CN107118373A - A kind of POSS PEG hybridized hydrogels, its preparation method and application - Google Patents

A kind of POSS PEG hybridized hydrogels, its preparation method and application Download PDF

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CN107118373A
CN107118373A CN201710391475.1A CN201710391475A CN107118373A CN 107118373 A CN107118373 A CN 107118373A CN 201710391475 A CN201710391475 A CN 201710391475A CN 107118373 A CN107118373 A CN 107118373A
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poss
peg
preparation
mal
arm
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CN107118373B (en
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卢翠芬
沈金瑞
李鹤玲
余晶晶
董念国
刘宗涛
胡行健
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Hubei University
Tongji Medical College of Huazhong University of Science and Technology
Union Hospital Tongji Medical College Huazhong University of Science and Technology
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Hubei University
Union Hospital Tongji Medical College Huazhong University of Science and Technology
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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
    • C08J3/24—Crosslinking, e.g. vulcanising, of macromolecules
    • C08J3/245—Differential crosslinking of one polymer with one crosslinking type, e.g. surface crosslinking
    • 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
    • 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
    • A61L27/52—Hydrogels or hydrocolloids
    • 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
    • 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
    • C08J2371/00—Characterised by the use of polyethers obtained by reactions forming an ether link in the main chain; Derivatives of such polymers
    • C08J2371/02—Polyalkylene oxides

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Dispersion Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oral & Maxillofacial Surgery (AREA)
  • Organic Chemistry (AREA)
  • Dermatology (AREA)
  • Polymers & Plastics (AREA)
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Abstract

The present invention relates to a kind of preparation method of POSS PEG hybridized hydrogels, comprise the following steps：4 arm PEG MAL and POSS SH are subjected to Michael addition reactions and obtain POSS PEG prepolymers；POSS PEG hybridized hydrogels are obtained by Micheal addition reaction salt resis with POSS PEG prepolymers using matrix metalloproteinase peptide substrate as crosslinking agent.The POSS PEG hybridized hydrogels mechanical strengths of the present invention are good, and its mechanical strength can carry out finely regulating by changing 4 arm PEG MAL molecular weight, POSS SH and 4 arm PEG MAL molar ratio, it need to be only prepared from simultaneously in the Triethanolamine buffer of low concentration, gelation time quickly, reduces the infringement or loss of the seed cell or medicine to carrying thereon as much as possible on the premise of basic physicochemical property is ensured.

