CN107413395A - A kind of agglomeration type high-hydrophilic strong anion exchanger, preparation method and its application in liquid chromatographic packing materials - Google Patents
A kind of agglomeration type high-hydrophilic strong anion exchanger, preparation method and its application in liquid chromatographic packing materials Download PDFInfo
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- CN107413395A CN107413395A CN201710760467.XA CN201710760467A CN107413395A CN 107413395 A CN107413395 A CN 107413395A CN 201710760467 A CN201710760467 A CN 201710760467A CN 107413395 A CN107413395 A CN 107413395A
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- polyvinyl alcohol
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J41/00—Anion exchange; Use of material as anion exchangers; Treatment of material for improving the anion exchange properties
- B01J41/08—Use of material as anion exchangers; Treatment of material for improving the anion exchange properties
- B01J41/12—Macromolecular 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
- C08F8/00—Chemical modification by after-treatment
- C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
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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
- C08F8/00—Chemical modification by after-treatment
- C08F8/34—Introducing sulfur atoms or sulfur-containing groups
- C08F8/36—Sulfonation; Sulfation
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- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
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Abstract
The invention belongs to liquid chromatographic packing materials preparing technical field, and in particular to a kind of agglomeration type high-hydrophilic strong anion exchanger, preparation method and its application in liquid chromatographic packing materials.The agglomeration type high-hydrophilic strong anion exchanger is carried out agglomeration to the polymer microballoon of sulfonation by quaternized polyvinyl alcohol and is made.Quaternized polyvinyl alcohol is made by following steps：Polyvinyl alcohol is dispersed in water, adds that sodium hydroxide is molten and the hydroxypropyl-trimethyl ammonium chloride of 3 chlorine 2, successive reaction is carried out under agitation, filters drying after washing.Advantage of the invention is that：High-hydrophilic strong anion exchanger is prepared using quaternized polyvinyl alcohol agglomeration aromatic olefin organic copolymer base ball; preparation speed is fast, operating process is simply green; avoid and using hypertoxicity reagents such as chloromethylether or dichlormetbylethers, also eliminate the drawbacks of being short of using the anionite hydrophily caused by nano particle or carbon nano-tube modification.
Description
Technical field
The invention belongs to liquid chromatographic packing materials preparing technical field, and in particular to a kind of agglomeration type high-hydrophilic it is strong cloudy from
Sub- exchanger, preparation method and its application in liquid chromatographic packing materials.
Technical background
High-hydrophilic strong anion chromatograph packing material is mostly based on organic polymer matrix, and functional group is mostly quaternary amine base, so
And to introduce quaternary amine base in organic polymer-based ball surface, then preparation process usually requires to use chloromethylether and dichlormetbylether
Chloromethylation is carried out to organic polymer etc. hypertoxicity reagent and introduces Active Chlorine, is subsequently reacted again with tertiary amine reagent and introduces quaternary amine
Base, the preparation process complex steps, and chloromethylether and dichlormetbylether are poisoned very big to human and environment.
To solve this drawback, the conventional method of prior art is exactly micro- using quaternary ammoniated nano particle and the polymer of sulfonation
Ball (particle diameter is micron order) by agglomeration reaction formed a surface richness quaternary amines core-shell microspheres (core be sulfonation polymerization
Thing microballoon, shell are quaternary ammoniated nano particle), such as United States Patent (USP) US4119580,4376047,4351909, all it is to use this
Strategy process prepares strong anion chromatograph packing material.Although the quaternary amine type chromatographic stationary phases that this method can obtain high power capacity are filled out
Material, but its deficiency is：Nano particle is difficult equably agglomeration in micrograde polymer microsphere due to mutual Coulomb repulsion
Surface, cause its surface portion exposed and without nano particle agglomeration.And because polymer microballoon surface sheet is as strong hydrophobicity,
Therefore using the chromatograph packing material hydrophily shortcoming obtained by this method.Another deficiency is：It is difficult to accurately control nanometer
Grain particle diameter, therefore the batch reproducibility deficiency for causing the type chromatograph packing material to prepare.
