CN110105477A - A kind of responsiveness quaternization polyvinyl alcohol of tetraphenylethylene label and preparation and application - Google Patents
A kind of responsiveness quaternization polyvinyl alcohol of tetraphenylethylene label and preparation and application Download PDFInfo
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- CN110105477A CN110105477A CN201910343330.3A CN201910343330A CN110105477A CN 110105477 A CN110105477 A CN 110105477A CN 201910343330 A CN201910343330 A CN 201910343330A CN 110105477 A CN110105477 A CN 110105477A
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- polyvinyl alcohol
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
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- 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
- C08F8/00—Chemical modification by after-treatment
- C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
- C08F8/32—Introducing nitrogen atoms or nitrogen-containing groups by reaction with amines
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- 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
- C08F8/00—Chemical modification by after-treatment
- C08F8/44—Preparation of metal salts or ammonium salts
Abstract
The invention belongs to biological medicine Material Field, responsiveness quaternization polyvinyl alcohol and the preparation and application of a kind of tetraphenylethylene label are disclosed.The responsiveness quaternization polyvinyl alcohol of the tetraphenylethylene label has structural formula described in formula (I).Preparation method are as follows: PVA is dissolved in organic solvent, be added activator CDI activated, then be added DEEDA reacted, clean, precipitate, purifying, dry after obtain PVA-DEEDA；PVA-DEEDA is dissolved in organic solvent, TPE-CH is then added2Br heating reaction, precipitates, purifies, dry, obtains PVA-TPE.The material has both temperature, pH response and AIE photoluminescent property simultaneously in the present invention, and the polymer being prepared belongs to quaternary ammonium salt polymer antibacterial agent, superior with anti-microbial property, safe and non-toxic, anti-microbial property is stablized, and the in situ of bacterium may be implemented and kill and be imaged.
Description
Technical field
The invention belongs to biological medicine Material Fields, and in particular to a kind of responsiveness quaternization of tetraphenylethylene label
Polyvinyl alcohol and preparation and application.
Background technique
Microbial pathogens can cause the infection and disease of animal, plant and the mankind, for a long time be always strong to the mankind
The threat of health and social development.Human mortality's number as caused by bacterium, virus and fungal infection accounts for global death toll every year
A quarter.Since microorganism exists everywhere and can be propagated by empty gas and water and food etc., control and pre- preventing microorganism
Infection is a very big challenge.For combating microorganisms pathogen, various antibacterial agents, including antibiotic, disinfectant and anti-corrosion
Agent is widely used.However, universal and improper use of antibiotic and disinfectant has induced antibiotic property microorganism
New strains lead to sharply increasing for antibacterial problem.Therefore, there is an urgent need to develop low toxicity, efficiently, be not likely to produce the novel of drug resistance
Antibacterial agent.
Conventional anti-microbial agents are prepared based on natural or low molecular weight compound.Since low molecular weight antibacterial agent holds
Easy diffusion couple human body causes toxicity, while being used for a long time and being easy to produce drug resistance and its lead to environmental pollution, and limits
It is further used.The antibacterial polymer of high molecular weight avoids what low molecular weight antibacterial agent permeated from polymer substrate from asking
Topic, guarantees the durability of its antibacterial in environmentally friendly manner.Polyvinyl alcohol (PVA) is containing numerous hydroxyls and has preferable water-soluble
Property.PVA has good biocompatibility and a biological degradability, while its spinning, film forming and excellent at gelling performance, to current
It is used in fields such as wound sutures, artificial skin, bone repair material, drug conveying carrier, contact lenses and packaging materials for food
Way is extensively.Therefore traditional small molecule antibacterial agent is combined with PVA, the antibacterial agent of exploitation PVA base has tempting prospect.
Since two thousand one, with aggregation-induced emission (Aggregation-induced emission, AIE) characteristic
Fluorescent material causes the extensive concern of people.Its main feature is that do not shine under such molecular dispersed state, and in the collected state
Strong light can be issued.Even to this day, AIE material is almost applied in numerous field of light emitting materials, especially in biosystem
Organelle, virus or bacterium, the fields such as blood vessel imaging show more and more advantages.In view of the advantage of this uniqueness, base
In the fluorescent molecule of AIE, such as tetraphenylethylene (TPE) is also widely introduced into the design of functional material as hydrophobic patch and works as
In.But currently, the antibacterial agent that tetraphenylethylene is introduced into PVA base is had not been reported.
