CN103980403A - Styrene system ion exchange resin as well as preparation method and application thereof - Google Patents
Styrene system ion exchange resin as well as preparation method and application thereof Download PDFInfo
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- CN103980403A CN103980403A CN201410209486.XA CN201410209486A CN103980403A CN 103980403 A CN103980403 A CN 103980403A CN 201410209486 A CN201410209486 A CN 201410209486A CN 103980403 A CN103980403 A CN 103980403A
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Abstract
The invention provides a styrene system ion exchange resin as well as a preparation method and application thereof. The styrene system ion exchange resin is prepared by taking styrene and toluylene as monomers and is a milk-white nontransparent spherical particle; the diameter is 0.05-1.20 mm; the density is as follows: the true wet density is 1.06-1.10 g/ml, and the apparent wet density is 0.65-0.75 g/ml; the strength (attrited sphericity) is more than or equal to 95%; the surface active group is -N+(CH3)2; the aperture is 80-100 nanometers; the porosity is 45%-22%; the pore volume is 0.75-0.84 ml/g; the specific area is 850-1000 m<2>/g; the full exchange capacity of dry resin is 3.7 mmol/g, and the full exchange capacity of wet resin is 1.1 mmol/g. The styrene system ion exchange resin provided by the invention is an effective cell factor adsorbing material, achieves outstanding adsorption effect on endotoxins and inflammatory factors which are contained in blood and can be applied to the aspect of resin hemoperfusion apparatus.
Description
Technical field
The present invention relates to a kind of copolymer material and preparation method thereof and application, especially a kind of styrene ion exchange resin and preparation method thereof and application.
Background technology
Severe infection can cause multiple conditions of human body, as endotoxemia, seriously can cause organ necrosis, irreversible shock even dead, serious harm patient health and life.The methods for the treatment of of severe infection is the important topic of medicine clinical research.
In recent years, use blood perfusion (Hemoperfusion, HP) method treatment severe infection to obtain some progress both at home and abroad.The researchist of Japan is by PXB (Polymyxin B, PMB) be coated on the inwall of blood filter tubular fibre, make PMB blood fibers adsorption post (PMX-F, trade(brand)name Toraymyxin, Toray Industried Inc.Japan), its clinical test results shows, PMX-F can effectively treat severe infection.But PXB is expensive, and there is renal toxicity, if split away off and enter blood of human body from carrier, have direct toxic side effect.Therefore, developing safer effective blood perfusion surrogate has important practical significance.
Summary of the invention
Technical problem to be solved by this invention is to provide a kind of styrene ion exchange resin.
Another technical problem to be solved by this invention is to provide the preparation method of above-mentioned styrene ion exchange resin.
Another technical problem to be solved by this invention is to provide the application of above-mentioned styrene ion exchange resin.
For solving the problems of the technologies described above, technical scheme of the present invention is:
A kind of styrene ion exchange resin, it is a kind of cross-linked polystyrene beads body, for the opaque spherical particle of oyster white, diameter is 0.05～1.20mm, density is wet true density 1.06～1.10g/ml, wet volume density 0.65～0.75g/ml, intensity (rate of small round spheres after mill)>=95%, surface active groups is-N
+(CH
3)
2, aperture is 80～100nm, and porosity is 45～52%, and pore volume is 0.75～0.84ml/g, and specific surface area is 850～1000m
2/ g, full exchange capacity is that dried resin is that 3.7mmol/g, wet resin are 1.1mmol/g.
Preferably, above-mentioned styrene ion exchange resin, use temperature≤100 DEG C.
Preferably, above-mentioned styrene ion exchange resin, be in water, to carry out suspension polymerization by styrene monomer and divinylbenzene monomer to obtain multipolymer pearl body, then repeatedly introduce ionizable group (ammonia, primary amine or secondary amine) and synthetic cross-linked polystyrene beads body to multipolymer pearl body.
