CN108715644A - A kind of preparation method of aldehyde radical and amino phosphoryl choline polymer bionic adhesion coating - Google Patents
A kind of preparation method of aldehyde radical and amino phosphoryl choline polymer bionic adhesion coating Download PDFInfo
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- CN108715644A CN108715644A CN201810615338.6A CN201810615338A CN108715644A CN 108715644 A CN108715644 A CN 108715644A CN 201810615338 A CN201810615338 A CN 201810615338A CN 108715644 A CN108715644 A CN 108715644A
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- phosphoryl choline
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Abstract
The present invention is the preparation method of a kind of aldehyde radical and amino phosphoryl choline polymer bionic adhesion coating.By the vinyl monomer containing Phosphorylcholine hydrophilic radical and the vinyl monomer containing aldehyde radical by simple solution free radical polymerization, the phosphoryl choline polymer containing aldehyde radical is synthesized.Vinyl monomer containing Phosphorylcholine hydrophilic radical and the vinyl monomer containing amino are subjected to free radical polymerization, synthesize the phosphoryl choline polymer containing amino.Two kinds of phosphoryl choline polymers and dopamine are dissolved in polar solvent, chitosan film surface is coated in, heats in Tris-HCl solution after dry, you can prepare the bionic adhesion coating with imitating cell outer-layer membrane structure.This method preparation is simple and convenient to operate, and a kind of new approach is provided to obtain the excellent bionic adhesion coating of blood compatibility.
Description
Technical field
The invention belongs to material surface science and biological medical polymer material technical field, and in particular to it is a kind of prepare it is viscous
The method of attached imitating cell outer-layer membrane structure coating.
Background technology
Chitosan has many advantages, such as degradability, antibiotic property, nontoxic, non-stimulated, pH responses (Carbohydrate
Polymers 2010,79:724-730), it has been widely used in the fields such as biomedicine.It is more and more research shows that：
Chitosan and its derivative material can be used for blood purification.Amino in chitosan molecule contributes to a variety of toxin in blood
Absorption, can be used for blood Absorbent (Chemical Journal of Chinese Universities 2002,23:75-77；Journal of
Microencapsulation 1993,10:475-486).Chitosan film has high dialysance, selectivity and intensity, can be with
As haemodialysis material (Journal of Applied Polymer Science 1992,46:255-261；263-269).
Although chitosan and its derivative has many advantages as blood purification material, there is also protein absorption, and blood is small
Plate sticks, the problems such as eventually leading to blood coagulation, form thrombus, so the blood compatibility for improving chitosan and its derivative material is compeled
In the eyebrows and eyelashes (Applied Surface Science 2005,241:485-492；Biomaterials 2002,23:2561-
2568；Biomaterials 2003,24:3213-3220).
Phosphorylcholine (phosphorylcholine, PC) is the terminal hydrophyllic group for forming cell membrane basic unit lecithin, is
Outer layer functional group in extracellular tunic, simultaneous with positive and negative xenogenesis charge, ability and hydrophily with stronger combination water
Can, the surface of this structure and composition will not only be adsorbed with physiological environment interaction and depositing proteins, will not cause
Platelet activation leads to the adverse reactions such as blood coagulation, has good biocompatibility.In recent years studies have shown that using phosphinylidyne
Choline group and its polymer have imitating cell outer-layer membrane structure in material surface structure, can significantly improve the blood phase of material
Capacitive.
In recent years, using approach (the Carbohydrate Polymers 2007,70 of grafting Phosphorylcholine small molecule:82-
88；Biomacromolecules 2007,8:3169-3176；Biomacromolecules 2006,7:3151-3156；
Journal of Applied Polymer Science 2003,88:489-493；Polymer International
2003,52:81-85；Journal of biomaterials science,Polymer edition 2002,13:501-
510；Colloids and Surfaces B:Biointerfaces 2009,71:268-274) modification of chitosan so that shell is poly-
The blood compatibility of sugar significantly improves.But these modes are not often high in the density of the Phosphorylcholine group of material surface, limit
It has made it and has been modified the application in field and further increasing for blood compatibility in bio-medical material.
For this purpose, by the methacrylic acid containing Phosphorylcholine group-methylacryoyloxyethyl Phosphorylcholine binary copolymerization
Object (PMA) polyanion carries out layer upon layer electrostatic self assembly with chitosan (polycation), obtains with imitating cell outer-layer film knot
Coating surface (the Colloids and Surfaces B of structure:Biointerfaces 2011,85:48-55).Protein adsorbs
With platelet adhesion reaction the experimental results showed that：The blood compatibility of modified rear surface is obviously improved.In view of this modification side
The all the advantages of method will provide technical support to promote the blood compatibility of bio-medical material.However, with physical absorption side
Formula is incorporated in the polymer with simulated cellulosa membrane structure coating of transplanting device surface, inevitably occurs in complex environment in vivo molten
It solves, fall off.For this purpose, Lewis and Xu build equality (Biomaterials 2001,22:99-111；Biomaterials 2004,
25:3099-3108；European Polymer Journal 2004,40:291-298) respectively to containing trimethoxy silicon substrate
The polymer coating of group and Phosphorylcholine group is studied.The result shows that trimethoxy on polymer molecular chain in coating
Silicon group, which meets water, can occur hydrolysis, crosslinking, also covalent bond can be formed with the active group of substrate surface, to make Phosphorylcholine class
The stability of polymer coating is significantly improved.It can be seen that crosslinking between polymer and its with substrate surface functional group
Reaction, be improve Phosphorylcholine Type of Collective object coating stability key factor.
