CN109232833A - A kind of preparation method of low bacterial adhesion, bacterium release and reproducible high-strength nano composite hydrogel - Google Patents
A kind of preparation method of low bacterial adhesion, bacterium release and reproducible high-strength nano composite hydrogel Download PDFInfo
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- CN109232833A CN109232833A CN201810870918.XA CN201810870918A CN109232833A CN 109232833 A CN109232833 A CN 109232833A CN 201810870918 A CN201810870918 A CN 201810870918A CN 109232833 A CN109232833 A CN 109232833A
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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
- C08F285/00—Macromolecular compounds obtained by polymerising monomers on to preformed graft polymers
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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
- C08F292/00—Macromolecular compounds obtained by polymerising monomers on to inorganic materials
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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
- C08F2438/00—Living radical polymerisation
- C08F2438/03—Use of a di- or tri-thiocarbonylthio compound, e.g. di- or tri-thioester, di- or tri-thiocarbamate, or a xanthate as chain transfer agent, e.g . Reversible Addition Fragmentation chain Transfer [RAFT] or Macromolecular Design via Interchange of Xanthates [MADIX]
Abstract
The invention discloses a kind of low bacterial adhesions, reproducible high-strength nano composite hydrogel preparation method, the following steps are included: 1) polymerization reaction: radical initiator is added in nanoparticle, it is mixed to get the nanoparticle of surface grafting initiator, it adds stimuli responsive type monomer to be reacted, obtains the nanoparticle of surface grafting response type polymer brush；2) UV is crosslinked: dispersing the nanoparticle of surface grafting response type polymer brush in solvent, add hydrophilic monomer, initiator and crosslinking agent, UV crosslinking with radiation is carried out after mixing, obtains a kind of low bacterial adhesion, reproducible high-strength nano composite hydrogel.The method of the present invention preparation process is simple and efficient, and obtained Nanometer composite hydrogel bacterial adhesion amount is low, releasable bacterium and function of surface regeneration, and imparts the excellent mechanical property of material, provides new approaches for the preparation of functional material.
Description
Technical field
The present invention relates to the preparation fields of Nanometer composite hydrogel, and in particular to there is one kind low bacterial adhesion, bacterium to release
It puts and the preparation method of reproducible high-strength nano composite hydrogel.
Background technique
Tissue infection caused by bacterium attachment and breeding, equipment fault is that biomedical applications field is long-standing asks
Topic, seriously threatens the life and health of the mankind, so, by the prevention of building antimicrobial surface or reduce material surface biological pollution tool
There are important social and economic implications.There are mainly three types of current antimicrobial modes, be respectively sterilization surface, antibacterium stick and
Bacterium release surface, due to the defect that single function antimicrobial surface has itself that can not overcome, antimicrobial surface is gradually by single function
It can be to multi-functional development.
Macromolecule hydrogel is a kind of high absorbency material with three-dimensional internet structure, wherein using hydrogel as base
The anti-biotic material at bottom due to good biocompatibility, gas permeability and wetability, wound dressing, conduit coating and
The application fields such as implant have received widespread attention.But conventional hydrogels are due to the hydrophilic radical in polymer segment
The characteristics of making it have good swelling behavior, but being easily broken after its water suction limits its development.
Currently, researcher constructs a series of multifunctional antibiotic water of intelligent responses using stimulus responsive polymers brush
Gel rubber material, Chinese invention patent CN107868260A disclose a kind of low bacterial adhesion, sterilization and reproducible novel water-setting
The preparation method of glue specifically includes 1) UV polymerization reaction；2) esterification；3) ATRP reacts；4) silver reaction is carried；ATRP method
It ensure that the effective controllable of functional polymer brush length, also utilize the environment-responsive of functional polymer brush, it is outer to realize change
Boundary's environment causes polymer brush to shrink elongation, and dead bacterium is driven to be desorbed in turn, to realize the renewable of hydrogel anti-microbial property；
Long-term antibacterial is also achieved the effect that by the slow release of silver ion, product has Escherichia coli, staphylococcus aureus
Apparent fungistatic effect has obtained a kind of Multifucntional hydrogel.
But that there are synthetic methods is complicated, preparation time is tediously long and poor mechanical property for existing multifunctional antibiotic hydrogel
The problems such as, it is very limited in practical applications.Therefore, a kind of simply and efficiently multi-functional high intensity hydrogel preparation side
Method has wide application background and potential value in field of biomedicine.