The preparation method of above-mentioned styrene ion exchange resin, concrete preparation process is as follows:
(1) adopt free radical suspending copolymerization to prepare cross-linked styrene-divinylbenzene copolymer by styrene monomer and divinylbenzene monomer:
1. the vinylbenzene and the divinylbenzene mixture that contain initiator benzoyl peroxide are suspended in the water that contains dispersion agent, and described dispersion agent is polyvinyl alcohol or carbonyl bearing polymer;
2. under agitation condition, make the drop major part suspending within the scope of 30-70 object, organic phase (state of a kind of solution that vinylbenzene and divinylbenzene are mixed to form) is dispersed into pearl body;
3. be heated to 95 DEG C, make initiator benzoyl peroxide decompose and initiated polymerization obtains pearl styrene-divinylbenzene copolymer;
4. after polymerization completes, then with sig water cleaning cleaning polyalcohol cross-linked polystyrene beads body to remove the dispersion agent sticking, then dewater, dry;
(2) functionalizing of crosslinked polystyrene-prepare macroporous anion exchange resin:
Cross-linked styrene-divinylbenzene copolymer that 4. above-mentioned steps is prepared carries out functionalizing, make cross-linked polystyrene beads body by chloroethyl crosslinked polystyrene amination, wherein, the chloromethylation of crosslinked polystyrene being introduced to chloromethyl by Knut Fridell-Kerafyrm thatch alkylated reaction on the phenyl ring of crosslinked polystyrene realizes; When chloromethyl resin forms quaternary amine type strong basic ion exchange resin with reactive tertiary amine again, when chloromethyl resin reacts and forms weak base anion-exchange resin with ammonia, primary amine or secondary amine.
Preferably, the preparation method of above-mentioned styrene ion exchange resin introduces chloromethyl realization to the chloromethylation of crosslinked polystyrene by Knut Fridell-Kerafyrm thatch alkylated reaction in described step (2) and refers to that crosslinked polystyrene and chloromethyl ether are at ZnCl on the phenyl ring of crosslinked polystyrene
2do in the situation of catalyzer, carry out chloromethylation.
Preferably, the preparation method of above-mentioned styrene ion exchange resin, step (1) the 4. pearl body size of gained cross-linked polystyrene beads body and homogeneity depends on type and the consumption of ratio, suspension stabilizer, initiator and the monomer of size, stirring velocity, temperature, water and the monomer mixture of reactor and agitator; Specifically, Church and Shinner propose following three equations and describe the droplet-size distribution in suspension polymerization process:
In formula, d
minfor the minimum grain size of drop stable existence, less will merging; d
maxfor the maximum particle diameter of drop existence, then will brokenly disperse greatly; D '
maxfor the maximum particle diameter that can keep suspending, more greatly just there will be two phase stratification; P
cand P
dbe respectively the density of external phase and disperse phase; D is agitating vane diameter; σ is interfacial tension; N is stirring velocity.
Preferably, the preparation method of above-mentioned styrene ion exchange resin, described step (1) 3. obtains after vinylbenzene-diethylbenzene alkene copolymer, add when dissolving each other with styrene monomer and divinylbenzene monomer and not participating in the inert compound (being called pore-creating agent) of polymerization, after polymerization completes, this inert compound is removed by distillation method, formed macroporous type cross-linked styrene-divinylbenzene copolymer.
Preferably, the preparation method of above-mentioned styrene ion exchange resin, described inert compound is toluene or dimethylbenzene.
The application of above-mentioned styrene ion exchange resin aspect adsorb cell factor.
Preferably, the application of above-mentioned styrene ion exchange resin, described cytokine is intracellular toxin or inflammatory factor.
Preferably, above-mentioned styrene ion exchange resin is in the application of preparing aspect blood perfusion device.
The invention has the beneficial effects as follows:
Above-mentioned styrene ion exchange resin, it is a kind of effectively cytokine sorbing material, it all significantly reduces (P < 0.05) for intracellular toxin in experiment in vitro blood plasma and inflammatory cytokine content, intracellular toxin, tumor necrosis factor alpha, interleukin 1,6,8 adsorption rate are respectively 99.2%, 55.0%, 57.0%, 75.0%, 42.0%; Styrene ion exchange resin plasma perfusion treatment group Endotoxin Levels obviously decline (P < 0.05) in experimentation on animals, rate of descent exceedes 90%, empty perfusion control group level of endotoxin is without obviously decline (P > 0.05), two groups of comparing differences have significance (P > 0.05), visible remarkable to the intracellular toxin in blood and inflammatory factor adsorption effect; Its preparation method is simple, is applicable to clinical prolonged application.
