CN109612808B - Hydrophilic glass slide for medical detection - Google Patents

Hydrophilic glass slide for medical detection Download PDF

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CN109612808B
CN109612808B CN201910113114.XA CN201910113114A CN109612808B CN 109612808 B CN109612808 B CN 109612808B CN 201910113114 A CN201910113114 A CN 201910113114A CN 109612808 B CN109612808 B CN 109612808B
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glass slide
medical detection
hydrophilic glass
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polymer intermediate
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CN109612808A (en
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王丽丽
谭举朋
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    • GPHYSICS
    • G01MEASURING; TESTING
    • G01NINVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N1/00Sampling; Preparing specimens for investigation
    • G01N1/28Preparing specimens for investigation including physical details of (bio-)chemical methods covered elsewhere, e.g. G01N33/50, C12Q
    • G01N1/30Staining; Impregnating ; Fixation; Dehydration; Multistep processes for preparing samples of tissue, cell or nucleic acid material and the like for analysis
    • G01N1/31Apparatus therefor

Abstract

The invention discloses a hydrophilic glass slide for medical detection, which is characterized in that a condensation polymer intermediate is prepared by carrying out condensation polymerization on bis [2- (dimethylamino) ethyl ] (2Z) -2-butenedioic acid ester and 4, 5-dichloro-1, 3-dioxolane-2-one, then a condensation polymer intermediate is prepared by copolymerizing the condensation polymer intermediate, hydrogen furfuryl acrylate, acrylonitrile and ethylene glycol dimethacrylate according to the mass ratio of 2:1 (3-5):1, and finally the condensation polymer intermediate is prepared by soaking the condensation polymer intermediate in a gluconic acid aqueous solution for ion exchange. The hydrophilic glass slide for medical detection disclosed by the invention has the advantages of excellent comprehensive performance, low manufacturing cost, excellent adhesion and wettability, good mechanical property and weather resistance, and safety and environmental friendliness in use.