Chinese patent CN201210426077.6, disclose a kind of using quaternized carbon nanotube agglomeration micrograde polymer
Anion chromatographic filling material is prepared in microballoon.This method is only that quaternary ammonium carbon nano tube is substituted into quaternized nano particle, above-mentioned
The problem of uneven agglomeration of nano particle agglomeration polymer microballoon method and hydrophily are short of still has.
The B of Chinese patent Authorization Notice No. CN 104226283, disclose a kind of polyvinylalcohol coats type chromatographic stationary phases and
Its preparation method and application, there is provided a kind of method modified by physics coating stromal surfaces such as silica gel, although should
Method can obtain strongly hydrophilic polarity chromatograph packing material, and preparation process is also relatively simple, green.However, this method is profit
In polar group ball surface be copolymerized the principle of film forming with polyvinyl alcohol, due to the strongly hydrophilic of polyvinyl alcohol, it is desirable to internal
Base ball surface contains enough polar sites.Therefore this method be difficult to be applicable strong hydrophobicity with 1-chloro-4-methyl-benzene-divinyl
Base benzene is the polymer microballoon of representative, therefore limits species and the development of the ion-exchanger.Even if pass through multiple polyethylene
Filler obtained by alcohol coating polymer microballoon remains as inert filler, is not used to Anion separation.
The present invention, which is mixed quaternized poly-vinyl alcohol solution with the organic copolymer microspheres solution of sulfonation by innovation, to shake
High-hydrophilic strong anion exchanger is obtained after swinging, and is applied in liquid chromatographic packing materials.
The content of the invention
For shortcoming present in above-mentioned preparation method, the invention provides a kind of high-hydrophilic strong anion exchanger.
Present invention also offers a kind of preparation method of high-hydrophilic strong anion exchanger, the letter of this method preparation process
It is single, green.
To realize an above-mentioned goal of the invention, the present invention adopts the technical scheme that：A kind of agglomeration type high-hydrophilic it is strong cloudy from
Sub- exchanger, the agglomeration type high-hydrophilic strong anion exchanger are entered by quaternized polyvinyl alcohol to the polymer microballoon of sulfonation
Row agglomeration and be made.
Preferably, described quaternized polyvinyl alcohol is made by following steps：Polyvinyl alcohol is dispersed in water, added
Sodium hydroxide and 3- chloro-2-hydroxypropyl-trimethyl ammonium chlorides, successive reaction is carried out under agitation, dried after filtering washing,
It can obtain quaternized polyvinyl alcohol.
Preferably, the mass volume ratio of the polyvinyl alcohol and water is 1g：15mL, the polyvinyl alcohol, sodium hydroxide, 3-
The mass ratio of chloro-2-hydroxypropyl-trimethyl ammonium chloride is 4：1：5, continuous reaction time 7-9h.
It is further preferred that the agglomeration, specific reactions steps are：, will be quaternized under the conditions of 50-70 DEG C of reaction temperature
Polyvinyl alcohol, sulfonation polymer microballoon and water stir, after suction filtration, by filtration cakes torrefaction.
It is highly preferred that polymer microballoon is 1-chloro-4-methyl-benzene and divinyl benzene copolymer microballoon.