Summary of the invention
In place of the above shortcoming and defect of the existing technology, the primary purpose of the present invention is that providing a kind of four benzene
The responsiveness quaternization polyvinyl alcohol of base ethylene label.
Another object of the present invention is to provide the responsiveness quaternization polyvinyl alcohol of above-mentioned tetraphenylethylene label
Preparation method.
A further object of the present invention is to provide the responsiveness quaternization polyvinyl alcohol works of above-mentioned tetraphenylethylene label
For the application of antibacterial agent.
The responsiveness quaternization polyvinyl alcohol of tetraphenylethylene label of the invention overcomes quaternary ammonium salt small molecule antibacterial
The defect of agent has and stablizes antibacterial ability and environment-responsive, while assigning long-acting tracer of the material for bacterium.
The object of the invention is achieved through the following technical solutions:
A kind of responsiveness quaternization polyvinyl alcohol of tetraphenylethylene label, has the structural formula as described in following formula (I):
X in formula, y, z indicate the degree of polymerization of each repetitive unit.
Preferably, x+y+z=1932~2818 in formula (I).
The preparation method of the responsiveness quaternization polyvinyl alcohol of above-mentioned tetraphenylethylene label, including step is prepared as follows
It is rapid:
(1) polyvinyl alcohol (PVA) is dissolved in organic solvent, activator N is added, N'- carbonyl dimidazoles (CDI) are lived
Change, N is then added, N- diethyl ethylenediamine (DEEDA) is reacted, clean, precipitate, purifying, dry after obtain diethyl second
The modified polyvinyl alcohol (PVA-DEEDA) of diamines；
(2) PVA-DEEDA is dissolved in organic solvent, bromomethyl tetraphenylethylene (TPE-CH is then added2Br) heating is anti-
It answers, precipitates, purify, it is dry, obtain the responsiveness quaternization polyvinyl alcohol (PVA-TPE) of tetraphenylethylene label.
The reaction route of above-mentioned preparation method is shown below:
Preferably, the weight average molecular weight of polyvinyl alcohol described in step (1) is 85000~124000.
Preferably, organic solvent described in step (1) is dimethyl sulfoxide (DMSO).
Preferably, reaction temperature described in step (1) is 22 DEG C, and the reaction time is 20~36h.
Preferably, removal of impurities described in step (1) is that ammonia spirit is added into solution, removes unreacted activator N,
N'- carbonyl dimidazoles (CDI)；The precipitating refers to be precipitated in acetone；The purifying, which refers to, dissolves sediment with water, then
Dialysis, obtains purified product；The drying is freeze-drying.
Preferably, the ratio of hydroxyl mole and activator CDI are 1:(0.4~0.6 in PVA in step (1))；Hydroxyl in PVA
Base mole and the molar ratio of DEEDA are 1:(0.4~0.6).
Preferably, organic solvent described in step (2) is dimethyl sulfoxide (DMSO).
Preferably, PVA-DEEDA and TPE-CH in step (2)2The molar ratio of Br is 1:(0.005~0.015).
Preferably, heating reaction described in step (2), which refers to, reacts 24~36h in 50~70 DEG C of heating.
Preferably, the precipitating reagent of precipitating described in step (2) is acetone；The purifying, which refers to, dissolves sediment with water,
Then it dialyses, obtains purified product；The drying is freeze-drying.
Application of the responsiveness quaternization polyvinyl alcohol of above-mentioned tetraphenylethylene label as antibacterial agent.
The present invention is first with polyvinyl alcohol (PVA) for main chain, and using N, N'- carbonyl dimidazoles (CDI) activate PVA
Intermediate is formed, then it is modified with nucleophilic species N, the N- diethyl ethylenediamine (DEEDA) with primary amine, is obtained
Polyvinyl alcohol with hydrophilic amide (- CO-NH-) and hydrophobicity ethamine group.This two parts alternately controls polymer and exists
Property in aqueous solution makes it have temperature and pH response.Then pass through tertiary ethamine group and the tetraphenyl second for having bromomethyl
Alkene molecule (TPE-CH2Br the quaternary amine that) further the collection temperature of TPE label is prepared in quaternary ammonium reaction, pH is responded is birdsed of the same feather flock together second
Enol.Tetraphenylethylene (TPE) molecule has aggregation-induced emission (AIE) property, which can effectively control
The degree of quaternary amine and TPE label processed.