However, polymer crosslinkable groups facile hydrolysis, crosslinking in the synthesis process so that its building-up process condition is excessively
Harshness is difficult to preserve, and causes its application range limited.Yao et al. reacts the DOPA for adhering to imitative mussel using amino with carboxyl
Amine is grafted to the coating studied on the phosphoryl choline polymer containing carboxyl in titanium alloy surface, but the content of dopamine is only
4%, attachment of polymers power is relatively low.For this purpose, with the approach of active ester monomer to have synthesized DOPAMINE CONTENT IN RABBIT high and controllable by Gong et al.
Phosphoryl choline polymer, and use it for the surfaces of various materials such as polypropylene, polytetrafluoroethylene (PTFE) modification.Dang et al. will contain
Eight arm PEG of dopamine and phosphoryl choline polymer are for surfaces of various materials coating modification.This bionic adhesion method is one
Determine can to increase in degree the stability of coating, but the adhesion strength of imitative bivalves adherent coating is not strong, stability need to be improved.
Invention content
Technical problem to be solved by the present invention lies in view of the above shortcomings of the prior art, provide a kind of aldehyde radical and amino
The preparation method of phosphoryl choline polymer bionic adhesion coating.By the vinyl monomer containing Phosphorylcholine hydrophilic radical with contain
There is the vinyl monomer of aldehyde radical by simple solution free radical polymerization, synthesizes the phosphoryl choline polymer containing aldehyde radical.It will contain
The vinyl monomer and the vinyl monomer containing amino for having Phosphorylcholine group pass through simple solution free radical polymerization, synthesis
Phosphoryl choline polymer containing amino.Then two kinds of phosphoryl choline polymers and dopamine are dissolved in polar solvent, are coated
On chitosan film surface, dry be placed in Tris-HCl solution is heated, you can preparing has imitating cell outer-layer membrane structure
Bionic adhesion coating.The preparation method of imitating cell outer-layer membrane structure coating is simple and convenient to operate, and is imitated to obtain stable having
The coating surface of cell outer-layer membrane structure provides a kind of new approach.
In order to solve the above technical problems, the technical solution adopted by the present invention is：
A kind of preparation method of aldehyde radical and amino phosphoryl choline polymer bionic adhesion coating, includes the following steps：
Step 1: under nitrogen protection, by the vinyl monomer containing aldehyde radical and containing the vinyl monomer of Phosphorylcholine
Free radical solution polymerization reaction is carried out under the action of initiator, synthesizes the phosphoryl choline polymer containing aldehyde radical；
Step 2: under nitrogen protection, by the vinyl monomer containing amino and containing the vinyl monomer of Phosphorylcholine
Free radical solution polymerization reaction is carried out under the action of initiator, synthesizes the phosphoryl choline polymer containing aldehyde radical；
Step 3: two kinds of phosphoryl choline polymers and dopamine are dissolved with polar solvent, and it is coated in chitosan film table
Face, dry be placed in Tris-HCl solution are heated, that is, prepare the bionic adhesion coating with imitating cell outer-layer membrane structure.
The vinyl monomer containing Phosphorylcholine hydrophilic radical is with the vinyl monomer molar ratio containing aldehyde radical
(9.5:0.5)~(6:4).
The vinyl monomer containing Phosphorylcholine hydrophilic radical and the vinyl monomer molar ratio containing amino are about
It is (9.5:0.5)~(6:4).
The vinyl monomer containing Phosphorylcholine hydrophilic radical is methylacryoyloxyethyl Phosphorylcholine, is contained
The vinyl monomer of aldehyde radical is methacrolein, and the vinyl monomer containing amino is 2- aminoethyl methacrylate hydrochloric acid
Salt.
In step 1, solvent is methanol and tetrahydrofuran mixed solvent, and initiator is azodiisobutyronitrile, and reaction temperature is
65~80 DEG C, the reaction time is 20~26h, and the bag filter for being 7000 with molecular cut off is dialysed, and is freezed at -50 DEG C dry
It is dry.
In step 2, the solvent of the phosphoryl choline polymer of the synthesis containing amino is distilled water, and initiator is over cure
Sour potassium, reaction temperature are 65~80 DEG C, and the reaction time is 20~26h, and the bag filter for being 7000 with molecular cut off is dialysed,
It is freeze-dried at -50 DEG C.
In step 3, two kinds of phosphoryl choline polymers containing aldehyde radical and amino are configured to a concentration of 1~8mg/mL solution,
Two kinds of phosphoryl choline polymer mass ratioes containing aldehyde radical and amino are (9.5:0.5)~(6:4), dopamine is that the two dosage is total
The 1~8% of quality.
In step 3, the volume for being coated in chitosan film surface drop coating is 10~45 μ L/cm2/ face, 30 DEG C of vacuum drying
24h。
The polar solvent is methanol or ethyl alcohol.
The painting is placed on pH value of solution=8~9 Tris-HCl, and heating temperature is processing 17 in 40~75 DEG C~for 24 hours.
