CN107778496A - High-strength conducting hydrogel doped with polyaniline and its preparation method and application - Google Patents
High-strength conducting hydrogel doped with polyaniline and its preparation method and application Download PDFInfo
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- CN107778496A CN107778496A CN201610740498.4A CN201610740498A CN107778496A CN 107778496 A CN107778496 A CN 107778496A CN 201610740498 A CN201610740498 A CN 201610740498A CN 107778496 A CN107778496 A CN 107778496A
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- polyaniline
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
- C08J3/03—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in aqueous media
- C08J3/075—Macromolecular gels
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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
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/06—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polyethers, polyoxymethylenes or polyacetals
- C08F283/065—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polyethers, polyoxymethylenes or polyacetals on to unsaturated polyethers, polyoxymethylenes or polyacetals
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L51/00—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
- C08L51/08—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers grafted on to macromolecular compounds obtained otherwise than by reactions only involving unsaturated carbon-to-carbon bonds
Abstract
The present invention is disclosed doped with high-strength conducting hydrogel of polyaniline and its preparation method and application, with 2 vinyl 4,6 diaminourea 1,3,5 triazines and the hydrogel that vinyl imidazole is main body, and one layer of doped polyaniline is coated on gel, assign gel electric conductivity, by the stimulation of weak current, promote the differentiation of Neural Stem Cells direction.
Description
Technical field
The present invention relates to it is a kind of can conductive high-strength hydrogel that directly induced nerve stem cells break up to neuron direction
Prepare, specially a kind of 2- vinyl -4,6- diamino-1,3,5-triazines-vinyl imidazole-polyaniline (PVDT-VI-PANI)
The preparation method and application of hydrogel, the hydrogel can be conductive by doped polyaniline, by the stimulation of electric current, promote god
Break up through stem cell to neuron direction.
Background technology
The nervous system disease affects the life of many people, but neuron lacks the ability of self-regeneration and regeneration.God
It is a kind of multi-functional cell through stem cell, neuron, spongiocyte etc. can be divided into.So stem cell transplantation turns into treatment god
A kind of advantageous methods through systemic disease.But NSC is under normal operation, it is intended to spongiocyte direction point
Change, many inconvenience are brought to its practical application.Hydrogel has some similitudes with human body overall situation, and can support nerve
The growth and differentiation of stem cell, cause the extensive concern of researcher.But its often mechanical property is poor, with human body
Musculature mechanical property lack matching, equally also limit its application to a certain extent.
The content of the invention
It is an object of the invention to overcome the deficiencies of the prior art and provide the high-strength conducting hydrogel doped with polyaniline and
Its preparation method and application, the hydrogel with 2- vinyl -4,6- diamino-1,3,5-triazines and vinyl imidazole for main body,
Specially 2- vinyl -4,6- diamino-1,3,5-triazines, imidazoles copolymer (PVDT-co-VI), the copolymer are removed and shown
The inherent characteristic of hydrogel, one layer of doped polyaniline can also be coated on gel, assign gel electric conductivity, pass through faint electricity
The stimulation of stream, promote the differentiation of Neural Stem Cells direction.
The technical purpose of the present invention is achieved by following technical proposals：
Doped with the high-strength conducting hydrogel of polyaniline, be made up of hydrogel and polyaniline, hydrogel by 2- vinyl -4,
6- diamino-1,3,5-triazines, vinyl imidazole and crosslinking agent are formed by radical polymerization copolymerization, the cross-linker molecules
Strand both ends are with backbone structure (i.e. (CH2CH2O) n among carbon-carbon double bond, strand being peg molecule；Polyaniline
For doped polyaniline, it is dispersed in by impregnation method in hydrogel.
In the inventive solutions, with 2- vinyl -4,6- diamino-1,3,5-triazines and vinyl imidazole conduct
Comonomer, with cross-linking agents comonomer, the strand both ends of cross-linker molecules among double bond, strand for " oxygen-
The connected skeleton structure (i.e. the backbone structure of peg molecule, (CH2CH2O) n) of carbon-to-carbon-oxygen " singly-bound, using thermal source or
Light source makes initiator provide free radical, then triggers 2- vinyl -4,6- diamino-1,3,5-triazines, vinyl miaow by free radical
Double bond in azoles and crosslinking agent, make three almost while trigger, polymerisation occurs, in the hydrogel material finally prepared, tool
Have poly- 2- vinyl -4,6- diamino-1,3,5-triazines, a segment of three kinds of materials of polyimidazole and crosslinking agent, wherein 2- vinyl -
4,6- diamino-1,3,5-triazines provide the mechanical property in skeleton, and vinyl imidazole can adsorb polyaniline, in crosslinking agent
Polyethylene glycol structures provide soft segment, above-mentioned a few part synergies, whole hydrogel material is embodied high intensity and is led
The effect of electricity.
