an initiator to initiate monomers to react. Wherein the initiator can be selected from thermal initiator under water phase condition commonly used in polymer polymerization field, such as Ammonium Persulfate (APS) and potassium persulfate (KPS), or photoinitiator, such as 2-hydroxy-2-methyl-1-phenyl-1-acetone (Irgacure1173) or Irgacure 2959. If a thermal initiator is selected, it is necessary to first remove oxygen from the reaction system by using an inert gas (such as nitrogen, argon or helium) to avoid inhibition of polymerization, and then, depending on the activity and amount of the initiator, to heat the reaction system to a temperature above the initiation temperature of the initiator used and for a considerable time (such as 1 hour or more or longer (1 to 5 hours)) to promote the initiator to generate enough radicals for a long time to initiate the reaction system for continuous radical polymerization, thereby finally preparing the hydrogel of the present invention. If a photoinitiator is selected, the photoinitiator is selected from 2-hydroxy-2-methyl-1-phenyl-1-propanone (Irgacure1173) or Irgacure 2959. A transparent closed reaction container can be selected for initiating free radical polymerization under the condition of ultraviolet irradiation, and because the photoinitiation efficiency is higher than that of thermal initiation, when the irradiation time is adjusted according to the activity and the dosage of the selected initiator, the irradiation time can be shorter than the heating time of thermal initiation, such as 20 minutes or longer (30min-1h), and compared with the thermal initiation, the experimental time can be greatly reduced.
The invention has the beneficial effects that: the molecular structure of N-acryloyl glycinamide (NAGA) contains two connected amide groups, so that poly N-acryloyl glycinamide (PNAGA) gel obtained by NAGA polymerization is of a double-hydrogen bond structure, and internal hydrogen bonds are compact and are orderly arranged, so that the PNAGA gel has good mechanical property and stability. However, the lack of functional groups in PNAGA gels limits their functional utility. Although the functional group is introduced into the polymer gel obtained by copolymerizing the functionalized vinyl monomer and the NAGA monomer, even a small amount of comonomer is introduced, the regularly arranged double hydrogen bond structure in the original PNAGA gel can be damaged, so that the mechanical property and the stability of the polymer gel are simultaneously reduced. The preparation method of the interpenetrating network gel of the invention obtains the PACG/PNAGA interpenetrating network gel, namely, a certain amount of carboxyl groups are introduced into a PNAGA gel system by introducing the first heavy PACG network with low concentration, and the mechanical property of the original PNAGA gel and the stability in aqueous solution are not damaged. The preparation method of the functional modified polymer hydrogel is simple, and is also suitable for modification of various functional groups, namely, vinyl monomers with various functional groups can be used as a first heavy network, so that a series of functionalized PNAGA gels with good mechanical properties and stability can be obtained.
Drawings
FIG. 1 is a graph comparing the equilibrium water content of N-acryloyl glycine (ACG) and N-acryloyl glycine amide (NAGA) copolymer gels and interpenetrating network structure hydrogels prepared according to the present invention;
FIG. 2 is a tensile test stress-strain curve of N-acryloyl glycinamide (PNAGA) with 25% solids content and interpenetrating network structure hydrogel prepared according to the present invention.
Detailed Description
The technical solution of the present invention is further illustrated by the following specific examples.
Example 1
0.025g N-acryloyl glycine (ACG) was weighed into a 4mL centrifuge tube using an electronic balance, 750. mu.L deionized water and 0.75. mu.L 1173 photoinitiator were accurately pipetted using a pipette gun and added to the mixture and mixed well.
Sealing, placing in an ultraviolet crosslinking instrument, and irradiating with ultraviolet light for 40min to obtain poly N-acryloyl glycine (PACG) sol.
0.225g N-acryloyl glycinamide (NAGA) was weighed into the poly N-acryloyl glycine (PACG) sol using an electronic balance, and N-acryloyl glycinamide (NAGA) was dissolved and mixed well by vortex stirring, and 4.5. mu.L 1173 photoinitiator was accurately pipetted using a pipette and mixed well.
