CN107652393A - Adsorption antibacterial sugar-containing polymer and preparation method thereof - Google Patents
Adsorption antibacterial sugar-containing polymer and preparation method thereof Download PDFInfo
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- CN107652393A CN107652393A CN201710986877.6A CN201710986877A CN107652393A CN 107652393 A CN107652393 A CN 107652393A CN 201710986877 A CN201710986877 A CN 201710986877A CN 107652393 A CN107652393 A CN 107652393A
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- 229920000642 polymer Polymers 0.000 title claims abstract description 60
- 230000000844 anti-bacterial effect Effects 0.000 title claims abstract description 49
- 238000001179 sorption measurement Methods 0.000 title claims abstract description 42
- 238000002360 preparation method Methods 0.000 title claims abstract description 19
- 239000000178 monomer Substances 0.000 claims abstract description 21
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 16
- 230000003291 dopaminomimetic effect Effects 0.000 claims abstract description 9
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 8
- -1 methacryl amine Chemical class 0.000 claims abstract description 6
- 239000002994 raw material Substances 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 10
- 238000005580 one pot reaction Methods 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 4
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 3
- 230000000977 initiatory effect Effects 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 150000007970 thio esters Chemical group 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 33
- 239000000758 substrate Substances 0.000 abstract description 26
- 239000000463 material Substances 0.000 abstract description 19
- FOIXSVOLVBLSDH-UHFFFAOYSA-N Silver ion Chemical compound [Ag+] FOIXSVOLVBLSDH-UHFFFAOYSA-N 0.000 abstract description 11
- 230000003115 biocidal effect Effects 0.000 abstract description 7
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical group OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 abstract description 7
- 238000011065 in-situ storage Methods 0.000 abstract description 6
- OVMJVEMNBCGDGM-UHFFFAOYSA-N iron silver Chemical compound [Fe].[Ag] OVMJVEMNBCGDGM-UHFFFAOYSA-N 0.000 abstract description 3
- 239000002861 polymer material Substances 0.000 abstract description 3
- 229910052751 metal Inorganic materials 0.000 abstract description 2
- 239000002184 metal Substances 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 15
- 241000894006 Bacteria Species 0.000 description 14
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 13
- 229910052710 silicon Inorganic materials 0.000 description 13
- 239000010703 silicon Substances 0.000 description 13
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 12
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 11
- 238000012545 processing Methods 0.000 description 11
- 239000004205 dimethyl polysiloxane Substances 0.000 description 9
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 9
- CXQXSVUQTKDNFP-UHFFFAOYSA-N octamethyltrisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)O[Si](C)(C)C CXQXSVUQTKDNFP-UHFFFAOYSA-N 0.000 description 9
- 238000004987 plasma desorption mass spectroscopy Methods 0.000 description 9
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- 238000012986 modification Methods 0.000 description 8
- 230000004048 modification Effects 0.000 description 8
- 239000010935 stainless steel Substances 0.000 description 8
- 229910001220 stainless steel Inorganic materials 0.000 description 8
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- 230000000845 anti-microbial effect Effects 0.000 description 6
- 238000011056 performance test Methods 0.000 description 6
- 238000010094 polymer processing Methods 0.000 description 6
- 229910052709 silver Inorganic materials 0.000 description 6
- 239000004332 silver Substances 0.000 description 6
- 229910001961 silver nitrate Inorganic materials 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 239000008367 deionised water Substances 0.000 description 5
- 229910021641 deionized water Inorganic materials 0.000 description 5
- 239000007983 Tris buffer Substances 0.000 description 4
- 238000007605 air drying Methods 0.000 description 4