Preparation method of the invention and obtained product have the following advantages that and the utility model has the advantages that
(1) synthesis material of the present invention is cheap and easy to get, and synthetic reaction condition is mild, and the reaction time is short, and technological operation is simple, raw
It produces at low cost.
(2) the responsiveness quaternization polyvinyl alcohol of tetraphenylethylene of the invention label has temperature and pH double-response
(including physiological environment temperature) can carry out phase transition temperature adjusting by control ratio.Aggregation-induced emission (AIE) property is had both simultaneously
Matter has excellent cell and bacterium imaging function, is a kind of good Biofunctional materials.
(3) the responsiveness quaternization polyvinyl alcohol of tetraphenylethylene label of the invention have excellent anti-microbial property,
Sterilization rate is fast, antimicrobial efficiency is high.Low concentration reaches 99% or more to the antibiotic rate of staphylococcus aureus, while can realize
The in situ of bacterium is killed and is imaged.
(4) the responsiveness quaternization polyvinyl alcohol of tetraphenylethylene of the invention label has water-soluble well, makees
To be not necessarily to that organic solvent hydrotropy, safe ready is added in antibacterial agent use process.
Detailed description of the invention
Fig. 1 is polyvinyl alcohol (PVA), modified polyvinyl alcohol (PVA-DEEDA) used in embodiment 1 and is successfully grafted AIE
The nuclear magnetic spectrogram of molecular polyethylene alcohol (PVA-TPE)；
The pH that Fig. 2 is 1 gained PVA-TPE of embodiment responds experimental result picture；
Fig. 3 is the cytotoxicity experiment result figure of 1 gained PVA-TPE of embodiment；
Fig. 4 is the antibacterial experiment result figure of 1 gained PVA-TPE of embodiment；
Fig. 5 is the bacterium imaging results figure of 1 gained PVA-TPE of embodiment.
Specific embodiment
Present invention will now be described in further detail with reference to the embodiments and the accompanying drawings, but embodiments of the present invention are unlimited
In this.
Embodiment 1
(1) it prepares PVA-DEEDA: polyvinyl alcohol (5.0g, hydroxyl mole are 0.12mol) is dissolved in 100mL DMSO,
90 DEG C of stirring and dissolvings.After being completely dissolved, room temperature is dropped to, it is small that CDI (7.8g, 0.048mol) is added to activation 3 in above-mentioned solution
When, 22 DEG C of DEEDA (6.7mL, 0.048mol), which are slowly added to, then to above-mentioned solution reacts 20 hours.It is added 50mL's 25%
Ammonia spirit stirs 1 hour, removes unreacted CDI.Reaction was completed, precipitates in acetone, and sediment is dissolved in deionized water
In, it dialyses 3 days, freeze-drying obtains modified polyvinylalcohol.The weight average molecular weight of polyvinyl alcohol is preferably 85000~124000.
(2) prepare PVA-TPE: the PVA-DEEDA (600mg, 16.4mmol) that step (1) obtains is dissolved in 12mL DMSO,
TPE-CH is then added until being completely dissolved in stirring2Br (35mg, 0.082mmol), 70 DEG C of heating are reacted 24 hours, and acetone is heavy
It forms sediment, sediment is dissolved in deionized water, dialyse 3 days, be lyophilized up to PVA-TPE.
Nuclear-magnetism test, the result is shown in Figure 1 are carried out to PVA-DEEDA, PVA-TPE of the preparation of this example.
PH responsiveness characterization is carried out to the PVA-TPE of this example preparation, as a result sees Fig. 2.