Compared with the prior art, the present invention has the following advantages：
The present invention passes through the vinyl monomer containing Phosphorylcholine hydrophilic radical and the vinyl monomer containing aldehyde radical
Simple solution free radical polymerization synthesizes the phosphoryl choline polymer containing aldehyde radical.By the vinyl containing Phosphorylcholine group
Monomer, by simple solution free radical polymerization, synthesizes the Phosphorylcholine polymerization containing amino with the vinyl monomer containing amino
Object.Then two kinds of phosphoryl choline polymers and dopamine are dissolved in polar solvent, are coated in chitosan film surface, dry postposition
Heat in Tris-HCl solution, keeps aldehyde radical and chitosan film surface amino groups in the phosphoryl choline polymer containing aldehyde radical anti-
When should be anchored base material, also with the amino cross-linking reaction in the phosphoryl choline polymer containing amino, while dopamine adherency and with
Chitosan film surface amino groups reaction anchoring base material when, also with the amino in two kinds of phosphoryl choline polymers containing amino and aldehyde radical
With aldehyde radical cross-linking reaction, the density of coating stability and surface Phosphorylcholine group is significantly improved, you can obtaining has imitative cell
The bionic adhesion coating of outer layer membrane structure.The preparation method of imitating cell outer-layer membrane structure coating is simple and convenient to operate, steady to obtain
The fixed coating surface with imitating cell outer-layer membrane structure provides a kind of new approach.The imitating cell outer-layer membrane structure of the present invention
Coating will be in blood purification, and material implanted, organizational project, the fields such as medicament slow release and biosensor have wide answer
Use foreground.
Description of the drawings
Fig. 1 is the dynamic contact angle of chitosan film of the present invention and Chitosan film.
Fig. 2 is the fine energy spectrum diagram of element of chitosan film of the present invention and Chitosan film.
Specific implementation mode
A kind of preparation method of aldehyde radical and amino phosphoryl choline polymer bionic adhesion coating of the present invention, including following step
Suddenly：
Step 1: under nitrogen protection, by the vinyl monomer (methacrolein) containing aldehyde radical and containing Phosphorylcholine
Vinyl monomer (methylacryoyloxyethyl Phosphorylcholine) free radical solution polymerization reaction is carried out under the action of initiator,
Synthesize the phosphoryl choline polymer containing aldehyde radical；Vinyl monomer containing Phosphorylcholine hydrophilic radical and the second containing aldehyde radical
Alkenyl monomer molar ratio is (9.5:0.5)~(6:4).Solvent is methanol and tetrahydrofuran mixed solvent, and initiator is azo two
Isobutyronitrile, reaction temperature are 65~80 DEG C, and the reaction time is 20~26h, and the bag filter for being 7000 with molecular cut off carries out
Analysis, is freeze-dried at -50 DEG C.
Step 2: under nitrogen protection, by vinyl monomer (the 2- aminoethyl methacrylate hydrochloric acid containing amino
Salt) and vinyl monomer (methylacryoyloxyethyl Phosphorylcholine) containing Phosphorylcholine carried out under the action of initiator from
It is reacted by radical solution polymerization, synthesizes the phosphoryl choline polymer containing aldehyde radical；Vinyl containing Phosphorylcholine hydrophilic radical
Monomer is about (9.5 with the vinyl monomer molar ratio containing amino:0.5)~(6:4).It is poly- to synthesize the Phosphorylcholine containing amino
The solvent for closing object is distilled water, and initiator is potassium peroxydisulfate, and reaction temperature is 65~80 DEG C, and the reaction time is 20~26h, with cutting
It is that 7000 bag filter is dialysed to stay molecular weight, is freeze-dried at -50 DEG C.
Step 3: two kinds of phosphoryl choline polymers and dopamine are dissolved with polar solvent (methanol or ethyl alcohol), and coat
On chitosan film surface, the volume for being coated in chitosan film surface drop coating is 10~45 μ L/cm2/ face, 30 DEG C of vacuum drying are for 24 hours.
Dry be placed in Tris-HCl solution is heated, and painting is placed on pH value of solution=8~9 Tris-HCl, and heating temperature is 40~
In 75 DEG C processing 17~for 24 hours.Prepare the bionic adhesion coating with imitating cell outer-layer membrane structure.Two containing aldehyde radical and amino
Kind phosphoryl choline polymer is configured to a concentration of 1~8mg/mL solution, two kinds of phosphoryl choline polymers containing aldehyde radical and amino
Mass ratio is (9.5:0.5)~(6:4), dopamine is the 1~8% of the two dosage gross mass.
The present invention optimal embodiment be：By the methylacryoyloxyethyl phosphinylidyne containing Phosphorylcholine hydrophilic radical
Choline monomer and the methacrolein monomers containing aldehyde radical in molar ratio 8:2 use solution free radical polymerization, synthesis to contain aldehyde radical
Phosphoryl choline polymer.Meanwhile by the methylacryoyloxyethyl Phosphorylcholine monomer containing Phosphorylcholine hydrophilic radical
With 2- aminoethyl methacrylate hydrochloric acid salt monomer in molar ratio 8:2 use solution free radical polymerization, synthesis to contain amino
Phosphoryl choline polymer.Then by two kinds of phosphoryl choline polymers in mass ratio 7 containing aldehyde radical and amino:3, then take dopamine
Both about the 3% of dosage is dissolved in methanol solvate and being uniformly mixed, then by its solution drop Tu on chitosan film surface, 30 DEG C
Vacuum drying is for 24 hours.Drying is placed in pH value of solution=8.5 Tris-HCl, and 22h is handled at 50 DEG C, you can obtaining has imitative cell
The bionic adhesion coating of outer layer membrane structure.
With reference to the accompanying drawings and examples, technical scheme of the present invention is described in further detail.