- 239000004599 antimicrobial Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- GSWPVNPGTONRRG-AMXXWBLWSA-N 2-methyl-N-[(3R,4S,5S,6R)-2,3,4,5-tetrahydroxy-6-(hydroxymethyl)oxan-3-yl]prop-2-enamide Chemical compound CC(=C)C(=O)N[C@]1(O)C(O)O[C@H](CO)[C@@H](O)[C@@H]1O GSWPVNPGTONRRG-AMXXWBLWSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 230000015271 coagulation Effects 0.000 description 3
- 238000005345 coagulation Methods 0.000 description 3
- 238000000799 fluorescence microscopy Methods 0.000 description 3
- 239000011159 matrix material Substances 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 230000001376 precipitating effect Effects 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000002352 surface water Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- 241000193830 Bacillus <bacterium> Species 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- 230000001580 bacterial effect Effects 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 210000002429 large intestine Anatomy 0.000 description 2
- 229960004502 levodopa Drugs 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 2
- 230000002688 persistence Effects 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 208000035473 Communicable disease Diseases 0.000 description 1
- WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 description 1
- 241000237536 Mytilus edulis Species 0.000 description 1
- 235000009754 Vitis X bourquina Nutrition 0.000 description 1
- 235000012333 Vitis X labruscana Nutrition 0.000 description 1
- 240000006365 Vitis vinifera Species 0.000 description 1
- 235000014787 Vitis vinifera Nutrition 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 210000000170 cell membrane Anatomy 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- MHUWZNTUIIFHAS-CLFAGFIQSA-N dioleoyl phosphatidic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(COP(O)(O)=O)OC(=O)CCCCCCC\C=C/CCCCCCCC MHUWZNTUIIFHAS-CLFAGFIQSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 235000013601 eggs Nutrition 0.000 description 1
- 238000002389 environmental scanning electron microscopy Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 210000003495 flagella Anatomy 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007769 metal material Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 235000020638 mussel Nutrition 0.000 description 1
- NQIMONOHVBBZKE-UHFFFAOYSA-N n-[2-(3,4-dihydroxyphenyl)ethyl]-2-methylprop-2-enamide Chemical compound CC(=C)C(=O)NCCC1=CC=C(O)C(O)=C1 NQIMONOHVBBZKE-UHFFFAOYSA-N 0.000 description 1
- 239000002086 nanomaterial Substances 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 230000007096 poisonous effect Effects 0.000 description 1
- 229920001690 polydopamine Polymers 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/52—Amides or imides
- C08F220/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
- C08F220/58—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide containing oxygen in addition to the carbonamido oxygen, e.g. N-methylolacrylamide, N-(meth)acryloylmorpholine
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/38—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Treatments Of Macromolecular Shaped Articles (AREA)
Abstract
The invention discloses adsorption antibacterial sugar-containing polymer and preparation method, sugar monomer, carboxylic acid type monomer and Dopaminergics monomer are contained as raw material using methacryl amine, chain-transferring agent is added, is prepared in sunshine or the next footwork of simulated solar irradiation with approximate wave band.Sugar-containing polymer prepared by the present invention is not only with water solubility also with preferable surface adsorption property, and can surface in situ reduce silver ion, available for prepare functional antibiosis sugar-containing polymer material and for the materials such as inorganic, organic and metal later stage antibacterial surface handle.Dopaminergics monomer has catechol functional group, and sugar-containing polymer prepared by the present invention forms covalent bond or strong non-covalent bond to adsorb in material surface by catechol functional group and material surface；Carboxylic acid chelated silver iron, silver ion can be fixed in above-mentioned substrate；There is reproducibility containing sugar monomer and Dopaminergics monomer, above-mentioned silver ion in-situ reducing can be produced antibiotic property.
Description
Technical field
Present invention relates particularly to a kind of adsorption antibacterial sugar-containing polymer and preparation method thereof.