Brief description of the drawings
Fig. 1 is styrene ion exchange resin blood perfusion absorption animal experimental model schematic flow sheet in experimental example.
Embodiment
Below in conjunction with specific embodiment, technical scheme of the present invention is further described.
Embodiment 1
A kind of preparation example of styrene ion exchange resin
The preparation method of above-mentioned styrene ion exchange resin, concrete preparation process is as follows:
(1) adopt free radical suspending copolymerization to prepare cross-linked styrene-divinylbenzene copolymer by styrene monomer and divinylbenzene monomer:
1. the vinylbenzene 40g and the divinylbenzene 10g mixture that contain initiator benzoyl peroxide 0.4g are suspended in the water that contains dispersion agent, and described dispersion agent is polyvinyl alcohol or carbonyl bearing polymer;
2. under agitation condition, make the drop major part suspending within the scope of 30-70 object, organic phase (state of a kind of solution that vinylbenzene and divinylbenzene are mixed to form) is dispersed into pearl body;
3. be heated to 95 DEG C, make benzoyl peroxide (initiator) decompose and initiated polymerization obtains pearl styrene-divinylbenzene copolymer; Add toluene, after polymerization completes, toluene is removed by distillation method, form macroporous type cross-linked styrene-divinylbenzene copolymer;
4. after polymerization completes, then with sig water cleaning cleaning polyalcohol cross-linked polystyrene beads body to remove the dispersion agent sticking, then dewater, dry;
(2) functionalizing of crosslinked polystyrene-prepare macroporous anion exchange resin:
Cross-linked styrene-divinylbenzene copolymer that 4. above-mentioned steps is prepared carries out functionalizing, make cross-linked polystyrene beads body by chloroethyl crosslinked polystyrene amination, wherein, to the chloromethylation of crosslinked polystyrene, by Knut Fridell-Kerafyrm thatch alkylated reaction, crosslinked polystyrene and chloromethyl ether are at ZnCl
2do in the situation of catalyzer, carry out chloromethylation, on the phenyl ring of crosslinked polystyrene, introduce chloromethyl; When chloromethyl resin forms quaternary amine type strong basic ion exchange resin with reactive tertiary amine again, when chloromethyl resin reacts and forms weak base anion-exchange resin with ammonia, primary amine or secondary amine, after testing, the diameter of prepared cross-linked polystyrene beads body (the opaque spherical particle of oyster white) is 0.05～1.20mm, density is wet true density 1.06～1.10g/ml, wet volume density 0.65～0.75g/ml, intensity (rate of small round spheres after mill)>=95%, surface active groups is-N
+(CH
3)
2, aperture is 80～100nm, and porosity is 45～52%, and pore volume is 0.75～0.84ml/g, and specific surface area is 850～1000m
2/ g, full exchange capacity is that dried resin is that 3.7mmol/g, wet resin are 1.1mmol/g.