Using initiator provide free radical trigger 2- vinyl -4,6- diaminostilbenes, 3,5- triazines, vinyl imidazole and
Crosslinking agent reacts.Wherein initiator can select the thermal initiator commonly used in field of macromolecule polymerization, such as the isobutyl of azo two
Nitrile (ABIN), benzoyl peroxide (BPO), or light trigger, as 1- [4- (2- hydroxy ethoxies)-phenylene] -2- hydroxyls -
2 ', 2 '-dimethyl ethyl ketone (Irgacure 2959), methyl vinyl ketone, styrax.If selecting thermal initiator, head is needed
The oxygen in reaction system is excluded first with inert gas (such as nitrogen, argon gas or helium), to avoid its inhibition, then
According to the activity and dosage of initiator, reaction system is heated on the initiation temperature of initiator used and keeps considerably long
Time, such as more than 1h or longer (1-5h), to promote initiator to produce enough free radicals, initiation reaction for a long time
Raolical polymerizable persistently occurs for system, the final water hydrogel for preparing the present invention.If selecting light trigger, can select
With transparent closed reaction vessel, trigger radical polymerization under conditions of ultraviolet light, because light-initiated efficiency is higher than heat
Trigger, when adjusting irradiation time with dosage because of the activity of initiator selected by, when irradiation time can be shorter than the heating of thermal initiation
Between, it is such as 20 minutes or longer (30min-1h).
In the inventive solutions, should be according to 2- vinyl -4,6- diamino-1,3,5-triazines, vinyl miaow
Azoles selection use initiator, the dissolubility of crosslinking agent, selection can be completely dissolved above-mentioned four kinds of materials or can with it is above-mentioned
The solvent that four kinds of materials dissolve each other completely, to be well mixed reaction system.Due to 2- vinyl -4,6- diaminostilbenes, 3,5- triazines,
Vinyl imidazole polarized, initiator and crosslinking agent be able to will be also dissolved in polar solvent, therefore may be selected in organic solvent
Polar solvent, such as dimethylformamide, dimethyl acetamide, tetrahydrofuran, dimethyl sulfoxide (DMSO).
Doped with the preparation method of the high-strength conducting hydrogel of polyaniline, carry out as steps described below：
By 2- vinyl -4,6- diaminostilbenes, 3,5- triazines, vinyl imidazole, crosslinking agent and initiator are dissolved in solvent
In, triggered by initiator in 2- vinyl -4,6- diamino-1,3,5-triazines, vinyl imidazole and cross-linker molecules not
Saturated bond, hydrogel is prepared by Raolical polymerizable under conditions of anoxybiotic；Hydrogel is immersed in doped polyaniline
1-METHYLPYRROLIDONE solution in so that doped polyaniline enter hydrogel in.
In the above-mentioned technical solutions, monomer 2- vinyl -4,6- diamino-1,3,5-triazines, the quality of vinyl imidazole
Than 1：(1-1.2), preferably wait mass ratio.
In the above-mentioned technical solutions, the quality of initiator is 3%-the 5% of monomer and crosslinking agent gross mass.
In the above-mentioned technical solutions, crosslinking agent quality accounts for 20%-the 30% of two kinds of monomer mass sums, preferably 25-30%,
Crosslinking agent is polyethyleneglycol diacrylate, number-average molecular weight 3000-5000.
After the completion of reaction, copolymer is taken out from reaction vessel, removes the monomer, initiator, crosslinking for not participating in reaction
After agent and solvent, in immersion in deionized water until reaching swelling equilibrium (such as immersion 7 days, a water is changed every 12h, is reached
To swelling equilibrium).After the 1-METHYLPYRROLIDONE solution of immersion doped polyaniline, fully embathed, gone using PBS after taking-up
Except responseless monomer and solvent.