Description

A kind of POSS-PEG hybridized hydrogels, its preparation method and application
Technical field
The present invention relates to field of tissue engineering technology is related to, more specifically it relates to a kind of POSS-PEG hybridized hydrogels and its system Preparation Method and the tissue engineering bracket prepared with it.
Background technology
Tissue engineering technique possesses huge potentiality in biomedical applications, such as repairs, replaces impaired or illing tissue Biological function.One of successful key factor of tissue engineering technique is one suitable timbering material of selection.In order to realize group Reconstruction is knitted, timbering material should possess following condition：(1) good biocompatibility；(2) stronger mechanical performance；(3) it is higher Porosity and enough apertures；(4) biodegradability and suitable degradation rate.
Polyethylene glycol (PEG) hydrogel is the tissue engineering bracket material that a class haves a great attraction, its biocompatibility Good, nontoxic, immunogenicity is low, to the anti-absorption of protein, can be excreted by kidney, not have accumulation in vivo.PEG-hydrogel Structure, mechanical behavior and degradability can be controlled by PEG chemistry and processing conditions；Its biological function then can by PEG-hydrogel is internally embedded bioactive molecule to obtain, for example, be embedded in matrix metalloproteinase (MMP) peptide substrate (MMP (W)X), make PEG-hydrogel that there is enzyme sensitiveness, the protease (especially MMPs) secreted using seed cell itself is promoted thin Extracellular matrix is degraded, and promotes bioactive molecule to discharge, and is conducive to growth, adhesion of the seed cell in support.However, PEG-hydrogel Bad mechanical strength, its mechanical strength be much smaller than biological tissue.
Polyhedral oligomeric silsesquioxane (POSS) is the nano-hybrid material on a kind of molecular level, and molecular dimension is in 1- Between 3nm, the inorganic skeleton and the organic substituent of periphery being made up of the Si-O-Si keys of core constitute hybrid inorganic-organic knot Structure, peripheral organic substituent imparts the good molecules of POSS and can designed.POSS nano-particles can strengthen toughness of polymers, resistance to Warm nature energy, mechanical property, and its is nonpoisonous and tasteless, with good biocompatibility, it is considered to be new-generation Biomedical Materials. The POSS hybridized hydrogels studied at present are all by photopolymerization or the hexamethylene diisocyanate used (HDI) or hexichol Dicyclohexylmethane diisocyanate (MDI) etc. carries out condensation reaction as crosslinking agent and prepared.The major defect of these preparation methods It is that light trigger used, HDI, MDI etc. have toxicity, and reaction needs to carry out in organic solvent, the external life to material Thing Study on Compatibility can only be confined in 2D cell culture.
Accordingly, it would be desirable to the hydrogel with more preferable mechanical property is developed, and without using organic molten in preparation process Agent plastic, so that cell is packaged into material while maximum activity is kept.
The content of the invention
To solve problem above, the invention provides a kind of preparation method of POSS-PEG hybridized hydrogels, including it is following Step：
S1：Four arm polyethylene glycol (4-arm-PEG-MAL) of Maleimido functionalization and POSS-SH are carried out Michael addition reactions obtain POSS-PEG prepolymers；
S2：Use the sensitive matrix metalloproteinase peptide substrate (MMP (W) of enzymeX) it is used as crosslinking agent and the POSS-PEG Prepolymer obtains the POSS-PEG hybridized hydrogels by Micheal addition reaction salt resis.Specific course of reaction is as schemed Shown in 10 reaction equation.
In a preferred embodiment, MMP (W)XThe sequence of peptide is：Ac-GCRD-GPQG↓IWGQ-DGCG-NH2。
In a preferred embodiment, the molecular weight of the 4-arm-PEG-MAL is 10kDa~40kDa.
In one embodiment, the Michael additions between 4-arm-PEG-MAL described in S1 and the POSS-SH Reaction is carried out in tetrahydrofuran.
In a preferred embodiment, the mol ratio between POSS-SH described in S1 and the 4-arm-PEG-MAL is 0.25-1。
In a preferred embodiment, S1 comprises the following steps：
S11：The 4-arm-PEG-MAL and the POSS-SH are dissolved in tetrahydrofuran；
S12：Being stirred at room temperature makes the 4-arm-PEG-MAL and POSS-SH generation Michael additions anti-for 3.5 hours Should；
S13：The tetrahydrofuran is removed, that is, obtains the POSS-PEG prepolymers.
In one embodiment, MMP described in S2 (W)XCross-linking reaction between the POSS-PEG prepolymers exists Carried out in the aqueous solution of monoethanolamine.
In a preferred embodiment, the concentration of the monoethanolamine is 3-10mM.
In a preferred embodiment, the pH of the ethanolamine solutions is 7-8, preferably 7.4.
In a preferred embodiment, MMP described in S2 (W)XWeight ratio is between the POSS-PEG prepolymers 1:3-20, it is highly preferred that can be by MMP (W)XFunction base and POSS-PEG prepolymers function base ratio be 1:1.
In one embodiment, the reaction temperature in S2 is 37 DEG C.
In one embodiment, medicine or seed cell be also added in the aqueous ethanolamine in S2.
The invention further relates to POSS-PEG hybridized hydrogels prepared by the above method.
The invention further relates to application of the above-mentioned POSS-PEG hybridized hydrogels in tissue engineering bracket is prepared.
The POSS-PEG hybridized hydrogels mechanical strength of the present invention is good, and its mechanical strength can be by changing maleimide ammonia The molar ratio of four arm polyethylene glycol (4-arm-PEG-MAL) molecular weight of base functionalization, POSS-SH and 4-arm-PEG-MAL Finely regulating is carried out, while need to be only prepared from the Triethanolamine buffer of low concentration, gelation time quickly, is ensureing base The infringement or loss of the seed cell or medicine to carrying thereon are reduced on the premise of this physicochemical property as much as possible.
Brief description of the drawings
Fig. 1 is the stereoscan photograph of POSS-PEG hybridized hydrogels；
Fig. 2 is the oscillatory stress scanning spectra of the storage modulus (G ') of POSS-PEG hybridized hydrogels；
Fig. 3 is the dynamic frequency scanning collection of illustrative plates of the storage modulus (G ') of POSS-PEG hybridized hydrogels；
Fig. 4 is POSS-PEG hybridized hydrogel swelling curves；
Fig. 5 compares block diagram for the equilibrium swelling of POSS-PEG hybridized hydrogels；
Fig. 6 is POSS-PEG hybridized hydrogel degradation rate statistical charts；
Fig. 7 is the 4 weeks interior degradation curves of POSS-PEG hybridized hydrogels prepared with 4-arm-PEG-MAL molecular weight 20kDa；
Fig. 8 is that POSS-PEG hybridized hydrogel Cell culture invitro CCK cell viabilities determine figure；