And putting the mixed solution into a mold, sealing, putting into an ultraviolet crosslinking instrument, and irradiating for 40min by ultraviolet light to obtain the interpenetrating network structure hydrogel.
The interpenetrating network gel of monomer mass ratio of N-acryloyl glycine (ACG) to N-acryloyl glycine amide (NAGA) is 1:9 is obtained in the above process, and the gel process is similar in other monomer ratio.
The preparation process of the copolymer gel is similar to the above process except that N-acryloyl glycine (ACG) and N-acryloyl glycine amide (NAGA) monomers are simultaneously dissolved in deionized water at the beginning, and then a photoinitiator is added to irradiate ultraviolet light to polymerize the copolymer gel.
The equilibrium water content of the copolymeric gel of N-Acryloylglycine (ACG) and N-acryloylglycinamide (NAGA) and the interpenetrating network hydrogel was measured at 37 ℃ in Phosphate Buffered Saline (PBS) at pH 7.4
Firstly, soaking a gel sample in a PBS (phosphate buffer solution) with the pH value of 7.4, and placing the gel sample in a constant-temperature incubator at 37 ℃ until the gel is in swelling balance; the gel was then removed, the excess liquid on the surface of the gel was gently wiped with filter paper and weighed quickly. The gel was then dried in a vacuum oven at 60 ℃ until the mass of the gel sample remained constant. The gel Equilibrium Water Content (EWC) was calculated as follows:
(mwet-mdry)/mwet×100％
wherein m iswetDenotes the wet weight of the gel, mdryThe dry weight of each gel sample is indicated.
As can be seen from FIG. 1, the equilibrium water content of the interpenetrating network gel is lower in the same proportion compared to the N-Acryloylglycine (ACG), N-acryloylglycinamide (NAGA) copolymer gel, that is to say the latter is more stable in solution; and the equilibrium water content of the two is similar with the change trend of the monomer proportion, and is also improved with the increase of the monomer proportion of the N-acryloyl glycine (ACG) in the gel. It is noted here that the copolymeric gel having a monomer ratio of N-Acryloylglycine (ACG) to N-acryloylglycinamide (NAGA) of 1:9 swells heavily in phosphate buffered saline solution and the gel cannot maintain a fixed morphology, at which time the equilibrium water content measured by this method is inaccurate and no specific data are obtained.
Testing mechanical properties of interpenetrating network structure hydrogel
Adopting a universal tensile testing machine, wherein gel samples subjected to tensile test are dumbbell-shaped gel samples with the thickness of 0.5mm, the width of a parallel part of 2mm and the gauge length of 10mm at room temperature, and the tensile rate is fixed at 50mm min-1. All gel samples were stretchedBefore testing, the test pieces were soaked in deionized water and fully reached swelling equilibrium.
As can be seen from fig. 2, the presence of poly-N-acryloylglycine (PACG) network has a certain effect on the mechanical properties of poly-N-acryloylglycine amide (PNAGA) gel, depending on the monomer ratio of N-Acryloylglycine (ACG) and N-acryloylglycine amide (NAGA), but the effect is not so great that the original mechanical properties of poly-N-acryloylglycine amide (PNAGA) gel are not substantially lost. With reference to fig. 2, the method for preparing the hydrogel with the interpenetrating network structure introduces a certain amount of carboxyl groups into a poly N-acryloyl glycinamide (PNAGA) gel system, and does not destroy the mechanical properties of the original poly N-acryloyl glycinamide (PNAGA) gel and the stability in an aqueous solution. The copolymer gel, however, cannot maintain good stability of the gel, although it has a carboxyl group introduced therein.
Example 2
0.0192g of N-acryloyl glycine (ACG) was weighed into a 4mL centrifuge tube using an electronic balance, 750. mu.L of deionized water and 0.5. mu.L of Irgacure2959 photoinitiator were accurately pipetted using a pipette gun, added thereto, and mixed well.
Sealing, placing in ultraviolet crosslinking instrument, and irradiating with ultraviolet light for 50min to obtain poly N-acryloyl glycine (PACG) sol.