Background technology
In recent years due to a large amount of uses of antibiotic, disinfectant etc., cause the variation of drug tolerant bacteria, cause pathogen,
The outburst of infectious disease, cause researcher actively found in anti-biotic material field it is new it is safe, persistence is good, hypotoxicity
Novel antibacterial material.In current antibacterial strategy, Nano Silver and silver ion are entered inside bacterium by the cell membrane of bacterium
Sterilization or bacteriostasis are played, therefore silver-colored based compound or silver-carrying nano material have broad-spectrum antibacterial property, persistence, security
The advantages that.The preparation method of Nano Silver is mainly the method for microwave radiation, ultrasonic radiation and micro-reduction at present, is ground both at home and abroad
The Nano Silver studied carefully, it is more silver-colored to make ball-type, the silver-colored cluster of particle or parcel in the solution, preferable bactericidal effect is shown, and
And find that the Nano Silver with large specific surface area can be combined preferably with bacterium in clinical practice.But these methods,
Using substantial amounts of organic solvent or poisonous reducing agent, environment and biozone can be injured, are not suitable for further clinical
Using.Have scholar's research report, make the method for reducing agent by maltose, prepare Nano Silver and with good antibiotic property and
Security.We therefrom gain enlightenment, and glucose equally has reproducibility, can green, effectively reduce Ag+, based on grape
The design of material of sugar, which can develop into, prepares the effective method of Ag-carried antibacterial material.In addition, the specificity of sugar and protein
Molecular recognition plays very important effect in vital movement, and there are many eggs combined with sugar specificity on bacterial flagellum surface
In vain, long-chain and have a repeat unit show stronger combination effect for bacterium containing sugared polymers.At the same time, it is actual medical
With in life, it is necessary to which the material of antibacterial includes the different types of material such as surgical knife tool, glassware, daily necessities, development one
General, easy, the green surface coating method of kind is significant.It can be adhered in a variety of matrix surfaces and obtained according to marine mussel
To inspiration, catechol group is oxidized to the quinoid structure of complexity and forms poly-dopamine in substrate material surface under alkalescence condition
Layer.We design preparation amine functional group containing DOPA, glucose primitive and can be complexed Ag+Carboxyl functional group it is multi-functional poly-
Compound, a step realizes the modification to different matrix material surface, while grappling and in-situ reducing Ag on the surface, so as to prepare pin
To the purpose of different surfaces antimicrobial coating.
The content of the invention
It is an object of the present invention to provide adsorption antibacterial sugar-containing polymer and preparation method thereof, solve the above problems.
The present invention a kind of technical scheme be：A kind of adsorption antibacterial sugar-containing polymer, its structure such as following formula（）：
（）
Wherein, m span is 1-40, and n span is 1-100, and q span is 10-200.
The preparation method of said structure is：Sugar monomer, carboxylic acid type monomer and Dopaminergics list are contained with methacryl amine
Body is raw material, adds chain-transferring agent, irradiates under light, prepared by one kettle way, reaction equation is：
Wherein, a span is 1-40, and b span is 1-100, and c span is 10-200.Further, the first
Mol ratio of the base acrylic amide containing sugar monomer, carboxylic acid type monomer, Dopaminergics monomer, chain-transferring agent is 10-200：1-100:
1-40: 1。
Further, the irradiation under light is to be irradiated under sunshine or simulated solar irradiation.
Further, the sunshine or simulated solar irradiation are initiation system.
Further, the chain-transferring agent is thio esters chain-transferring agent.
Further, the chain-transferring agent is selected from two thio naphthoic acid isobutyronitrile ester or 4- cyano group -4- (phenyl formyls
Sulfenyl) any one in valeric acid.
Further, the reaction time of the one kettle way is 35-45h.
Further, the reaction condition of the one kettle way is 20-30 DEG C of oxygen-free environment.
