CN104060311A - Method for functionally modifying surface of conductive substrate - Google Patents
Method for functionally modifying surface of conductive substrate Download PDFInfo
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- CN104060311A CN104060311A CN201410267358.0A CN201410267358A CN104060311A CN 104060311 A CN104060311 A CN 104060311A CN 201410267358 A CN201410267358 A CN 201410267358A CN 104060311 A CN104060311 A CN 104060311A
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- catecholamine
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Abstract
The invention discloses a method for functionally modifying a surface of a conductive substrate. The method comprises the following steps: (1) decorating a catecholamine polymer coating on the surface of the conductive substrate by using a three-electrode working system which takes a platinum electrode as a counter electrode, takes a saturated calomel electrode as a reference electrode, takes the conductive substrate as a working electrode, takes a phosphate buffer solution containing 10<-5>-1g/mL of catecholamine as electrolyte or takes a trihydroxy methyl-aminomethane hydrochloride buffer solution containing 10<-5>-1g/mL of catecholamine as electrolyte; and (2) putting the conductive substrate obtained in the step (1) and decorated by the catecholamine polymer coating in a functional molecule solution for reacting, and thus obtaining the conductive substrate with functionalized surface. The functional molecules are silver nitrate, polymer containing amino or sulfydryl, polypeptide or protein. The method disclosed by the invention is capable of regulating physical and chemical properties of the surface of the conductive substrate and has the advantages of being simple, convenient, efficient, environmentally-friendly and capable of easily achieving industrialized application.
Description
Technical field
The present invention relates to solid material surface modification field, be specifically related to the method for the surface-functionalized modification of a kind of conductive substrates.
Background technology
Because metallic substance has good mechanical property, anti-fatigue performance and excellent erosion resistance, and be convenient to processing, it is widely used in the medicine equipments such as joint prosthesis, artificial bone, intravascular stent.But, because the metal material surface of biologically inert lacks the functional motif that human body cell can be identified, poor with the consistency of tissue, finally usually cause the generation of various clinical adverse events.
The Surface Physical Chemistry character of metallic substance has vital effect for the normal performance of its function.The method of current metal surface properties modification mainly contains the method such as fixed function molecule after plasma method, molten glue – gel method, self-assembly layer by layer, surface silicon alkanisation.Although these methods can realize the regulation and control to metal material surface physico-chemical property to a certain extent, but also there is significant limitation simultaneously, for example, need special expensive device, operation steps complexity, consuming time, less stable, is subject to the restriction of metal species and shape or needs to use poisonous and hazardous reagent etc.
Be subject to nature mussel to adhere to machine-processed inspiration, recently there are some researches show that Dopamine HCL molecule, under alkaline condition, oxidation auto-polymerization can occur, can form firmly poly-Dopamine HCL coating of a combination in various solid substrate surface.Because reaction conditions gentleness, operation steps are simple, the method attracts wide attention as a kind of novel surface-functionalized modified method.
But the method also exists many shortcomings that are difficult to overcome.First, alkaline condition causes the method not to be suitable for the surface modification of easy generation alkaline corrosion material; Secondly, poly-Dopamine HCL is slower in the sedimentation rate of substrate surface; Again, the oxidation auto-polymerization of Dopamine HCL under alkaline condition not only can form poly-Dopamine HCL coating at substrate surface, and in solution, also can form a large amount of poly-Dopamine HCL particles.The formation of these poly-Dopamine HCL particles has not only greatly reduced the effective rate of utilization of Dopamine HCL molecule, and is adsorbed in the increase that can cause coatingsurface roughness after poly-Dopamine HCL coatingsurface.These shortcomings have seriously hindered the application of poly-Dopamine HCL surface modification technology.
Therefore, the deficiency existing for current techniques, necessary seek a kind of quick, efficient and there is the method for the functionalizing material surface modification of good applicability.
Summary of the invention
The invention provides the method for the surface-functionalized modification of a kind of conductive substrates, by carry out the electrochemically oxidative polymerization of catecholamine and fixing of functional molecular on conductive substrates surface, realize the regulation and control to conductive substrates Surface Physical Chemistry character, there is easy, efficient, environmental friendliness, be easy to the advantages such as industrial applications.