Cytotoxicity characterization is carried out to the PVA-TPE that this example is prepared, chooses l cell
(L929cells) it is tested.By L929 cell with 5 × 103The density of cells/well is seeded in 96 orifice plates, in 5%CO2、37
It is cultivated 24 hours under the conditions of DEG C, abandons culture medium, the culture medium solution that the PVA-TPE containing various concentration is added continues culture 48 hours,
Culture medium is removed, three times, 100 μ L CCK-8 working solutions are added in every hole to PBS rinse cell, and cell are further cultivated 1 hour,
Every hole absorbance is measured at 450nm using microplate reader and calculates cell survival rate.As a result see Fig. 3.It should be the result shows that this example
The polyvinyl alcohol quaternary ammonium material of preparation has good biocompatibility.
Anti-microbial property research is carried out for the PVA-TPE being prepared in this example.The germy experiment consumptive material of institute is all made of
Autoclave sterilization processing, prevents foreign aid bacterium from having an impact to experimental result.LB culture medium and LB nutrient agar are according to explanation
Book is dissolved in deionized water, is then sterilized using autoclave.After sterilizing, LB culture medium is placed in 4 DEG C of refrigerators and saves；LB
Nutrient agar pours into fabric swatch in batch cultur ware, after solidification to be cooled, collects and is stored in 4 DEG C of refrigerators.
In the culture of bacterium, first with a small amount of bacteria Staphylococcus aureus (ATCC29213) of transfer needle picking and greatly
Enterobacteria (ATCC 15224) is added in 15mL LB culture medium, and culture (220rpm) in shaking table is placed at 37 DEG C, bacterium is set and reaches
To intermediate concentration.Bacterium solution is subjected to gradient dilution, and applies and invests on agar plate.Attached agar plate will be applied and be placed in 37 DEG C of mould trainings
Feeding case is incubated overnight, until agar plate surface grows bacterium colony.The suitable agar plate of bacterium colony concentration is chosen, transfer needle picking list is utilized
A bacterium colony is placed in 15mL and shakes in tube, and 3-5mL fresh LB is added, and it is small that culture (220rpm) 5 in shaking table is placed at 37 DEG C
When, so that bacterial concentration is reached medium level.
The PVA-TPE solution of various concentration is placed in 1.5mL centrifuge tube, 200 μ l diluted concentrations are added in each hole is
106The bacterial solution of cfu/mL is placed in shaking table 150rpm at 37 DEG C and cultivates 2 hours.After 2 hours, bacterium solution gradient dilution, and point
It does not take 10 μ l painting to invest on agar plate, then places it in mold incubator and be incubated overnight, when bacterium colony size is suitable,
The agar plate for choosing suitable concentration gradient carries out count of bacteria.As a result see Fig. 4.It should be the result shows that compared to Gram-negative
Bacterium, material have better antibiotic property for gram-positive bacteria.
Bacterium imaging representation is carried out to the PVA-TPE of this example preparation.Choose staphylococcus aureus (ATCC29213) into
Row experiment, PVA-TPE solution is placed in 1.5mL centrifuge tube, and it is 10 that 200 μ l diluted concentrations are added in each hole6Cfu/mL's
Bacterial solution is placed in shaking table 150rpm at 37 DEG C and cultivates 2 hours, will mixing drop on laser co-focusing ware, be used for laser
Confocal microscopy.Its bacterium imaging results is shown in Fig. 5.Should the result shows that material have to gram-positive bacteria it is good thin
Bacterium imaging function.
Embodiment 2
(1) it prepares PVA-DEEDA: polyvinyl alcohol (5.0g, hydroxyl mole are 0.12mol) is dissolved in 100mL DMSO,
90 DEG C of stirring and dissolvings.After being completely dissolved, room temperature is dropped to, it is small that CDI (9.2g, 0.06mol) is added to middle activation 3 in above-mentioned solution
When, 22 DEG C of DEEDA (8mL, 0.06mol), which are slowly added to, then to above-mentioned solution reacts 20 hours.The ammonium hydroxide of 50mL 25% is added
Solution stirs 1 hour, removes unreacted CDI.Reaction was completed, precipitates in acetone, and sediment is dissolved in deionized water,
Dialysis 3 days, freeze-drying obtain modified polyvinylalcohol.The weight average molecular weight of polyvinyl alcohol is preferably 85000~124000.
