CN105218847A - A kind of bill of material interface function method of modifying based on polyphenolic compound - Google Patents
A kind of bill of material interface function method of modifying based on polyphenolic compound Download PDFInfo
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Abstract
The invention discloses a kind of bill of material interface function method of modifying based on polyphenolic compound.The method is the base material of modification to be soaked in the mixing solutions of polyphenolic compound, silane coupling agent and functional molecular, polyphenolic compound react with substrate surface and autohemagglutination process in react with functional molecular, finally form one deck polyphenolic compound/functional molecular compound coating; Or be soaked in the solution of polyphenolic compound and silane coupling agent want the base material of modification, the autohemagglutination of polyphenolic compound is utilized to form a strata polyphenolic compound layer at substrate surface, then react with functional molecular solution, obtain that there is functional coating.That the surface-functionalized modification that the present invention is differing materials provides a kind of universality, simple novel method, is almost applicable to the surface modification of any base material.The functional firm coating finally obtained, can obviously improve substrate surface performance.
Description
Technical field
The invention belongs to field of material surface modification, be specifically related to polyphenolic compound and several functions molecular reaction and then the broad spectrum method to differing materials modifying surface.
Background technology
The method of surface modification is varied, cuts both ways.Physical method and the large class of chemical process two can be divided into generally.Physical method comprises blended and simple spraying; Chemical process comprises carries out covalent bonding, surface grafting etc. to material surface.Along with raising to material performance requirement under the discovery application of various novel material and various complex environment, environmental protection also in urgent need to be improved, simple to the requirement of material surface modifying, efficient energy-saving are basic demands.
Containing multiple phenolic group group in polyphenolic compound, in field of surface modification with Dopamine HCL and Weibull for representative.Contain a large amount of pyrocatechol functional groups in Dopamine HCL and Weibull molecule, make their solution can form one deck from poly layer at material surface under the environment of aerobic.We can by polyphenolic compound in the middle of collecting process or a large amount of active group in autohemagglutination rear surface carry out functional modification.In Chinese invention patent CN104194023A, Dopamine HCL is used to improve medical polyurethane material surface hydrophilicity and biocompatibility.In Chinese invention patent CN104524986A, surface-coated Dopamine HCL and the cationic method of polymine is used to prepare hydrophilic antimicrobial film.Although above-mentioned patent uses polyphenolic compound Dopamine HCL to improve the wetting ability etc. of material, method is complicated, and coating is very infirm.
Summary of the invention
The present invention is directed to the shortcomings such as complex steps that existing surface modifying method exists, inefficiency, coating be insecure, provide a kind of pervasive method of modifying of bill of material interface functionization based on polyphenolic compound.The present invention adds silane coupling agent in Process of Surface Modification.Silane coupling agent comprises hydrolysable group OMe, OEt, and functional end-group NH
2, SH, epoxy etc.In the middle of the process of polyphenolic compound autohemagglutination, the quinoid that silane coupling agent can be formed in collecting process with Polyphenols is on the one hand reacted, on the one hand can with material surface reaction bonded, thus form a kind of silane coupling agent-polyphenolic compound cross-linked structure, and be fixed on substrate surface firmly.This structure has possessed polyphenolic compound in the simple advantage of field of surface modification, possesses again the performance that the simple polyphenolic compound of analogy is more solid and reliable.In modifying process, add different functional moleculars, as polymine, amino polyvinyl alcohol, chitosan etc., make the further functionalization of material surface, be applicable to the demands such as hydrophilic modifying, antibacterial modified, anti-/ protein stimulatory be adhesion modified.Compared with existing method of modifying, step of the present invention is simple, and suitability is strong, and the functional coating of preparation is more firm, material can be applied to more maintain performance in rugged environment constant.Wide potential application foreground is had in the field such as medicine equipment, material antiseptic.