The method have the advantages that：
(1) method that the present invention realizes active free radical polymerization using sunlight irradiation in system existing for chain-transferring agent, system
The controllable sugar-containing polymer of standby compound with regular structure;
(2) sugar-containing polymer for preparing of the present invention not only good water solubility, also with preferable surface adsorption property, is modified on surface
Silver ion, and in-situ reducing can be arrested after upper, available for preparation multifunctionality and has the sugar-containing polymer material of excellent anti-bacterium capability
Material;
(3) Dopaminergics monomer has catechol functional group, and sugar-containing polymer prepared by the present invention passes through catechol function
Group with material surface formation covalent bond or strong non-covalent bond and adsorb in material surface, and carboxylic acid can chelated silver iron,
It is fixed on above-mentioned substrate, and under the reduction of sugar, form silver nano-grain, surface is possessed anti-microbial property;
(4) sugar-containing polymer prepared by the present invention can preferably be adsorbed in different types of matrix surface, have good table
Universality is modified in face, and forms silver nano-grain in material surface, material is had antibacterial surface;
(5) the inventive method is easy to operate, is advantageous to save cost of manufacture, promotes to promote.
Brief description of the drawings
Fig. 1 is the gpc measurement curve map of the antibacterial sugar-containing polymer with adsorption of the embodiment of the present invention 1；
Fig. 2 is that the surface test water of the silicon chip of the processing of the antibacterial sugar-containing polymer with adsorption of the embodiment of the present invention 1 connects
The comparison figure of feeler；
Fig. 3 is that the antibacterial sugar-containing polymer with adsorption of the embodiment of the present invention 1 modifies front and rear sweep on silicon chip surface
Retouch Electronic Speculum and compare figure;
Fig. 4 is that the antibacterial sugar-containing polymer with adsorption of the embodiment of the present invention 1 modifies front and rear resist on silicon chip surface
Bacterium performance test com-parison and analysis figure;
The surface test water that Fig. 5 is the PDMS of the processing of the antibacterial sugar-containing polymer with adsorption of the embodiment of the present invention 2 connects
The comparison figure of feeler；
Fig. 6 is before and after the antibacterial sugar-containing polymer with adsorption of the embodiment of the present invention 2 is modified on PDMS pieces surface
Anti-microbial Performance Tests com-parison and analysis figure；
Fig. 7 is the surface test of the stainless steel substrates of the processing of the antibacterial sugar-containing polymer with adsorption of the embodiment of the present invention 3
The comparison figure of water contact angle；
Fig. 8 is before and after the antibacterial sugar-containing polymer with adsorption of the embodiment of the present invention 3 is modified on stainless steel substrates surface
Anti-microbial Performance Tests com-parison and analysis figure.
Embodiment
In order to facilitate the understanding of the purposes, features and advantages of the present invention, with reference to the accompanying drawings and examples
Further illustrate technical scheme.But the invention is not restricted to listed embodiment, it should also be included in institute of the present invention
It is required that interest field in other any known change.
First, " one embodiment " or " embodiment " referred to herein refers to may be included at least one realization side of the present invention
Special characteristic, structure or characteristic in formula." in one embodiment " that different places occur in this manual not refers both to
Same embodiment, nor the single or selective embodiment mutually exclusive with other embodiment.
Secondly, the present invention is described in detail using structural representation etc., when the embodiment of the present invention is described in detail, for ease of saying
Bright, schematic diagram can disobey general proportion and make partial enlargement, and the schematic diagram is example, and it should not limit the present invention herein
The scope of protection.In addition, the three dimensions of length, width and depth should be included in actual fabrication.
In addition, present invention is to study to complete by a large amount of creative experiments, said with following specific embodiments
It is bright.
Embodiment 1：
Weigh 0.15g 2-（Methacryl amido）Glucopyranose, 27mg dopamine Methacrylamide, 11mL first
Base acrylic acid and 1.2mg 4- cyano group -4- (phenyl formyl sulfenyl) valeric acid is dissolved in 1mL dimethyl sulfoxide (DMSO), 25
Under DEG C room temperature oxygen free condition, one pot reaction 40h is irradiated under sunshine or simulated solar irradiation, then using methanol as precipitating
Agent, product is slowly added dropwise in 200mL precipitation agent methanols and is allowed to coagulation, obtain white precipitate, centrifuged, dried, weigh.