Fig. 9 is the work dead cell stain photo of POSS-PEG hybridized hydrogel Cell culture invitro cells；
Figure 10 is the chemical equation of the method for the present invention.
Embodiment
The principle and feature of the present invention are described below in conjunction with example, the given examples are served only to explain the present invention, and It is non-to be used to limit the scope of the present invention.
The preparation of 1.POSS-PEG hybridized hydrogels
POSS-PEG hybridized hydrogels are prepared by the following method：By 4-arm-PEG-MAL, (it is limited that triumphant science and technology is good in Beijing Company) and POSS-SH (Sigma companies) be dissolved in 3mL tetrahydrofurans, be stirred at room temperature after 3.5 hours remove solvent obtain POSS- PEG prepolymers；Then it is POSS-PEG prepolymers and matrix metalloproteinase peptide substrate (Shanghai gill biochemical technology company) is molten Solution is well mixed in 3mL pH 7.4 triethanolamine, obtains pre- gelling solution；Above-mentioned pre- gelling solution is finally transferred to 5 In individual 600 μ l moulds, reacted in 37 DEG C of biochemical cultivation cases, prepare hydrogel.In POSS-PEG prepolymer preparation process 4-arm-PEG-MAL molecular weight, 4-arm-PEG-MAL, POSS-SH amount are as shown in table 1；POSS-PEG hybridized hydrogel systems Amount, triethanolamine concentrations and the gelation time of POSS-PEG prepolymers and matrix metalloproteinase peptide substrate during standby are such as Shown in table 2.
4-arm-PEG-MAL molecular weight, 4-arm-PEG-MAL, POSS-SH amount in the embodiment 1-5 of table 1
In the embodiment 1-5 of table 2 amount of POSS-PEG prepolymers and matrix metalloproteinase peptide substrate, triethanolamine concentrations with And gelation time
In embodiment 1-5, can plastic, and gelation time is all within 20min.Resulting POSS-PEG hydridization Hydrogel is observed under ESEM, as a result as shown in figure 1, being in POSS-SH and 4-arm-PEG-MAL mol ratio 0.25th, in the case of 0.5 and 1, the 4-arm-PEG-MAL for each molecular weight tested can react with POSS-SH, and it reacts Product can be cross-linked to form cavernous cross-linked structure with matrix metalloproteinase peptide substrate.
The physicochemical property of 2.POSS-PEG hybridized hydrogels
1) mechanical strength
Hydrogel test specimens (n=3) are swelling to balance with ultra-pure water, filter paper dries surface moisture, using rheometer solution Bleed gel mechanical property, 3 test specimens are averaged.Fig. 2 sweeps for the oscillatory stress of the storage modulus (G ') of hydrogel material Tracing spectrum, Fig. 3 is the dynamic frequency scanning collection of illustrative plates of storage modulus (G ').It can be seen that, prepared using the inventive method by Fig. 2 and 3 Hydrogel material when suffered stress increases to 20Pa from 0.1Pa, storage modulus (G ') does not substantially become with the change of stress Change, storage modulus (G ') shows that hydrogel material crosslinking is good also without significant change when range of scanned frequencies is 1Hz to 2Hz.Phase Compared with the pure PEG-hydrogel for not adding POSS, POSS-PEG hybridized hydrogel mechanical strengths are bigger, and mechanical strength contains with POSS Amount increases and increased.
2) hydrophily
By hydrogel test specimens (n=3) freeze-drying, its weight is accurately weighed.Dry hydrogel is immersed in 0.9% chlorination In sodium injection (10mL), 37 DEG C of water-baths are placed in.In the predetermined time, the hydrogel being swelled is taken out, surface water is dried with filter paper Weighed after point, until hydrogel constant weight is constant.The swollen percentage (%) of hydrogel=(be swelled rear hydrogel quality-molten Swollen preceding hydrogel quality)/be swelled before hydrogel quality × 100%, 3 test specimens average.Fig. 4 is swelled for hydrogel material Curve；Fig. 5 compares block diagram for the equilibrium swelling of hydrogel material.Water-setting glue material prepared by the inventive method is can be seen that by Figure 4 and 5 Material has reached higher swelling ratio in preceding 10h, and reaches after 168h swelling equilibrium.Although POSS-PEG hybridized hydrogels Equilibrium swelling ratio increases and reduced with POSS contents, but hydrogel material equilibrium swelling ratio prepared by the inventive method is 12 to 33 Between, show that it still has good hydrophily.
3) enzyme degradability
By hydrogel test specimens (n=3) freeze-drying, its weight is accurately weighed.Dry hydrogel is immersed in 0.01M phosphoric acid Salt buffer (PBS, pH=7.4,9mL) and recombinant human MMP-2 (200ng/mL, 1mL), pure PEG-hydrogel as blank group, It is placed in 37 DEG C of water-baths.Distilled water is rinsed after 30 days, freeze-drying, is weighed.Calculate the accumulative degraded of every group of hydrogel in the solution Hydrogel quality × 100%, 3 test before percentage (%)=(hydrogel quality-residue hydrogel quality before degraded)/degraded Sample is averaged.A is degradation rate figure in Fig. 6；Fig. 7 is the POSS-PEG hydridization prepared with 4-arm-PEG-MAL molecular weight 20kDa 4 weeks interior degradation curves of hydrogel.By Fig. 6 and 7 can be seen that the inventive method prepare hydrogel material degradation rate 28% to Between 48%, show that hydrogel material has enzyme degradability, and with the increase of POSS contents, POSS-PEG hybridized hydrogels Degradation rate is lower, degradation speed is slower.
3. carry the POSS-PEG hybridized hydrogels of Human umbilical vein endothelial cells (HUVEC)
Obtained different POSS-SH and 4-arm-PEG-MAL molar ratio each 3mL of preformation glue, in human umbilical vein Chrotoplast (HUVEC) is uniformly mixed, and cell density is 1 × 106/mL.Take 64 μ L to be placed in 96 porocyte culture plates, be highly 2mm, 5%CO237 DEG C of incubation 30min of constant incubator, add the low sugar DMEM culture mediums that 200uL contains 10% hyclone, after It is continuous to be incubated, sample was taken out at the 1st day and the 4th day, dead cell stain test cell activity of living is carried out, using fluorescence microscopy Image, observation cytoactive and form；And cell viability test is carried out with CCK-8, pushed away using spectrophotometer detection absorbance Calculate number of viable cells.Pure PEG-hydrogel is control group.Fig. 8 is that CCK cell viabilities determine figure；Fig. 9 is that Cell culture invitro is lived extremely Cell dyeing figure.As a result show, cell is uniform in hydrogel enclosed inside, culture has higher cell viability, table after four days Bright POSS-PEG hydrogel materials are nontoxic and with good biocompatibility.
The foregoing is only presently preferred embodiments of the present invention, be not intended to limit the invention, it is all the present invention spirit and Within principle, any modification, equivalent substitution and improvements made etc. should be included in the scope of the protection.

