CN102417778A - Preparation method of antibacterial and anti-protein adsorption soft coating - Google Patents

Preparation method of antibacterial and anti-protein adsorption soft coating Download PDF

Info

Publication number
CN102417778A
CN102417778A CN2011102894467A CN201110289446A CN102417778A CN 102417778 A CN102417778 A CN 102417778A CN 2011102894467 A CN2011102894467 A CN 2011102894467A CN 201110289446 A CN201110289446 A CN 201110289446A CN 102417778 A CN102417778 A CN 102417778A
Authority
CN
China
Prior art keywords
soft coating
water
protein adsorption
preparation
mixture
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
CN2011102894467A
Other languages
Chinese (zh)
Inventor
杜淼
王平
郑强
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Zhejiang University ZJU
Original Assignee
Zhejiang University ZJU
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Zhejiang University ZJU filed Critical Zhejiang University ZJU
Priority to CN2011102894467A priority Critical patent/CN102417778A/en
Publication of CN102417778A publication Critical patent/CN102417778A/en
Pending legal-status Critical Current

Links

Images

Landscapes

  • Materials For Medical Uses (AREA)

Abstract

The invention discloses a preparation method of an antibacterial and anti-protein adsorption soft coating. The method comprises the following steps of: (1) dissolving an electrolyte monomer in water, adjusting the pH value to 6.5-7.5 to obtain a mixture A; and dispersing a functional monomer in water, using a surfactant to perform pre-emulsification and obtain a mixture B; (2) mixing the mixture A and the mixture B, adding an initiator to polymerize at 30-55 DEG C and obtain a crude product; (3) adding the crude product obtained in the step (2) in water to prepare a crude product solution, mixing the crude product solution with a curing agent to coat, and curing to obtain a coating; and (4) placing the coating obtained in the step (3) in water to realize swelling balance and obtain the antibacterial and anti-protein adsorption soft coating. The preparation method provided by the invention can be performed at the room temperature, the technology is simple and practical, the raw material is available, the cost is lower and the coating has a very good application prospect in the antibacterial and anti-protein adsorption biomedical coating material.