Method of modifying of the present invention is divided into single stage method and two-step approach.Single stage method is wanting the base material of modification to be soaked in the mixing solutions of polyphenolic compound, silane coupling agent and functional molecular, polyphenolic compound react with substrate surface and autohemagglutination process in react with functional molecular, finally form one deck polyphenolic compound/functional molecular compound coating.Two-step approach is wanting the base material of modification to be soaked in the solution of polyphenolic compound and silane coupling agent, the autohemagglutination of polyphenolic compound is utilized to form a strata polyphenolic compound layer at substrate surface, then react with functional molecular solution, obtain that there is functional coating.
The method one of the bill of material interface function method of modifying based on polyphenolic compound of the present invention is:
(1) functional molecular being dissolved in pH value is in the trishydroxymethylaminomethane-hydrochloride buffer of 8-10, polyphenolic compound and silane coupling agent is added after standby function molecular melting, the concentration of functional molecular is 1-5g/L, the concentration of polyphenolic compound is 0.5-5g/L, and the concentration of silane coupling agent is 0.1-0.5g/L;
(2) base material to be modified is soaked in the mixing solutions that step (1) prepares, at 30-60 DEG C, reacts 6-48 hour;
(3), after reaction terminates, base material is taken out, clean with deionized water rinsing, dry, obtain the polyphenolic compound of substrate surface coating polymerization and the compound coating of functional molecular.
When dissolving in the step (1) of described method one, required temperature range is 37-50 DEG C.
The method two of the bill of material interface function method of modifying based on polyphenolic compound of the present invention is:
1) polyphenolic compound and silane coupling agent being dissolved in pH value is in the trishydroxymethylaminomethane-hydrochloride buffer of 8-10, and the concentration of polyphenolic compound is 0.5-5g/L, and the concentration of silane coupling agent is 0.1-0.5g/L; Base material is soaked in 6-24 hour in above-mentioned solution, then takes out, and clean with deionized water rinsing, obtain the base material that surface-coated has polyphenolic compound;
2) functional molecular being dissolved in pH value is in the phosphate buffer soln of 8-10, and the concentration of functional molecular is 1-5g/L; Surface-coated there is the base material of polyphenolic compound to be immersed in the phosphate buffer soln of above-mentioned functions molecule, at 30-60 DEG C, react 6-48 hour;
3), after reaction terminates, base material is taken out, clean with deionized water rinsing, dry, obtain the polyphenolic compound of substrate surface coating polymerization and the compound coating of functional molecular.
Described base material is selected from glass, pottery, polypropylene, polyethylene, polymeric amide, urethane, stainless steel, aluminium alloy.
First surface decontamination process is carried out before described substrate modifications.
Described polyphenolic compound is Dopamine HCL, Weibull.
Described functional molecular is Quaternary Polyethyleneimine, chitosan, amino-polyethyleneglycols, gelatin, heparin, heparin sodium, gentamicin.
Described silane coupling agent is selected from KH540, KH550, KH560, KH580, KH590.
Described base material immersion way for all immerse solution and want facing up of modification.
Single stage method of the present invention utilizes polyphenolic compound in the middle of the process of autohemagglutination, its abundant active group, such as amino, hydroxyl etc., react with the active function groups of difference in functionality molecule, such as amino, carboxyl, sulfydryl etc., and add a small amount of silane coupling agent, form one deck polyphenolic compound/functional molecular compound coating.This single stage method can be applicable to the hydrophilic modifying of material surface, promotes protein adherence, cell adhesion, surperficial anti-soil, anticorrosive modification etc.Two-step approach first fixes one deck polyphenolic compound at substrate surface, utilizes the active function groups of the abundant active group in polyphenolic compound surface and difference in functionality molecule to react subsequently, thus functional molecular is fixed on substrate surface firmly.This two-step approach modified substrate surface, except having function that single stage method modification can possess, can also carry out anti-protein, cell adhesion to different substrate materials surface, antibacterial etc. function modified.That the surface-functionalized modification that the present invention is differing materials provides a kind of universality, simple novel method, is almost applicable to the surface modification of any base material.The functional firm coating finally obtained, can obviously improve substrate surface performance.