Embodiment 2
A kind of preparation example of styrene ion exchange resin
The preparation method of above-mentioned styrene ion exchange resin, concrete preparation process is as follows:
(1) adopt free radical suspending copolymerization to prepare cross-linked styrene-divinylbenzene copolymer by styrene monomer and divinylbenzene monomer:
1. the vinylbenzene 40g and the divinylbenzene 10g mixture that contain initiator benzoyl peroxide 0.4g are suspended in the water that contains dispersion agent, and described dispersion agent is polyvinyl alcohol or carbonyl bearing polymer;
2. under agitation condition, make the drop major part suspending within the scope of 30-70 object, organic phase is dispersed into pearl body;
3. be heated to 95 DEG C, make benzoyl peroxide (initiator) decompose and initiated polymerization obtains pearl styrene-divinylbenzene copolymer;
4. after polymerization completes, then with sig water cleaning cleaning polyalcohol cross-linked polystyrene beads body to remove the dispersion agent sticking, then dewater, dry;
(2) functionalizing of crosslinked polystyrene-prepare macroporous anion exchange resin:
Cross-linked styrene-divinylbenzene copolymer that 4. above-mentioned steps is prepared carries out functionalizing, make cross-linked polystyrene beads body by chloroethyl crosslinked polystyrene amination, wherein, to the chloromethylation of crosslinked polystyrene, by Knut Fridell-Kerafyrm thatch alkylated reaction, crosslinked polystyrene and chloromethyl ether are at ZnCl
2do in the situation of catalyzer, carry out chloromethylation, on the phenyl ring of crosslinked polystyrene, introduce chloromethyl; When chloromethyl resin forms quaternary amine type strong basic ion exchange resin with reactive tertiary amine again, when chloromethyl resin reacts and forms weak base anion-exchange resin with ammonia, primary amine or secondary amine, after testing, the diameter of prepared cross-linked polystyrene beads body (the opaque spherical particle of oyster white) is 0.05～1.20mm, density is wet true density 1.06～1.10g/ml, wet volume density 0.65～0.75g/ml, intensity (rate of small round spheres after mill)>=95%, surface active groups is-N
+(CH
3)
2, aperture is 80～100nm, and porosity is 45～52%, and pore volume is 0.75～0.84ml/g, and specific surface area is 850～1000m
2/ g, full exchange capacity is that dried resin is that 3.7mmol/g, wet resin are 1.1mmol/g.
Experimental example
1, as follows for realizing the experimental procedure that human vitronectin is tested and animal model experiment institute adopts:
(1) human vitronectin experiment
Accurately measure styrene ion exchange resin described in 10 parts of embodiment 1, every part of 1ml, mixes with intracellular toxin positive patients blood plasma 1:10 (v/v) ratio in resin, puts 37 DEG C of water bath with thermostatic control vibration 150min, according to absorption Plasma Before And After intracellular toxin, cytokine concentration, calculate adsorption rate.
Adsorption rate L (%)=(C
0-C)/C
0× 100%
In formula, C
0concentration before being respectively absorption with C and after absorption.
(2) animal model experiment
Adopt bacterium infection method to prepare endotoxemia type severe infection animal model (raising experiment, with rabbit, infects two kinds of methods by endotoxin injection/bacterium and prepares model).With styrene ion exchange resin described in embodiment 1 by this endotoxemia animal model of hemoperfusion treatment.Check adsorption effect and the security thereof of induced by endotoxin and inflammatory factor.Experiment flow is shown in Fig. 1, and by link perfusion device, and with 3000ml normal saline flushing pipeline, row Femoral arterial and venous cannulation, forms whole blood circulation and plasma circulation: employing plasma separator carries out separating plasma; Blood plasma is through adsorption tanks; Be that 20-30ml/min carries out plasma perfusion by blood pump control plasma flow rate, Hemoperfusion time is 2 hours, and before perfusion, adsorption tanks perfusion 30min, 60min and 120min sampling, measure level of plasma endotoxin, calculates adsorption rate.
2, experimental result
(1) human vitronectin experimental result
After the external Static Adsorption of styrene ion exchange resin described in embodiment 1, in blood plasma, intracellular toxin and inflammatory cytokine content all significantly reduce (P < 0.05), intracellular toxin, tumor necrosis factor alpha, interleukin 1,6,8 adsorption rate are respectively 99.2%, 55.0%, 57.0%, 75.0%, 42.0%; Safety experiment shows: total protein, albumin, sphaeroprotein and change of electrolyte be not obvious (P > 0.05) all; Resin immersion liquid, without leachable, without heat source response, the results are shown in following table 1-4.
