CN110101907A - The modified polyarylether class bone implant material containing diazanaphthalene terphenyl structure and preparation method thereof of surface physics - Google Patents
The modified polyarylether class bone implant material containing diazanaphthalene terphenyl structure and preparation method thereof of surface physics Download PDFInfo
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- CN110101907A CN110101907A CN201910369918.6A CN201910369918A CN110101907A CN 110101907 A CN110101907 A CN 110101907A CN 201910369918 A CN201910369918 A CN 201910369918A CN 110101907 A CN110101907 A CN 110101907A
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
- A61L27/14—Macromolecular materials
- A61L27/18—Macromolecular materials obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
- A61L27/28—Materials for coating prostheses
- A61L27/34—Macromolecular materials
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
- A61L27/50—Materials characterised by their function or physical properties, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
- A61L27/54—Biologically active materials, e.g. therapeutic substances
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
- A61L2300/20—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices containing or releasing organic materials
- A61L2300/252—Polypeptides, proteins, e.g. glycoproteins, lipoproteins, cytokines
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- A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
- A61L2300/40—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a specific therapeutic activity or mode of action
- A61L2300/412—Tissue-regenerating or healing or proliferative agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61L2430/00—Materials or treatment for tissue regeneration
- A61L2430/02—Materials or treatment for tissue regeneration for reconstruction of bones; weight-bearing implants
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Abstract
The present invention provides a kind of modified polyarylether class bone implant materials containing diazanaphthalene terphenyl structure and preparation method thereof of surface physics.A kind of surface has the Phthalazinone poly (arylene ether nitrile) of osteogenic activity coating, prepares functional coating on Phthalazinone polyarylether surface, functional coating includes the biologically active bone morphogenetic protein layer of physical absorption.The biologically active protein layer includes bone morphogenetic protein, collagen, osteopontin, plasma fibrin etc., and albumin layer loads to Phthalazinone polyarylether surface by way of physical absorption.The surface physics absorption of protein includes that protein is adsorbed onto the functional group on Phthalazinone polyarylether surface or the monolayer of active functional group.Three-dimensional surface structure of the present invention and functional coating can improve the osteogenic activity of polyarylether.
Description
Technical field
The present invention relates to the modified phthalazones that contains of a kind of medical high polymer implantation material more particularly to surface physics to join
Polyarylether class bone implant material of benzene structure and preparation method thereof.
Background technique
Bone renovating material is one of maximum bio-medical material of clinical demand amount, and bone implant material is as bone renovating material
One kind, be constantly subjected to the attention of people.Macromolecule bone implant material is with its distinctive property and advantage, in bone implant material
Occupy very big specific gravity.Vivo environment is the environment of liquid, macromolecule bone implant material, it is necessary to meet non-toxic, excellent biology
The requirement such as compatibility, chemical stability, suitable physical mechanical property, easy processing molding, preferable property/valence ratio.Wherein, excellent
Biocompatibility and osteogenic activity be most inappeasable, but most important, be that can high molecular material be used for bone implant
The key of material.
Polyether-ether-ketone (PEEK) is widely used as bone as a kind of novel semi-crystalline state aromatic thermoplastic engineering plastics
It is implanted into material.However, the problems such as biocompatibility is not high and osteogenic activity is undesirable is always to influence PEEK implantation body life time
Problem, for the these problems for improving material, researcher carries out surface modification treatment to PEEK, prepares osteoid apatite on surface
Coating and protein layer with osteogenic activity, biocompatibility and osteogenic activity are improved.
The monomer of this full heteroaromatic of diazanaphthalene terphenyl, distortion, non-co-planar structure is introduced into polyarylether molecule
In chain, a series of Phthalazinone type polyarylethers are synthesized, have been the important member in high performance engineering plastics family.Because of its structure
It is similar with PEEK, and then be possible to be used as bio-medical material.Phthalazinone polyarylether is Dalian University of Technology's independent research
A kind of novel high-performance thermoplastic resin with independent intellectual property rights, in previous research work, to contain phthalazone
The poly (aryl ether sulfone ketone) of structure has carried out surface and has been modified, and the biocompatibility and osteogenic activity of material are greatly improved.