The obtained antibacterial sugar-containing polymer PDMAG for possessing adsorption structural formula is as follows：
Wherein m:n:q=1:1:5, molecular weight 24700, referring to Fig. 1, Fig. 1, which is the embodiment of the present invention 1, has an adsorption
Antibacterial sugar-containing polymer gpc measurement curve map.As shown in figure 1, molecular weight distribution is 1.1 or so.
By 50mL, 0.1mol/L tris solution（Tris）Mixed with 22.9mL, 0.1mol/L hydrochloric acid
Afterwards, 100mL is diluted with water to, the pH value for adjusting mixed liquor is 8.2, is configured to Tris-Hcl solution.
Take 0.1g that there is the antibacterial sugar-containing polymer PDMAG of adsorption to be dissolved in the Tris-Hcl solution 5mL shapes prepared
Into mixed liquor, silicon chip is placed in culture dish, mixed liquor is added drop-wise in substrate, is submerged, is placed on normal temperature shady place, is used after 4h
Deionized water washing surface three times, then air drying.As shown in figure 1, water contact angle test is carried out to the surface after processing, please
Refering to Fig. 2, Fig. 2 is the surface test of the silicon chip of the processing of the antibacterial sugar-containing polymer with adsorption of the embodiment of the present invention 1
The comparison figure of water contact angle.As shown in Fig. 2 the water contact angle of the silicon chip surface shown above without by sugar-containing polymer processing
Picture, the water contact angle picture of the silicon chip surface handled by sugar-containing polymer is expressed below, is shown by contrast, by containing sugar
The silicon chip surface water contact angle of polymer treatment changes significantly, and the water contact angle of substrate is reduced to 24 ° by 55 °, shows this reality
Apply example preparation sugar-containing polymer surface adsorption property it is stronger, the water solubility on surface is improved.
By the substrate of above-mentioned modification sugar-containing polymer, 0.5 mg/mL silver nitrate solution is added dropwise in its surface, makes base
Basal surface is submerged completely.It is washed with deionized after 3h, air drying.Then the micro- Microscopic observations of SEM are placed the substrate above.
Referring to Fig. 3, before the antibacterial sugar-containing polymer with adsorption that Fig. 3 is the embodiment of the present invention 1 is modified on silicon chip surface
ESEM afterwards compares figure.As shown in figure 3, compared with bare silicon wafer before, have on the silicon chip surface after modification substantial amounts of
Silver nano-grain, show that silver ion is fixed and effectively reduced on material substrate surface by this method.
Above-mentioned silicon chip is placed in alcohol and submerged 3 hours.After take out, will contaminate in lustful Escherichia coli drop loaded surfaces,
Place 15 minutes, then with deionized water rinsing surface, be placed on the situation of fluorescence microscopy Microscopic observation bacterial death.Refer to figure
4, Fig. 4 be that the antibacterial sugar-containing polymer with adsorption of the embodiment of the present invention 1 modifies front and rear antibacterial on silicon chip surface
Performance test com-parison and analysis figure.As shown in figure 4, by the collective effect of polymer and silver nitrate, have in substrate plus pernitric acid silver
Surface on, have it is substantial amounts of red occur for dead bacterium, and left side one arranges, only big on only polymer-modified surface
The green of amount is bacterium living, and it is good to show that sugar-containing polymer manufactured in the present embodiment can be used for modification inorganic material surface to make it have
Good bactericidal effect.
Embodiment 2：
Weigh 0.15g 2-（Methacryl amido）Glucopyranose mannose, 27mg dopamines Methacrylamide, 11 μ L
4.7mg 4- cyano group -4- (phenyl formyl sulfenyl) valeric acid of methacrylic acid is dissolved in 1mL dimethyl sulfoxide (DMSO), at 25 DEG C
Under room temperature oxygen free condition, one pot reaction 40h is irradiated under sunshine or simulated solar irradiation, then using methanol as precipitating reagent,
Product is slowly added dropwise in 200mL precipitation agent methanols and is allowed to coagulation, obtains white precipitate, is centrifuged, dries, weighs.