A method for the surface-functionalized modification of conductive substrates, comprises the following steps:
(1) adopt three electrode work systems at conductive substrates finishing catecholamine polymeric coating, wherein, platinum electrode (platinum plate electrode or platinum wire electrode) conduct is to electrode, and saturated calomel electrode is as reference electrode, and conductive substrates is working electrode;
Electrolytic solution is for containing 10
-5the phosphate buffered saline buffer of～1g/mL catecholamine, or contain 10
-5the Tri(Hydroxymethyl) Amino Methane Hydrochloride damping fluid of～1g/mL catecholamine.
Electrochemically oxidative polymerization is a kind of effective ways of preparing polymeric film, the catecholamines such as Dopamine HCL have very strong electrochemical activity, using conductive substrates to be finished as working electrode, can deposit fast and controllably a polymeric coating with potential reaction at substrate surface by the electrochemically oxidative polymerization of catecholamine.Utilize the chemical reactivity of this polymeric coating, various functional moleculars can be introduced to conductive substrates material surface, thereby realize the regulation and control for substrate surface physicochemical property.
Catecholamine is the aminated compounds that a class contains pyrocatechol basic structural unit, comprise DOPA, Dopamine HCL, norepinephrine and suprarenin and their derivative, such material has very strong electrochemical activity, in the catecholamine polymeric coating that catecholamine obtains through electrochemical polymerization, be rich in quinonyl, phenolic hydroxyl group isoreactivity group, and there is certain reductibility, can various functional moleculars be incorporated into by chemical reaction to the surface of conductive substrates.
In step (1); catecholamine carries out electrochemically oxidative polymerization reaction by the potentiostatic method under three-electrode system condition or cyclic voltammetry on the surface of conductive substrates, and electrochemically oxidative polymerization reaction is carried out under the condition of room temperature, nitrogen atmosphere protection.
As preferably, the electrochemically oxidative polymerization of catecholamine adopts cyclic voltammetry to carry out.Than potentiostatic method, the prepared catecholamine polymeric coating of cyclic voltammetry and conductive substrates adhere to more firm, and can effectively avoid generated catecholamine polymkeric substance excessively oxidated.For the ease of the generation of electrochemically oxidative polymerization reaction, before modifying, conductive substrates is cleaned up.
In order to increase the electroconductibility of electrolyte solution, as preferably, in described Tri(Hydroxymethyl) Amino Methane Hydrochloride damping fluid, contain supporting electrolyte.
Phosphate buffered saline buffer and Tri(Hydroxymethyl) Amino Methane Hydrochloride damping fluid are mainly used in maintaining pH value, there is no particular requirement for its ionic strength.
As preferably, described catecholamine is the one in DOPA, DOPA derivative, Dopamine HCL, Dopamine HCL derivative, norepinephrine or norepinephrine derivative.These catecholamines can be reacted and be formed firmly by electrochemically oxidative polymerization on conductive substrates surface, and have potential chemically reactive catecholamine polymeric coating.
As the conductive substrates of working electrode, its kind and shape do not have particular requirement, can conduct electricity or surperficial chip or the medicine equipment etc. that can conduct electricity for various.
The content of catecholamine is very few, and it is slower that catecholamine carries out the speed of electrochemically oxidative polymerization, and the formation speed of catecholamine polymeric coating is slower; Add-on is too much, can increase production cost, and as preferably, in electrolytic solution, the content of catecholamine is 10
-3～500mg/mL, further preferred, in electrolytic solution, the content of catecholamine is 10
-3～500mg/mL.
As preferably, the pH value of described electrolytic solution is 6～11.Further preferably, the pH value of described electrolytic solution is 6.5～7.5.
PH is too low, and the reaction of the electrochemically oxidative polymerization of catecholamine is difficult to carry out; PH is too high, can cause some metallic substance generation alkaline corrosion.
The electrochemical polymerization reaction times to catecholamine in the present invention there is no particular determination, but polymerization time is too short, complete, covering uniformly that the catecholamine polymeric coating of formation is difficult to realize on whole conductive substrates surface; Polymerization time is long, can increase energy consumption, improve production cost.By controlling the time of electrochemical polymerization reaction, can accurately regulate and control the thickness of catecholamine polymeric coating, to meet its concrete service requirements.