Description

A kind of preparation method of antibiotic anti-protein adsorption soft coating
Technical field
The present invention relates to bio-medical material and chemical field, be specifically related to a kind of preparation method of antibiotic anti-protein adsorption soft coating.
Background technology
In recent years; Biomaterial, artificial implanted device, Wicresoft's PCI are increasingly extensive in the application of medicine and hygiene fields, in use since the defective of surgical instrument surfacing itself easily initiation cause many serious consequences such as repeated infection of postoperative bacterium and tissue necrosis because of bacterial infection.This requires used surgical instrument surfacing to have the biological activity that suppresses bacterial adhesion and growth, and effective control and therapeutic action are played in postoperative infection and inflammatory reaction that embedded material causes.In addition, improve biomaterial and implanted device surfaces for biocompatibility is the focus of studying both at home and abroad always, is the effective way of improving the material surface biocompatibility and suppress nonspecific proteins absorption.On the other hand; Protein also can cause a lot of unwanted results in the absorption of material surface; Understand impact analysis precision etc. behind the non-specific adsorption albumen on the biological example chip, therefore be necessary that modification is carried out on the surface of bioelectronics device makes it have good anti-protein adsorption characteristic.
The glycocalix structure is the interactional important structure of iuntercellular specificity on the surface of cell membrane, and its compact arranged high-hydrophilic sugar chain can the nonspecific action of virtual impedance cell surface through the entropy repulsive interaction.Cell surface glycoprotein gives-and then repel and reach specific recognition and adhesion between acceptor through offset entropy based on the electrostatic attraction of specific three dimensional structure.Research shows characteristics such as high-hydrophilic that some polysaccharide macromoleculars, zwitter-ion electrolyte molecule, some water-soluble macromolecules itself are had, kindliness; Make they can the virtual impedance material surface to proteinic non-specific adsorption (Langmuir; 2006,22,10072-10077; Adv Mater.2008,20,335-338).For example the carboxymethyl derivant with VISOSE is fixed on silicon wafer surface, have anti-protein adsorption and anti-cell adhesive capacity (Langmuir, 2002,18,2483-2494).Chinese patent document CN101463139A is grafted to the polyurethane material surface with fungi Pachymose carboxyl methylation derivant through chemical process, makes it have the material of anti-protein adsorption and antibacterial.Chinese patent document CN102040742A discloses and has a kind ofly carried out the modification of zwitter-ion chemistry on the organosilicon material surface, and then forms the surface of anti-protein adsorption.It is worthy of note that with polysaccharide macromolecular or the modification of zwitter-ion chemistry material surface is handled, its operability is relatively poor, difficulty is big, can only handle the material surface of small area, aspect applying, has certain difficulty.
Summary of the invention
The invention provides a kind of preparation method of antibiotic anti-protein adsorption soft coating, this method is easy to handle, and is workable, is easy to promote the use of; And it is, practical by effectively arrestin absorption and the bacterium absorption of soft coating that this method prepares.
A kind of preparation method of antibiotic anti-protein adsorption soft coating comprises:
(1) electrolyte monomer is dissolved in the water, regulates pH value to 6.5～7.5, obtain mixture A; Function monomer is scattered in the water with the preparatory emulsification of tensio-active agent, obtains mixture B;
(2) mixture A and mixture B are mixed, add initiator,, obtain head product 30～55 ℃ of following polymerizations;
(3) head product that step (2) is obtained adds and is mixed with head product solution in the entry, with head product solution with film after solidifying agent mixes, solidify and obtain coating;
(4) coating that step (3) is obtained is put into water, until swelling equilibrium, obtains antibiotic anti-protein adsorption soft coating.
Among the above-mentioned preparation method; In the step (1); The ratio of described electrolyte monomer consumption and Total Water is 3～30: 100g/ml, and the ratio of function monomer consumption and Total Water is 0.15～8.5: 100g/ml water, the ratio of dosage of surfactant and Total Water are 0.15～8.5: 100g/ml; Above-mentioned Total Water is the summation of electrolyte monomer solution water consumption and function monomer emulsion water consumption, i.e. the summation of mixture A and mixture B water consumption; In the step (2), the mass ratio of electrolyte monomer and function monomer total amount is 0.005～0.1: 1 in described initiator amount and the step (1).
In the step (3), the ratio of head product and water is 3～20 in the described head product solution: 100g/ml, the mass ratio of function monomer consumption is 0.02～0.50: 1 in described hardener dose and the step (1).Described curing reaction generally carries out at normal temperatures.
In the step (4), described swelling equilibrium generally through measuring the thickness decision of film, when the thickness of film no longer changes, promptly reaches swelling equilibrium.
