CN108192020A - A kind of preparation method of intelligent amphoteric ion polymer material - Google Patents
A kind of preparation method of intelligent amphoteric ion polymer material Download PDFInfo
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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
- 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
- C08F220/10—Esters
- C08F220/34—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate
- C08F220/36—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate containing oxygen in addition to the carboxy oxygen, e.g. 2-N-morpholinoethyl (meth)acrylate or 2-isocyanatoethyl (meth)acrylate
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- C—CHEMISTRY; METALLURGY
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F230/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
- C08F230/02—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing phosphorus
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- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/38—Boron-containing compounds
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- 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
- C08F220/10—Esters
- C08F220/34—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate
- C08F220/36—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate containing oxygen in addition to the carboxy oxygen, e.g. 2-N-morpholinoethyl (meth)acrylate or 2-isocyanatoethyl (meth)acrylate
- C08F220/365—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate containing oxygen in addition to the carboxy oxygen, e.g. 2-N-morpholinoethyl (meth)acrylate or 2-isocyanatoethyl (meth)acrylate containing further carboxylic moieties
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/38—Boron-containing compounds
- C08K2003/387—Borates
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Abstract
A kind of preparation method of intelligent amphoteric ion polymer material, includes the following steps：(1) it is zwitterionic monomer, function monomer, reinforcing agent, crosslinking agent and catalyst is soluble in water, accelerator reaction is then added dropwise at 20~40 DEG C；(2) 40~55 DEG C are warming up to again the reaction was continued after being flowed to system unobvious gradually heating is dried to obtain the intelligent amphoteric ion polymer material.The method of the present invention prepares while has the function of the intelligent macromolecule material of shape memory, selfreparing and antipollution etc. using glycine betaine monomer as primary raw material.
Description
Technical field
The present invention relates to a kind of preparation methods of intelligent amphoteric ion polymer material, remember more particularly to shape
Recall, selfreparing, the high molecular material of functions such as resistance tocrocking preparation method, belong to biomimetic material, biomedicine, drug release
Technical field.
Background technology
At present, more and more artificial materials are in biological detection, biochemical equipment, biological engineering material and body implanting material
It is used widely in the fields of grade.In biomaterial, high molecular material is with raw material is extensive, MOLECULE DESIGN is flexible, performance is various
The advantages such as change and easy processing.Wherein, intelligent polymer material is one of material with the fastest developing speed.So-called intellectual material is
Change the stimuli responsive material for generating kickback to microenvironment around, these reactions show as change in shape, surface characteristics
Or dissolubility, complicated molecule self assembly, solution is to phase transition of gel etc..
Stimulating responsive polymer is the macromolecular system with " intelligence " behavior, when the stimulus signal for receiving external environment
Afterwards, the certain physical properties of its own or chemical property such as molecular configuration, dissolubility, formation of chemical bond fracture etc. embody spy
Some intelligent behavior.External environment stimulation mode is broadly divided into chemical stimulation and physical stimulation two types.Chemical stimulation mode
Polymer molecule chain structure can be changed, change polymer molecular chain between or polymer molecular chain and solvent between interact
Chemical factor, such as pH value, ionic strength and redox.Physical stimulation, which refers to, can cause interaction and various energy between molecule
Measure the factor changed, such as temperature, light, electric field and mechanical stress.These outside stimulus modes so that polymer architecture generation can
Inverse or irreversible variation, the body phase or liquid phase behavior for causing system change.Therefore, stimulus responsive polymers are in nanometer material
It has a wide range of applications in material science, life science and clinical medicine domain.
In stimulus responsive polymers, shape memory high molecule, self-healing polymers etc. are all several important intellectual materials.