The absorption result of table 1HB-H-7 resin to plasma endotoxin
Before and after note: * absorption, comparing difference has statistical significance, P<0.05
The absorption result of table 2HB-H-7 resin to plasma levels of cytokines
Before and after note: * absorption, comparing difference has statistical significance, P<0.05
The adsorption effect of table 3HB-H-7 resin to protein
Table 4HB-H-7 resin is to electrolytical adsorption effect
(2) animal model experiment result
Before and after Plasma perfusion, compare, styrene ion exchange resin plasma perfusion treatment group Endotoxin Levels obviously decline (P < 0.05) described in embodiment 1, rate of descent exceedes 90%, empty perfusion control group level of endotoxin is without obviously declining (P > 0.05), and two groups of comparing differences have significance (P > 0.05).Before and after the absorption for the treatment of group perfusion, relatively, protein, white corpuscle, red corpuscle, thrombocyte and ionogen do not have considerable change.All long-term health survivals after the experiment for the treatment of group dog, 14-22h death after all dog experiments of control group finish, the results are shown in following table 5.
Table 5 animal model experiment result
pg/ml
Before and after note: * absorption, comparing difference has statistical significance, P<0.05
Experimental result shows there is unusual effect with intracellular toxin and inflammatory factor that styrene ion exchange resin described in embodiment 1 is removed in severe infection blood samples of patients by blood perfusion, and safe.For the severe infection that is difficult to treatment provides one very valuable methods for the treatment of.
Above-mentioned detailed description of this kind of styrene ion exchange resin and preparation method thereof and application being carried out with reference to embodiment; illustrative instead of determinate; can list several embodiment according to institute's limited range; therefore in the variation and the amendment that do not depart under general plotting of the present invention, within should belonging to protection scope of the present invention.
Claims (10)
1. a styrene ion exchange resin, it is characterized in that: be a kind of cross-linked polystyrene beads body, for the opaque spherical particle of oyster white, diameter is 0.05～1.20mm, density is wet true density 1.06～1.10g/ml, wet volume density 0.65～0.75g/ml, intensity counts to grind rear rate of small round spheres>=and 95%, surface active groups is-N
+(CH
3)
2, aperture is 80～100nm, and porosity is 45～52%, and pore volume is 0.75～0.84ml/g, and specific surface area is 850～1000m
2/ g, full exchange capacity is that dried resin is that 3.7mmol/g, wet resin are 1.1mmol/g.
2. styrene ion exchange resin according to claim 1, is characterized in that: use temperature≤100 DEG C.
3. styrene ion exchange resin according to claim 1, it is characterized in that: be in water, to carry out suspension polymerization by styrene monomer and divinylbenzene monomer to obtain multipolymer pearl body, then repeatedly introduce ionizable group and synthetic cross-linked polystyrene beads body to multipolymer pearl body.
4. the preparation method of styrene ion exchange resin claimed in claim 1, is characterized in that: concrete preparation process is as follows:
(1) adopt free radical suspending copolymerization to prepare cross-linked styrene-divinylbenzene copolymer by styrene monomer and divinylbenzene monomer:
1. the vinylbenzene and the divinylbenzene mixture that contain initiator benzoyl peroxide are suspended in the water that contains dispersion agent, and described dispersion agent is polyvinyl alcohol or carbonyl bearing polymer;
2. under agitation condition, make the drop major part suspending within the scope of 30-70 object, organic phase is dispersed into pearl body;
3. be heated to 95 DEG C, make initiator benzoyl peroxide decompose and initiated polymerization obtains pearl styrene-divinylbenzene copolymer;
4. after polymerization completes, then with sig water cleaning cleaning polyalcohol cross-linked polystyrene beads body to remove the dispersion agent sticking, then dewater, dry;
(2) functionalizing of crosslinked polystyrene-prepare macroporous anion exchange resin:
Cross-linked styrene-divinylbenzene copolymer that 4. above-mentioned steps is prepared carries out functionalizing, make cross-linked polystyrene beads body by chloroethyl crosslinked polystyrene amination, wherein, the chloromethylation of crosslinked polystyrene being introduced to chloromethyl by Knut Fridell-Kerafyrm thatch alkylated reaction on the phenyl ring of crosslinked polystyrene realizes; When chloromethyl resin forms quaternary amine type strong basic ion exchange resin with reactive tertiary amine again, when chloromethyl resin reacts and forms weak base anion-exchange resin with ammonia, primary amine or secondary amine.