The Phthalazinone polyarylether that the present invention uses is a kind of High performance plastic resin haveing excellent performance, mechanical property with
The mechanical property of bone matches.However, the biocompatibility of Phthalazinone polyarylether and osteogenic activity lower limit its as bone
It is implanted into the application of material, the present invention intends preparing the coating with osteogenic activity on Phthalazinone polyarylether surface, to improve its life
Object compatibility and osteogenic activity.
Summary of the invention
The object of the present invention is to provide a kind of novel Phthalazinone polyarylethers with osteogenic activity, it is characterised in that miscellaneous
The preparation of naphthalene biphenyl polyarylether surface has the coating of osteogenic activity, and coating is included in plane surface or three-dimensional surface physical absorption tool
There is the protein layer of bioactivity.Biologically active protein layer is adsorbed on Phthalazinone by the method for physical absorption and gathers
Aryl oxide surface.The biocompatibility and bioactivity of Phthalazinone polyarylether can be improved in surface modified coat.
Technical solution of the present invention:
A kind of modified polyarylether class bone implant material containing diazanaphthalene terphenyl structure of surface physics, including substrate and
Coating, the two are combined as a whole by physical absorption；The substrate is the polyarylether containing diazanaphthalene terphenyl structure, described
Coating be biologically active protein.
The protein includes bone morphogenetic protein, collagen, osteopontin, plasma fibrin etc..
The polyarylether containing diazanaphthalene terphenyl structure, structure expression are as follows:
The glass transition temperature of the polyarylether containing diazanaphthalene terphenyl structure is not less than 250 DEG C, thermal weight loss
5% decomposition temperature is not less than 480 DEG C, and the polyarylether inherent viscosity is 0.1-0.9dL/g.
Wherein, Ar1It is any one in having structure or two or more combinations for the main structure of double halogen monomers:
Ar2It is any one in having structure or two or more combinations for the main structure of biphenol monomer:
Wherein, R1、R2、R3、R4It is hydrogen, halogenic substituent, phenyl, phenoxy group, the straight chain alkane containing at least one carbon atom
Base, the branched alkyl containing at least one carbon atom or the branched alkoxy containing at least one carbon atom, R1、R2、R3
And R4Structure it is identical or different；
M is positive integer；
N is 0 or positive integer.
The preparation method of the modified polyarylether class bone implant material containing diazanaphthalene terphenyl structure of surface physics, step
It is as follows:
The first step obtains polyarylether product by polyarylether powder by hot-forming；
The sand paper that polyarylether product passes through different meshes respectively is polished, keeps its surface uniform, obtain a variety of tables by second step
The different polyarylether product of surface roughness；Then the polyarylether product that will have been polished, successively using deionized water, ethyl alcohol, acetone,
Deionized water washing, drying for standby；
Third step immerses the pH=7.4 of biologically active protein respectively by the polyarylether product of different roughness
PBS solution, magnetic agitation 12 hours~2 days at room temperature；
4th step removes polyarylether product from solution, not higher than drying in 37 DEG C of convection ovens, is placed on 4 DEG C
It is spare in refrigerator.
It is 24 hours that the immersion, which has the time of the solution of the protein of osteogenic activity,.
The protein layer thickness has osteogenic activity less than 1 μm.
The concentration of the protein solution with osteogenic activity is 100ng/mL.
Beneficial outcomes of the invention:
(1) Phthalazinone polyarylether preparation method of the surface with osteogenic activity coating is not necessarily to equipment, at low cost, can be to multiple
It is modified that the bone implant part of miscellaneous shape carries out surface.
(2) modified coating prepared by the present invention have osteogenic activity protein layer, have preferable biocompatibility and
Osteogenic activity can improve the biocompatibility and skeletonization of polyarylether material under the premise of not influencing polyarylether mechanical property
Activity has broad application prospects in terms of bone implant material.
(3) for this method by the way of physical absorption, the micro-nano structure formed using surface is not changing Bones morphology
Bone morphogenetic protein is loaded under the premise of protein structure, effectively keeps its bioactivity in a short time.