As preferably, the current potential of described working electrode relative saturation mercurous chloride electrode is-1～1V, and the time that obtains catecholamine polymeric coating in conductive substrates finishing is 1～300 minute.The catecholamine electrochemically oxidative polymerization reaction of carrying out on conductive substrates surface 1～300 minute obtains catecholamine polymeric coating.
Under normal circumstances, the thickness of described catecholamine polymeric coating is 1～200nm.Preferably, the thickness of described catecholamine polymeric coating is 1～100nm.
Further preferably, the time that obtains catecholamine polymeric coating in conductive substrates finishing is 120～180 minutes.
(2) solution that the conductive substrates that is modified with catecholamine polymeric coating step (1) being obtained is placed in functional molecular reacts, obtain surface-functionalized conductive substrates, described functional molecular is Silver Nitrate, polymkeric substance (for example at least PEG2000 with a sulfydryl of end, sulfydryl reacts with the active group in catecholamine polymeric coating), polypeptide or albumen with amino or sulfydryl.
After catecholamine polymeric coating reacts with functional molecular, dry up post-processing step through washed with de-ionized water, nitrogen, obtain surface-functionalized conductive substrates.
The equal wide material sources of described functional molecular, be easy to get, and can be with catecholamine polymeric coating generation chemical reaction, to realize surface fixing, thereby give conductive substrates surface various physicochemical property.
According to the difference of functional molecular kind, adopt corresponding solvent to dissolve, the strength of solution of functional molecular is without particular determination, but concentration is too low, can greatly reduce surface-functionalized effect, excessive concentration can increase cost, therefore, as preferably, the strength of solution of described functional molecular is 10
-5～1g/mL.Further preferably, the strength of solution of described functional molecular is 0.5～200g/mL.
The reaction times of step (2) is without particular determination, but the reaction times is too short, and catecholamine polymeric coating may be insufficient with reacting of functional molecular, affects the even modification on conductive substrates surface; Reaction times is long, can increase time cost.
As preferably, the reaction times of step (2) is 1～48h.Further preferably, the reaction times of step (2) is 12～24h.
The temperature of reaction of step (2) is without particular determination, but temperature of reaction is too low, sluggish between catecholamine polymeric coating and functional molecular; Temperature of reaction is too high, can increase energy consumption, raise the cost.
As preferably, temperature of reaction is 4～60 DEG C.Further preferably, temperature of reaction is 25～37 DEG C.
Compared with prior art, the present invention has following beneficial effect:
The present invention adopts the electrochemically oxidative polymerization reaction of catecholamine to realize the surface modification to conductive substrates, reaction conditions gentleness, raw material and all nontoxic, environmental protections of reagent easy and simple to handle, used, all without particular requirement, be particularly useful for the surface-functionalized modification to complicated shape conductive substrates for the type of conductive substrates and shape.
The catecholamine electrochemically oxidative polymerization that the present invention adopts can be realized under neutrallty condition, compared with the oxidation auto-polymerization method of Dopamine HCL under classical alkaline condition, there is polymeric coating faster and form speed, thereby can significantly shorten polymerization time, meanwhile, neutral reaction conditions can also effectively be avoided problem in classical way, the problem includes: material alkaline corrosion problem.
Under classical alkaline condition, Dopamine HCL oxidation auto-polymerization method not only can form on conductive substrates surface poly-Dopamine HCL coating, and in solution, also can form a large amount of poly-Dopamine HCL particles, the formation of these poly-Dopamine HCL particles has not only greatly reduced the utilising efficiency of Dopamine HCL molecule, but also be easily adsorbed on poly-Dopamine HCL coatingsurface, cause the increase of coating roughness.In the present invention by neutral catecholamine solution the electrochemically oxidative polymerization under inert gas atmosphere condition, make the polyreaction of catecholamine mainly occur in conductive substrates surface to be finished, can effectively avoid the formation of polymer beads in solution, therefore can significantly improve the utilising efficiency of free catecholamine molecule in solution.
The catecholamine polymeric coating obtaining by the electrochemical polymerization of catecholamine in the present invention has good chemical reactivity, can various functional moleculars be incorporated into material surface to realize different functions by further chemical reaction.