Description

Hydrophilic glass slide for medical detection
Technical Field
The invention relates to the technical field of biomedical articles, in particular to a hydrophilic glass slide for medical detection.
Background
With the development of science and technology, slides for medical and biological detection are widely applied to cytological diagnosis, pathological experiments, HPV detection and the like, and people have high requirements on the performance and large market demands. At present, a common glass slide is a glass slide with hydrophobic adhesion, and the problem of tissue cell dropping is often caused when the glass slide is applied to the processes of histology, immune tissue cytochemistry, frozen section, specimen preparation, tissue cell section, in-situ hybridization and the like. In addition, the glass specimen cannot be reused after being sealed and used, and certain medical waste is caused by damaged and abandoned glass specimens, so that the glass specimen is very difficult to treat.
Pathological techniques are changing day by day, especially in recent years, rapid development of immunohistochemistry and liquid-based cytology. In the staining process, cells and tissue sections are stained by different methods, and particularly when complex staining such as special staining, Feulgen staining, immunohistochemistry and the like is encountered, the cells and the tissue sections are affected by factors such as high temperature, high pressure, radiation, acid-base corrosion and the like, and the tissue cells are easy to fall off from the glass slide. The treatment of the slide with an adhesive is a common approach to solve this problem, but the prior art adhesive may have problems such as staining of the background of the slide, contamination, etc. Not only influences the daily work of technicians, but also is not beneficial to the diagnosis of pathologists. The method is an effective way for solving the defect, can ensure that the tissue is uniformly dyed, has accurate medical detection, ensures that cells and tissue sections are firmly adhered to the glass slide, and prevents the slide from falling off due to a plurality of factors such as peracid, high temperature, high pressure and the like in the dyeing process.
In medical and biological research, conventional tissue preparation includes fixing proper tissue material with formaldehyde solution, dewatering with alcohol step by step, embedding paraffin, slicing tissue with slicer, mounting on glass slide, coloring with hematoxylin-eosin dye, and sealing in optical resin glue. The used glass slide needs to be boiled in water, soaked in alkali liquor, acid liquor and the like. Therefore, ideal medical examination slides also need to be resistant to xylene, butanone wiping, boiling, acid, base, and dye testing, among other things. The hydrophilic glass slides in the prior art do not have the properties, and in addition, the hydrophilic glass slides generally have the problems of thinness, brittleness, easy breakage, poor mechanical property and poor weather resistance, so the hydrophilic glass slides need to be carefully made and used, can be broken by taking little attention, damage specimens, and particularly, the precious specimens are difficult to recover, and cause difficult-to-compensate loss.
Therefore, the development of a hydrophilic glass slide for medical detection with excellent comprehensive performance becomes an urgent problem to be solved in the industry, and has a very important significance in promoting the development of medical biotechnology.
Disclosure of Invention
In order to overcome the defects in the prior art, the invention provides a hydrophilic glass slide for medical detection, which overcomes the technical defects that the surface of the traditional glass slide is not enough in wettability, cells and tissue slices cannot be firmly adhered to the glass slide in the using process, and the slices are dropped due to multiple factors such as peracid, high temperature, high pressure and the like in the dyeing process, cannot simultaneously resist xylene and butanone wiping, resist boiling, acid, alkali and dye tests, are thin and brittle, are easy to break, have poor mechanical properties and poor weather resistance, and have the advantages of excellent comprehensive performance, low manufacturing cost, excellent adhesion and wettability, good mechanical properties and weather resistance, and safe and environment-friendly use.
In order to achieve the purpose, the technical scheme is that the hydrophilic glass slide for medical detection is characterized in that a condensation polymer intermediate is prepared by carrying out condensation polymerization on bis [2- (dimethylamino) ethyl ] (2Z) -2-butenedioate and 4, 5-dichloro-1, 3-dioxolane-2-one, then the condensation polymer intermediate, hydrogen furfuryl acrylate, acrylonitrile and ethylene glycol dimethacrylate are copolymerized according to the mass ratio of 2:1 (3-5):1 to prepare an addition polymer intermediate, and finally the addition polymer intermediate is soaked in a gluconic acid aqueous solution for ion exchange to prepare the hydrophilic glass slide for medical detection.