Detailed description of the invention
Fig. 1 (a) is scanning electron microscope (SEM) photograph of the PPENS after the polishing of 400 mesh sand paper.
Fig. 1 (b) is scanning electron microscope (SEM) photograph of the PPENS after the polishing of 2000 mesh sand paper.
Fig. 2 (a) is scanning electron microscope (SEM) photograph of the PPENK after the polishing of 400 mesh sand paper.
Fig. 2 (b) is scanning electron microscope (SEM) photograph of the PPENK after the polishing of 2000 mesh sand paper.
Fig. 3 is the contact angle that PPBES and PPENK were polished and adsorbed bone morphogenetic protein.
Fig. 4 is albumen In-vitro release curves.
Fig. 5 is mtt assay detection and the modified print leaching liquor culture cell survival rate of BMP-2.
Specific embodiment
Below in conjunction with attached drawing and technical solution, a specific embodiment of the invention is further illustrated.
One the present invention is further elaborated in conjunction with specific embodiments.
PPBES structural formula is as follows:
PPENK structural formula is as follows:
Embodiment one
The first step obtains PPBES product by PPBES powder by hot-forming；
The sand paper that PPBES product passes through 400 mesh and 2000 mesh respectively is polished, keeps its surface uniform, obtain table by second step
The different PPBES product of surface roughness, PPBES-400 and PPBES-2000；Then the PPBES product that will have been polished, makes respectively
It is washed with deionized water, ethyl alcohol, acetone, deionized water, drying for standby；
Third step immerses the pH=7.4 of bone morphogenesis protein-2 respectively by PPBES-400 and PPBES-2000 product
PBS solution, magnetic agitation 24 hours at room temperature.
Finally, product is removed from solution, dry, is placed on spare in 4 DEG C of refrigerators in 37 DEG C of convection ovens.
Embodiment two
By the PPBES in embodiment one, it is changed to PPENK, with step with embodiment one
Pass through awkward silence at a meeting scanning electron microscopic observation different roughness polyarylether material surface topography.Pass through water contact angle measuring instrumentss
Levy the hydrophilic and hydrophobic of sample surfaces.By using BMP-2 content kit, test bone morphogenesis protein-2 loading efficiency and
Release in vitro efficiency determines the content of surface BMP-2.Using MC3T3-E1 mice embryonic pre-osteoblast as test cell
To characterize the biocompatibility of material.
The surface of above method preparation has PPBES the and PPENK product of osteogenic activity protein, and performance is as follows:
Test case one:
It to obtained four kinds of materials, is observed under awkward silence at a meeting scanning electron microscope, as illustrated in fig. 1 and 2, never with the scanning of sample
As can be seen that PPESK is similar to PPENK surface topography in electron microscope, do not distinguish significantly.Meanwhile when two kinds of materials pass through
After the sand paper polishing for crossing different meshes, the roughness significant change of material surface, after the polishing of 2000 mesh sand paper, sample table
Surface evenness is higher.
Test case two:
To four kinds of materials, surveyed in the water contact angle after polishing and after absorption bone morphogenesis protein-2
Examination, it is as shown in the table:
As can be seen from the table, with the raising of two kinds of material surface roughness, the hydrophily of material is better, meanwhile,
The hydrophily of PPBES is better than PPENK, this may be related with the group contained by material.Occur by adsorption Bones morphology
After -2 albumen of albumen, the hydrophily of two kinds of materials has apparent raising, illustrates that material surface has adsorbed a certain amount of albumen.
Test case three:
Using bright BMP-2 protein quantity kit, the quantity of two kinds of material absorption bone morphogenesis protein-2s is carried out
Measurement, the initial concentration of bone morphogenesis protein-2 is 100ng/mL, and as a result it is as shown in the table:
As can be seen from the table, with the increase of roughness, material surface has adsorbed more Bones morphologies and egg occurs
White -2.Meanwhile under identical roughness, the adsorbance of PPBES is higher than PPENK.