To realize above-mentioned another goal of the invention, the present invention adopts the technical scheme that：A kind of agglomeration type high-hydrophilic is cloudy by force
The preparation method of ion-exchanger, it includes preparation process：
1) preparation of polymer microballoon；
Polymer microballoon is prepared from suspension polymerization, the polymer microballoon is that 1-chloro-4-methyl-benzene and divinylbenzene are total to
Polymers base ball；
2) sulfonation of polymer microballoon；
Under conditions of ice-water bath, 1-chloro-4-methyl-benzene and divinyl benzene copolymer base ball prepared by step 1) disperse
In sulfuric acid solution；Then reaction being continuously stirred at ambient temperature suspension being made, the suspension is poured into ice-water bath solution
Middle terminating reaction, filter cake is washed to neutrality after suction filtration, produces the polymer microballoon of sulfonation；
3) preparation of quaternized polyvinyl alcohol；
Polyvinyl alcohol is dispersed in water, sodium hydroxide and the chloro- 2- hydroxypropyl trimethylammoniums of 3- are added at a temperature of 80-95 DEG C
Ammonium chloride, the successive reaction under the conditions of magnetic agitation, dried after filtering washing, produce quaternized polyvinyl alcohol；
4) agglomeration；
Under the conditions of 50-70 DEG C of reaction temperature, by sulfonation made from quaternized polyvinyl alcohol made from step 3), step 2)
Polymer microballoon and water stir, after suction filtration, by filtration cakes torrefaction, that is, agglomeration type high-hydrophilic strong anion is made and exchanges
Agent.
Wherein, in step 1), described polyalcohol microspherulite diameter is 8 μm；In step 2), the 1-chloro-4-methyl-benzene and two
The mass volume ratio of divinylbenzene copolymer base ball and sulfuric acid solution is 1g：2mL, the mass fraction of the sulfuric acid solution are
60%, stirring reaction 20-40min.
Wherein, in step 3), the mass volume ratio of the polyvinyl alcohol and water is 1g：15mL, the polyvinyl alcohol, hydrogen-oxygen
Change sodium solution, the mass volume ratio of 3- chloro-2-hydroxypropyl-trimethyl ammonium chloride solution is 4：1：5, continuous reaction time 7-
9h；In step 4), the mass volume ratio of described quaternized polyvinyl alcohol, the polymer microballoon of sulfonation and water is 2g：4g：
50mL。
The present invention also provides a kind of application of agglomeration type high-hydrophilic strong anion exchanger in liquid chromatographic packing materials,
Agglomeration type high-hydrophilic strong anion exchanger is scattered in homogenate, and chromatographic column is put under hydraulics.Preferably, hydraulic pressure
Condition is 5000psi.
The technological merit of the present invention is：
1) present invention using the quaternized nano particle used in quaternized poly-vinyl alcohol solution substitution conventional method or
CNT carries out agglomeration to the polymer microballoon of sulfonation.Quaternized polyvinyl alcohol is still homogeneous phase solution system, is contributed to gram
Take the defects of nano particle agglomeration is uneven, hydrophily shortcoming, while from quaternized polyvinyl alcohol can ensure that to obtain strong
Anionite possesses high hydrophily.
2) agglomeration type high-hydrophilic strong anion exchanger of the invention, having for quaternized polyvinyl alcohol and sulfonation is passed through
Machine polymer microballoon obtains high-hydrophilic strong anion by the method for agglomeration and exchanges filler, avoids chloromethylether and dichloromethane
The use of the poisonous reagents such as base ether, and preparation speed is fast, operating process is simply green, and especially, polyvinyl alcohol is carried out
When quaternized, the quaternizing agent with different anions cation exchange groups species and structure may be selected, present invention preferably employs 3-
Chloro-2-hydroxypropyl-trimethyl ammonium chloride carries out quaternized modification to polyvinyl alcohol and obtains quaternary ammoniated polyethylene in the basic conditions
Alcohol, this method provide a kind of new approaches to prepare high hydrophilic anionic exchanger.
3) 3- chloro-2-hydroxypropyl-trimethyl ammonium chlorides of the present invention carry out season to polyvinyl alcohol in the basic conditions
Ammoniumization is modified, although preparation method, than more conventional, there is presently no by quaternized poly-vinyl alcohol solution of the present invention
High-hydrophilic strong anion exchanger is made applied to the report in chromatographic column filler in polymer microballoon agglomeration with sulfonation, adopts
With the anion-exchange chromatography filler that quaternized polyvinyl alcohol agglomeration sulfonated polymer microballoon proposed by the present invention obtains to separation
Inorganic anion shows good separating property, and this is the innovative content of the present invention.