After 50mL, 0.1mol/L tris solution and 22.9mL, 0.1mol/L hydrochloric acid are mixed, add water
100mL is diluted to, the pH value for adjusting mixed liquor is 8.2, is configured to Tris-Hcl solution.
Take 0.1g that there is the antibacterial sugar-containing polymer PDMAG of adsorption to be dissolved in the Tris-Hcl solution 5mL shapes prepared
Into mixed liquor, PDMS is placed in culture dish, mixed liquor is added drop-wise in substrate, is submerged, is placed on normal temperature shady place, is used after 4h
Deionized water washing surface three times, then air drying.Water contact angle test is carried out to the surface after processing, referring to Fig. 5, figure
5 be the PDMS of the processing of the antibacterial sugar-containing polymer with adsorption of the embodiment of the present invention 2 surface test water contact angle
Compare figure.As shown in figure 5, above figure represents the water contact angle picture without the PDMS surfaces by sugar-containing polymer processing, under
Face figure represents the water contact angle picture on the surface of the PDMS by sugar-containing polymer processing, is shown by contrast, by poly- containing sugar
The PDMS surface water contact angles of compound processing change significantly, and the water contact angle of substrate is reduced to 66 ° by 105 °, shows this implementation
The surface adsorption property of sugar-containing polymer prepared by example is stronger, and the water solubility on surface is improved.
By the substrate of above-mentioned modification sugar-containing polymer, 0.5 mg/mL silver nitrate solution is added dropwise in its surface, makes base
Basal surface is submerged completely.It is washed with deionized after 3h, is placed in alcohol and submerges 3 hours.After take out, lustful large intestine will be contaminated
In bacillus drop loaded surfaces, place 15 minutes, then with deionized water rinsing surface, it is dead to be placed on fluorescence microscopy Microscopic observation bacterium
Situation about dying.Referring to Fig. 6, Fig. 6 is the antibacterial sugar-containing polymer with adsorption of the embodiment of the present invention 2 in PDMS piece tables
Front and rear Anti-microbial Performance Tests com-parison and analysis figure is modified on face.As shown in fig. 6, by the collective effect of polymer and silver nitrate,
Have in substrate on the surface for adding pernitric acid silver, the bacterium for having substantial amounts of red to be death occurs, and left side one arranges, only polymer
Only substantial amounts of green is bacterium living on the PDMS surfaces of modification, shows that sugar-containing polymer manufactured in the present embodiment can be used for modifying
Organic material surface simultaneously makes it have good bactericidal effect.
Experimental example 3：
Weigh 0.15g 2-（Methacryl amido）Glucopyranose, 27mg dopamines Methacrylamide, 11 μ L methyl
Acrylic acid and 0.8mg two thio naphthoic acid isobutyronitrile esters are dissolved in 1mL dimethyl sulfoxide (DMSO), in 25 DEG C of room temperature oxygen free conditions
Under, one pot reaction 40h is irradiated under sunshine or simulated solar irradiation, then using methanol as precipitating reagent, product is slowly dripped
Add in 200mL precipitation agent methanols and be allowed to coagulation, obtain white precipitate, centrifuge, dry, weigh.
After 50mL, 0.1mol/L tris solution and 22.9mL, 0.1mol/L hydrochloric acid are mixed, add water
100mL is diluted to, the pH value for adjusting mixed liquor is 8.2, is configured to Tris-Hcl solution.