Continue the material to absorption bone morphogenesis protein-2, carries out release in vitro efficiency test, test result such as Fig. 3 institute
Show, can be seen that from the cumulative release amount of bone morphogenesis protein-2 in release in first day, when 12 is small after, cumulative release
Amount obviously increases, and reaches 90% or more of the adsorbance of bone morphogenesis protein-2, and explosion release phenomenon occurs.When with release
Time continues to extend, and Cumulative release amount no longer occurs significantly to increase, and illustrates material surface still residual fraction rhBMP-2.
Test case four:
Cytotoxicity experiment is carried out to two kinds of materials using mtt assay, material is impregnated in cell culture medium, material is obtained
Leaching liquor after, using various concentration leaching liquor with mouse preosteoblast co-incubation one day, it is as a result as shown in figure 4, thin
Cellular toxicity the results show that four kinds of materials of surface physics absorption bone morphogenesis protein-2, cell reaches with respect to appreciation rate
90% or more, meet requirement of the national standard ISO 10993 to cytotoxicity, obtained material is non-toxic.
Claims (4)
1. a kind of modified polyarylether class bone implant material containing diazanaphthalene terphenyl structure of surface physics, including substrate and painting
Layer, the two are combined as a whole by physical absorption；The substrate is the polyarylether containing diazanaphthalene terphenyl structure, described
Coating is the protein with osteogenic activity；
The protein includes bone morphogenetic protein, collagen, osteopontin and plasma fibrin；
The polyarylether containing diazanaphthalene terphenyl structure, structure expression are as follows:
Wherein, Ar1It is any one in having structure or two or more combinations for the main structure of double halogen monomers:
Ar2It is any one in having structure or two or more combinations for the main structure of biphenol monomer:
Wherein, R1、R2、R3、R4It is hydrogen, halogenic substituent, phenyl, phenoxy group, the straight chained alkyl containing at least one carbon atom, contains
There are the branched alkyl of at least one carbon atom or the branched alkoxy containing at least one carbon atom, R1、R2、R3And R4
Structure it is identical or different；
M is positive integer；
N is 0 or positive integer；
The protein layer thickness has osteogenic activity less than 1 μm.
2. a kind of preparation method of the modified polyarylether class bone implant material containing diazanaphthalene terphenyl structure of surface physics,
It is characterized in that, steps are as follows:
The first step obtains polyarylether product by polyarylether powder by hot-forming；
The sand paper that polyarylether product passes through different meshes respectively is polished, keeps its surface uniform, it is thick to obtain a variety of surfaces by second step
The different polyarylether product of rugosity；Then the polyarylether product that will have been polished, successively using deionized water, ethyl alcohol, acetone, go from
Sub- water washing, drying for standby；
Third step immerses the PBS solution of biologically active protein respectively by the polyarylether product of different roughness,
Magnetic agitation 12 hours~2 days at room temperature；Wherein, PBS solution pH=7.4；
4th step removes polyarylether product from solution, dries in 37 DEG C of convection ovens, is placed on spare in 4 DEG C of refrigerators.
3. preparation method according to claim 2, which is characterized in that the protein solution with osteogenic activity
Concentration is 100ng/mL~1mg/mL.
4. preparation method according to claim 2 or 3, which is characterized in that the immersion has the albumen of osteogenic activity
The time of the solution of matter is 24 hours.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN112221360A (en) * | 2020-09-15 | 2021-01-15 | 大连理工大学 | Copolymerized ether sulfone hemodialysis membrane containing phthalazinone structure and preparation method thereof |
| CN112221361A (en) * | 2020-09-15 | 2021-01-15 | 大连理工大学 | Polyether sulfone/copolyether sulfone blended hollow fiber hemodialysis membrane with phthalazinone structure and preparation method thereof |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112221360A (en) * | 2020-09-15 | 2021-01-15 | 大连理工大学 | Copolymerized ether sulfone hemodialysis membrane containing phthalazinone structure and preparation method thereof |
| CN112221361A (en) * | 2020-09-15 | 2021-01-15 | 大连理工大学 | Polyether sulfone/copolyether sulfone blended hollow fiber hemodialysis membrane with phthalazinone structure and preparation method thereof |
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