(2) prepare PVA-TPE: the PVA-DEEDA (600mg, 16.4mmol) that step (1) obtains is dissolved in 12mL DMSO,
TPE-CH is then added until being completely dissolved in stirring2Br (35mg, 0.082mmol), 70 DEG C of heating are reacted 24 hours, and acetone is heavy
It forms sediment, sediment is dissolved in deionized water, dialyse 3 days, be lyophilized up to PVA-TPE.
Embodiment 3
(1) it prepares PVA-DEEDA: polyvinyl alcohol (5.0g, hydroxyl mole are 0.12mol) is dissolved in 100mL DMSO,
90 DEG C of stirring and dissolvings.After being completely dissolved, room temperature is dropped to, it is small that CDI (11.7g, 0.072mol) is added to activation 3 in above-mentioned solution
When, 22 DEG C of DEEDA (10mL, 0.072mol), which are slowly added to, then to above-mentioned solution reacts 20 hours.The ammonia of 50mL 25% is added
Aqueous solution stirs 1 hour, removes unreacted CDI.Reaction was completed, precipitates in acetone, and sediment is dissolved in deionized water
In, it dialyses 3 days, freeze-drying obtains modified polyvinylalcohol.The weight average molecular weight of polyvinyl alcohol is preferably 85000~124000.
(2) prepare PVA-TPE: the PVA-DEEDA (600mg, 16.4mmol) that step (1) obtains is dissolved in 12mL DMSO,
TPE-CH is then added until being completely dissolved in stirring2Br (35mg, 0.082mmol), 70 DEG C of heating are reacted 24 hours, and acetone is heavy
It forms sediment, sediment is dissolved in deionized water, dialyse 3 days, be lyophilized up to PVA-TPE.
Embodiment 4
(1) it prepares PVA-DEEDA: polyvinyl alcohol (5.0g, hydroxyl mole are 0.12mol) is dissolved in 100mL DMSO,
90 DEG C of stirring and dissolvings.After being completely dissolved, room temperature is dropped to, it is small that CDI (9.2g, 0.06mol) is added to activation 3 in above-mentioned solution
When, it is slowly added to DEEDA (8mL, 0.06mol) then to above-mentioned solution, 22 DEG C are reacted 20 hours.The ammonia of 50mL 25% is added
Aqueous solution stirs 1 hour, removes unreacted CDI.Reaction was completed, precipitates in acetone, and sediment is dissolved in deionized water
In, it dialyses 3 days, freeze-drying obtains modified polyvinylalcohol.The weight average molecular weight of polyvinyl alcohol is preferably 85000~124000.
(2) prepare PVA-TPE: the PVA-DEEDA (600mg, 16.4mmol) that step (1) obtains is dissolved in 12mL DMSO,
TPE-CH is then added until being completely dissolved in stirring2Br (70mg, 0.164mmol), 70 DEG C of heating are reacted 24 hours, and acetone is heavy
It forms sediment, sediment is dissolved in deionized water, dialyse 3 days, be lyophilized up to PVA-TPE.
Embodiment 5
(1) it prepares PVA-DEEDA: polyvinyl alcohol (5.0g, hydroxyl mole are 0.12mol) is dissolved in 100mL DMSO,
90 DEG C of stirring and dissolvings.After being completely dissolved, room temperature is dropped to, it is small that CDI (9.2g, 0.06mol) is added to activation 3 in above-mentioned solution
When, it is slowly added to DEEDA (8mL, 0.06mol) then to above-mentioned solution, 22 DEG C are reacted 20 hours.The ammonia of 50mL 25% is added
Aqueous solution stirs 1 hour, removes unreacted CDI.Reaction was completed, precipitates in acetone, and sediment is dissolved in deionized water
In, it dialyses 3 days, freeze-drying obtains modified polyvinylalcohol.The weight average molecular weight of polyvinyl alcohol is preferably 85000~124000.
(2) prepare PVA-TPE: the PVA-DEEDA (600mg, 16.4mmol) that step (1) obtains is dissolved in 12mL DMSO,
TPE-CH is then added until being completely dissolved in stirring2Br (105mg, 0.246mmol), 70 DEG C of heating are reacted 24 hours, acetone
Precipitating, sediment is dissolved in deionized water, is dialysed 3 days, is lyophilized up to PVA-TPE.