In the above-mentioned technical solutions, in the 1-METHYLPYRROLIDONE solution of doped polyaniline, doped polyaniline
Mass percent is 0.1%-1%, soak time at least 2 hours, preferably 4-6 hours.
Reach a MPa rank, conductance doped with the tensile strength and compressive strength of the high-strength conducting hydrogel of polyaniline
Average reachable 10-15mS/cm, resistance is average up to 1-5 Ω, the application in induced nerve stem cells Differentiating Into Neurons.
It is provided by the invention it is a kind of can conductive high-strength water-setting that directly induced nerve stem cells break up to neuron direction
Glue is for raw material, in the presence of crosslinking agent and initiator with 2- vinyl -4,6- diamino-1,3,5-triazines and vinyl imidazole
Copolymerization is made, and realizes 2- vinyl -4,6- diamino-1,3,5-triazines humidifications, is adsorbed by vinyl imidazole doped poly-
Aniline, obtained product have high intensity and electric conductivity concurrently simultaneously.Product preparation method is simple, is easy to long-term and preserves and long-distance fortune
It is defeated.
Brief description of the drawings
Fig. 1 be the present invention gel adsorption doped polyaniline after gel photo.
Fig. 2 be the present invention gel adsorption doped polyaniline after gel surface scanning electron microscopic picture.
Fig. 3 is the infared spectrum of gel gel after doped polyaniline is adsorbed of the present invention.
Fig. 4 be the present invention gel after doped polyaniline is adsorbed, impose 75mV electro photoluminescence, after 7 days, gel table
The microphoto of face cell.
Fig. 5 be the present invention gel after doped polyaniline is adsorbed, impose 75mV electro photoluminescence, after 7 days, gel table
The stream data of face cell, undifferentiated living cells are dyed with nestin, and the living cells of differentiation is dyed with the tubulins of β 3.
Embodiment
Technical scheme is further illustrated with reference to specific embodiment.Doped polyaniline selects direct city
Purchase, is dissolved in solvent N-methyl pyrilidone after ground sieving.
By monomer 2- vinyl -4,6- diamino-1,3,5-triazines (80mg, Tokyo Kasei Kogyo), vinyl miaow
Azoles (80mg, about 80 μ l, sigma), and crosslinking agent polyethyleneglycol diacrylate (40mg, number-average molecular weight 4000, sigma) add
Enter into 1.5ml centrifuge tubes, after dissolving monomer and crosslinking agent with 1000 μ l dimethyl sulfoxide (DMSO) (DMSO), add light trigger
Irgacure2959 (5mg, 1- [4- (2- hydroxy ethoxies)-phenylene] -2- hydroxyls -2 ', 2 '-dimethyl ethyl ketone, sigma).Will
Containing monomer, in the solvent of crosslinking agent and initiator injection closed mold, mould ultra-violet curing case (XL-1000UV,
Spectronics Corporation) in irradiation 30min, fully to trigger radical polymerization.Then turn on mould and take out water-setting
Glue, rinsed for several times, and soaked 7 days repeatedly with deionized water, above-mentioned deionized water is changed every 12h.Then by gained hydrogel
It is immersed in 4 in the 1-METHYLPYRROLIDONE solution (mass percent of doped polyaniline is 0.2wt%) of doped polyaniline
Individual hour, take out, gel is fully embathed with PBS, removes responseless monomer and solvent, macroscopical shape as shown in Figure 1
Looks.
High-strength conducting gel will be prepared to be quenched in liquid nitrogen, then gel will be freezed, utilize SEM (FEI
Quanta S-4800FE-SEM) observation Signa Gel surface Polyaniline, it can be seen that gel surface is adsorbed with largely
Polyaniline particulate, as shown in Figure 2.High-strength conducting gel will be prepared to dry in an oven, be all-trans using PerkinElmer decay
Penetrate the infrared spectrum of FTIS determination sample.Monomer 2- vinyl -4,6- diaminostilbenes, in 3,5- triazines
NH2Peak appear in 3299 and 1631cm-1Place, the characteristic peak of imidazoles appear in 3100cm-1Place, 1736 and 1082cm-1Represent and hand over
Join the absworption peak of C=O and C-O-C in agent, 1120cm-1The characteristic peak of quinoid ring in polyaniline, show the successful conjunction of Signa Gel
Into as shown in Figure 3.