Embodiment 1
16mmol 2- methylacryoyloxyethyls Phosphorylcholines and 4mmol methacrolein are weighed, with 0.1mmol azos
Bis-isobutyronitrile is initiator, volume ratio 4:1 methanol and tetrahydrofuran is solvent, under nitrogen protection, 70 DEG C of polymerisations
For 24 hours, after reaction, concentration of reaction solution, with molecular cut off be 6000~8000D bag filter dialyse, then at -50 DEG C it is cold
It is lyophilized dry, obtains the phosphoryl choline polymer containing aldehyde radical.
Weigh 16mmol 2- methylacryoyloxyethyls Phosphorylcholines and 4mmol 2- aminoethyl methacrylate hydrochloric acid
Salt, using 0.1mmol potassium peroxydisulfates as initiator, distilled water is solvent, under nitrogen protection, 70 DEG C of polymerisation 12h, reaction knot
It dialyses after beam, is then freeze-dried at -50 DEG C, obtain amino-containing phosphoryl choline polymer.
Phosphoryl choline polymer manufactured in the present embodiment containing aldehyde radical and the phosphoryl choline polymer containing amino are pressed
Mass ratio 7:3, it is configured to the methanol solution of 4mg/mL.Then adding dopamine makes its concentration be about that 0.12mg/mL mixing is equal
It is even.Then by the mixed solutions of above-mentioned two kinds of phosphoryl choline polymers and dopamine drop Tu on chitosan film surface, drop coating
Volume is 30 μ L/cm2/ face.It is dried in vacuo for 24 hours at 30 DEG C again.Later, it is placed in pH value of solution=8.5 Tris-HCl at 50 DEG C
Manage 22h, when making in the phosphoryl choline polymer containing aldehyde radical aldehyde radical react with chitosan film surface amino groups to be anchored base material, also with containing
There is the amino cross-linking reaction in the phosphoryl choline polymer of amino, while dopamine is adhered to and reacted with chitosan film surface amino groups
Be anchored base material when, also with the amino and aldehyde radical cross-linking reaction in two kinds of phosphoryl choline polymers containing amino and aldehyde radical, significantly
Improve the density of coating stability and surface Phosphorylcholine group, you can obtain the bionic adhesion with imitating cell outer-layer membrane structure
Coating.
As shown in Figure 1, chitosan film of the present embodiment through coating treatment compared with the chitosan film without coating treatment, passes through
The advancing angle and receding angle of the chitosan of coating treatment decrease, this is because the phosphoryl choline polymer of good hydrophilic property is logical
Reacting for amino in phosphoryl choline polymer of the aldehyde radical with chitosan surface amino groups and containing amino is crossed, the viscous of dopamine is also passed through
Phosphorylcholine group is fixed on the surface of chitosan film by attached and anchoring effect, obtains the table with imitating cell outer-layer membrane structure
Face so that its hydrophily significantly improves, and advancing angle and receding angle are substantially reduced.In addition, the presence of dopamine increases modified shell
The hydrophily of glycan film, advancing angle and receding angle all reduce.This illustrates that dopamine increases chitosan film surface Phosphorylcholine base
The density of group, so modified advancing angle receding angle decreases.
As shown in Fig. 2, chitosan film of the present embodiment through coating treatment compared with the chitosan film without coating treatment, passes through
There is N on Phosphorylcholine group on the chitosan film surface of modification+With P characteristic absorption peaks, this illustrates the phosphinylidyne courage of good hydrophilic property
Base groups are fixed on chitosan film surface.Amino and chitosan film surface amino groups and the Phosphorylcholine containing aldehyde radical in dopamine
In polymer aldehyde radical react while dopamine crosslinking and the phosphoryl choline polymer containing amino in amino and poly-dopamine
Middle carbonyl reaction, the anchoring reacted with chitosan film surface amino groups by aldehyde radical in phosphoryl choline polymer and amino and and DOPA
The reaction of amine is adhered to is fixed on chitosan film surface by Phosphorylcholine group, can prepare the table with imitating cell outer-layer membrane structure
Face so that its hydrophily significantly improves, and N on Phosphorylcholine group occurs+With P characteristic absorption peaks.
Embodiment 2
19mmol 2- methylacryoyloxyethyls Phosphorylcholines and 1mmol methacrolein are weighed, with 0.1mmol azos
Bis-isobutyronitrile is initiator, volume ratio 4:1 methanol and tetrahydrofuran is solvent, under nitrogen protection, 70 DEG C of polymerisations
For 24 hours, after reaction, concentration of reaction solution, with molecular cut off be 6000~8000D bag filter dialyse, then at -50 DEG C it is cold
It is lyophilized dry, obtains the phosphoryl choline polymer containing aldehyde radical.
Weigh 12mmol 2- methylacryoyloxyethyls Phosphorylcholines and 8mmol 2- aminoethyl methacrylate hydrochloric acid
Salt, using 0.1mmol potassium peroxydisulfates as initiator, distilled water is solvent, under nitrogen protection, 70 DEG C of polymerisation 12h, reaction knot
It dialyses after beam, is then freeze-dried at -50 DEG C, obtain amino-containing phosphoryl choline polymer.