The above embodiment is a preferred embodiment of the present invention, but embodiments of the present invention are not by above-described embodiment
Limitation, other any changes, modifications, substitutions, combinations, simplifications made without departing from the spirit and principles of the present invention,
It should be equivalent substitute mode, be included within the scope of the present invention.
Claims (10)
1. a kind of responsiveness quaternization polyvinyl alcohol of tetraphenylethylene label, it is characterised in that: the tetraphenylethylene mark
The responsiveness quaternization polyvinyl alcohol of note has the structural formula as described in following formula (I):
X in formula, y, z indicate the degree of polymerization of each repetitive unit.
2. a kind of responsiveness quaternization polyvinyl alcohol of tetraphenylethylene label according to claim 1, feature exist
In: x+y+z=1932~2818 in formula (I).
3. a kind of preparation method of the responsiveness quaternization polyvinyl alcohol of tetraphenylethylene label of any of claims 1 or 2,
It is characterized by comprising following preparation steps:
(1) PVA is dissolved in organic solvent, activator CDI is added and is activated, DEEDA is then added and is reacted, removal of impurities,
PVA-DEEDA is obtained after precipitating, purifying, drying；
(2) PVA-DEEDA is dissolved in organic solvent, TPE-CH is then added2Br heating reaction, precipitates, purifies, dry, obtains
PVA-TPE。
4. a kind of preparation side of the responsiveness quaternization polyvinyl alcohol of tetraphenylethylene label according to claim 3
Method, it is characterised in that: the weight average molecular weight of polyvinyl alcohol described in step (1) is 85000~124000；The organic solvent is
DMSO；The reaction temperature is 22 DEG C, and the reaction time is 20~36h.
5. a kind of preparation side of the responsiveness quaternization polyvinyl alcohol of tetraphenylethylene label according to claim 3
Method, it is characterised in that: removal of impurities is that ammonia spirit is added into solution described in step (1), removes unreacted activator CDI；
The precipitating refers to be precipitated in acetone；The purifying, which refers to, dissolves sediment with water, then dialyses, obtains purified product；
The drying is freeze-drying.
6. a kind of preparation side of the responsiveness quaternization polyvinyl alcohol of tetraphenylethylene label according to claim 3
Method, it is characterised in that: the molar ratio of PVA and activator CDI is 1:(0.4~0.6 in step (1))；Mole of PVA and DEEDA
Than for 1:(0.4~0.6).
7. a kind of preparation side of the responsiveness quaternization polyvinyl alcohol of tetraphenylethylene label according to claim 3
Method, it is characterised in that: organic solvent described in step (2) is DMSO；The heating reaction refers to reacts in 50~70 DEG C of heating
24~36h.
8. a kind of preparation side of the responsiveness quaternization polyvinyl alcohol of tetraphenylethylene label according to claim 3
Method, it is characterised in that: PVA-DEEDA and TPE-CH in step (2)2The molar ratio of Br is 1:(0.005~0.015).
9. a kind of preparation side of the responsiveness quaternization polyvinyl alcohol of tetraphenylethylene label according to claim 3
Method, it is characterised in that: the precipitating reagent of precipitating described in step (2) is acetone；The purifying, which refers to, dissolves sediment with water, so
After dialyse, obtain purified product；The drying is freeze-drying.
10. a kind of responsiveness quaternization polyvinyl alcohol of tetraphenylethylene label of any of claims 1 or 2 is as antibacterial agent
Application.
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| CN110845662A (en) * | 2019-11-28 | 2020-02-28 | 华南理工大学 | Polymer with highest critical solution temperature and aggregation-induced emission fluorescence property, and preparation and application thereof |
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| CN111718435A (en) * | 2020-06-17 | 2020-09-29 | 西北大学 | Antibacterial high-molecular polyvinyl alcohol material, and method and application thereof |
| CN116531557A (en) * | 2023-05-26 | 2023-08-04 | 中国人民解放军南部战区总医院 | Polymer antibacterial material and preparation method and application thereof |
| CN116763977A (en) * | 2023-05-26 | 2023-09-19 | 中国人民解放军南部战区总医院 | Dressing doped with rubidium-containing mesoporous bioactive glass loaded with AIE and preparation method thereof |
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