The manufacturing method of the hydrophilic glass slide for medical detection is realized by the following steps:
adding bis [2- (dimethylamino) ethyl ] (2Z) -2-butenedioate and 4, 5-dichloro-1, 3-dioxolane-2-one into an organic solvent, stirring and reacting at 30-40 ℃ for 6-8 hours, then performing rotary evaporation to remove the solvent, washing with diethyl ether for 3-5 times, and then performing rotary evaporation to remove the diethyl ether again to obtain a polycondensate intermediate;
II, mixing the polycondensate intermediate prepared in the step I, hydrogen furfuryl acrylate, acrylonitrile, ethylene glycol dimethacrylate and an emulsifier, performing ultrasonic treatment for 15-25 minutes, adding the mixture into a mold, placing the mold into a radiation field in the atmosphere of nitrogen or inert gas, performing radiation by adopting a cobalt 60-gamma radiation method, and performing polymerization reaction for 35-45 minutes to obtain a polyadduct intermediate;
and III, soaking the addition polymer intermediate prepared in the step II in 2-3mol/L gluconic acid aqueous solution for ion exchange for 30-50 hours, then soaking in water for 3-5 hours, taking out and placing in a vacuum drying oven for drying at the temperature of 100-110 ℃ for 18-24 hours, and obtaining the hydrophilic glass slide for medical detection.
Preferably, the mass ratio of the bis [2- (dimethylamino) ethyl ] (2Z) -2-butenedioate to the 4, 5-dichloro-1, 3-dioxolan-2-one to the organic solvent in the step I is 1.8:1 (10-15).
Preferably, the organic solvent is selected from one or more of diethyl ether, dichloromethane and tetrahydrofuran.
Preferably, the mass ratio of the polycondensate intermediate, the hydrogen furfuryl acrylate, the acrylonitrile, the ethylene glycol dimethacrylate and the emulsifier is 2:1 (3-5: 1 (0.1-0.3).
Preferably, the emulsifier is one or more selected from sodium dodecyl benzene sulfonate, polyoxypropylene polyoxyethylene glycerol ether and nonylphenol polyoxyethylene ether.
Preferably, the inert gas is selected from one of helium, neon and argon.
Adopt the produced beneficial effect of above-mentioned technical scheme to lie in:
(1) the hydrophilic glass slide for medical detection provided by the invention has the advantages of simple and easily-operated manufacturing method, easily-obtained raw materials, rich sources, low preparation cost and low dependence on equipment, and is suitable for large-scale production.
(2) The hydrophilic glass slide for medical detection provided by the invention overcomes the defects of insufficient surface wettability of the traditional glass slide, cells and tissue slices can not be firmly adhered to the glass slide in the using process, and the slices can not be simultaneously wiped with dimethylbenzene and butanone due to the dropping caused by various factors such as peracid, high temperature, high pressure and the like in the dyeing process, and have the technical defects of thinness, brittleness, easy breakage, poor mechanical property and poor weather resistance.
(3) The hydrophilic glass slide for medical detection provided by the invention has better wettability and adhesion because of more hydrophilic groups and alkoxy groups in the molecular structure, and contains a diene structure, so that a three-dimensional network structure is formed in an addition polymerization stage, and the comprehensive performance of the glass slide is improved.
(4) The hydrophilic glass slide for medical detection provided by the invention is excellent in material taking, good in biocompatibility, excellent in mechanical property, anti-falling and anti-collision and strong in practicability.
Detailed Description
In order to make the technical solutions of the present invention better understood and make the above features, objects, and advantages of the present invention more comprehensible, the present invention is further described with reference to the following examples. The examples are intended to illustrate the invention only and are not intended to limit the scope of the invention.
Wherein the raw materials are all purchased commercially.
Example 1
A hydrophilic glass slide for medical detection is characterized in that a condensation polymer intermediate is prepared by carrying out condensation polymerization on bis [2- (dimethylamino) ethyl ] (2Z) -2-butenedioate and 4, 5-dichloro-1, 3-dioxolan-2-one, an addition polymer intermediate is prepared by copolymerizing the condensation polymer intermediate, hydrogen furfuryl acrylate, acrylonitrile and ethylene glycol dimethacrylate in a mass ratio of 2:1:3:1, and the addition polymer intermediate is soaked in a gluconic acid aqueous solution for ion exchange.
The manufacturing method of the hydrophilic glass slide for medical detection is realized by the following steps:
adding 18g of bis [2- (dimethylamino) ethyl ] (2Z) -2-butenedioic acid ester and 10g of 4, 5-dichloro-1, 3-dioxolan-2-one into 100g of diethyl ether, stirring and reacting at 30 ℃ for 6 hours, then performing rotary evaporation to remove the solvent, washing with the diethyl ether for 3 times, and then performing rotary evaporation again to remove the diethyl ether to obtain a polycondensate intermediate;