Phosphoryl choline polymer manufactured in the present embodiment containing aldehyde radical and the phosphoryl choline polymer containing amino are pressed
Mass ratio 9.5:0.5, it is configured to the ethanol solution of 8mg/mL.Then adding dopamine makes its concentration be about 0.08mg/mL mixed
It closes uniform.Then by the mixed solution drop Tu of above-mentioned two kinds of phosphoryl choline polymers and dopamine in chitosan film surface, drop
The volume of painting is 10 μ L/cm2/ face.It is dried in vacuo for 24 hours at 30 DEG C again.Later, it is placed in pH value of solution=8.5 Tris-HCl 40
DEG C processing for 24 hours, you can prepare with imitating cell outer-layer membrane structure bionic adhesion coating.
Embodiment 3
18mmol 2- methylacryoyloxyethyls Phosphorylcholines and 2mmol methacrolein are weighed, with 0.1mmol azos
Bis-isobutyronitrile is initiator, volume ratio 4:1 methanol and tetrahydrofuran is solvent, under nitrogen protection, 70 DEG C of polymerisations
For 24 hours, after reaction, concentration of reaction solution, with molecular cut off be 6000~8000D bag filter dialyse, then at -50 DEG C it is cold
It is lyophilized dry, obtains the phosphoryl choline polymer containing aldehyde radical.
Weigh 13mmol 2- methylacryoyloxyethyls Phosphorylcholines and 7mmol 2- aminoethyl methacrylate hydrochloric acid
Salt, using 0.1mmol potassium peroxydisulfates as initiator, distilled water is solvent, under nitrogen protection, 70 DEG C of polymerisation 12h, reaction knot
It dialyses after beam, is then freeze-dried at -50 DEG C, obtain amino-containing phosphoryl choline polymer.
Phosphoryl choline polymer manufactured in the present embodiment containing aldehyde radical and the phosphoryl choline polymer containing amino are pressed
Mass ratio 9:1, it is configured to the methanol solution of 7mg/mL.Then adding dopamine makes its concentration be about that 0.14mg/mL mixing is equal
It is even.Then by the mixed solutions of above-mentioned two kinds of phosphoryl choline polymers and dopamine drop Tu on chitosan film surface, drop coating
Volume is 15 μ L/cm2/ face.It is dried in vacuo for 24 hours at 30 DEG C again.Later, it is placed in pH value of solution=8.5 Tris-HCl at 45 DEG C
Manage 23h, you can prepare the bionic adhesion coating with imitating cell outer-layer membrane structure.
Embodiment 4
17mmol 2- methylacryoyloxyethyls Phosphorylcholines and 3mmol methacrolein are weighed, with 0.1mmol azos
Bis-isobutyronitrile is initiator, volume ratio 4:1 methanol and tetrahydrofuran is solvent, under nitrogen protection, 70 DEG C of polymerisations
For 24 hours, after reaction, concentration of reaction solution, with molecular cut off be 6000~8000D bag filter dialyse, then at -50 DEG C it is cold
It is lyophilized dry, obtains the phosphoryl choline polymer containing aldehyde radical.
Weigh 14mmol 2- methylacryoyloxyethyls Phosphorylcholines and 6mmol 2- aminoethyl methacrylate hydrochloric acid
Salt, using 0.1mmol potassium peroxydisulfates as initiator, distilled water is solvent, under nitrogen protection, 70 DEG C of polymerisation 12h, reaction knot
It dialyses after beam, is then freeze-dried at -50 DEG C, obtain amino-containing phosphoryl choline polymer.
Phosphoryl choline polymer manufactured in the present embodiment containing aldehyde radical and the phosphoryl choline polymer containing amino are pressed
Mass ratio 8:2, it is configured to the ethanol solution of 6mg/mL.Then adding dopamine makes its concentration be about that 0.24mg/mL mixing is equal
It is even.Then by the mixed solutions of above-mentioned two kinds of phosphoryl choline polymers and dopamine drop Tu on chitosan film surface, drop coating
Volume is 20 μ L/cm2/ face.It is dried in vacuo for 24 hours at 30 DEG C again.Later, it is placed in pH value of solution=8.5 Tris-HCl at 55 DEG C
Manage 21h, you can prepare the bionic adhesion coating with imitating cell outer-layer membrane structure.
Embodiment 5
15mmol 2- methylacryoyloxyethyls Phosphorylcholines and 5mmol methacrolein are weighed, with 0.1mmol azos
Bis-isobutyronitrile is initiator, volume ratio 4:1 methanol and tetrahydrofuran is solvent, under nitrogen protection, 70 DEG C of polymerisations
For 24 hours, after reaction, concentration of reaction solution, with molecular cut off be 6000~8000D bag filter dialyse, then at -50 DEG C it is cold
It is lyophilized dry, obtains the phosphoryl choline polymer containing aldehyde radical.
Weigh 15mmol 2- methylacryoyloxyethyls Phosphorylcholines and 5mmol 2- aminoethyl methacrylate hydrochloric acid
Salt, using 0.1mmol potassium peroxydisulfates as initiator, distilled water is solvent, under nitrogen protection, 70 DEG C of polymerisation 12h, reaction knot
It dialyses after beam, is then freeze-dried at -50 DEG C, obtain amino-containing phosphoryl choline polymer.
Phosphoryl choline polymer manufactured in the present embodiment containing aldehyde radical and the phosphoryl choline polymer containing amino are pressed
Mass ratio 6:4, it is configured to the methanol solution of 5mg/mL.Then adding dopamine makes its concentration be about that 0.25mg/mL mixing is equal
It is even.Then by the mixed solutions of above-mentioned two kinds of phosphoryl choline polymers and dopamine drop Tu on chitosan film surface, drop coating
Volume is 25 μ L/cm2/ face.It is dried in vacuo for 24 hours at 30 DEG C again.Later, it is placed in pH value of solution=8.5 Tris-HCl at 60 DEG C
Manage 20h, you can prepare the bionic adhesion coating with imitating cell outer-layer membrane structure.