Typical shape-memory polymer (SMP) " can remember " macroscopical (permanent) shape, fixed under the conditions of extraneous temperature and pressure
For interim and static in shape, then by being returned to original state under the environmental Kuznets Curves such as temperature, light, water.SMP is this in different condition
Lower tool gives material in the fields such as sensor, smart machine application value there are two types of performance of different shapes.Selfreparing macromolecule
Material (SHP) is then inspired by the Nature, and the healing of mimic biology bulk damage by substance supply or energy supply mechanism, makes
The indiscoverable microfissure of naked eyes can be healed automatically into the micro-damage for exercising material during material processing or use.
This characteristic extends the materials'use service life, reduces use cost.Therefore, shape memory and selfreparing be all material " intelligence " and
" it is desirable that " feature, this just causes more and more researchers structure to have selfreparing and the research of shape memory property.
It is both at home and abroad that intelligent macromolecule is applied to biomedical sector in the research tendency of intellectual material.However, mostly
Number shape-memory polymer does not all have ideal biocompatibility, by taking shape memory polyurethane as an example, meeting in implantation human body
Cause the inflammatory reaction of body.Amphoteric ion polymer is as a kind of special high molecular material, because it has excellent biofacies
Capacitive has caused extensive concern.
Invention content
For this purpose, the purpose of the present invention is to provide a kind of preparation method of intelligent amphoteric ion polymer material, the party
Method prepares while has the function of the intelligent high score of shape memory, selfreparing and antipollution etc. using glycine betaine monomer as primary raw material
Sub- material.
In order to achieve the above object, the present invention adopts the following technical scheme that：
A kind of preparation method of intelligent amphoteric ion polymer material, includes the following steps：
(1) it is zwitterionic monomer, function monomer, reinforcing agent, crosslinking agent and catalyst is soluble in water, then 20~40
Accelerator reaction is added dropwise at DEG C；
(2) being warming up to 40~50 DEG C, the reaction was continued to the flowing of system unobvious；Heating in the step can improve monomer and turn
Rate increases material molecule amount and intensity；
(3) further heating is dried to obtain the intelligent amphoteric ion polymer material.
The method of the present invention is primary raw material with zwitterionic monomer, such as betaine type amphoteric ion monomer, passes through freedom
Base copolyreaction makes polymer formation dual-network structure that intelligent amphoteric ion polymer material be made, and preparation process has item
The advantages such as part is mild, simple for process and operating condition is stablized.
Amphoteric ion polymer (also known as both sexes betaine polymer or polyampholyte) is one kind while has yin, yang
The polymer of ionic group, positive and negative charge number is identical on side chain and electroneutral is presented.The solvent of these negative ions groups
Change effect is very strong, and can be acted on by oxygen key makes polymer surfaces form one layer of hydrated sheath, so as to effectively impedance non-protein
Absorption etc..Therefore, amphoteric ion polymer has critically important biological nature, in nanometer material science, life science and clinical doctor
In field have a wide range of applications.
Intelligent amphoteric ion polymer material produced by the present invention not only has good shape memory and selfreparing work(
Can, it is adsorbed herein in connection with the excellent biological nature of amphoteric ion polymer and anti-non-protein, makes it in bionic material, medicine etc.
There is certain application prospect in field, and high molecular material " intelligent " feature finds full expression.
Preferably, the addition for counting each component in step (1) in parts by weight is 18~35 parts of zwitterionic monomer, work(
2~8 parts of monomer of energy, 40~75 parts of water, 0.1~2 part of crosslinking agent, 0.2~2.5 part of catalyst, 0.4~4 part of accelerator, reinforcing agent
1~5 part, preferably 18~35 parts of zwitterionic monomer, 2~8 parts of function monomer, 55~75 parts of water, 0.1~2 part of crosslinking agent are urged
0.2~2.5 part of agent, 1~4 part of accelerator, 1.5~4 parts of reinforcing agent.
Preferably, the water is deionized water.
Preferably, zwitterionic monomer, function monomer, reinforcing agent, crosslinking agent and catalyst rear stirring 2~10 soluble in water
Hour makes up to substantially uniformity.