II, mixing 20g of the polycondensate intermediate prepared in the step I, 10g of hydrogen furfuryl acrylate, 30g of acrylonitrile, 10g of ethylene glycol dimethacrylate and 1g of sodium dodecyl benzene sulfonate, performing ultrasonic treatment for 15 minutes, adding the mixture into a mold, placing the mold into a radiation field in a nitrogen atmosphere, and performing radiation by adopting a cobalt 60-gamma radiation method for 35 minutes to perform polymerization reaction to obtain a polyadduct intermediate;
and III, soaking the addition polymer intermediate prepared in the step II in 2mol/L gluconic acid aqueous solution for ion exchange for 30 hours, then soaking in water for 3 hours, taking out, placing in a vacuum drying oven, and drying at 100 ℃ for 18 hours to obtain the hydrophilic glass slide for medical detection.
Example 2
A hydrophilic glass slide for medical detection is characterized in that a condensation polymer intermediate is prepared by carrying out condensation polymerization on bis [2- (dimethylamino) ethyl ] (2Z) -2-butenedioate and 4, 5-dichloro-1, 3-dioxolan-2-one, an addition polymer intermediate is prepared by copolymerizing the condensation polymer intermediate, hydrogen furfuryl acrylate, acrylonitrile and ethylene glycol dimethacrylate in a mass ratio of 2:1:3.5:1, and the addition polymer intermediate is soaked in a gluconic acid aqueous solution for ion exchange.
The manufacturing method of the hydrophilic glass slide for medical detection is realized by the following steps:
i, adding 18g of bis [2- (dimethylamino) ethyl ] (2Z) -2-butenedioate and 10g of 4, 5-dichloro-1, 3-dioxolan-2-one into 110g of dichloromethane, stirring and reacting at 32 ℃ for 6.5 hours, then performing rotary evaporation to remove the solvent, washing with diethyl ether for 4 times, and then performing rotary evaporation again to remove the diethyl ether to obtain a polycondensate intermediate;
II, mixing 20g of the polycondensate intermediate prepared in the step I, 10g of hydrogen furfuryl acrylate, 35g of acrylonitrile, 10g of ethylene glycol dimethacrylate and 1.5g of polyoxypropylene polyoxyethylene glycerol ether, performing ultrasonic treatment for 17 minutes, adding the mixture into a mold, placing the mold into a radiation field in a helium atmosphere, and performing radiation by adopting a cobalt 60-gamma radiation method for 37 minutes to perform polymerization reaction to obtain a polycondensate intermediate;
and III, soaking the addition polymer intermediate prepared in the step II in 2.3mol/L gluconic acid aqueous solution for ion exchange for 35 hours, then soaking in water for 3.5 hours, taking out, and drying in a vacuum drying oven at 103 ℃ for 20 hours to obtain the hydrophilic glass slide for medical detection.
Example 3
A hydrophilic glass slide for medical detection is characterized in that a condensation polymer intermediate is prepared by carrying out condensation polymerization on bis [2- (dimethylamino) ethyl ] (2Z) -2-butenedioate and 4, 5-dichloro-1, 3-dioxolan-2-one, an addition polymer intermediate is prepared by copolymerizing the condensation polymer intermediate, hydrogen furfuryl acrylate, acrylonitrile and ethylene glycol dimethacrylate in a mass ratio of 2:1:4:1, and the addition polymer intermediate is soaked in a gluconic acid aqueous solution for ion exchange.
The manufacturing method of the hydrophilic glass slide for medical detection is realized by the following steps:
adding 18g of bis [2- (dimethylamino) ethyl ] (2Z) -2-butenedioic acid ester and 10g of 4, 5-dichloro-1, 3-dioxolan-2-one into 130g of tetrahydrofuran, stirring and reacting at 35 ℃ for 7 hours, then performing rotary evaporation to remove the solvent, washing with diethyl ether for 4 times, and then performing rotary evaporation again to remove the diethyl ether to obtain a polycondensate intermediate;
II, mixing 20g of polycondensate intermediate prepared in the step I, 10g of hydrogen furfuryl acrylate, 40g of acrylonitrile, 10g of ethylene glycol dimethacrylate and 2g of nonylphenol polyoxyethylene ether, performing ultrasonic treatment for 19 minutes, adding the mixture into a mold, placing the mold into a radiation field in a neon atmosphere, and performing radiation by adopting a cobalt 60-gamma radiation method for 39 minutes to perform polymerization reaction to obtain a polyadduct intermediate;
and III, soaking the addition polymer intermediate prepared in the step II in 2.5mol/L gluconic acid aqueous solution for ion exchange for 40 hours, then soaking in water for 4 hours, taking out, placing in a vacuum drying oven, and drying at 105 ℃ for 21 hours to obtain the hydrophilic glass slide for medical detection.
Example 4
A hydrophilic glass slide for medical detection is characterized in that a condensation polymer intermediate is prepared by carrying out condensation polymerization on bis [2- (dimethylamino) ethyl ] (2Z) -2-butenedioate and 4, 5-dichloro-1, 3-dioxolan-2-one, an addition polymer intermediate is prepared by copolymerizing the condensation polymer intermediate, hydrogen furfuryl acrylate, acrylonitrile and ethylene glycol dimethacrylate in a mass ratio of 2:1:4.5:1, and the addition polymer intermediate is soaked in a gluconic acid aqueous solution for ion exchange.