Embodiment 6
14mmol 2- methylacryoyloxyethyls Phosphorylcholines and 6mmol methacrolein are weighed, with 0.1mmol azos
Bis-isobutyronitrile is initiator, volume ratio 4:1 methanol and tetrahydrofuran is solvent, under nitrogen protection, 70 DEG C of polymerisations
For 24 hours, after reaction, concentration of reaction solution, with molecular cut off be 6000~8000D bag filter dialyse, then at -50 DEG C it is cold
It is lyophilized dry, obtains the phosphoryl choline polymer containing aldehyde radical.
Weigh 17mmol 2- methylacryoyloxyethyls Phosphorylcholines and 3mmol 2- aminoethyl methacrylate hydrochloric acid
Salt, using 0.1mmol potassium peroxydisulfates as initiator, distilled water is solvent, under nitrogen protection, 70 DEG C of polymerisation 12h, reaction knot
It dialyses after beam, is then freeze-dried at -50 DEG C, obtain amino-containing phosphoryl choline polymer.
Phosphoryl choline polymer manufactured in the present embodiment containing aldehyde radical and the phosphoryl choline polymer containing amino are pressed
Mass ratio 6.5:3.5, it is configured to the ethanol solution of 3mg/mL.Then adding dopamine makes its concentration be about 0.18mg/mL mixed
It closes uniform.Then by the mixed solution drop Tu of above-mentioned two kinds of phosphoryl choline polymers and dopamine in chitosan film surface, drop
The volume of painting is 35 μ L/cm2/ face.It is dried in vacuo for 24 hours at 30 DEG C again.Later, it is placed in pH value of solution=8.5 Tris-HCl 65
DEG C processing 19h, you can prepare with imitating cell outer-layer membrane structure bionic adhesion coating.
Embodiment 7
13mmol 2- methylacryoyloxyethyls Phosphorylcholines and 7mmol methacrolein are weighed, with 0.1mmol azos
Bis-isobutyronitrile is initiator, volume ratio 4:1 methanol and tetrahydrofuran is solvent, under nitrogen protection, 70 DEG C of polymerisations
For 24 hours, after reaction, concentration of reaction solution, with molecular cut off be 6000~8000D bag filter dialyse, then at -50 DEG C it is cold
It is lyophilized dry, obtains the phosphoryl choline polymer containing aldehyde radical.
Weigh 18mmol 2- methylacryoyloxyethyls Phosphorylcholines and 2mmol 2- aminoethyl methacrylate hydrochloric acid
Salt, using 0.1mmol potassium peroxydisulfates as initiator, distilled water is solvent, under nitrogen protection, 70 DEG C of polymerisation 12h, reaction knot
It dialyses after beam, is then freeze-dried at -50 DEG C, obtain amino-containing phosphoryl choline polymer.
Phosphoryl choline polymer manufactured in the present embodiment containing aldehyde radical and the phosphoryl choline polymer containing amino are pressed
Mass ratio 7.5:2.5, it is configured to the methanol solution of 2mg/mL.Then adding dopamine makes its concentration be about 0.14mg/mL mixed
It closes uniform.Then by the mixed solution drop Tu of above-mentioned two kinds of phosphoryl choline polymers and dopamine in chitosan film surface, drop
The volume of painting is 40 μ L/cm2/ face.It is dried in vacuo for 24 hours at 30 DEG C again.Later, it is placed in pH value of solution=8.5 Tris-HCl 70
DEG C processing 18h, you can prepare with imitating cell outer-layer membrane structure bionic adhesion coating.
Embodiment 8
12mmol 2- methylacryoyloxyethyls Phosphorylcholines and 8mmol methacrolein are weighed, with 0.1mmol azos
Bis-isobutyronitrile is initiator, volume ratio 4:1 methanol and tetrahydrofuran is solvent, under nitrogen protection, 70 DEG C of polymerisations
For 24 hours, after reaction, concentration of reaction solution, with molecular cut off be 6000~8000D bag filter dialyse, then at -50 DEG C it is cold
It is lyophilized dry, obtains the phosphoryl choline polymer containing aldehyde radical.
Weigh 19mmol 2- methylacryoyloxyethyls Phosphorylcholines and 1mmol 2- aminoethyl methacrylate hydrochloric acid
Salt, using 0.1mmol potassium peroxydisulfates as initiator, distilled water is solvent, under nitrogen protection, 70 DEG C of polymerisation 12h, reaction knot
It dialyses after beam, is then freeze-dried at -50 DEG C, obtain amino-containing phosphoryl choline polymer.
Phosphoryl choline polymer manufactured in the present embodiment containing aldehyde radical and the phosphoryl choline polymer containing amino are pressed
Mass ratio 8.5:1.5, it is configured to the ethanol solution of 1mg/mL.Then adding dopamine makes its concentration be about 0.08mg/mL mixed
It closes uniform.Then by the mixed solution drop Tu of above-mentioned two kinds of phosphoryl choline polymers and dopamine in chitosan film surface, drop
The volume of painting is 45 μ L/cm2/ face.It is dried in vacuo for 24 hours at 30 DEG C again.Later, it is placed in pH value of solution=8.5 Tris-HCl 75
DEG C processing 17h, you can prepare with imitating cell outer-layer membrane structure bionic adhesion coating.