Preferably, zwitterionic monomer, function monomer, reinforcing agent, crosslinking agent and catalyst rear deoxygenation soluble in water, it is such as logical
Cross at least one of vacuum nitrogen gas or inert gas and repeated multiple times with deoxygenation.
Preferably, the zwitterionic monomer is carboxylic acid glycine betaine methyl methacrylate, methacryloylethyl sulfo group
One kind or two or more combination in glycine betaine or methacryloxyethyl Phosphorylcholine.
Preferably, the function monomer for hydroxyethyl methacrylate, 2- methyl -2- acrylic acid -2,3- dihydroxy propyl ester,
One kind or two or more combination in 3,4- dihydroxy benzenes acrylic or methacrylic acid hydroxypropyl acrylates.
Preferably, the crosslinking agent be phenyl boric acid, borax, N, in N- methylene-bisacrylamides or boric acid a kind or 2 kinds with
On combination, preferably phenyl boric acid and/or boric acid.Borate ester cross-linking system is introduced into polymeric system, has network material
There is reversible transformation function, regulate and control in performance and control the application function enhancing in release field.
Preferably, the catalyst agent is overcurrent acid potassium, hydrogen peroxide, isopropyl benzene hydroperoxide, sodium chlorate or persulfuric acid
Ammonium.
Preferably, the accelerator is sodium thiosulfate, ferrous sulfate, lauryl mercaptan or tetramethylethylenediamine.
Preferably, the reinforcing agent is polyvinyl alcohol, polyethylene glycol oxide or polyacrylic acid.
Preferably, the time that accelerator reaction is added dropwise is 0.5~1.5 hour.Reaction preferably carries out under stiring.
Preferably, reaction mixture is transferred in cuboid Teflon mould step (1) after reaction.
Preferably, a height of 70mm*15mm*10mm of the length and width of cuboid Teflon mould.
Preferably, it is 20~24 hours that step (2), which is warming up to 40~50 DEG C of times that the reaction was continued,.
Preferably, the mode of step (3) heating drying is dried 8~10 hours, then heat up to be first warming up to 50~65 DEG C
It is 20~24 hours dry to 65~90 DEG C.Cool down after drying from the polymer samples being removed from the molds.In order to allow
Water volatilization is by the way of stage heating drying, to prevent from generating the performance of aeration material, above-mentioned liter in water volatilization process
Warm mode then can farthest reduce the generation of bubble so that it is best that material property is made.
Preferably, the preparation method of the present invention includes the following steps：
By the zwitterionic monomer measured, function monomer, reinforcing agent, crosslinking agent, catalyst is dissolved in closed reactor
With a certain amount of deionized water dissolving, stirring makes up to substantially uniformity for 2~10 hours, and vacuum nitrogen gas simultaneously repeated multiple times is removed
Oxygen；It controls 20~40 DEG C of temperature that quantitative accelerator is added dropwise, and size is poured into after reacting 0.5~1.5 hour under stiring as 70mm*
In 15mm*10mm Teflon moulds, then it is warming up to 40~50 DEG C and stands reaction 20~24 hours；When reaction system unobvious
50~65 DEG C and 8~10 hours dry are gradually warming up to during flowing, then is warming up to 65~90 DEG C of dryings 20~24 hours, after cooling
The amphoteric ion polymer sample being removed from the molds.
The present invention has the advantages that compared with the prior art：
1st, the present invention provides the preparation method of " intelligent " amphoteric ion network structure polymer material, the material is not only
Possess the properties such as shape memory and selfreparing, and amphoteric ion polymer introducing makes material have excellent biological nature
With the functions such as antipollution, there is certain application prospect in fields such as bionic material, medicine.
2nd, borate ester cross-linking system is introduced polymeric system by the present invention, and network material is made to have the function of reversible transformation,
Regulate and control in performance and control the application function enhancing in release field.