Figure of description
Fig. 1 is the surface water contact angle of polypropylene base before modified in embodiment 1 and the surface water contact angle after Dopamine HCL/gelatin coating modification; Left figure is 104.3 ° before modified, and right figure is modified 51.6 °;
Fig. 2 is the adhesion growing state on HEK293 cell the adhesion growing state on the surface of polypropylene base and the surface after Dopamine HCL/gelatin coating modification before modification in embodiment 1; Left figure is before modified, and right figure is modified;
Fig. 3 is the surface water contact angle of stainless steel substrate before modified in embodiment 2 and the surface water contact angle after Dopamine HCL/gelatin coating modification; Left figure is 86.5 ° before modified, and right figure is modified 46.5 °;
Fig. 4 is the surface water contact angle of glass baseplate before modified in embodiment 5 and the surface water contact angle after poly-Dopamine HCL-activated polyethylene glycol coating modification; Left figure is 44.9 ° before modified, and right figure is modified 32.3 °;
Fig. 5 is the HEK293 cell adhesion growing state on the surface of glass baseplate and the adhesion growing state through gathering the surface after Dopamine HCL-amino-polyethyleneglycols coating modification before modification in embodiment 5.Left figure is before modified, and right figure is modified;
Fig. 6 is the surface water contact angle of glass baseplate before modified in embodiment 6 and the surface water contact angle after poly-Dopamine HCL-polymine coating modification; Left figure is 42.7 ° before modified, and right figure is modified 36.2 °;
Fig. 7 is the HEK293 cell adhesion growing state on the surface of glass baseplate and the adhesion growing state through gathering the surface after Dopamine HCL-Quaternary Polyethyleneimine coating modification before modification in embodiment 6; Left figure is before modified, and right figure is modified.
Embodiment
Further illustrate the present invention below by embodiment, but be not limited to following embodiment.After the content of having read the present invention's instruction, those skilled in the art can make various changes or modifications the present invention, as long as within the spirit and principles in the present invention, the change, amendment etc. of these equivalent form of values all should be included within protection scope of the present invention.
Embodiment 1
Single stage method gathers Dopamine HCL/gelatin-compounded coating at polypropylene base surface construction: joined by 5g gelatin in 1L trishydroxymethylaminomethane-hydrochloride buffer (pH=8.5), solution is heated to 37 DEG C and makes Gelatin; 2g Dopamine HCL and 0.5g silane coupling agent KH540 are joined in above-mentioned solution, stirs; Sheet-like polypropylene base material (2cm × 2cm) is first carried out surface decontamination process, then all to immerse in the mixing solutions of above-mentioned preparation and want facing up of modification, take out polypropylene base after 12h, with deionized water rinsing 5 times, after drying, obtain poly-Dopamine HCL/gelatin-compounded coating.Sharp instrument scraped finish is used not come off.Measure water contact angle, unmodified polypropylene base water contact angle is 104.3 °, and modified polypropylene base water contact angle is 51.6 ° (Fig. 1).HEK293 cell is on unmodified polypropylene base surface and apply the growing state on the polypropylene base surface after modification as shown in Figure 2 through poly-Dopamine HCL/gelatin.Obviously can find out unmodified polypropylene base surface not adherent cell, and substrate surface cell adhesion after modification and well-grown.This shows that the polypropylene base after poly-Dopamine HCL/gelatin surface modification has good biocompatibility, can promote adhesion and the growth of cell.
Embodiment 2
Single stage method forms poly-Dopamine HCL/gelatin-compounded coating on stainless steel substrate surface: stainless steel substrate is placed in deionized water, acetone, ethanolic soln ultrasonic cleaning 5min respectively.Polypropylene base in embodiment 1 is replaced to stainless steel substrate, and other experiment conditions are identical with embodiment 1, prepare the stainless steel substrate that can promote the biocompatibility that cell adhesion grows.As shown in Figure 3, stainless steel substrate water contact angle is before modified 86.5 °, and after modification, water contact angle becomes 46.5 °.