Described electrolyte monomer is at least a in the compound shown in structural formula (I), (II), (III):
In the formula (I), R 1Be H or CH 3, R 2, R 3Independently be H or C separately 1～C 3Alkyl, n=0～3, Z 1Be Phenylsulfonic acid base, sulfonic group, phosphate, Phenylsulfonic acid alkali (like Supragil GN base, Phenylsulfonic acid ammonium etc.), sulphonate-base, phosphate base, hydroxyl, dimethylamino etc.
Figure BDA0000094559240000031
In the formula (II), R 4Be H or CH 3, X is H, basic metal, ammonium, hydroxyalkyl or end alkyl polyethylene glycol groups etc.
Figure BDA0000094559240000032
In the formula (III), R 5Be H or CH 3, Y is any one in following three kinds of structures:
Figure BDA0000094559240000033
In above-mentioned three kinds of structures, R 6, R 13And R 9Independently be C separately 2～C 5The fat segment, R 7, R 8, R 10, R 11And R 14Independently be C separately 1～C 5Alkyl, R 16, R 12Be C 1～C 5Alkyl or phenyl, R 15Be C 2～C 5The fat segment, Z 2Be halogen, OSO 2, OSO 3, OPO 2, OPO 3Or CH 3COO etc., Z 3For-OSO 2,-OSO 3,-OPO 2,-OPO 3Or-COO.
In the electrolyte monomer, the compound shown in the formula (I) is trimethyl-glycine (betaine) analog derivative, the research proof, and it is active that its polymkeric substance has good antibiotic and anti-protein adsorption; Formula (II) and formula (III) are water-soluble fabulous monomer, and after polymerization, the film forming, the film surface forms the fine and close hydration layer of one deck, can antibiotic and anti-protein adsorption.
Said function monomer is at least a among structural formula (IV), (V):
Figure BDA0000094559240000034
In the formula (IV), G 1, G 2, G 4And G 6Independently be H or C separately 1～C 3Alkyl, G 3And G 5Independently be H or CH separately 3, m, q independently are 0～3 separately;
Figure BDA0000094559240000041
In the formula V, G 7, G 8, G 10And G 12Independently be H or C separately 1～C 3Alkyl, G 9And G 11Independently be H or CH separately 3, p=0～6, v=0 or 1, w=0～6.
Function monomer contains two keys and epoxide group, and wherein, curing reaction can take place epoxide group, has both had good adhesiveproperties, makes the electrolytic polymer film forming again; Two keys then can referring to the polyreaction of electrolyte monomer.
Because function monomer is an oil-soluble monomer, for improving the dispersity of function monomer in water, be convenient to the smooth completion of subsequent polymerisation reaction, described function monomer carries out preparatory emulsification with non-ionics in water; Selectable non-ionics comprises arlacels non-ionics or polyoxyethylene non-ionics.Further preferred arlacels non-ionics comprises polyoxyethylene 20 sorbitan monolaurate, polyoxyethylene sorbitan lipid acid ketone, polyoxyethylene 20 sorbitan monooleate, polyoxyethylene 20 sorbitan trioleate etc.; Further preferred polyoxyethylene non-ionics comprises: TX10, polyoxyethylene nonylphenol, high-carbon fatty alcohol polyoxyethylene ether, polyoxyethylene carboxylate, T 46155 amine etc.
A kind of in the water-soluble persulfate initiator, the water-soluble azo initiator that under 30～55 ℃ of temperature, have greater activity, the water soluble oxidized reduction initiator etc. of said initiator.Further preferred water-soluble persulfate initiator comprises (NH 4) 2S 2O 8, K 2S 2O 8, Na 2S 2O 8Further preferred water-soluble azo initiator comprises azo diisobutyl amidine hydrochloride, azo two isobutyl imidazoline salt hydrochlorates, azo dicyano valeric acid, azo di-isopropyl tetrahydroglyoxaline etc.Further preferred water soluble oxidized reduction initiator comprises (NH 4) 2S 2O 8/ Na 2SO 3, K 2S 2O 8/ NaHSO 3, hydrogen peroxide/Fe 2SO 4, (NH 4) 2S 2O 8/ NaHSO 3, Na 2S 2O 8/ NaHSO 3Deng.Above-mentioned initiator is participated in polyreaction at two keys that the pH value can optionally cause in electrolyte monomer and the function monomer in 6.5～7.5 scopes.
Said solidifying agent is one or more in amino acids solidifying agent, amidates solidifying agent, cashew nut oil modified amine curing agent, polyethyleneimine: amine hardener, chitosan solidifying agent, urea solidifying agent, melamine cured dose etc.Above-mentioned solidifying agent can solidify under near low temperature (room temperature) condition, and nontoxic.Further preferred amino acids class solidifying agent comprises l-arginine, ornithine, Methionin, glycocoll, L-Ala etc.; Further preferred amino acids salt solidifying agent comprises spermine hydrochlorate, ornithine salt, lysine salt, glycinate etc.Further preferred said cashew nut oil modified amine curing agent comprises cashew pnenolic aldehyde amine.
In polymerization process, different according to pH, initiator can decompose according to different decomposed forms, thereby with different triggering mechanism trigger monomer polymerizations.Among the present invention, adjusting pH value is in 6.5～7.5 scopes and control kick off temperature, prevents that epoxide group is participated in polyreaction in the function monomer.The present invention adopts the method for emulsion copolymerization in the electrolyte monomer polymerization process, to introduce curable function monomer, through regulating the pH value, guarantees that initiator carries out according to required triggering mechanism, and the defencive function group is not participated in reaction.Through this method, on macromolecular main chain, introduce hydrophobic little block, its side chain is a curable groups.With product that obtains and corresponding curing agent uniform mixing, film-forming is put into water then at normal temperatures, reaches swelling equilibrium, promptly gets antibiotic anti-protein adsorption soft coating.