3rd, preparation method provided by the invention is simple, and reaction condition is mild, and technological operation is stablized, and exploitativeness is strong, comprehensive
It is at low cost, remarkable in economical benefits.
Specific embodiment
Of the invention for ease of understanding, it is as follows that the present invention enumerates embodiment.Those skilled in the art are it will be clearly understood that the implementation
Example is used only for helping to understand the present invention, is not construed as the concrete restriction to the present invention.
80 DEG C of conditions of selection carry out shape fixed rate and recovery rate performance test；Fragmentation polymerization is measured by universal testing machine
Self-repair efficiency after object material selfreparing 24 hours；Pass through the anti-hemoglobin adsorptivity of ultraviolet specrophotometer test material
Energy.
Embodiment 1
A kind of preparation method of intelligent amphoteric ion polymer material, includes the following steps：
(1) preparation of function monomer：By 13 parts of glycidyl methacrylate, 87 parts of deionized waters and 1 part to benzene two
Phenol is added in the reactor with condenser pipe.It is warming up to 85 DEG C and forms homogeneous phase aqueous solution after stirring initial latex 11 hours, revolve
Turn moisture in evaporation mixed liquor, hydroquinone is removed with neutral alundum (Al2O3), obtain weak yellow liquid as function monomer：2- first
Base -2- acrylic acid -2,3- dihydroxy propyl ester.
(2) preparation of intelligent amphoteric ion polymer：It will be on 20 parts of carboxylic acid glycine betaine methyl methacrylates, 6.5 parts
Self-control function monomer, 64 parts of deionized waters, 2 parts of boric acid are stated, 3 parts of polyvinyl alcohol, 1.5 parts of ammonium persulfates, which weigh, adds in reactor,
Stirring is allowed to dissolve and be uniformly mixed for 2 hours or so, vacuum nitrogen gas, repeated multiple times abundant deoxygenation.Control 30 DEG C of drops of temperature
Add 3 parts of tetramethylethylenediamines, poured into Teflon mould after stirring lower reaction 1h, then to be warming up to 40 DEG C of arrest reactions 24 small
When.55 DEG C of dry 10h are warming up to when reaction system unobvious flow, then are warming up to 85 DEG C of dryings for 24 hours, after cooling from mold
Take out polymer samples.
Shape fixed rate 96% under the conditions of 80 DEG C after measured, shape recovery rate 91%, for 24 hours after self-repair efficiency 81%, blood
The anti-adsorption rate 95% of albumin.
Embodiment 2
A kind of preparation method of intelligent amphoteric ion polymer material, includes the following steps：
(1) preparation of function monomer is the same as embodiment 1.
(2) preparation of intelligent amphoteric ion polymer：By 22 parts of methacryloylethyl sulfobetaines, 3 parts it is above-mentioned
Make function monomer, 65 parts of deionized waters, 3 parts of polyacrylic acid by oneself, 2 parts of boric acid, it is small that 2 parts of ammonium persulfates add in three-necked flask stirring 3
When be allowed to be completely dissolved, vacuum nitrogen gas, repeated multiple times abundant deoxygenation.Temperature 30 DEG C of dropwise additions, 3 parts of tetramethylethylenediamines are controlled,
The lower reaction of stirring is poured into after 1 hour in Teflon mould.It is warming up to 40 DEG C of arrest reactions again 22 hours.When reaction system into
55 DEG C of dryings 10 hours are warming up to after gel, then are warming up to 85 DEG C of dryings 24 hours, are taken out after cooling from mold polymer-like
Product.
Shape fixed rate 95% under the conditions of 80 DEG C after measured, shape recovery rate 92%, self-repair efficiency 82% after 24 hours,
The anti-adsorption rate 96% of haemocyanin.