Mechanics Performance Testing is carried out to the high-strength conductive gel of preparation, Mechanics Performance Testing is in electronic universal tester
Carried out in (Jinan epoch Co., Ltd), the size for the sample of compression performance test is diameter 10mm, high 8mm, is compressed
Speed is 10mm min-1.Size for the sample of tensile property test is long 30mm, wide 4mm, thickness 0.2mm, rate of extension
For 100mm min-1.The mechanical strength of gel is greatly improved in obtained mineralising gel, as shown in the table, stretching and compression
Intensity can reach a MPa rank：
Conducting performance test is carried out to the high-strength conductive gel of preparation, electrical performance testing is in electrochemical workstation
Tested on (New Zealand PGSTAT302N types electrochemical workstation) using impedance method is crosslinked, the conductive hydrogel before test be
Reach swelling equilibrium in neutral buffer (pH=7.4).The sample size of electrical performance testing is diameter 10mm, high 1mm's
Sequin, it is as shown in the table：
NSC is inoculated into gel surface with 5 × 104per mL density, 75mV electricity is then imposed to gel
Stimulate (200HZ, B2912A precision source/measure unit, Agilent).Seen after 7 days with fluorescence microscope
Examine the form of (OLYMPUS, Japan) gel surface NSC, it can be seen that NSC there are many Synaptic formations, shows
Stem cell breaks up to neuron direction, as shown in Figure 4.
NSC is inoculated into gel surface with 5 × 104per mL density, 75mV electricity is then imposed to gel
Stimulate (200HZ, B2912A precision source/measure unit, Agilent).Gel surface is collected after 7 days
Cell, the Neural Stem Cells direction differentiation of gel surface is detected with flow cytometer (Becton Dickinson)
Cell quantity, the stem cell for having 61.1% break up to neuron direction, and demonstrating faint electro photoluminescence can be thin with induced nerve stem
Born of the same parents break up to neuron direction, as shown in Figure 5.
Recorded according to present invention and the preparation technology of Signa Gel is adjusted, the Signa Gel of preparation is surveyed
Examination, the effect of faint electro photoluminescence induction differentiation can be achieved, and stretching and compressive strength can reach a MPa rank, conductance is put down
It is average up to 1-5 Ω up to 10-15mS/cm, resistance.
Exemplary description has been done to the present invention above, it should explanation, in the situation for the core for not departing from the present invention
Under, any simple deformation, modification or other skilled in the art can not spend the equivalent substitution of creative work equal
Fall into protection scope of the present invention.
Claims (10)
1. doped with the high-strength conducting hydrogel of polyaniline, it is characterised in that be made up of hydrogel and polyaniline, hydrogel is by 2-
Vinyl -4,6- diamino-1,3,5-triazines, vinyl imidazole and crosslinking agent are formed by radical polymerization copolymerization, the friendship
Join the strand both ends of agent molecule with the backbone structure among carbon-carbon double bond, strand being peg molecule；Polyaniline is
Doped polyaniline, it is dispersed in by impregnation method in hydrogel；Monomer 2- vinyl -4,6- diaminostilbenes, 3,5- triazines, second
The mass ratio 1 of alkenyl imidazoles：(1-1.2)；Crosslinking agent quality accounts for 20%-the 30% of two kinds of monomer mass sums, and crosslinking agent is poly- second
Omega-diol diacrylate, number-average molecular weight 3000-5000.
2. the high-strength conducting hydrogel according to claim 1 doped with polyaniline, it is characterised in that monomer 2- ethene
The mass ratioes such as base -4,6- diaminostilbenes, 3,5- triazines, vinyl imidazole.
3. the high-strength conducting hydrogel according to claim 1 doped with polyaniline, it is characterised in that crosslinking agent quality accounts for
25-the 30% of two kinds of monomer mass sums.