Claims (10)

1. a kind of preparation method of POSS-PEG hybridized hydrogels, it is characterised in that comprise the following steps：
S1：4-arm-PEG-MAL and POSS-SH is subjected to Michael addition reactions and obtains POSS-PEG prepolymers；
S2：Pass through Micheal additions with the POSS-PEG prepolymers using matrix metalloproteinase peptide substrate as crosslinking agent Cross-linking reaction plastic, obtains the POSS-PEG hybridized hydrogels.
2. preparation method according to claim 1, it is characterised in that 4-arm-PEG-MAL described in the S1 and POSS- SH Michael addition reactions are carried out in tetrahydrofuran.
3. preparation method according to claim 1, it is characterised in that POSS-SH described in the S1 and 4-arm-PEG- Mol ratio between MAL is 0.25-1.
4. preparation method according to claim 1, it is characterised in that S1 comprises the following steps：
S11：The 4-arm-PEG-MAL and the POSS-SH are dissolved in tetrahydrofuran；
S12：Being stirred at room temperature makes the 4-arm-PEG-MAL and POSS-SH occur Michael addition reactions；
S13：The tetrahydrofuran is removed, that is, obtains the POSS-PEG prepolymers.
5. preparation method according to claim 1, it is characterised in that matrix metalloproteinase peptide substrate described in S2 and institute The cross-linking reaction between POSS-PEG prepolymers is stated to carry out in the aqueous solution of monoethanolamine.
6. preparation method according to claim 5, it is characterised in that the concentration of the monoethanolamine is 3-10mM.
7. preparation method according to claim 5, it is characterised in that the pH of the ethanolamine solutions is 7-8.
8. the preparation method according to any one of claim 1-7, it is characterised in that in the aqueous ethanolamine in S2 also It with the addition of medicine or seed cell.
9. a kind of POSS-PEG hybridized hydrogels, it is characterised in that be prepared into by the preparation method described in claim 1-8 Arrive.
10. application of the POSS-PEG hybridized hydrogels in tissue engineering bracket is prepared described in claim 9.
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Cited By (7)