Summary of the invention
That the object of the present invention is to provide a kind of bacterial adhesion rates is low, can discharge accompanying bacterium and reproducible
The preparation method of high-strength nano composite hydrogel.
A kind of preparation method of low bacterial adhesion, bacterium release and reproducible high-strength nano composite hydrogel, including
Following steps:
(1) polymerization reaction: radical initiator is added in nanoparticle, is mixed to get receiving for surface grafting initiator
Rice corpuscles adds stimuli responsive type monomer and is reacted, obtains the nanoparticle of surface grafting response type polymer brush；
(2) UV is crosslinked: being dispersed the nanoparticle of surface grafting response type polymer brush in solvent, is added hydrophily
Monomer, initiator and crosslinking agent carry out UV crosslinking with radiation, obtain the Nanometer composite hydrogel after mixing.
The method of the present invention utilizes active free radical polymerization in the surface grafting stimulating responsive polymer brush of nanoparticle, then
The multifunctional antibiotic aquogel system of nano particle hybridization is prepared for by UV crosslinking with radiation.When the grafting responsiveness of load polymerize
The nanoparticle content of object brush reaches a timing, and polymer brush may spread to hydrogel surface, in the polymerization of nanoparticle surface
Object brush can change itself in response to environmental stimuli physically or chemically, thus the characteristics of assigning hydrogel intelligent response,
Changing external environment causes polymer brush to shrink elongation, and then drives dead bacterium desorption, realizes the bacterium of Nanometer composite hydrogel
It discharges and renewable.
Nanoparticle can pass through physical absorption since skin effect with higher makes it have higher surface-active
It is present on polymer segment, while the polymer brush of nanoparticle surface grafting and hydrogel substrate polymer segment will generate
Entanglement effect, therefore can be improved the intensity of hydrogel；In addition, being combined using UV crosslinking and chemical crosslinking, while load is received
Rice corpuscles, the multifunctional antibiotic Nanometer composite hydrogel that can also make have stronger mechanical property.
In step (1), the polymerization reaction is atom transition free radical polymerization reaction, reversible addition chain transfer polymerization is anti-
It answers or light-initiated transfer terminates polymerization reaction.
The specific steps of the atom transition free radical polymerization reaction are as follows: ATRP initiator is added to nanoparticle
In, the nanoparticle of graft initiator is stirred to get, stimuli responsive type monomer, catalyst, ligand and solvent are added, wait disperse
After uniformly, 6h-48h is reacted under anaerobic, obtains the nanoparticle of surface grafting response type polymer brush；
The ATRP initiator is organohalogen compounds；The solvent is the mixing of trifluoroethanol and water that volume ratio is 1:1
Mixed liquor, deionized water or the 2- isopropanol of liquid, the isopropanol that volume ratio is 1:1 and water；The catalyst is stannous chloride；Institute
Stating ligand is Me6TREN or bipyridyl.
The specific steps of the reversible addition chain transfer polymerization reaction are as follows: RAFT reagent is added in nanoparticle,
The nanoparticle for stirring to get grafting RAFT reagent, adds stimuli responsive type monomer, radical initiator and solvent, wait disperse
After uniformly, 6h-48h is reacted under anaerobic, obtains the nanoparticle of surface grafting response type polymer brush；
The RAFT initiator is 2- (dodecyl trithiocarbonate) -2 Methylpropionic acid (DDMAT).
The light-initiated transfer terminates the specific steps of polymerization reaction are as follows: photoinitiator is added in nanoparticle,
60 DEG C of -80 DEG C of reaction 1h-2h are warming up to, the nanoparticle of grafting photoinitiator is obtained, add stimuli responsive type monomer and molten
Agent reacts 30min-60min under ultraviolet lighting and nitrogen protection after being uniformly dispersed, and obtains the polymerization of surface grafting response type
The nanoparticle of object brush；
The photoinitiator is 2- [p- (2- hydroxy-2-methyl propiophenone)]-glycolmethacrylate.
In step (1), the nanoparticle is nano-silicon dioxide particle, nano-titania particle, nano-scale gold particle
Son or polymer nano-particle.
In step (1), the stimulating responsive monomer is that salt responds monomer DVBAPS, temperature-responsive monomer NIPAM
Or pH responsiveness monomer MAA.
In step (1), the response type polymer brush with a thickness of 60nm-200nm, the polymer of nanoparticle surface
Brush thickness is too short, can make polymer brush that can not extend to hydrogel surface, and the too long response performance that will lead to of polymer brush weakens.