0.2308g N-acryloyl glycinamide (NAGA) is weighed by an electronic balance and is added into the poly N-acryloyl glycin (PACG) sol, the N-acryloyl glycinamide (NAGA) is dissolved and uniformly mixed through vortex stirring, and 4.5 mu L of Irgacure2959 photoinitiator is accurately transferred by a liquid transfer gun and uniformly mixed.
And putting the mixed solution into a mold, sealing, putting into an ultraviolet crosslinking instrument, and irradiating for 50min by ultraviolet light to obtain the interpenetrating network structure hydrogel.
The interpenetrating network gel of the monomer mass ratio of N-acryloyl glycine (ACG) to N-acryloyl glycine amide (NAGA) of 1:12 is obtained in the above process, and the gel process is similar in other monomer ratio.
Example 3
0.0156g of N-acryloyl glycine (ACG) was weighed into a 4mL centrifuge tube with an electronic balance, 750. mu.L of deionized water and 0.5. mu.L of Irgacure2959 photoinitiator were accurately pipetted with a pipette gun and added to the mixture and mixed well.
Sealing, and irradiating in ultraviolet crosslinking instrument for 60min to obtain poly N-acryloyl glycine (PACG) sol.
0.2344g N-acryloyl glycinamide (NAGA) is weighed by an electronic balance and is added into the poly N-acryloyl glycin (PACG) sol, the N-acryloyl glycinamide (NAGA) is dissolved and uniformly mixed through vortex stirring, and 4.5 mu L of Irgacure2959 photoinitiator is accurately transferred by a liquid transfer gun and uniformly mixed.
And (3) putting the mixed solution into a mold, sealing, and then putting into an ultraviolet crosslinking instrument to be irradiated by ultraviolet light for 60min to obtain the hydrogel with the interpenetrating network structure.
The interpenetrating network gel of the monomer mass ratio of N-acryloyl glycine (ACG) to N-acryloyl glycine amide (NAGA) is 1:15 is obtained in the above process, and the gel process is similar in other monomer ratio.
Example 4
0.0119g of N-acryloyl glycine (ACG) were weighed into a 4mL centrifuge tube using an electronic balance, and 750. mu.L of deionized water and 0.5. mu.L of 1173 photoinitiator were accurately pipetted using a pipette gun and added thereto and mixed well.
Sealing, and irradiating in ultraviolet crosslinking instrument for 30min to obtain poly N-acryloyl glycine (PACG) sol.
0.2381g N-acryloyl glycinamide (NAGA) is weighed by an electronic balance and is added into the poly N-acryloyl glycin (PACG) sol, the N-acryloyl glycinamide (NAGA) is dissolved and uniformly mixed by vortex stirring, and 4.5 mu L1173 photoinitiator is accurately transferred by a liquid transfer gun and uniformly mixed.
And (3) putting the mixed solution into a mold, sealing, and then putting into an ultraviolet crosslinking instrument to be irradiated by ultraviolet light for 30min to obtain the hydrogel with the interpenetrating network structure.
The interpenetrating network gel of the monomer mass ratio of N-acryloyl glycine (ACG) to N-acryloyl glycine amide (NAGA) is 1:20 is obtained in the above process, and the gel process is similar in other monomer ratio.
The invention has been described in an illustrative manner, and it is to be understood that any simple variations, modifications or other equivalent changes which can be made by one skilled in the art without departing from the spirit of the invention fall within the scope of the invention.
Claims (10)
1. The hydrogel with the interpenetrating network structure is characterized in that: firstly, N-acryloyl glycine (ACG) is used as a comonomer to carry out free radical polymerization by initiating a carbon-carbon double bond on the N-acryloyl glycine (ACG) monomer to prepare the N-acryloyl glycine (PACG), secondly, adding an N-acryloyl glycinamide (NAGA) monomer into the poly-N-acryloyl glycinamide (PACG) to initiate carbon-carbon double bonds on the N-acryloyl glycinamide (NAGA), and carrying out free radical polymerization to prepare the hydrogel with the interpenetrating network structure, wherein the molecules of the hydrogel with the interpenetrating network structure are the carbon-carbon main chain of the poly-N-acryloyl glycinamide (PACG) and the carbon-carbon main chain of the poly-N-acryloyl glycinamide (PNAGA) which are mutually interpenetrated to form a three-dimensional crosslinking network structure, and the side chains are amide groups and carboxyl groups, wherein the mass ratio of N-acryloyl glycine (ACG) to N-acryloyl glycine amide (NAGA) is 1: (8-22), preferably 1: (9-20) a solid content of 20-30%, preferably 20-25%, (the solid content being the sum of the masses of N-Acryloylglycine (ACG) and N-acryloylglycinamide (NAGA)/the sum of the masses of both monomers and the solvent).