The manufacturing method of the hydrophilic glass slide for medical detection is realized by the following steps:
i, adding 18g of bis [2- (dimethylamino) ethyl ] (2Z) -2-butenedioate and 10g of 4, 5-dichloro-1, 3-dioxolan-2-one into 140g of an organic solvent, stirring and reacting at 38 ℃ for 7.5 hours, then performing rotary evaporation to remove the solvent, washing with diethyl ether for 5 times, and performing rotary evaporation again to remove the diethyl ether to obtain a polycondensate intermediate; the organic solvent is a mixture formed by mixing diethyl ether, dichloromethane and tetrahydrofuran according to a mass ratio of 1:2: 4;
II, mixing 20g of the polycondensate intermediate prepared in the step I, 10g of hydrogen furfuryl acrylate, 45g of acrylonitrile, 10g of ethylene glycol dimethacrylate and 2.5g of emulsifier, performing ultrasonic treatment for 23 minutes, adding the mixture into a mold, placing the mold into a radiation field in an argon atmosphere, and performing radiation by adopting a cobalt 60-gamma radiation method for 43 minutes to perform polymerization reaction to obtain a polyadduct intermediate; the emulsifier is a mixture formed by mixing sodium dodecyl benzene sulfonate, polyoxypropylene polyoxyethylene glycerol ether and nonylphenol polyoxyethylene ether according to a mass ratio of 1:3: 2;
and III, soaking the addition polymer intermediate prepared in the step II in 2.8mol/L gluconic acid aqueous solution for ion exchange for 45 hours, then soaking in water for 4.5 hours, taking out, and placing in a vacuum drying oven for drying at 108 ℃ for 23 hours to obtain the hydrophilic glass slide for medical detection.
Example 5
A hydrophilic glass slide for medical detection is characterized in that a condensation polymer intermediate is prepared by carrying out condensation polymerization on bis [2- (dimethylamino) ethyl ] (2Z) -2-butenedioate and 4, 5-dichloro-1, 3-dioxolan-2-one, an addition polymer intermediate is prepared by copolymerizing the condensation polymer intermediate, hydrogen furfuryl acrylate, acrylonitrile and ethylene glycol dimethacrylate in a mass ratio of 2:1:5:1, and the addition polymer intermediate is soaked in a gluconic acid aqueous solution for ion exchange.
The manufacturing method of the hydrophilic glass slide for medical detection is realized by the following steps:
i, adding 18g of bis [2- (dimethylamino) ethyl ] (2Z) -2-butenedioic acid ester and 10g of 4, 5-dichloro-1, 3-dioxolan-2-one into 150g of diethyl ether, stirring and reacting at 40 ℃ for 8 hours, then performing rotary evaporation to remove the solvent, washing with the diethyl ether for 5 times, and then performing rotary evaporation again to remove the diethyl ether to obtain a polycondensate intermediate;
II, mixing 20g of polycondensate intermediate prepared in the step I, 10g of hydrogen furfuryl acrylate, 50g of acrylonitrile, 10g of ethylene glycol dimethacrylate and 3g of nonylphenol polyoxyethylene ether, performing ultrasonic treatment for 25 minutes, adding the mixture into a mold, placing the mold into a radiation field in a nitrogen atmosphere, and performing radiation by adopting a cobalt 60-gamma radiation method for 45 minutes to perform polymerization reaction to obtain a polyadduct intermediate;
and III, soaking the addition polymer intermediate prepared in the step II in 3mol/L gluconic acid aqueous solution for ion exchange for 50 hours, then soaking in water for 5 hours, taking out, placing in a vacuum drying oven, and drying at 110 ℃ for 24 hours to obtain the hydrophilic glass slide for medical detection.
Comparative example
A hydrophilic glass slide is prepared according to the formula and the preparation method of embodiment 1 of Chinese patent 201610823285.8.
The performance of the glass slides obtained in examples 1 to 5 and comparative example was tested, and the test methods and test results are shown in Table 1.
TABLE 1
Item Contact angle Tensile Properties Biocompatibility
Unit of Degree of rotation MPa
Test standard ISO15989-2004 GB/T14344-2003 GB/T16886
Example 1 64 85 Without rejection
Example 2 62 88 Without rejection
Example 3 60 92 Without rejection
Example 4 58 95 Without rejection
Example 5 56 99 Without rejection
Comparative example 78 72 Slight allergy
As can be seen from table 1, the hydrophilic slide glass for medical examination disclosed in the embodiment of the present invention has better hydrophilicity and biocompatibility and more excellent mechanical properties than the comparative example.
The foregoing shows and describes the general principles and broad features of the present invention and advantages thereof. It will be understood by those skilled in the art that the present invention is not limited to the embodiments described above, which are described in the specification and illustrated only to illustrate the principle of the present invention, but that various changes and modifications may be made therein without departing from the spirit and scope of the present invention, which fall within the scope of the invention as claimed. The scope of the invention is defined by the appended claims and equivalents thereof.