Embodiment 9
10mmol 2- methylacryoyloxyethyls Phosphorylcholines and 1mmol methacrolein are weighed, with 0.1mmol azos
Bis-isobutyronitrile is initiator, volume ratio 4:1 methanol and tetrahydrofuran is solvent, under nitrogen protection, 65 DEG C of polymerisations
20h, after reaction, concentration of reaction solution, with molecular cut off be 6000~8000D bag filter dialyse, then at -50 DEG C it is cold
It is lyophilized dry, obtains the phosphoryl choline polymer containing epoxy.
Weigh 10mmol 2- methylacryoyloxyethyls Phosphorylcholines and 1mmol2- aminoethyl methacrylate hydrochloric acid
Salt, using 0.1mmol potassium peroxydisulfates as initiator, distilled water is solvent, under nitrogen protection, 65 DEG C of polymerisation 20h, reaction knot
It dialyses after beam, is then freeze-dried at -50 DEG C, obtain amino-containing phosphoryl choline polymer.
Phosphoryl choline polymer manufactured in the present embodiment containing aldehyde radical and the phosphoryl choline polymer containing amino are pressed
Mass ratio 9.5:0.5, it is configured to the methanol solution of 8mg/mL.Then adding dopamine makes its concentration be about 0.5mg/mL mixing
Uniformly.Then the mixed solution of above-mentioned two kinds of phosphoryl choline polymers and dopamine is dripped into Tu in chitosan film surface, drop coating
Volume be 10 μ L/cm2/ face.It is dried in vacuo for 24 hours at 30 DEG C again.Later, it is placed in pH value of solution=8 Tris-HCl at 75 DEG C
Manage 17h, you can prepare the bionic adhesion coating with imitating cell outer-layer membrane structure.
Embodiment 10
6mmol 2- methylacryoyloxyethyls Phosphorylcholines and 4mmol methacrolein are weighed, with 0.1mmol azos two
Isobutyronitrile is initiator, volume ratio 4:1 methanol and tetrahydrofuran is solvent, under nitrogen protection, 80 DEG C of polymerisations
20h, after reaction, concentration of reaction solution, with molecular cut off be 6000~8000D bag filter dialyse, then at -50 DEG C it is cold
It is lyophilized dry, obtains the phosphoryl choline polymer containing epoxy.
Weigh 6mmol 2- methylacryoyloxyethyls Phosphorylcholines and 4mmol 2- aminoethyl methacrylate hydrochloric acid
Salt, using 0.1mmol potassium peroxydisulfates as initiator, distilled water is solvent, under nitrogen protection, 80 DEG C of polymerisation 20h, reaction knot
It dialyses after beam, is then freeze-dried at -50 DEG C, obtain amino-containing phosphoryl choline polymer.
Phosphoryl choline polymer manufactured in the present embodiment containing aldehyde radical and the phosphoryl choline polymer containing amino are pressed
Mass ratio 6:4, it is configured to the ethanol solution of 2.5mg/mL.Then adding dopamine makes its concentration be about that 0.2mg/mL mixing is equal
It is even.Then by the mixed solutions of above-mentioned two kinds of phosphoryl choline polymers and dopamine drop Tu on chitosan film surface, drop coating
Volume is 27 μ L/cm2/ face.It is dried in vacuo for 24 hours at 30 DEG C again.Later, it is placed in pH value of solution=9 Tris-HCl and is handled at 40 DEG C
17h, you can prepare the bionic adhesion coating with imitating cell outer-layer membrane structure.
In short, the present invention is the preparation method of a kind of aldehyde radical and amino phosphoryl choline polymer bionic adhesion coating.It will contain
There are the phosphoryl choline polymer, the phosphoryl choline polymer containing amino and dopamine mixed solution of aldehyde radical to be coated in material table
Face is prepared with this with the excellent bionic adhesion coating of imitating cell outer-layer membrane structure, blood compatibility.The present invention will contain phosphinylidyne
The vinyl monomer of choline hydrophilic radical passes through simple solution free radical polymerization, synthesis with the vinyl monomer containing aldehyde radical
Phosphoryl choline polymer containing aldehyde radical.By the vinyl monomer containing Phosphorylcholine hydrophilic radical and contain the ethylene of amino
Base monomer carries out free radical polymerization, synthesizes the phosphoryl choline polymer containing amino.By two kinds of phosphoryl choline polymers and DOPA
Amine is dissolved in polar solvent, is coated in chitosan film surface, is heated in Tris-HCl solution after dry, you can prepares tool
There is the bionic adhesion coating of imitating cell outer-layer membrane structure.This method preparation is simple and convenient to operate, excellent to obtain blood compatibility
Different bionic adhesion coating provides a kind of new approach.The modified material of this imitating cell outer-layer membrane structure, will be net in blood
Change, material implanted, organizational project, the fields such as medicament slow release and biosensor have broad application prospects.
The above is only presently preferred embodiments of the present invention, not does any restrictions to the present invention, every according to invention skill
Art essence changes any simple modification, change and equivalent structure made by above example, still falls within the technology of the present invention
In the protection domain of scheme.