Take 0.1g that there is the antibacterial sugar-containing polymer of adsorption to be dissolved in the Tris-Hcl solution 5mL prepared and form mixing
Liquid, stainless steel substrates are placed in culture dish, mixed liquor is added drop-wise in substrate, submerged, be placed on normal temperature shady place, spent after 4h
Ionized water washing surface three times, then air drying.Water contact angle test is carried out to the surface after processing, referring to Fig. 7, Fig. 7
It is the surface test water contact angle of the stainless steel substrates of the processing of the antibacterial sugar-containing polymer with adsorption of the embodiment of the present invention 3
Comparison figure.As shown in fig. 7, upper figure represents the water contact angle figure without the stainless steel substrates surface by sugar-containing polymer processing
Piece, figure below represents the water contact angle picture on the surface of the stainless steel substrates by sugar-containing polymer processing, shown by contrast, passes through
The stainless steel substrates surface water contact angle of sugar-containing polymer processing changes significantly, and the water contact angle of substrate is reduced to 54 ° by 82 °,
Show that the surface adsorption property of sugar-containing polymer manufactured in the present embodiment is stronger, the water solubility on surface is improved.
By the substrate of above-mentioned modification sugar-containing polymer, 0.5 mg/mL silver nitrate solution is added dropwise in its surface, makes base
Basal surface is submerged completely.It is washed with deionized after 3h, is placed in alcohol and submerges 3 hours.After take out, lustful large intestine will be contaminated
In bacillus drop loaded surfaces, place 15 minutes, then with deionized water rinsing surface, it is dead to be placed on fluorescence microscopy Microscopic observation bacterium
Situation about dying.Referring to Fig. 8, Fig. 8 is the antibacterial sugar-containing polymer with adsorption of the embodiment of the present invention 3 in stainless steel substrates
Front and rear Anti-microbial Performance Tests com-parison and analysis figure is modified on surface.As shown in figure 8, by polymer and the common work of silver nitrate
With, have in substrate on the surface for adding pernitric acid silver, there is the substantial amounts of red bacterium for death to occur, and left side one arranges, it is only poly-
Only substantial amounts of green is bacterium living on the surface of compound modification, shows that sugar-containing polymer manufactured in the present embodiment can be used for modifying
Metal material surface simultaneously makes it have good bactericidal effect.
In summary, the invention discloses adsorption antibacterial sugar-containing polymer and preparation method thereof, the sugar-containing polymer
Not only with water solubility also with preferable surface adsorption property, and can be in surface in situ reduction silver ion, available for preparing
Functional antibiosis sugar-containing polymer material and the later stage antibacterial surface processing for materials such as inorganic, organic and metals；DOPA
Amine monomers have catechol functional group, and sugar-containing polymer prepared by the present invention passes through catechol functional group and material surface
Form covalent bond or strong non-covalent bond and adsorb in material surface；Carboxylic acid chelated silver iron, can be in above-mentioned substrate
Fixed silver ion；There is reproducibility containing sugar monomer and Dopaminergics monomer, can above-mentioned silver ion in-situ reducing so as to
Produce antibiotic property.
It should be noted that the above embodiments are merely illustrative of the technical solutions of the present invention and it is unrestricted, although with reference to preferable
The present invention is described in detail embodiment, it will be understood by those within the art that, can be to the technology of the present invention
Scheme is modified or equivalent substitution, and without departing from the spirit and scope of technical solution of the present invention, it all should cover in this hair
Among bright right.
Claims (9)
1. adsorption antibacterial sugar-containing polymer, its structure such as following formula（）：
（）
Wherein, m span is 1-40, and n span is 1-100, and q span is 10-200.
2. the preparation method of adsorption antibacterial sugar-containing polymer according to claim 1, it is characterised in that：With methyl-prop
Acrylamide is raw material containing sugar monomer, carboxylic acid type monomer and Dopaminergics monomer, adds chain-transferring agent, irradiates, pass through under light
Prepared by one kettle way, reaction equation is：
Wherein, a span is 1-40, and b span is 1-100, and c span is 10-200.
3. the preparation method of adsorption antibacterial sugar-containing polymer according to claim 2, it is characterised in that：The methyl
Mol ratio of the acrylic amide containing sugar monomer, carboxylic acid type monomer, Dopaminergics monomer, chain-transferring agent is 10-200：1-100: 1-
40: 1。
4. the preparation method of adsorption antibacterial sugar-containing polymer according to claim 2, it is characterised in that：It is described in light
Lower irradiation is to be irradiated under sunshine or simulated solar irradiation.