Embodiment 3
A kind of preparation method of intelligent amphoteric ion polymer material, includes the following steps：
1.5 parts of N, N- methylene-bisacrylamides and 67 parts of deionized waters are added in three-necked flask and are stirred 1~2 hour.It treats
Again by 20 parts of carboxylic acid glycine betaine methyl methacrylates, 5 parts of hydroxyethyl methacrylates, 2.5 parts of polyoxyethylenes after being completely dissolved
Alkene, the metered three-necked flask of 2 parts of ammonium persulfates simultaneously continue stirring and are allowed to be completely dissolved for 1 hour, and vacuum nitrogen gas is repeatedly more
Secondary abundant deoxygenation.It controls 35 DEG C of temperature and adds in 2 parts of sodium thiosulfate, and polytetrafluoroethyl-ne is poured into after reacting 1 hour under stiring
In alkene mold, 45 DEG C of heating arrest reaction 24 hours.Be warming up to when reaction system unobvious flow 60 DEG C of dryings 9 it is small when, then
90 DEG C of dryings 24 hours are warming up to, polymer samples are taken out after cooling.
Shape fixed rate 90% under the conditions of 80 DEG C after measured, shape recovery rate 90%, self-repair efficiency 80% after 24 hours,
The anti-adsorption rate 96% of haemocyanin.
Embodiment 4
A kind of preparation method of intelligent amphoteric ion polymer material, includes the following steps：
By 25 parts of methacryloxyethyl Phosphorylcholines, 4 parts of hydroxy propyl methacrylates, 60 parts of deionized waters, 2 parts
Phenyl boric acid, 3 parts of polyvinyl alcohol, 2 parts of potassium peroxydisulfates add in three-necked flask stirring and are allowed to be completely dissolved within 3 hours or so and mix
It is even, vacuum nitrogen gas, repeated multiple times abundant deoxygenation.Temperature 33 DEG C of dropwise additions, 4 parts of tetramethylethylenediamines are controlled, and anti-under stiring
It is poured into Teflon mould after answering 0.5 hour, then is warming up to 40 DEG C of arrest reactions 24 hours.When reaction system unobvious stream
55 DEG C of dryings 10 hours are warming up to when dynamic, then are warming up to 85 DEG C of dryings 24 hours, polymer samples are taken out after cooling.
Shape fixed rate 91% under the conditions of 80 DEG C after measured, shape recovery rate 92%, 24 hours self-repair efficiencies 80%, blood
The anti-adsorption rate 94% of albumin.
The obtained material of the present invention has high shape fixed rate and shape recovery rate, makes it in medical bionics material as propped up
The fields such as frame, bionic glue band are using more.The shape of this intellectual material can change with outside stimulus condition；Self-healing properties
Crackle, micro-damage that material generates when applying is enable to obtain to heal automatically under conditions of renovation agent is not added with, is prolonged the service life；
Possible contaminated wound or adsorbed proteins etc., zwitterionic materials prepared by the present invention have water to general biomimetic material when in use
Cooperation becomes the outstanding person of stain resistant material with that can eliminate these negative effects.
Obviously, the above embodiments are merely examples for clarifying the description, and is not intended to limit the embodiments.It is right
For those of ordinary skill in the art, can also make on the basis of the above description it is other it is various forms of variation or
It changes.There is no necessity and possibility to exhaust all the enbodiments.And the obvious variation thus extended out or
Among changing still in the protection domain of the invention.
Claims (10)
1. a kind of preparation method of intelligent amphoteric ion polymer material, includes the following steps：
(1) it is zwitterionic monomer, function monomer, reinforcing agent, crosslinking agent and catalyst is soluble in water, then at 20~40 DEG C
Accelerator reaction is added dropwise；
(2) being warming up to 40~50 DEG C, the reaction was continued to the flowing of system unobvious；；
(3) further heating is dried to obtain the intelligent amphoteric ion polymer material.
2. preparation method according to claim 1, which is characterized in that count the addition of each component in step (1) in parts by weight
It measures as 18~35 parts of zwitterionic monomer, 2~8 parts of function monomer, 40~75 parts of water, 0.1~2 part of crosslinking agent, catalyst 0.2~
2.5 parts, 0.4~4 part of accelerator, 1~5 part of reinforcing agent.