In step (2), the condition of the UV radiation are as follows: UV optical wavelength 365nm, irradiation time 3min-120min, if instead
It is too short between seasonable, gel can not be formed, hydrogel can be formed within this range.
In step (2), the nanoparticle of the surface grafting response type polymer brush, initiator, crosslinking agent and hydrophilic
Property monomer mass ratio be 0.2-10:0.1-10:0.1-5:100；
The hydrophilic monomer is HEAA, HEMA or SBMA；The crosslinking agent is MBA, DTA, di-tert-butyl peroxide
Object；The initiator is 2- hydroxyl -4'- (2- hydroxy ethoxy) -2- methyl phenyl ketone, AIBA, AIP or ACVA；
The solvent is that the volume ratio of the methanol aqueous solution that the volume ratio of water, water and methanol is 10:1 or water and ethyl alcohol is
The ethanol water of 10:1.
Compared with the prior art, the present invention has the following beneficial effects:
(1) the method for the present invention uses modified nanometer particle load hydrogel, and Conventional nano particle can be overcome to load
Nanoparticle agglomeration traits in hydrogel preferably promote the performance of obtained Nanometer composite hydrogel；
(2) present invention prepares multifunctional antibiotic water using the method for the modified nano particle hybridization of stimulus responsive polymers brush
Gel, blending method prepare Nanometer composite hydrogel method and are simple and efficient, and cost is lower；
(3) in the method for the present invention, the polymer brush and hydrogel substrate polymer segment of nanoparticle surface grafting are generated
Entanglement effect, the multifunctional antibiotic Nanometer composite hydrogel made have stronger mechanical property；
(4) product that the method for the present invention obtains has the function of that long-acting antibacterium is sticked, when bacterial adhesion amount reaches certain
When degree, change the bacterium that external condition, that is, releasable surface is sticked, realizes functional regeneration.
Detailed description of the invention
Fig. 1 is the structural schematic diagram of the low bacterial adhesion, bacterium release and reproducible Nanometer composite hydrogel；
Fig. 2 is Nanometer composite hydrogel surface fluorescence micrograph obtained in embodiment 1；
Fig. 3 is the stress-strain diagram of Nanometer composite hydrogel obtained in embodiment 1.
Specific embodiment
The invention is further illustrated by the examples, but the present invention is not limited by following embodiment.
Embodiment 1
(1) it takes 5g nano-silicon dioxide particle to be placed in 50ml round-bottomed flask, the dry pyridine of 0.3ml is added, is added dropwise at 0 DEG C
The organohalogen compounds 2- bromine isobutyl acylbromide of 0.25ml after 30min to be mixed, is reacted 12 hours, 8000rpm centrifuge washing at room temperature
Collect solid particle；
(2) the solid particle 80mg for taking step (1) to obtain sequentially adds response monomer DVBAPS, 2ml polymerization of 1.48g salt
Object good solvent trifluoroethanol, 2ml deionized water, 20 μ L ligand Me6TREN, 18mg transition metal halide CuCl, by multiple
Vacuum suction, logical N2After circulation, reacts system for 24 hours under the conditions of 25 DEG C, obtain modified Nano particle；
(3) beaker of 50mL is taken, modified Nano particle is sequentially added thereto and (is separately added into and accounts for hydrophilic monomer quality
0,0.5wt%, 1wt%, 2wt%), 1.8g hydrophilic monomer HEAA, 0.039g photoinitiator 2- hydroxyl -4'- (2- hydroxyl ethoxy
Base) -2- methyl phenyl ketone, 0.005g crosslinking agent MBA, 2g ultrapure water, it is to be mixed to after completely dissolution, solution is transferred to spare
Mold in, and with the UV illumination 60min that wavelength is 365nm, obtain the Nanometer composite hydrogel.
The Nanometer composite hydrogel surface fluorescence micrograph that Fig. 2 is, in order to further study Nanometer composite hydrogel
Mechanical property, stretching experiment has been carried out to it under hygrometric state, the stress-strain diagram of obtained Nanometer composite hydrogel is shown in figure
3；When wherein polyHEAA@SNPs-g-polyDVBAPS-1 is that modified Nano mass particle accounts for the 0.5% of hydrophilic monomer quality
Nanometer composite hydrogel, pol yHEAA@SNPs-g-polyDVBAPS-2 be modified Nano mass particle account for hydrophilic monomer
Quality 1% when Nanometer composite hydrogel, polyHEAA@SNPs-g-polyDVBAPS-3 be modified Nano mass particle account for
Hydrophilic monomer quality 2% when Nanometer composite hydrogel.