5. the preparation method of adsorption antibacterial sugar-containing polymer according to claim 2, it is characterised in that：The sun
Light or simulated solar irradiation are initiation system.
6. the preparation method of adsorption antibacterial sugar-containing polymer according to claim 2, it is characterised in that：The chain turns
Shifting agent is thio esters chain-transferring agent.
7. the preparation method of adsorption antibacterial sugar-containing polymer according to claim 6, it is characterised in that：The chain turns
Move any one that agent is selected from two thio naphthoic acid isobutyronitrile ester or 4- cyano group -4- (phenyl formyl sulfenyl) valeric acids.
8. the preparation method of adsorption antibacterial sugar-containing polymer according to claim 2, it is characterised in that：Described one pot
The reaction time of method is 35-45h.
9. the preparation method of adsorption antibacterial sugar-containing polymer according to claim 2, it is characterised in that：Described one pot
The reaction condition of method is 20-30 DEG C of oxygen-free environment.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109350739A (en) * | 2018-11-12 | 2019-02-19 | 苏州大学 | A kind of new type anticancer immunologic adjuvant and preparation method thereof |
| CN110204755A (en) * | 2019-06-12 | 2019-09-06 | 苏州大学 | Purposes of the dopamine containing sugar copolymer |
| CN113444201A (en) * | 2021-06-29 | 2021-09-28 | 苏州大学 | Fluorescent sugar-containing polymer and preparation method thereof |
| CN114216889A (en) * | 2021-11-10 | 2022-03-22 | 苏州大学 | SERS substrate with selective surface Raman enhancement and preparation method thereof |
| CN114702624A (en) * | 2022-01-20 | 2022-07-05 | 河南科技大学 | Polysaccharide polymer based antibacterial material and preparation method thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105176288A (en) * | 2015-10-22 | 2015-12-23 | 天津科技大学 | Preparation of polymer-brush-based composite material antimicrobial coating |
| CN106046252A (en) * | 2016-06-14 | 2016-10-26 | 苏州大学 | Sugar-containing polymer with surface adsorption property and method for manufacturing sugar-containing polymer |
-
2017
- 2017-10-20 CN CN201710986877.6A patent/CN107652393A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105176288A (en) * | 2015-10-22 | 2015-12-23 | 天津科技大学 | Preparation of polymer-brush-based composite material antimicrobial coating |
| CN106046252A (en) * | 2016-06-14 | 2016-10-26 | 苏州大学 | Sugar-containing polymer with surface adsorption property and method for manufacturing sugar-containing polymer |
Non-Patent Citations (1)
| Title |
|---|
| 彭伦等: ""固定并还原Ag+的含糖聚合物合成及抗菌性能研究"", 《2017全国高分子学术论文报告会》 * |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109350739A (en) * | 2018-11-12 | 2019-02-19 | 苏州大学 | A kind of new type anticancer immunologic adjuvant and preparation method thereof |
| CN109350739B (en) * | 2018-11-12 | 2021-11-05 | 苏州大学 | Novel anti-cancer immunologic adjuvant and preparation method thereof |
| CN110204755A (en) * | 2019-06-12 | 2019-09-06 | 苏州大学 | Purposes of the dopamine containing sugar copolymer |
| CN113444201A (en) * | 2021-06-29 | 2021-09-28 | 苏州大学 | Fluorescent sugar-containing polymer and preparation method thereof |
| CN114216889A (en) * | 2021-11-10 | 2022-03-22 | 苏州大学 | SERS substrate with selective surface Raman enhancement and preparation method thereof |
| CN114702624A (en) * | 2022-01-20 | 2022-07-05 | 河南科技大学 | Polysaccharide polymer based antibacterial material and preparation method thereof |
| CN114702624B (en) * | 2022-01-20 | 2024-01-19 | 河南科技大学 | Antibacterial material based on polysaccharide polymer and preparation method thereof |
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