3. preparation method according to claim 1 or claim 2, which is characterized in that zwitterionic monomer described in step (1) is carboxylic acid
1 in glycine betaine methyl methacrylate, methacryloylethyl sulfobetaines or methacryloxyethyl Phosphorylcholine
Kind or combination of more than two kinds.
4. according to any one of the claim 1-3 preparation methods, which is characterized in that function monomer described in step (1) is first
Base hydroxy-ethyl acrylate, 2- methyl -2- acrylic acid -2,3- dihydroxy propyl ester, Ferulic Acid or methacrylic acid
One kind or two or more combination in hydroxypropyl acrylate.
5. according to any one of the claim 1-4 preparation methods, which is characterized in that crosslinking agent described in step (1) is benzene boron
Acid, borax, N, one kind or two or more combination, preferably phenyl boric acid and/or boric acid in N- methylene-bisacrylamides or boric acid.
6. according to any one of the claim 1-5 preparation methods, which is characterized in that catalyst agent described in step (1) was
The sour potassium of stream, hydrogen peroxide, isopropyl benzene hydroperoxide, sodium chlorate or ammonium persulfate；
Preferably, the accelerator is sodium thiosulfate, ferrous sulfate, lauryl mercaptan or tetramethylethylenediamine；
Preferably, the reinforcing agent is polyvinyl alcohol, polyethylene glycol oxide or polyacrylic acid.
7. according to any one of the claim 1-6 preparation methods, which is characterized in that zwitterionic monomer, function in step (1)
Monomer, reinforcing agent, crosslinking agent and catalyst stirring 2~10 hours afterwards soluble in water；
Preferably, zwitterionic monomer, function monomer, reinforcing agent, crosslinking agent and catalyst rear deoxygenation soluble in water.
8. according to any one of the claim 1-7 preparation methods, which is characterized in that accelerator reaction is added dropwise in step (1)
Time is 0.5~1.5 hour；
Preferably, reaction mixture is transferred in cuboid Teflon mould step (1) after reaction；
Preferably, a height of 70mm*15mm*10mm of the length and width of cuboid Teflon mould.
9. according to any one of the claim 1-8 preparation methods, which is characterized in that be warming up in step (2) 40~50 DEG C after
The time of continuous reaction is 20~24 hours.
10. according to any one of the claim 1-9 preparation methods, which is characterized in that heating drying mode is first in step (3)
It is warming up to 50~65 DEG C, it is 8~10 hours dry, then it is warming up to 65~90 DEG C of dryings 20~24 hours.
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| CN109970999A (en) * | 2019-03-15 | 2019-07-05 | 浙江工业大学 | A kind of chitosan/polysulfonate acidic group beet basic ion is for valence double-network hydrogel and preparation method thereof |
| CN111714410A (en) * | 2019-12-27 | 2020-09-29 | 杭州薄尔道格科技有限公司 | Non-phosphoric acid oral care composition and preparation method thereof |
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| CN113045698A (en) * | 2019-12-27 | 2021-06-29 | 黄石市森尔新型材料有限公司 | Zwitterionic polymer and preparation method and application thereof |
| CN113073477A (en) * | 2021-03-22 | 2021-07-06 | 四川大学 | Super-hydrophilic anti-fouling cotton fabric for oil-water separation and zwitterionic hydrogel for cotton fabric |
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| CN114592350A (en) * | 2022-03-07 | 2022-06-07 | 盐城工业职业技术学院 | Knitted fabric with dual functions of warm keeping, ventilation and air purification and preparation method thereof |
| CN115181381A (en) * | 2022-06-02 | 2022-10-14 | 天津大学 | Hydrogel for preserving cells at low temperature and monitoring ROS content in real time, preparation and application thereof |
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