Brief description of the drawings
Fig. 1 is that the high-hydrophilic strong anion exchanger prepared by the present invention is packed into chromatogram post separation inorganic anion
Chromatogram.
Fig. 2 is that polyvinyl alcohol not quaternized in contrast test applies sulfonated polymer microballoon for separating inorganic anion
Chromatogram.
Wherein, the peak in Fig. 1 is followed successively by IO from left to right3 -、BrO3 -、NO2 -、NO3 -、I-、SCN-。
Embodiment
In order that present disclosure can more accurately be understood, below in conjunction with the accompanying drawings to a kind of high-hydrophilic of the present invention
The embodiment of strong anion exchanger elaborates.However, it is desirable to explanation, implementation of the invention be not limited to
Under embodiment.
A kind of agglomeration type high-hydrophilic strong anion exchanger of the present invention is by polymerization of the quaternized polyvinyl alcohol to sulfonation
Thing microballoon carries out agglomeration and is made.
Specifically preparation process is：
1) preparation of polymer microballoon；
Polymer microballoon is prepared from suspension polymerization, the polymer microballoon is that 1-chloro-4-methyl-benzene and divinylbenzene are total to
Polymers base ball；
2) sulfonation of polymer microballoon；
Under conditions of ice-water bath, 1-chloro-4-methyl-benzene and divinyl benzene copolymer base ball prepared by step 1) disperse
In sulfuric acid solution；Then reaction being continuously stirred at ambient temperature suspension being made, the suspension is poured into ice-water bath solution
Middle terminating reaction, filter cake is washed to neutrality after suction filtration, produces the polymer microballoon of sulfonation；
3) preparation of quaternized polyvinyl alcohol；
Polyvinyl alcohol is dispersed in water, sodium hydroxide and the chloro- 2- hydroxypropyl trimethylammoniums of 3- are added at a temperature of 80-95 DEG C
Ammonium chloride, the successive reaction under the conditions of magnetic agitation, dried after filtering washing, produce quaternized polyvinyl alcohol；
4) agglomeration；
Under the conditions of 50-70 DEG C of reaction temperature, by sulfonation made from quaternized polyvinyl alcohol made from step 3), step 2)
Polymer microballoon and water stir, after suction filtration, by filtration cakes torrefaction, that is, agglomeration type high-hydrophilic strong anion is made and exchanges
Agent.
Embodiment 1
1) preparation of polymer microballoon：The 1-chloro-4-methyl-benzene and two that particle diameter is about 8 μm is prepared by suspension polymerization
Divinylbenzene copolymer base ball.
2) sulfonation of polymer microballoon：Weigh 10g above-mentioned prepared 1-chloro-4-methyl-benzene and divinyl benzene copolymer
Base ball is placed in 50mL round-bottomed flask, and adding 20 mL weight/mass percentage compositions in round-bottomed flask under conditions of ice-water bath is
60% sulfuric acid solution, sulphur is fully dispersed in by magnetic agitation 1-chloro-4-methyl-benzene and divinyl benzene copolymer base ball
In acid solution, suspension is made after 30min is continuously stirred under conditions of 30 DEG C of room temperature, it is molten that the suspension is poured into ice-water bath
Terminating reaction in liquid, above-mentioned ice-water bath solution is filtered, gained filter cake be washed to after neutrality both needed for sulfonation polymer it is micro-
Ball.
3) polyvinyl alcohol is quaternized：10g polyvinyl alcohol is taken to be scattered in the three-neck flask of the 250mL equipped with 150mL water,
Appropriate sodium hydroxide is added at a temperature of 90 DEG C and that appropriate 3- chloro-2-hydroxypropyl-trimethyl ammonium chlorides are slowly added dropwise is molten
Liquid, the successive reaction 8h under conditions of magnetic agitation, filter 60 DEG C of drying after washing, you can obtain quaternized polyvinyl alcohol.