Claims (6)

1. A hydrophilic glass slide for medical detection is characterized by being manufactured by the following manufacturing method:
adding bis [2- (dimethylamino) ethyl ] (2Z) -2-butenedioate and 4, 5-dichloro-1, 3-dioxolane-2-one into an organic solvent, stirring and reacting at 30-40 ℃ for 6-8 hours, then performing rotary evaporation to remove the solvent, washing with diethyl ether for 3-5 times, and then performing rotary evaporation to remove the diethyl ether again to obtain a polycondensate intermediate;
II, mixing the polycondensate intermediate prepared in the step I, hydrogen furfuryl acrylate, acrylonitrile, ethylene glycol dimethacrylate and an emulsifier, performing ultrasonic treatment for 15-25 minutes, adding the mixture into a mold, placing the mold into a radiation field in the atmosphere of nitrogen or inert gas, performing radiation by adopting a cobalt 60-gamma radiation method, and performing polymerization reaction for 35-45 minutes to obtain a polyadduct intermediate;
and III, soaking the addition polymer intermediate prepared in the step II in 2-3mol/L gluconic acid aqueous solution for ion exchange for 30-50 hours, then soaking in water for 3-5 hours, taking out and placing in a vacuum drying oven for drying at the temperature of 100-110 ℃ for 18-24 hours, and obtaining the hydrophilic glass slide for medical detection.
2. The hydrophilic glass slide for medical examination as claimed in claim 1, wherein the mass ratio of bis [2- (dimethylamino) ethyl ] (2Z) -2-butenedioate, 4, 5-dichloro-1, 3-dioxolan-2-one and organic solvent in step I is 1.8:1 (10-15).
3. The hydrophilic glass slide for medical detection as claimed in claim 1, wherein the organic solvent is one or more selected from diethyl ether, dichloromethane and tetrahydrofuran.
4. The hydrophilic glass slide for medical detection as claimed in claim 1, wherein the mass ratio of the polycondensate intermediate, the hydrogen furfuryl acrylate, the acrylonitrile, the ethylene glycol dimethacrylate and the emulsifier is 2:1 (3-5) to 1 (0.1-0.3).
5. The hydrophilic glass slide for medical detection as claimed in claim 1, wherein the emulsifier is one or more selected from sodium dodecylbenzene sulfonate, polyoxypropylene polyoxyethylene glycerol ether and nonylphenol polyoxyethylene ether.
6. The hydrophilic slide for medical examination of claim 1, wherein the inert gas is selected from the group consisting of helium, neon, and argon.
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CN1529917A (en) * 2001-04-10 2004-09-15 三菱麻铁里亚尔株式会社 Lithium ion polymer secondary battery, its electrode and method for synthesizing polymer compound in binder used in adhesion layer thereof
CN105143292A (en) * 2013-03-25 2015-12-09 化工产品开发公司Seppic Novel amphiphilic polymers and use thereof in the treatment of surfaces made of hydrophobic materials
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CN108137999A (en) * 2015-09-29 2018-06-08 阪东化学株式会社 Optical clear adhesive sheet, laminated body, the manufacturing method of laminated body and the display device with touch screen

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Publication number Priority date Publication date Assignee Title
CN105694078B (en) * 2016-01-29 2018-08-24 深圳市晓龙新能源科技有限公司 A kind of fuel cell of fuel cell anion-exchange membrane and its preparation method and application the anion exchange
CN108676184B (en) * 2018-04-03 2019-08-27 利辛县雨若信息科技有限公司 A kind of polymer anion-exchange membrane and preparation method thereof

Patent Citations (4)

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Publication number Priority date Publication date Assignee Title
CN1529917A (en) * 2001-04-10 2004-09-15 三菱麻铁里亚尔株式会社 Lithium ion polymer secondary battery, its electrode and method for synthesizing polymer compound in binder used in adhesion layer thereof
CN105143292A (en) * 2013-03-25 2015-12-09 化工产品开发公司Seppic Novel amphiphilic polymers and use thereof in the treatment of surfaces made of hydrophobic materials
CN108137999A (en) * 2015-09-29 2018-06-08 阪东化学株式会社 Optical clear adhesive sheet, laminated body, the manufacturing method of laminated body and the display device with touch screen
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