4. the preparation method of the high-strength conducting hydrogel doped with polyaniline, it is characterised in that carry out as steps described below：
By the dissolving of 2- vinyl -4,6- diamino-1,3,5-triazines, vinyl imidazole, crosslinking agent and initiator in a solvent, lead to
Cross initiator and trigger 2- vinyl -4,6- diaminostilbenes, the unsaturation in 3,5- triazines, vinyl imidazole and cross-linker molecules
Key, hydrogel is prepared by Raolical polymerizable under conditions of anoxybiotic；Hydrogel is immersed in the N- of doped polyaniline
In methylpyrrolidone solution, so that doped polyaniline enters in hydrogel；Monomer 2- vinyl -4,6- diaminostilbenes, 3,
The mass ratio 1 of 5- triazines, vinyl imidazole：(1-1.2)；Crosslinking agent quality accounts for 20%-the 30% of two kinds of monomer mass sums, hands over
Connection agent is polyethyleneglycol diacrylate, number-average molecular weight 3000-5000；The quality of initiator is monomer and the total matter of crosslinking agent
3%-the 5% of amount.
5. the preparation method of the high-strength conducting hydrogel according to claim 4 doped with polyaniline, it is characterised in that single
The mass ratioes such as body 2- vinyl -4,6- diaminostilbenes, 3,5- triazines, vinyl imidazole；Crosslinking agent quality accounts for two kinds of monomer masses
25-the 30% of sum.
6. the preparation method of the high-strength conducting hydrogel according to claim 4 doped with polyaniline, it is characterised in that
In the 1-METHYLPYRROLIDONE solution of doped polyaniline, the mass percent of doped polyaniline is 0.1% -1%, immersion
Time at least 2 hours, preferably 4-6 hours.
7. the preparation method of the high-strength conducting hydrogel according to claim 4 doped with polyaniline, it is characterised in that molten
Agent is dimethylformamide, dimethyl acetamide, tetrahydrofuran, dimethyl sulfoxide (DMSO).
8. the preparation method of the high-strength conducting hydrogel according to claim 4 doped with polyaniline, it is characterised in that draw
The thermal initiator commonly used in agent selection field of macromolecule polymerization is sent out, such as azodiisobutyronitrile (ABIN), benzoyl peroxide
(BPO) thermal initiator, is selected, then needs to exclude in reaction system first with inert gas (such as nitrogen, argon gas or helium)
Oxygen, to avoid its inhibition, then according to the activity and dosage of initiator, reaction system is heated to initiator used
Initiation temperature on and keep for quite a long time, such as more than 1h or longer (1-5h), during promoting initiator long
Between produce enough free radicals, Raolical polymerizable persistently occurs for initiation reaction system.
9. the preparation method of the high-strength conducting hydrogel according to claim 4 doped with polyaniline, it is characterised in that draw
Send out agent selection field of macromolecule polymerization in commonly use light trigger, as 1- [4- (2- hydroxy ethoxies)-phenylene] -2- hydroxyls -2 ',
2 '-dimethyl ethyl ketone (Irgacure 2959), methyl vinyl ketone, styrax, light trigger is selected, then can be selected transparent
Closed reaction vessel, triggers radical polymerization under conditions of ultraviolet light, because light-initiated efficiency is higher than thermal initiation, because
During according to activity and dosage the adjustment irradiation time of selected initiator, irradiation time can be shorter than the heat time of thermal initiation, and such as 20
Minute is longer (30min-1h).
10. the high-strength conducting hydrogel doped with polyaniline as described in one of claim 1-3 induced nerve stem cells to
Application in neuron differentiation, it is characterised in that tensile strength and compressive strength reach a MPa rank, and conductance is average reachable
10-15mS/cm, resistance are average up to 1-5 Ω.
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| CN110295467A (en) * | 2019-07-03 | 2019-10-01 | 江南大学 | A kind of apparatus for continuous treatment of conduction textile material |
| CN113736100A (en) * | 2021-08-12 | 2021-12-03 | 湖南工业大学 | Nano metal organic framework toughened high-strength fluorescent hydrogel and preparation method thereof |
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| CN105085960A (en) * | 2015-07-27 | 2015-11-25 | 天津大学 | Zinc-ion-responding high-strength hydrogel tube, and preparation method and application thereof |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN110295467A (en) * | 2019-07-03 | 2019-10-01 | 江南大学 | A kind of apparatus for continuous treatment of conduction textile material |
| CN113736100A (en) * | 2021-08-12 | 2021-12-03 | 湖南工业大学 | Nano metal organic framework toughened high-strength fluorescent hydrogel and preparation method thereof |
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Application publication date: 20180309 |