4) agglomeration：150mL water is added in 250mL round-bottomed flask and is placed in 60 DEG C of oil bath pan, in magnetic force
Quaternized polyvinyl alcohol and the polymer microballoon of sulfonation made from being added in the presence of stirring, it is set uniformly to disperse wherein, to take out
Filter, gained filter cake, which is placed in 140 DEG C of baking oven, dries 2h.
Embodiment 2
High-hydrophilic strong anion exchanger obtained by the polymer matrix ball of quaternized polyvinyl alcohol agglomeration sulfonation is scattered in
In homogenate, chromatographic column is put under 5000psi hydraulics.It is 1mL/min in flow velocity, mobile phase is 5mM potassium carbonate, purple
IO is separated under outer detection pattern3 -、BrO3 -、NO2 -、NO3 -、I-And SCN-Ion, spectrogram are shown in accompanying drawing 1.It is obvious that used in this example
The anion-exchange chromatography filler that quaternized polyvinyl alcohol agglomeration sulfonated polymer microballoon proposed by the present invention obtains to it is above-mentioned from
Sublist reveals good separating property.
Contrast test：In order to further protrude the separating effect of chromatograph packing material of the present invention, with Chinese invention patent CN
The method being previously mentioned in 104226283 B, i.e., quaternised modified place (commercial reagents of purchase, is not carried out using polyvinyl alcohol
Reason) chromatograph packing material that sulfonated polymer microballoon obtains is applied, the same sample in above-described embodiment 2 is separated.Such as Fig. 2 institutes
Showing, it can be seen that the filler is very weak to sample reservation, and substantially without separating effect.
Specific implementation case described above, only it is that technical scheme and beneficial effect have been carried out further
Explanation, it is noted that, without departing from the inventive concept of the premise, can be with for those skilled in the art
Some improvements and modifications are made, these improvements and modifications also should be regarded as within protection scope of the present invention.
Claims (10)
- A kind of 1. agglomeration type high-hydrophilic strong anion exchanger, it is characterised in that：The agglomeration type high-hydrophilic strong anion is handed over Agent is changed to be carried out agglomeration to the polymer microballoon of sulfonation by quaternized polyvinyl alcohol and be made.
- 2. agglomeration type high-hydrophilic strong anion exchanger according to claim 1, it is characterised in that：Described is quaternized Polyvinyl alcohol, it is made by following steps：Polyvinyl alcohol is dispersed in water, adds sodium hydroxide and the chloro- 2- hydroxypropyls of 3- Trimethyl ammonium chloride is filtered after carrying out successive reaction, is washed, drying, you can obtain quaternized polyvinyl alcohol.
- 3. agglomeration type high-hydrophilic strong anion exchanger according to claim 2, it is characterised in that：The polyvinyl alcohol Mass volume ratio with water is 1g：15mL, the polyvinyl alcohol, sodium hydroxide, the matter of 3- chloro-2-hydroxypropyl-trimethyl ammonium chlorides Amount is than being 4：1：5, continuous reaction time 7-9h.
- 4. agglomeration type high-hydrophilic strong anion exchanger according to claim 1, it is characterised in that：The agglomeration, its Specifically reactions steps are：Under the conditions of 50-70 DEG C of reaction temperature, by quaternized polyvinyl alcohol, sulfonation polymer microballoon and Water stirs, after suction filtration, by filtration cakes torrefaction；Wherein, described quaternized polyvinyl alcohol, the polymer microballoon and water of sulfonation Mass volume ratio be 2g：4g：50mL.
- 5. the agglomeration type high-hydrophilic strong anion exchanger according to claim 1 or 4, it is characterised in that：Polymer is micro- Ball is 1-chloro-4-methyl-benzene and divinyl benzene copolymer microballoon.