The present invention adopts method of emulsion polymerization; In the electrolyte monomer polymerization process, introduce the function monomer that contains epoxide group and double bond structure; Process a kind of soft coating of antibiotic anti-protein adsorption, this soft coating main ingredient is a polyelectrolyte, and contains the side chain of some amount on the main chain; Contain curable hydrophobic little block, play the cross-linking set effect.The cross-linking set of soft coating distributes more even among the present invention; The outermost of soft coating partly forms charged molecular brush, through hydration of ion strong adsorption one deck water molecules, forms a fixed water layer; Get rid of principle according to volume, this water layer can effectively suppress bacterium and proteic absorption.This invention not only utilizes the soft coating surface to be difficult for by adherent characteristics, and has utilized the excellent adhesive power characteristics of epoxy resin again.
The method of the antibiotic anti-protein adsorption soft coating of preparation provided by the invention is with method and the electrolyte monomer copolymerization of function monomer with emulsion copolymerization, forms little block; Realize solidifying through epoxide group on the function monomer, but ambient operation is simple for process, raw material is easy to get, and cost is lower, has good application prospects in the antibiotic anti-protein adsorption bio-medical coated material of preparation field.
Description of drawings
The anti-adsorption experiment result of soft coating streptococcus aureus that Fig. 1 a makes for embodiment 1.
Fig. 1 b is the anti-adsorption experiment result of the streptococcus aureus of pellosil.
The anti-adsorption experiment result of soft coating intestinal bacteria that Fig. 2 a makes for embodiment 1.
Fig. 2 b is the anti-adsorption experiment results of the intestinal bacteria of pellosil.
The experimental result of the anti-bovine serum albumin absorption of the soft coating that Fig. 3 makes for embodiment 1.
The experimental result of the anti-N,O-Diacetylmuramidase absorption of the soft coating that Fig. 4 makes for embodiment 1.
The anti-adsorption experiment result of the soft coating streptococcus aureus that Fig. 5 makes for embodiment 2.
The anti-adsorption experiment result of the soft coating intestinal bacteria that Fig. 6 makes for embodiment 2.
The experimental result of the anti-bovine serum albumin absorption of the soft coating that Fig. 7 makes for embodiment 2.
The experimental result of the anti-N,O-Diacetylmuramidase absorption of the soft coating that Fig. 8 makes for embodiment 2.
The anti-adsorption experiment result of the soft coating streptococcus aureus that Fig. 9 makes for embodiment 3.
The anti-adsorption experiment result of the soft coating intestinal bacteria that Figure 10 makes for embodiment 3.
The experimental result of the anti-bovine serum albumin absorption of the soft coating that Figure 11 makes for embodiment 3.
The experimental result of the anti-N,O-Diacetylmuramidase absorption of the soft coating that Figure 12 makes for embodiment 3.
Embodiment
Utilize specific embodiment that the present invention is further specified below.
Embodiment 1:
Take by weighing 2-acrylamido-2-methyl propane sulfonic acid, 15g is dissolved in the 50ml deionized water, joins in the four-hole boiling flask, under condition of ice bath, neutralizes, and regulates pH to 7.0 with several sodium hydroxide.Take by weighing again after 2-methyl-2-acrylic acid epoxy ethyl group methyl ester 3.0g is dissolved in the 50ml deionized water that adds the 2.0g polyoxyethylene 20 sorbitan monolaurate in advance emulsification in advance, also be added in the four-hole boiling flask.Under the nitrogen protection, fully stir about is 30 minutes.Add 0.8g azo diisobutyl amidine hydrochloride then, react 7h down, get head product at 40 ℃.Be configured to the head product solution that concentration is 8g/100ml water with the head product that obtains is soluble in water; Get 2ml head product solution, add solidifying agent cashew pnenolic aldehyde amine (25 ℃ of viscositys, 400-800mPa.s) 0.007g; Stir about 5 minutes; Removed bubble, and then said mixture was coated in the slide glass ambient cure 24 hours equably, film forming in ultrasonic again 1 minute.Film is put into deionized water, and after about 2 hours, noticeable change (variation in thickness is less than 0.1mm) no longer takes place in film thickness, gets soft coating.Soft coating is carried out antibiotic absorption test; Experimental result show that soft coating can the better inhibited streptococcus aureus (see Fig. 1 a) and intestinal bacteria (see Fig. 2 adhesion a); Fig. 1 b and Fig. 2 b have provided the situation of these two kinds of bacteriums of pellosil surface adsorption respectively, can know that through contrast the soft coating that the method for utilizing embodiment 1 prepares has antibacterium adsorptive power preferably.In addition, compare with pellosil, the soft coating that is prepared by present embodiment has excellent anti-bovine serum albumin absorption (Fig. 3) and anti-N,O-Diacetylmuramidase absorption (Fig. 4) ability.
Wherein, the structural formula of 2-acrylamido-2-methyl propane sulfonic acid is following:
Figure BDA0000094559240000061
The structural formula of 2-methyl-2-acrylic acid epoxy ethyl group methyl ester is following:
Figure BDA0000094559240000071
Embodiment 2:
Take by weighing 2-acrylamido-2-methyl propane sulfonic acid 30g and be dissolved in the 50ml deionized water, join in the four-hole boiling flask, under condition of ice bath, neutralize, regulate about pH to 6.8 with several sodium hydroxide.Take by weighing again after 2-methyl-2-acrylic acid epoxy ethyl group methyl ester 8.5g is dissolved in the 50ml deionized water that adds the 8.5g polyoxyethylene 20 sorbitan monolaurate in advance emulsification in advance, also join in the four-hole boiling flask.Under the nitrogen protection, fully stir about is 30 minutes.Add 0.2g azo diisobutyl amidine hydrochloride then, react 7h down, get head product at 40 ℃.Be configured to the head product solution that concentration is 5g/100ml water with the head product that obtains is soluble in water; Get 2ml head product solution; Add solidifying agent polymine (molecular weight ranges is between 320～600) 0.015g, stir about 5 minutes, ultrasonic again 1 minute removal bubble; Then said mixture was coated on the slide glass ambient cure 24 hours equably, film forming.Film is put into deionized water, and after about 2 hours, noticeable change (variation in thickness is less than 0.1mm) no longer takes place in film thickness, gets soft coating.Soft coating is carried out antibiotic absorption test, compare with pellosil, soft coating shows better inhibited streptococcus aureus (Fig. 5) and colibacillary adhesion (Fig. 6).Soft coating is carried out anti-protein adsorption experiment, compare bovine serum albumin (Fig. 7) that the soft coating surface adsorption is less and N,O-Diacetylmuramidase (Fig. 8) with pellosil.
Embodiment 3:
Take by weighing 2-acrylamido-2-methyl propane sulfonic acid 3.0g and be dissolved in the 50ml deionized water, join in the four-hole boiling flask, under condition of ice bath, neutralize, regulate about pH to 7.0 with several sodium hydroxide.Take by weighing 1,2-epoxy-7-octene 0.15g also joins in the four-hole boiling flask after being dissolved in the 50ml deionized water that adds the 0.15g polyoxyethylene 20 sorbitan monolaurate in advance emulsification in advance.Under the nitrogen protection, fully stir about is 30 minutes.Add 0.3g azo diisobutyl amidine hydrochloride then, react 6h down, get head product at 45 ℃.Be configured to the head product solution that concentration is 15g/100ml water with the head product that obtains is soluble in water; Get 2ml head product solution, add solidifying agent cashew pnenolic aldehyde amine (25 ℃ of viscositys, 400-800mPa.s) 0.003g; Stir about 5 minutes; Remove bubble in ultrasonic again 1 minute, then said mixture was coated on the slide glass ambient cure 24 hours equably, film forming.Film is put into deionized water, and after about 2 hours, noticeable change (variation in thickness is less than 0.1mm) no longer takes place in film thickness, gets soft coating.Soft coating is carried out antibiotic absorption test, compare with pellosil, soft coating shows excellent inhibition streptococcus aureus (Fig. 9) and colibacillary adhesion (Figure 10).Soft coating is carried out anti-protein adsorption experiment, compare with pellosil, the soft coating surface is not adsorbed bovine serum albumin (Figure 11) and N,O-Diacetylmuramidase (Figure 12) basically.
Embodiment 4:
Take by weighing [2-(methacryloyl oxygen base) ethyl] dimethyl--(3-sulfonic acid propyl group) volatile caustic (CAS:3637-26-1); 20.0g be dissolved in the 50ml deionized water; Join in the four-hole boiling flask, under condition of ice bath, neutralize, regulate about pH to 6.8 with several sodium hydroxide.Take by weighing 2-methyl-2-acrylic acid epoxy ethyl group methyl ester 2.0g be dissolved in add in the polyoxyethylated 50ml deionized water of 3.0g emulsification in advance in advance after, also join in the four-hole boiling flask.Under the nitrogen protection, fully stir about is 30 minutes.Add dissolved 0.2g K in advance then 2S 2O 8With 0.14g Na 2SO 3, react 7h down at 40 ℃, get head product.Be configured to the head product solution that concentration is 10g/100ml water with the head product that obtains is soluble in water; Get 2ml head product solution; Add solidifying agent glycocoll 0.008g, stir about 5 minutes, ultrasonic again 1 minute removal bubble; Then said mixture is coated on the slide glass ambient cure more than 24 hours equably, film forming.Film is put into deionized water, and after about 2 hours, noticeable change (variation in thickness is less than 0.1mm) no longer takes place in film thickness, gets soft coating.Soft coating is carried out antibiotic absorption test, compare with pellosil, soft coating shows better inhibited streptococcus aureus and colibacillary adhesion, and (Fig. 1 a, Fig. 2 are a) basic identical for result and instance 1.Soft coating is carried out anti-protein adsorption experiment, compare with pellosil, bovine serum albumin bletilla N,O-Diacetylmuramidase is not adsorbed on the soft coating surface basically, and the result is identical with instance 1 (Fig. 3, Fig. 4).
Wherein, the structural formula of [2-(methacryloyl oxygen base) ethyl] dimethyl--(3-sulfonic acid propyl group) volatile caustic is following:
Figure BDA0000094559240000081
Embodiment 5:
Take by weighing [2-(methacryloyl oxygen base) ethyl] dimethyl--(3-sulfonic acid propyl group) volatile caustic 15.0g and be dissolved in the 50ml deionized water, join in the four-hole boiling flask, under condition of ice bath, neutralize, regulate about pH to 7.0 with several sodium hydroxide.Take by weighing after 2-methyl-2-acrylic acid epoxy ethyl group methyl ester 6.0g is dissolved in the 50ml deionized water that adds 1.8g polyoxyethylene sorbitan lipid acid ketone in advance emulsification in advance, also join in the four-hole boiling flask.Under the nitrogen protection, fully stir about is 30 minutes.Add 0.3g K then 2S 2O 8, react 7h down at 50 ℃, get head product.Be configured to the head product solution that concentration is 8g/100ml water with the head product that obtains is soluble in water; Get 2ml head product solution; Add solidifying agent cashew pnenolic aldehyde amine 0.016g, stir about 5 minutes, ultrasonic again 1 minute removal bubble; Then said mixture is coated on the slide glass ambient cure more than 24 hours equably, film forming.Film is put into deionized water, and after about 2 hours, noticeable change (variation in thickness is less than 0.1mm) no longer takes place in film thickness, gets soft coating.Soft coating is carried out antibiotic absorption test, compare with pellosil, soft coating shows better inhibited streptococcus aureus and colibacillary adhesion, and result and embodiment 2 (Fig. 5, Fig. 6) are basic identical.Soft coating is carried out anti-protein adsorption experiment, compare, the less absorption bovine serum albumin bletilla N,O-Diacetylmuramidase in soft coating surface, similar with instance 2 results (Fig. 7 and Fig. 8) with pellosil.
Embodiment 6:
Employing is with embodiment 1 same ingredients and condition; Difference is that ionogen property monomer adopts the 2-sodium acrylate, and the soft coating of acquisition shows the adhesion with instance 1 essentially identical inhibition streptococcus aureus, intestinal bacteria, bovine serum albumin bletilla N,O-Diacetylmuramidase.
Embodiment 7:
Employing is with embodiment 1 same ingredients and condition; Difference is that ionogen property monomer adopts N-(3-dimethylamino-propyl) USAF RH-1, and the soft coating of acquisition shows the adhesion with instance 1 essentially identical inhibition streptococcus aureus, intestinal bacteria, bovine serum albumin bletilla N,O-Diacetylmuramidase.
Wherein, the structural formula of N-(3-dimethylamino-propyl) USAF RH-1 is following:
Figure BDA0000094559240000091
Embodiment 8:
Employing is with embodiment 1 same ingredients and condition; Difference is that ionogen property monomer adopts N hydroxymethyl acrylamide, and the soft coating of acquisition shows the adhesion with instance 1 essentially identical inhibition streptococcus aureus, intestinal bacteria, bovine serum albumin bletilla N,O-Diacetylmuramidase.
Wherein, the structural formula of N hydroxymethyl acrylamide is following:
Embodiment 9:
Employing is with embodiment 1 same ingredients and condition; Difference is that ionogen property monomer adopts 2-hydroxyethyl methacrylate, and the soft coating of acquisition shows the adhesion with instance 1 essentially identical inhibition streptococcus aureus, intestinal bacteria, bovine serum albumin bletilla N,O-Diacetylmuramidase.
Wherein, the structural formula of 2-hydroxyethyl methacrylate is following:
Embodiment 10:
Employing is with embodiment 1 same ingredients and condition; Difference is that ionogen property monomer adopts polyethylene glycol methacrylate-styrene polymer (molecular weight 300～950), and the soft coating of acquisition shows the adhesion with instance 2 essentially identical inhibition streptococcus aureuses, intestinal bacteria, bovine serum albumin bletilla N,O-Diacetylmuramidase.
Wherein, the structural formula of polyethylene glycol methacrylate-styrene polymer is following:
Figure BDA0000094559240000103
Embodiment 11:
Employing is with embodiment 1 same ingredients and condition; Difference is that ionogen property monomer adopts [2-(methacryloyl oxygen base) ethyl] dimethyl--(2-carboxylic acid ethyl) volatile caustic, and the soft coating of acquisition shows the adhesion with instance 1 essentially identical inhibition streptococcus aureus, intestinal bacteria, bovine serum albumin bletilla N,O-Diacetylmuramidase.
Wherein, the structure of [2-(methacryloyl oxygen base) ethyl] dimethyl--(2-carboxylic acid ethyl) volatile caustic is as follows:
Figure BDA0000094559240000111
Embodiment 12:
Employing is with embodiment 1 same ingredients and condition; Difference is that function matter property monomer adopts acrylic acid epoxy ethyl group methyl ester, and the soft coating of acquisition shows the adhesion with instance 1 essentially identical inhibition streptococcus aureus, intestinal bacteria, bovine serum albumin bletilla N,O-Diacetylmuramidase.
Wherein, the structural formula of acrylic acid epoxy ethyl group methyl ester is following:
Figure BDA0000094559240000112
Embodiment 13:
Employing is with embodiment 1 same ingredients and condition, and difference is that function matter property monomer adopts the epoxy butylene, and the soft coating of acquisition shows the adhesion with instance 1 essentially identical inhibition streptococcus aureus, intestinal bacteria, bovine serum albumin bletilla N,O-Diacetylmuramidase.
Embodiment 14:
Employing is with embodiment 1 same ingredients and condition; Difference is that function matter property monomer adopts 1-allyloxy-2; 3-propylene oxide, the soft coating of acquisition show the adhesion with instance 1 essentially identical inhibition streptococcus aureus, intestinal bacteria, bovine serum albumin bletilla N,O-Diacetylmuramidase.
Wherein, 1-allyloxy-2, the structural formula of 3-propylene oxide is following:
Figure BDA0000094559240000113