As shown in Fig. 2, the composite hydrogel to Escherichia coli/staphylococcus aureus incubation (E.coli:
120h；S.aureus:60h in), have good anti-bacterial attachment effect (low bacterial adhesion), as incubation time is into one
Step extends, and at 120h (60h), the bacterial number on composite hydrogel surface still is below~106/cm2；Pass through the NaCl in 2.0M
After impregnating in solution, the bacterium of gel surface is returned to lower than~104/cm2State, illustrate obtained composite hydrogel
With desorption bacterium, the renewable clean performance in surface.
As shown in figure 3, being filled with the breaking strength of the hydrogel of modified Nano particle compared with pure HEAA hydrogel and breaking
Splitting elongation has very big promotion, and with the increase of loading, hydrogel modulus is continuously increased；But hydrogel toughness exists
One critical value, when the loading of modified Nano particle is 1wt%, compared with pure water gel, the drawing of Nanometer composite hydrogel
Stretch stress improve 5.5 times, elongation strain improve 4.3 times.
Embodiment 2
(1) nano-silicon dioxide particle 5g is taken, sequentially adding 2.6mmol free radical scavenger 2-, (dodecyl three is thio
Carbonic ester) -2 Methylpropionic acid (DDMAT), 75ml deionized water, excessive condensing agent 1- (3- dimethylamino-propyl) -3- ethyl carbon
Diimmonium salt hydrochlorate (EDC) is reacted for 24 hours at room temperature after ultrasonic disperse；
(2) the above-mentioned solid particle 80mg for being connected to RAFT reagent is taken, sequentially adds 0.95g SBMA, 0.072g free radical draws
Hair agent azo-bis-isobutyl cyanide (AIBN), 4ml deionized water lead to N by multiple vacuum suction-2After circulation, make system in 25 DEG C of items
It is reacted for 24 hours under part；
(3) beaker for taking 50mL, sequentially adds that sequentially add 0.18g modified Nano particle, 1.8g thereto hydrophilic to it
Property monomer HEAA, 0.04g radical initiator 2,2'- azo diisobutyl amidine dihydrochloride (AIBA), 0.005g DTA, 2g it is super
Pure water, it is to be mixed to be transferred to solution in spare mold to after completely dissolution, and the UV illumination 60min for being 365nm with wavelength
Obtain the Nanometer composite hydrogel.
Embodiment 3
(1) 0.1g lauryl sodium sulfate (SDS) is dissolved in 190ml deionized water, and 10g styrene monomer is added, adds
Enter and react 1h under 0.16g potassium peroxydisulfate (KPS) condition of nitrogen gas, is warming up to 90 DEG C of reaction 1.5h；4.5g photoinitiator is added dropwise
2- [p- (2- hydroxy-2-methyl propiophenone)]-glycolmethacrylate (HMEM), in 70 DEG C of reaction 1.5h；
(2) it takes in 50ml reaction tube, sequentially adds nanoparticle 100mg, 12ml the monomer DMAMMA for being connected to photoinitiator,
It after dispersion is sufficiently stirred, is placed under 350W ultraviolet lamp and irradiates, react 45min under nitrogen protection；
(3) beaker of 50mL is taken, sequentially adds 0.09g modified Nano particle, 1.8g HEAA, 0.039g 2- hydroxyl thereto
Base -4'- (2- hydroxy ethoxy) -2- methyl phenyl ketone, 0.005g MBA, 2g ultrapure water, it is to be mixed to after completely dissolution, by solution
It is transferred in spare mold, and the UV illumination 60min for being 365nm with wavelength obtains the Nanometer composite hydrogel.