Embodiment 3
Single stage method forms poly-Weibull/gelatin-compounded coating on polypropylene base surface: the Dopamine HCL in embodiment 1 is replaced to Weibull, other experiment conditions are identical with embodiment 1, prepare the stainless steel substrate of the poly-Weibull/gelatin coating that can promote the biocompatibility that cell adhesion grows.
Embodiment 4
Single stage method forms poly-Weibull/gelatin-compounded coating on stainless steel substrate surface: the polypropylene base in embodiment 1 is replaced to stainless steel substrate, Dopamine HCL replaces to Weibull, other experiment conditions are identical with embodiment 1, prepare the stainless steel substrate of the poly-Weibull/gelatin coating that can promote the biocompatibility that cell adhesion grows.
Embodiment 5
Two-step approach builds polyoxyethylene glycol functionalized surface at glass substrate surface: be dissolved in 1L trishydroxymethylaminomethane-hydrochloride buffer (pH=8.5) by 2g Dopamine HCL and 0.5g silane coupling agent KH590, glass baseplate (2cm × 2cm) is first carried out surface decontamination process, then all to immerse in above-mentioned dopamine solution and want facing up of modification, take out after 12h, clean with deionized water rinsing; By rinse well be coated with Dopamine HCL glass baseplate immerse concentration be in the phosphate buffered saline(PBS) (pH=8.5) of amino-polyethyleneglycols (molecular weight is 4000) of 5g/L, base material all immerse solution and want facing up of modification; Reaction is placed in the thermostat container 24h of 37 DEG C; After question response terminates, take out base material, with deionized water rinsing 5 times, after cleaning, obtain the glass baseplate that Surface coating has poly-Dopamine HCL-activated polyethylene glycol coating.Measure water contact angle, unmodified glass baseplate water contact angle is 44.9 °, and modified glass baseplate water contact angle is 32.3 ° (Fig. 4).HEK293 cell applies the growing state of the glass substrate surface after modification as shown in Figure 5 at unmodified glass substrate surface with through poly-Dopamine HCL-activated polyethylene glycol.Can obviously find out at unmodified glass substrate surface, cell can attach growth, and substantially can not attach growth at the glass substrate surface cell after poly-Dopamine HCL-activated polyethylene glycol coating modification.This show through by two-step approach after the activated polyethylene glycol of glass substrate surface grafting T suppression cell, glass baseplate possessed T suppression cell adhere to functional.
Embodiment 6
Two-step approach builds polymine functionalized surface at glass substrate surface: the activated polyethylene glycol in embodiment 5 is replaced to Quaternary Polyethyleneimine (molecular weight is 25000), other experiment conditions are identical with embodiment 5, prepare and both can adhere to by T suppression cell, glass baseplate that again can be antibacterial.Measure water contact angle, unmodified glass baseplate water contact angle is 42.7 °, and modified glass baseplate water contact angle is 36.2 ° (Fig. 6).HEK293 cell applies the growing state of the glass substrate surface after modification as shown in Figure 7 at unmodified glass substrate surface with through poly-Dopamine HCL-Quaternary Polyethyleneimine.Can obviously find out at unmodified glass substrate surface, cell can attach growth, and substantially can not attach growth at the glass substrate surface cell after poly-Dopamine HCL-Quaternary Polyethyleneimine coating modification.Carry out antibacterial experiment discovery to base material, the glass baseplate after poly-Dopamine HCL-Quaternary Polyethyleneimine coating modification has good antibacterial effect.
Embodiment 7
Two-step approach builds chitosan functionalized surface at glass substrate surface: the activated polyethylene glycol in embodiment 5 is replaced to chitosan, and other experiment conditions are identical with embodiment 5, prepare the glass baseplate with anti-microbial property.Carry out antibacterial experiment discovery to base material, the glass baseplate after poly-Dopamine HCL-chitosan coating modification has good antibacterial effect.