Claims (10)

1. the preparation method of an antibiotic anti-protein adsorption soft coating comprises:
(1) electrolyte monomer is dissolved in the water, regulates pH value to 6.5～7.5, obtain mixture A; Function monomer is scattered in the water with the preparatory emulsification of tensio-active agent, obtains mixture B;
(2) mixture A and mixture B are mixed, add initiator,, obtain head product 30～55 ℃ of following polymerizations;
(3) head product that step (2) is obtained adds and is mixed with head product solution in the entry, with head product solution with film after solidifying agent mixes, solidify and obtain coating;
(4) coating that step (3) is obtained is put into water, until swelling equilibrium, obtains antibiotic anti-protein adsorption soft coating.
2. the preparation method of antibiotic anti-protein adsorption soft coating according to claim 1; It is characterized in that; In the step (1): the ratio of described electrolyte monomer consumption and Total Water is 3～30: 100g/ml; The ratio of described function monomer consumption and Total Water is 0.15～8.5: 100g/ml, and the ratio of described dosage of surfactant and Total Water is 0.15～8.5: 100g/ml; Said Total Water is the summation of mixture A and mixture B water consumption.
3. the preparation method of antibiotic anti-protein adsorption soft coating according to claim 1 is characterized in that, in the step (2): the mass ratio of electrolyte monomer and function monomer total amount is 0.005～0.1: 1 in described initiator amount and the step (1).
4. the preparation method of antibiotic anti-protein adsorption soft coating according to claim 1; It is characterized in that; In the step (3): the ratio of head product and water is 3～20 in the described head product solution: 100g/ml, the mass ratio of function monomer consumption is 0.02～0.50: 1 in described hardener dose and the step (1).
5. the preparation method of antibiotic anti-protein adsorption soft coating according to claim 1 is characterized in that, described electrolyte monomer is at least a in the compound shown in structural formula (I), (II), (III):
In the formula (I), R 1Be H or CH 3, R 2, R 3Independently be H or C separately 1～C 3Alkyl, n=0～3, Z 1Be Phenylsulfonic acid base, sulfonic group, phosphate, Phenylsulfonic acid alkali, sulphonate-base, phosphate base, hydroxyl or dimethylamino;
In the formula (II), R 4Be H or CH 3, X is H, basic metal, ammonium, hydroxyalkyl or end alkyl polyethylene glycol groups;
Figure FDA0000094559230000022
In the formula (III), R 5Be H or CH 3, Y is any one in following three kinds of structures:
In above-mentioned three kinds of structures, R 6, R 9And R 13Independently be C separately 2～C 5The fat segment, R 7, R 8, R 10, R 11And R 14Independently be C separately 1～C 5Alkyl, R 12, R 16Be C 1～C 5Alkyl or phenyl, R 15Be C 2～C 5The fat segment, Z 2Be halogen, OSO 2, OSO 3, OPO 2, OPO 3Or CH 3COO, Z 3For-OSO 2,-OSO 3,-OPO 2,-OPO 3Or-COO.
6. the preparation method of antibiotic anti-protein adsorption soft coating according to claim 1 is characterized in that, said function monomer is at least a among structural formula (IV), (V):
Figure FDA0000094559230000024
In the formula (IV), G 1, G 2, G 4And G 6Independently be H or C separately 1～C 3Alkyl, G 3And G 5Independently be H or CH separately 3, m, q independently are 0～3 separately;
Figure FDA0000094559230000025
In the formula V, G 7, G 8, G 10And G 12Independently be H or C separately 1～C 3Alkyl, G 9And G 11Independently be H or CH separately 3, p=0～6, v=0 or 1, w=0～6.
7. the preparation method of antibiotic anti-protein adsorption soft coating according to claim 1 is characterized in that, described tensio-active agent is a non-ionics.
8. the preparation method of antibiotic anti-protein adsorption soft coating according to claim 7 is characterized in that, described non-ionics is polysorbate nonionogenic tenside or T 46155 nonionogenic tenside.
9. the preparation method of antibiotic anti-protein adsorption soft coating according to claim 1 is characterized in that, described initiator is water-soluble persulfate initiator, water-soluble azo initiator or water soluble oxidized reduction initiator.
10. the preparation method of antibiotic anti-protein adsorption soft coating according to claim 1; It is characterized in that described solidifying agent is one or more in the amino acid solidifying agent, amino acid salts solidifying agent, cashew nut oil modified amine hardener, polyethyleneimine: amine hardener, chitosan solidifying agent, urea solidifying agent, melamine cured dose.
CN2011102894467A 2011-09-27 2011-09-27 Preparation method of antibacterial and anti-protein adsorption soft coating Pending CN102417778A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN2011102894467A CN102417778A (en) 2011-09-27 2011-09-27 Preparation method of antibacterial and anti-protein adsorption soft coating