Brief description of the drawings
Fig. 1 is the x-ray photoelectron energy spectrogram that in embodiment 1, poly-Dopamine HCL (ePDA) is modified the gold-plated silicon chips in front and back (Au);
Fig. 2 is the thickness motive force of growth graphic representation of the poly-Dopamine HCL coating that in embodiment 1 prepared by electrochemically oxidative polymerization method and classical Dopamine HCL oxidation auto-polymerization method;
Fig. 3 is that bare metal stent in embodiment 2 (stent), poly-Dopamine HCL modification support (stent-ePDA) and the voltolisation Dopamine HCL of having fixed endothelial cell growth factor (ECGF) are modified the cytoskeleton fluorescent staining picture of Human umbilical vein endothelial cells cultivation after 6 days on support (stentt-ePDA-VEGF) surface.
Embodiment
Embodiment 1
(1) be placed in the Tri(Hydroxymethyl) Amino Methane Hydrochloride damping fluid (containing 25mM Tris, 140mM NaCl and 3mMKCl, pH=7.4) that contains 1mg/mL Dopamine HCL using the gold-plated silicon chip cleaning up as working electrode.
Electrochemical polymerization reaction is carried out on CHI660D type electrochemical workstation, adopts three-electrode system, and wherein, reference electrode is 232 type saturated calomel electrode, is platinum plate electrode to electrode.Under room temperature, nitrogen protection condition, adopt cyclic voltammetry to carry out the electrochemically oxidative polymerization of Dopamine HCL; select the interval Wei of electric potential scanning – 0.5～0.5V; sweep speed for 20mV/s, after polyase 13 hour, take out gold-plated silicon chip deionized water rinsing, nitrogen dries up rear for subsequent use.
(2) silver nitrate solution that the gold-plated silicon chip of poly-Dopamine HCL being modified is placed in 170mg/mL reacts 2 hours under room temperature, dries up through deionized water rinsing and nitrogen, and can obtain area load has the gold-plated silicon chip of nano-Ag particles.This surface has excellent killing effect for the common bacteria such as intestinal bacteria, streptococcus aureus.
Observing Fig. 1 can find, the constituent content variation that the gold-plated silicon chip surface in front and back is modified in Dopamine HCL electrochemical polymerization shows that Dopamine HCL at gold-plated silicon chip surface, galvanic deposit has occurred really.
Observing Fig. 2 can find, compared with Dopamine HCL auto-polymerization method in classical basic solution, poly-Dopamine HCL coat-thickness prepared by the electrochemical polymerization of Dopamine HCL gathers way obviously faster.
Embodiment 2
(1) be placed in the Tri(Hydroxymethyl) Amino Methane Hydrochloride damping fluid (containing 25mM Tris, 140mM NaCl and 3mM KCl, pH=7.4) that contains 1mg/mL Dopamine HCL using 316L stainless steel angiocarpy bracket as working electrode.
Electrochemical polymerization is carried out on CHI660D type electrochemical workstation, adopts three-electrode system, and wherein, reference electrode is 232 type saturated calomel electrode, is platinum plate electrode to electrode.Under room temperature, nitrogen protection condition, adopt cyclic voltammetry to carry out the electrochemically oxidative polymerization of Dopamine HCL; select the interval Wei of electric potential scanning – 0.5～0.5V; sweep speed for 20mV/s, after polyase 13 hour, take out angiocarpy bracket deionized water rinsing, nitrogen dries up rear for subsequent use.
(2) angiocarpy bracket of poly-Dopamine HCL being modified is placed in the Tri(Hydroxymethyl) Amino Methane Hydrochloride damping fluid (10mM of the vascular endothelial growth factor (VEGF) that contains 500ng/mL, pH=8.5) in, at 37 DEG C, react 12 hours, take out (the phosphoric acid buffer with PBS, pH=7.410mM) after cleaning, naturally dry, obtained being fixed with the functionalized surface of VEGF.
Observation Fig. 3 is known, and compared with the 316L stainless steel angiocarpy bracket (stent) of unmodified, the angiocarpy bracket (stent-ePDA) after poly-DOPA is modified can effectively promote the growth of Human umbilical vein endothelial cells; Support (stent-ePDA-VEGF) after VEGF functionalization can further significantly promote the growth of Human umbilical vein endothelial cells.