Embodiment 4
(1) it takes 5g Nano particles of silicon dioxide to be placed in 50ml round-bottomed flask, the dry pyridine of 0.3ml is added, is added dropwise at 0 DEG C
The 2- bromine isobutyl acylbromide of 0.25ml after 30min to be mixed, is reacted 12 hours at room temperature, and 8000rpm centrifuge washing collects solid
Grain；
(2) the solid particle 80mg for taking above-mentioned surface grafting initiator, sequentially add 0.62g NIPA, 2ml trifluoroethanol,
2ml deionized water, 20 μ L Me6TREN, 18mg CuCl lead to N by multiple vacuum suction-2After circulation, make system in 25 DEG C of items
It is reacted for 24 hours under part；
(3) beaker of 50mL is taken, sequentially adds 0.18g modified Nano particle, 1.8g HEAA, 0.039g 2- hydroxyl thereto
Base -4'- (2- hydroxy ethoxy) -2- methyl phenyl ketone, 0.005g MBA, 2g ultrapure water, it is to be mixed to after completely dissolution, by solution
It is transferred in spare mold, and the UV illumination 60min for being 365nm with wavelength obtains the Nanometer composite hydrogel.
In summary example, which is simple and efficient, low bacterial adhesion and can desorption and regeneration, also have
There is preferable mechanical property, there are wide Research Prospects in biomedical, field of tissue engineering technology.
Claims (10)
1. the preparation method of a kind of low bacterial adhesion, bacterium release and reproducible high-strength nano composite hydrogel, including such as
Lower step:
(1) polymerization reaction: radical initiator is added in nanoparticle, is mixed to get the nanoparticle of surface grafting initiator
Son adds stimuli responsive type monomer and is reacted, obtains the nanoparticle of surface grafting response type polymer brush；
(2) UV is crosslinked: being dispersed the nanoparticle of surface grafting response type polymer brush in solvent, is added hydrophily list
Body, initiator and crosslinking agent carry out UV crosslinking with radiation, obtain the Nanometer composite hydrogel after mixing.
2. the preparation method of Nanometer composite hydrogel as described in claim 1, which is characterized in that the polymerization reaction is original
Sub- transition free radical polymerization reaction, the reaction of reversible addition chain transfer polymerization or light-initiated transfer terminate polymerization reaction.
3. the preparation method of Nanometer composite hydrogel as claimed in claim 2, which is characterized in that the atom transfer is free
The specific steps of base polymerization reaction are as follows: ATRP initiator is added in nanoparticle, stirs to get the nanometer of graft initiator
Particle adds stimuli responsive type monomer, catalyst, ligand and solvent, after being uniformly dispersed, reacts 6h- under anaerobic
48h obtains the nanoparticle of surface grafting response type polymer brush.
4. the preparation method of Nanometer composite hydrogel as claimed in claim 2, which is characterized in that the reversible addition chain turns
Move the specific steps of polymerization reaction are as follows: RAFT reagent is added in nanoparticle, stirs to get the nanometer of grafting RAFT reagent
Particle adds stimuli responsive type monomer, radical initiator and solvent, after being uniformly dispersed, reacts 6h- under anaerobic
48h obtains the nanoparticle of surface grafting response type polymer brush.
5. the preparation method of Nanometer composite hydrogel as claimed in claim 2, which is characterized in that the light-initiated transfer is whole
The only specific steps of polymerization reaction are as follows: photoinitiator is added in nanoparticle, 60 DEG C of -80 DEG C of reaction 1h-2h is warming up to, obtains
To the nanoparticle of grafting photoinitiator, add stimuli responsive type monomer and solvent, after being uniformly dispersed, in ultraviolet lighting and
30min-60min is reacted under nitrogen protection, obtains the nanoparticle of surface grafting response type polymer brush.
6. the preparation method of the Nanometer composite hydrogel as described in any one of claim 1-5 claim, which is characterized in that institute
The nanoparticle stated is nano-silicon dioxide particle, nano-titania particle, nano Au particle or polymer nano-particle.
7. the preparation method of the Nanometer composite hydrogel as described in any one of claim 1-5 claim, which is characterized in that institute
The stimulating responsive monomer stated is that salt responds monomer DVBAPS, temperature-responsive monomer NIPAM or pH respond monomer MAA.
8. the preparation method of the Nanometer composite hydrogel as described in any one of claim 1-5 claim, which is characterized in that institute
The response type polymer brush stated with a thickness of 60nm-200nm.
9. the preparation method of the Nanometer composite hydrogel as described in any one of claim 1-5 claim, which is characterized in that step
Suddenly in (2), the condition of the UV radiation are as follows: UV optical wavelength 365nm, irradiation time 3min-120min.
10. the preparation method of the Nanometer composite hydrogel as described in any one of claim 1-5 claim, which is characterized in that
In step (2), the nanoparticle of the surface grafting response type polymer brush, initiator, crosslinking agent and hydrophilic monomer
Mass ratio is 0.2-10:0.1-10:0.1-5:100.
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