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN2011102894467A CN102417778A (en) 2011-09-27 2011-09-27 Preparation method of antibacterial and anti-protein adsorption soft coating

Publications (1)

Publication Number Publication Date
CN102417778A true CN102417778A (en) 2012-04-18

Family

ID=45942424

Family Applications (1)

Application Number Title Priority Date Filing Date
CN2011102894467A Pending CN102417778A (en) 2011-09-27 2011-09-27 Preparation method of antibacterial and anti-protein adsorption soft coating

Country Status (1)

Country Link
CN (1) CN102417778A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108727937A (en) * 2018-05-22 2018-11-02 浙江大学 A kind of preparation method and application of high-strength anti-fouling anti-drag hydrogel soft coating
US11560487B2 (en) 2020-09-22 2023-01-24 Swimc Llc Coating compositions containing low molecular weight chitosan composition

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102051101A (en) * 2010-11-18 2011-05-11 浙江大学 Method for preparing normal temperature-cured anti-fouling anti-drag hydrogel soft coating

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102051101A (en) * 2010-11-18 2011-05-11 浙江大学 Method for preparing normal temperature-cured anti-fouling anti-drag hydrogel soft coating

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108727937A (en) * 2018-05-22 2018-11-02 浙江大学 A kind of preparation method and application of high-strength anti-fouling anti-drag hydrogel soft coating
CN108727937B (en) * 2018-05-22 2020-01-14 浙江大学 Preparation method and application of high-strength antifouling and anti-drag hydrogel soft coating
US11560487B2 (en) 2020-09-22 2023-01-24 Swimc Llc Coating compositions containing low molecular weight chitosan composition

Similar Documents

Publication Publication Date Title
EP3551679B1 (en) Polymer comprising certain level of bio-based carbon
CN106687149B (en) Hydrogel composition
CN110484062B (en) Method for constructing anti-fouling, sterilizing and releasing surface coating by utilizing dopamine and product thereof
CN105968276B (en) The amphipathic cationic copolymer and its nanoparticle of a kind of acid-sensitive and application
US11384186B2 (en) Polymer comprising certain level of bio-based carbon
CN107286355B (en) Cation-zwitterion copolymer and polycaprolactone blended membrane and preparation method and application thereof
CN102174163A (en) Side chain functionalized amphiphilic polyurethane and preparation method and application thereof
WO2007070262A3 (en) Absorbent articles comprising thermoplastic coated superabsorbent polymer materials
CN106046382A (en) Nitric oxide loaded cationic polymer, preparation method therefor and application of nitric oxide loaded cationic polymer
WO2018108610A1 (en) Polymer comprising certain level of bio-based carbon
CN103881126A (en) Method for improving blood compatibility of material
CN103059215A (en) Glycine betaine ester intelligent hydrogel relatively controllable in structure and preparation method and application
CN102417778A (en) Preparation method of antibacterial and anti-protein adsorption soft coating
CN108294857A (en) A kind of antibacterial lubricant type sheath and preparation method thereof
Jimenez et al. Fundamental insights into free-radical polymerization in the presence of catechols and catechol-functionalized monomers
RU2013156293A (en) ADHESIVE COMPOSITION FOR SOFT TISSUES, ADHESIVE COMPOSITION FOR WOUND BANDING OR WOUND BAND COMPOSITION
BR0308892A (en) Copolymer, aqueous polymer dispersion, film, pharmaceutical formulation, and processes for the preparation of a polymer and formulation
CN102432745B (en) Method for preparing active copolymer containing double functional groups including epoxy and tertiary amine
CN101302258A (en) Acrylic ester high molecular type surfactant and preparation of porous resin
CN103275269B (en) A kind of phosphoryl choline polymer containing aldehyde radical and its preparation method and application
CN110511624B (en) Preparation method of coating with sterilization and bacterial release effects and product thereof
TWI743552B (en) Composition of temporary crown materials
CN118005529B (en) Supermolecule panthenol bisabolol and preparation method and application thereof
CN114989470B (en) Preparation method and application of humidity response anisotropic composite surface
CN116983254B (en) Polyphenol-stevioside traditional Chinese medicine small molecule hydrogel and preparation method and application thereof

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
C12 Rejection of a patent application after its publication
RJ01 Rejection of invention patent application after publication

Application publication date: 20120418