Embodiment 8
Two-step approach builds gentamicin functionalized surface at glass substrate surface: the activated polyethylene glycol in embodiment 5 is replaced to gentamicin, and other experiment conditions are identical with embodiment 5, prepare the glass baseplate with anti-microbial property.Carry out antibacterial experiment discovery to base material, the glass baseplate after poly-Dopamine HCL-chitosan coating modification has good antibacterial effect.
Embodiment 9
Two-step approach builds heparin sodium functionalized surface at glass substrate surface: the activated polyethylene glycol in embodiment 5 is replaced to heparin sodium, and other experiment conditions are identical with embodiment 5, prepare the glass baseplate with blood compatibility performance.Measured by activating part activated partial thromboplastin time (APTT) and find, clotting time on unmodified glass baseplate was less than 30 seconds, and obviously extend through gathering the clotting time on the glass baseplate after Dopamine HCL-heparin sodium coating modification, can more than 1 minute.Also can find that the thrombocyte of unmodified glass sheet surface is by activation to a certain extent by scanning electron microscope microphotograph, stretch out pseudopodium significantly, and comparing rounding through gathering the platelet PLA2 on the glass baseplate after Dopamine HCL-heparin sodium coating modification, the degree that is activated is lower.
Claims (9)
1. based on a bill of material interface function method of modifying for polyphenolic compound, it is characterized in that, the concrete steps of the method are:
(1) functional molecular being dissolved in pH value is in the trishydroxymethylaminomethane-hydrochloride buffer of 8-10, polyphenolic compound and silane coupling agent is added after standby function molecular melting, the concentration of functional molecular is 1-5g/L, the concentration of polyphenolic compound is 0.5-5g/L, and the concentration of silane coupling agent is 0.1-0.5g/L;
(2) base material to be modified is soaked in the mixing solutions that step (1) prepares, at 30-60 DEG C, reacts 6-48 hour;
(3), after reaction terminates, base material is taken out, clean with deionized water rinsing, dry, obtain the polyphenolic compound of substrate surface coating polymerization and the compound coating of functional molecular.
2. based on a bill of material interface function method of modifying for polyphenolic compound, it is characterized in that, the concrete steps of the method are:
1) polyphenolic compound and silane coupling agent being dissolved in pH value is in the trishydroxymethylaminomethane-hydrochloride buffer of 8-10, and the concentration of polyphenolic compound is 0.5-5g/L, and the concentration of silane coupling agent is 0.1-0.5g/L; Base material is soaked in 6-24 hour in above-mentioned solution, then takes out, and clean with deionized water rinsing, obtain the base material that surface-coated has polyphenolic compound;
2) functional molecular being dissolved in pH value is in the phosphate buffer soln of 8-10, and the concentration of functional molecular is 1-5g/L; Surface-coated there is the base material of polyphenolic compound to be immersed in the phosphate buffer soln of above-mentioned functions molecule, at 30-60 DEG C, react 6-48 hour;
3), after reaction terminates, base material is taken out, clean with deionized water rinsing, dry, obtain the polyphenolic compound of substrate surface coating polymerization and the compound coating of functional molecular.
3. method according to claim 1, is characterized in that, when dissolving in step (1), required temperature range is 37-50 DEG C.
4. method according to claim 1 and 2, is characterized in that, described base material is selected from glass, pottery, polypropylene, polyethylene, polymeric amide, urethane, stainless steel, aluminium alloy.
5. method according to claim 1 and 2, is characterized in that, first carries out surface decontamination process before described substrate modifications.
6. method according to claim 1 and 2, is characterized in that, described polyphenolic compound is Dopamine HCL, Weibull.
7. method according to claim 1 and 2, is characterized in that, described functional molecular is Quaternary Polyethyleneimine, chitosan, amino-polyethyleneglycols, gelatin, heparin, heparin sodium, gentamicin.
8. method according to claim 1 and 2, is characterized in that, described silane coupling agent is selected from KH540, KH550, KH560, KH580, KH590.
9. method according to claim 1 and 2, is characterized in that, described base material immersion way for all immerse solution and want facing up of modification.
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