The support of this functional modification has excellent endotheliocyte consistency, is conducive to angiocarpy bracket and inserts the quick endothelialization after human body, can significantly suppress the generation of in-stent restenosis.
Embodiment 3
(1) be placed in the phosphate buffered saline buffer that contains 2mg/mL norepinephrine using ITO conductive glass as working electrode (containing 137mM NaCl, 2.7mM KCl, 10mM Na
2hPO
4and 2mMKH
2pO
4, pH=7.4).
Electrochemical polymerization is carried out on CHI660D type electrochemical workstation, adopts three-electrode system, and wherein, reference electrode is 232 type saturated calomel electrode, is platinum plate electrode to electrode.Under room temperature, nitrogen protection condition, adopt cyclic voltammetry to carry out the electrochemically oxidative polymerization of norepinephrine, select the interval Wei of electric potential scanning – 0.3～0.8V, sweep speed for 10mV/s.After polyase 13 hour, take out ITO conductive glass deionized water rinsing, nitrogen dries up rear for subsequent use.
(2) the ITO conductive glass of poly-norepinephrine being modified is placed in and contains the Tri(Hydroxymethyl) Amino Methane Hydrochloride damping fluid (10mM, pH=8.5) that 50mg/mL end is the PEG2000 of sulfydryl, room temperature reaction 12 hours.After washed with de-ionized water, nitrogen dries up, and has obtained being fixed with the functionalized surface of PEG2000.
This surface can the non-specific biomolecules of virtual impedance adhesion, there is good stable against biological contamination performance, can be used for the dirt resistant surfaces modification of the equipment such as boats and ships.
Claims (9)
1. a method for the surface-functionalized modification of conductive substrates, is characterized in that, comprises the following steps:
(1) adopt three electrode work systems at conductive substrates finishing catecholamine polymeric coating, wherein, platinum electrode is as to electrode, and saturated calomel electrode is as reference electrode, and conductive substrates is working electrode;
Electrolytic solution is for containing 10
-5the phosphate buffered saline buffer of～1g/mL catecholamine, or contain 10
-5the Tri(Hydroxymethyl) Amino Methane Hydrochloride damping fluid of～1g/mL catecholamine;
(2) solution that the conductive substrates that is modified with catecholamine polymeric coating step (1) being obtained is placed in functional molecular reacts, obtain surface-functionalized conductive substrates, described functional molecular is Silver Nitrate, polymkeric substance, polypeptide or albumen with amino or sulfydryl.
2. the method for the surface-functionalized modification of conductive substrates as claimed in claim 1, is characterized in that, described catecholamine is the one in DOPA, DOPA derivative, Dopamine HCL, Dopamine HCL derivative, norepinephrine or norepinephrine derivative.
3. the method for the surface-functionalized modification of conductive substrates as claimed in claim 1, is characterized in that, the current potential of described working electrode relative saturation mercurous chloride electrode is-1～1V.
4. the method for the surface-functionalized modification of conductive substrates as claimed in claim 1, is characterized in that, the time that obtains catecholamine polymeric coating in conductive substrates finishing is 1～300 minute.
5. the method for the surface-functionalized modification of conductive substrates as claimed in claim 1, is characterized in that, the thickness of described catecholamine polymeric coating is 1～200nm.
6. the method for the surface-functionalized modification of conductive substrates as claimed in claim 1, is characterized in that, the reaction times of step (2) is 1～48h.
7. the method for the surface-functionalized modification of conductive substrates as claimed in claim 1, is characterized in that, the temperature of reaction of step (2) is 4～60 DEG C.
8. the method for the surface-functionalized modification of conductive substrates as claimed in claim 1, is characterized in that, the pH value of described electrolytic solution is 6～11.
9. the method for the surface-functionalized modification of conductive substrates as claimed in claim 1, is characterized in that, in described Tri(Hydroxymethyl) Amino Methane Hydrochloride damping fluid, contains supporting electrolyte.
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| CN109343309A (en) * | 2018-12-03 | 2019-02-15 | 深圳市华星光电技术有限公司 | Negative photoresist and its application |
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