- A kind of 6. method for preparing agglomeration type high-hydrophilic strong anion exchanger as claimed in claim 1, it is characterised in that：Bag Include preparation process：1) preparation of polymer microballoon；Polymer microballoon is prepared from suspension polymerization, the polymer microballoon is 1-chloro-4-methyl-benzene and divinyl benzene copolymer Base ball；2) sulfonation of polymer microballoon；Under conditions of ice-water bath, 1-chloro-4-methyl-benzene and divinyl benzene copolymer base ball prepared by step 1) are scattered in sulphur In acid solution；Then reaction being continuously stirred at ambient temperature suspension being made, the suspension is poured into ice-water bath solution eventually Only react, filter cake is washed to neutrality after suction filtration, produce the polymer microballoon of sulfonation；3) preparation of quaternized polyvinyl alcohol；Polyvinyl alcohol is dispersed in water, sodium hydroxide and the chloro- 2- Hydroxyproyl Trimethyls chlorine of 3- are added at a temperature of 80-95 DEG C Change ammonium, the successive reaction under the conditions of magnetic agitation, dried after filtering washing, produce quaternized polyvinyl alcohol；4) agglomeration；Under the conditions of 50-70 DEG C of reaction temperature, by the poly- of sulfonation made from quaternized polyvinyl alcohol made from step 3), step 2) Compound microballoon and water stir, and after suction filtration, by filtration cakes torrefaction, that is, agglomeration type high-hydrophilic strong anion exchanger are made.
- 7. a kind of preparation method of agglomeration type high-hydrophilic strong anion exchanger according to claim 6, it is special Sign is：In step 1), described polyalcohol microspherulite diameter is 8 μm；In step 2), the 1-chloro-4-methyl-benzene and divinyl The mass volume ratio of benzene copolymer matrix ball and sulfuric acid solution is 1g：2mL, the mass fraction of the sulfuric acid solution is 60%, stirring Reaction time is 20-40min.
- 8. a kind of preparation method of agglomeration type high-hydrophilic strong anion exchanger according to claim 6, it is special Sign is：In step 3), the mass volume ratio of the polyvinyl alcohol and water is 1g：15mL, the polyvinyl alcohol, sodium hydroxide, The mass ratio of 3- chloro-2-hydroxypropyl-trimethyl ammonium chlorides is 4：1：5；In step 4), described quaternized polyvinyl alcohol, sulfonation The mass volume ratio of polymer microballoon and water is：2g：4g：50mL.
- A kind of 9. answering in liquid chromatographic packing materials of agglomeration type high-hydrophilic strong anion exchanger as claimed in claim 1 With, it is characterised in that：Agglomeration type high-hydrophilic strong anion exchanger is scattered in homogenate, and chromatogram is put under hydraulics Post.
- 10. application of the agglomeration type high-hydrophilic strong anion exchanger in liquid chromatographic packing materials according to claim 9, It is characterized in that：Hydraulics are 5000psi.
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Cited By (2)
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| CN109248715A (en) * | 2018-09-26 | 2019-01-22 | 安徽皖仪科技股份有限公司 | Anion exchange resin and its preparation method and application |
| CN112584924A (en) * | 2018-08-31 | 2021-03-30 | 昭和电工株式会社 | Filler for ion chromatography and method for producing same |
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Cited By (3)
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| CN112584924A (en) * | 2018-08-31 | 2021-03-30 | 昭和电工株式会社 | Filler for ion chromatography and method for producing same |
| CN112584924B (en) * | 2018-08-31 | 2023-07-14 | 株式会社力森诺科 | Packing for ion chromatography and method for producing the same |
| CN109248715A (en) * | 2018-09-26 | 2019-01-22 | 安徽皖仪科技股份有限公司 | Anion exchange resin and its preparation method and application |
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| CN107413395B (en) | 2020-05-19 |
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