Claims (10)
1. the preparation method of a kind of aldehyde radical and amino phosphoryl choline polymer bionic adhesion coating, it is characterised in that including following step
Suddenly：
Step 1: under nitrogen protection, the vinyl monomer containing aldehyde radical and the vinyl monomer containing Phosphorylcholine are being drawn
Free radical solution polymerization reaction is carried out under the action of hair agent, synthesizes the phosphoryl choline polymer containing aldehyde radical；
Step 2: under nitrogen protection, the vinyl monomer containing amino and the vinyl monomer containing Phosphorylcholine are being drawn
Free radical solution polymerization reaction is carried out under the action of hair agent, synthesizes the phosphoryl choline polymer containing amino；
Step 3: two kinds of phosphoryl choline polymers and dopamine are dissolved with polar solvent, and it is coated in chitosan film surface, done
Dry be placed in Tris-HCl solution is heated, that is, prepares the bionic adhesion coating with imitating cell outer-layer membrane structure.
2. the preparation method of a kind of aldehyde radical according to claim 1 and amino phosphoryl choline polymer bionic adhesion coating,
It is characterized in that, the vinyl monomer containing Phosphorylcholine hydrophilic radical and the vinyl monomer molar ratio containing aldehyde radical
It is (9.5:0.5)~(6:4).
3. the preparation method of a kind of aldehyde radical according to claim 1 and amino phosphoryl choline polymer bionic adhesion coating,
It is characterized in that, the vinyl monomer containing Phosphorylcholine hydrophilic radical and the vinyl monomer molar ratio containing amino
About (9.5:0.5)~(6:4).
4. the preparation method of a kind of aldehyde radical according to claim 1 and amino phosphoryl choline polymer bionic adhesion coating,
It is characterized in that, the vinyl monomer containing Phosphorylcholine hydrophilic radical is methylacryoyloxyethyl Phosphorylcholine,
Vinyl monomer containing aldehyde radical is methacrolein, and the vinyl monomer containing amino is 2- aminoethyl methacrylate salt
Hydrochlorate.
5. the preparation method of a kind of aldehyde radical according to claim 1 and amino phosphoryl choline polymer bionic adhesion coating,
It is characterized in that, in step 1, solvent is methanol and tetrahydrofuran mixed solvent, and initiator is azodiisobutyronitrile, reaction temperature
Degree is 65~80 DEG C, and the reaction time is 20~26h, and the bag filter for being 7000 with molecular cut off is dialysed, cold at -50 DEG C
It is lyophilized dry.
6. the preparation method of a kind of aldehyde radical according to claim 1 and amino phosphoryl choline polymer bionic adhesion coating,
It is characterized in that, in step 2, the solvent of the phosphoryl choline polymer of the synthesis containing amino is distilled water, and initiator was
Potassium sulfate, reaction temperature are 65~80 DEG C, and the reaction time is 20~26h, and the bag filter for being 7000 with molecular cut off carries out
Analysis, is freeze-dried at -50 DEG C.
7. the preparation method of a kind of aldehyde radical according to claim 1 and amino phosphoryl choline polymer bionic adhesion coating,
It is characterized in that, in step 3, it is molten that two kinds of phosphoryl choline polymers containing aldehyde radical and amino are configured to a concentration of 1~8mg/mL
Liquid, two kinds of phosphoryl choline polymer mass ratioes containing aldehyde radical and amino are (9.5:0.5)~(6:4), dopamine is that the two is used
Measure the 1~8% of gross mass.
8. the preparation method of a kind of aldehyde radical according to claim 1 and amino phosphoryl choline polymer bionic adhesion coating,
It is characterized in that, in step 3, the volume for being coated in chitosan film surface drop coating is 10~45 μ L/cm2/ face, 30 DEG C of vacuum are dry
It is dry for 24 hours.
9. the preparation method of a kind of aldehyde radical according to claim 1 and amino phosphoryl choline polymer bionic adhesion coating,
It is characterized in that, in step 3, the polar solvent is methanol or ethyl alcohol.
10. the preparation method of a kind of aldehyde radical according to claim 1 and amino phosphoryl choline polymer bionic adhesion coating,
It is characterized in that, in step 3, the painting is placed on pH value of solution=8~9 Tris-HCl, and heating temperature is in 40~75 DEG C
Reason 17~for 24 hours.
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| CN106380990A (en) * | 2016-08-27 | 2017-02-08 | 西安科技大学 | Preparation method of aldehyde-containing phosphorylcholine polymer and dopamine cross-linked coating |
| CN106750450A (en) * | 2016-11-07 | 2017-05-31 | 西安科技大学 | Preparation method containing epoxy phosphoryl choline polymer and dopamine crosslinking adhesion bionic coating |
| CN106866883A (en) * | 2017-03-01 | 2017-06-20 | 西安科技大学 | A kind of method that double Biomimetic Polymers are synthesized based on aldehyde radical and amino |
| CN107674225A (en) * | 2017-10-09 | 2018-02-09 | 西安科技大学 | The preparation method of two kinds of phosphoryl choline polymers crosslinking bionic coating containing aldehyde radical and amino |
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| CN106380990A (en) * | 2016-08-27 | 2017-02-08 | 西安科技大学 | Preparation method of aldehyde-containing phosphorylcholine polymer and dopamine cross-linked coating |
| CN106750450A (en) * | 2016-11-07 | 2017-05-31 | 西安科技大学 | Preparation method containing epoxy phosphoryl choline polymer and dopamine crosslinking adhesion bionic coating |
| CN106866883A (en) * | 2017-03-01 | 2017-06-20 | 西安科技大学 | A kind of method that double Biomimetic Polymers are synthesized based on aldehyde radical and amino |
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