2. The interpenetrating network structure hydrogel of claim 1, wherein: the mass ratio of N-acryloyl glycine (ACG) to N-acryloyl glycine amide (NAGA) is 1: (9-20) and the solid content is 20-25%.
3. The interpenetrating network structure hydrogel of claim 1, wherein: the solvent adopts deionized water, and N-acryloyl glycine (ACG) is dissolved in the deionized water to initiate free radical polymerization.
4. The interpenetrating network structure hydrogel of claim 1, wherein: the amount of initiator used is 1-5%, preferably 2-3% of N-acryloyl glycine (ACG) and N-acryloyl glycine amide (NAGA).
5. The interpenetrating network structure hydrogel of claim 1, wherein: the initiator is Ammonium Persulfate (APS), potassium persulfate (KPS), 2-hydroxy-2-methyl-1-phenyl-1-acetone (Irgacure1173) or Irgacure2959, and the reaction is initiated by heat for 1 to 5 hours; photo-initiation is adopted, and the reaction time is 20-60 min.
6. A method of preparing the interpenetrating network structure hydrogel of claims 1 to 5, wherein: firstly, N-acryloyl glycine (ACG) is used as a comonomer to carry out free radical polymerization by initiating a carbon-carbon double bond on the N-acryloyl glycine (ACG) monomer to prepare the N-acryloyl glycine (PACG), secondly, adding an N-acryloyl glycinamide (NAGA) monomer into the poly-N-acryloyl glycinamide (PACG) to initiate carbon-carbon double bonds on the N-acryloyl glycinamide (NAGA), and carrying out free radical polymerization to prepare the hydrogel with the interpenetrating network structure, wherein the molecules of the hydrogel with the interpenetrating network structure are the carbon-carbon main chain of the poly-N-acryloyl glycinamide (PACG) and the carbon-carbon main chain of the poly-N-acryloyl glycinamide (PNAGA) which are mutually interpenetrated to form a three-dimensional crosslinking network structure, and the side chains are amide groups and carboxyl groups, wherein the mass ratio of N-acryloyl glycine (ACG) to N-acryloyl glycine amide (NAGA) is 1: (8-22) a solids content of 20-30%, preferably 20-25%.
7. The method for preparing the hydrogel with the interpenetrating network structure according to claim 6, wherein the method comprises the following steps: the mass ratio of N-acryloyl glycine (ACG) to N-acryloyl glycine amide (NAGA) is 1: (9-20) and the solid content is 20-25%.
8. The method for preparing the hydrogel with the interpenetrating network structure according to claim 6, wherein the method comprises the following steps: the solvent adopts deionized water, and N-acryloyl glycine (ACG) is dissolved in the deionized water to initiate free radical polymerization.
9. The method for preparing the hydrogel with the interpenetrating network structure according to claim 6, wherein the method comprises the following steps: the amount of initiator used is 1-5%, preferably 2-3% of N-acryloyl glycine (ACG) and N-acryloyl glycine amide (NAGA).
10. The method for preparing the hydrogel with the interpenetrating network structure according to claim 6, wherein the method comprises the following steps: the initiator is Ammonium Persulfate (APS), potassium persulfate (KPS), 2-hydroxy-2-methyl-1-phenyl-1-acetone (Irgacure1173) or Irgacure2959, and the reaction is initiated by heat for 1 to 5 hours; photo-initiation is adopted, and the reaction time is 20-60 min.
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Application publication date: 20200331 |