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CN108129668A (en) * 2017-12-25 2018-06-08 徐州工程学院 A kind of thermoplastic elastomer (TPE) PA66-b-PEG compounds and its synthetic method and application
CN108164713A (en) * 2017-12-07 2018-06-15 湖北大学 Degradable and water soluble POSS-PEG hybridized hydrogels and its preparation method and application
CN109134866A (en) * 2018-08-02 2019-01-04 湖北大学 A kind of starlike POSS-PEG-ACRYL macromolecule polyalcohol and its preparation method and application
CN109762181A (en) * 2019-01-16 2019-05-17 湖南华腾制药有限公司 Modified Artecoll, hydrogel and preparation method and shaping and beauty material
CN109876194A (en) * 2019-04-11 2019-06-14 湖北大学 A kind of POSS-PEG hybridized hydrogel of adjustable degradation rate and preparation method thereof and its application
WO2019126781A1 (en) * 2017-12-21 2019-06-27 Revlon Consumer Products Corporation Silsesquioxanes and use in nail coatings thereof
CN113995887A (en) * 2021-10-14 2022-02-01 四川大学华西医院 Preparation method and application of cartilage repair nanogel composite system

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CN105601954A (en) * 2016-01-28 2016-05-25 湖南工业大学 Preparation method of biological friendly hydrogel with excellent rebound resilience
CN105669924A (en) * 2016-04-21 2016-06-15 厦门大学 Organic-inorganic linear-dendritic hybrid copolymer containing POSS structure and synthetic method of organic-inorganic linear-dendritic hybrid copolymer
CN106519632A (en) * 2016-09-30 2017-03-22 华中科技大学同济医学院附属协和医院 PEG hydrogel and preparation method thereof as well as tissue engineering scaffold prepared by PEG hydrogel

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CN103113735A (en) * 2013-02-04 2013-05-22 厦门大学 Nanometer noble metal/POSS hybridized polymer micro sphere and preparation method thereof
CN105601954A (en) * 2016-01-28 2016-05-25 湖南工业大学 Preparation method of biological friendly hydrogel with excellent rebound resilience
CN105669924A (en) * 2016-04-21 2016-06-15 厦门大学 Organic-inorganic linear-dendritic hybrid copolymer containing POSS structure and synthetic method of organic-inorganic linear-dendritic hybrid copolymer
CN106519632A (en) * 2016-09-30 2017-03-22 华中科技大学同济医学院附属协和医院 PEG hydrogel and preparation method thereof as well as tissue engineering scaffold prepared by PEG hydrogel

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108164713A (en) * 2017-12-07 2018-06-15 湖北大学 Degradable and water soluble POSS-PEG hybridized hydrogels and its preparation method and application
CN108164713B (en) * 2017-12-07 2021-04-16 湖北大学 Hydrolyzable degradable POSS-PEG hybrid hydrogel and preparation method and application thereof
WO2019126781A1 (en) * 2017-12-21 2019-06-27 Revlon Consumer Products Corporation Silsesquioxanes and use in nail coatings thereof
US10603264B2 (en) 2017-12-21 2020-03-31 Revlon Consumer Products Corporation Silsesquioxanes and use in nail coatings thereof
CN108129668A (en) * 2017-12-25 2018-06-08 徐州工程学院 A kind of thermoplastic elastomer (TPE) PA66-b-PEG compounds and its synthetic method and application
CN109134866A (en) * 2018-08-02 2019-01-04 湖北大学 A kind of starlike POSS-PEG-ACRYL macromolecule polyalcohol and its preparation method and application
CN109762181A (en) * 2019-01-16 2019-05-17 湖南华腾制药有限公司 Modified Artecoll, hydrogel and preparation method and shaping and beauty material
CN109876194A (en) * 2019-04-11 2019-06-14 湖北大学 A kind of POSS-PEG hybridized hydrogel of adjustable degradation rate and preparation method thereof and its application
CN109876194B (en) * 2019-04-11 2021-04-02 湖北大学 POSS-PEG hybrid hydrogel capable of adjusting degradation rate, and preparation method and application thereof
CN113995887A (en) * 2021-10-14 2022-02-01 四川大学华西医院 Preparation method and application of cartilage repair nanogel composite system

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