5. the preparation method of styrene ion exchange resin according to claim 4, it is characterized in that: described step (1) 3. obtains after vinylbenzene-diethylbenzene alkene copolymer, add when dissolving each other and do not participate in the inert compound of polymerization with styrene monomer and divinylbenzene monomer, after polymerization completes, this inert compound is removed by distillation method, formed macroporous type cross-linked styrene-divinylbenzene copolymer.
6. the preparation method of styrene ion exchange resin according to claim 5, is characterized in that: described inert compound is toluene or dimethylbenzene.
7. the preparation method of styrene ion exchange resin according to claim 4, is characterized in that: in described step (2), the chloromethylation of crosslinked polystyrene is introduced to chloromethyl realization by Knut Fridell-Kerafyrm thatch alkylated reaction on the phenyl ring of crosslinked polystyrene and refer to that crosslinked polystyrene and chloromethyl ether are at ZnCl
2do in the situation of catalyzer, carry out chloromethylation.
8. the application of styrene ion exchange resin claimed in claim 1 aspect adsorb cell factor.
9. the application of styrene ion exchange resin according to claim 8, is characterized in that: described cytokine is intracellular toxin or inflammatory factor.
10. the application of styrene ion exchange resin according to claim 8, is characterized in that: described styrene ion exchange resin is in the application of preparing aspect blood perfusion device.
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Cited By (12)
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|---|---|---|---|---|
| CN104264453A (en) * | 2014-09-09 | 2015-01-07 | 天津工业大学 | Manufacturing method of adsorption cationic fiber membrane |
| CN104403040A (en) * | 2014-09-29 | 2015-03-11 | 苏州赛分科技有限公司 | Ion exchange resin |
| CN104892920A (en) * | 2015-05-26 | 2015-09-09 | 安徽皖东树脂科技有限公司 | Macroporous strong-acidity styrene cation exchange resin |
| CN107262057A (en) * | 2016-04-08 | 2017-10-20 | 中国科学院大连化学物理研究所 | A kind of preparation method of bilirubin resin anion (R.A.) adsorbent |
| CN107321199A (en) * | 2016-04-29 | 2017-11-07 | 辽宁易辰膜科技有限公司 | A kind of manufacture method of rolling ion exchange homogeneous membrane |
| WO2018053696A1 (en) * | 2016-09-21 | 2018-03-29 | 于杰 | Nanocarrier for treating endotoxemia |
| CN108371945A (en) * | 2018-05-04 | 2018-08-07 | 南开大学 | For in removing in uremic patient body, the adsorbent of macromolecular toxins and preparation method |
| CN109174208A (en) * | 2018-08-30 | 2019-01-11 | 深圳市纯水号水处理科技有限公司 | A kind of resin adsorption removal trace metal ion solution |
| CN109833854A (en) * | 2019-03-04 | 2019-06-04 | 蚌埠市天星树脂有限责任公司 | A kind of macroporous absorbent resin and preparation method thereof |
| CN113042113A (en) * | 2021-03-22 | 2021-06-29 | 中国科学院广州能源研究所 | Preparation method of macroporous weak base anion exchange resin special for gold extraction |
| CN113501901A (en) * | 2021-07-23 | 2021-10-15 | 核工业北京化工冶金研究院 | Preparation method of uranium-adsorbing strongly-basic resin with narrow distribution particle size |
| CN116586048A (en) * | 2023-07-17 | 2023-08-15 | 江苏恰瑞生物科技有限公司 | Modified polystyrene adsorption resin for blood perfusion device and preparation method thereof |
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| CN104264453A (en) * | 2014-09-09 | 2015-01-07 | 天津工业大学 | Manufacturing method of adsorption cationic fiber membrane |
| CN104403040A (en) * | 2014-09-29 | 2015-03-11 | 苏州赛分科技有限公司 | Ion exchange resin |
| CN104892920A (en) * | 2015-05-26 | 2015-09-09 | 安徽皖东树脂科技有限公司 | Macroporous strong-acidity styrene cation exchange resin |
| CN107262057A (en) * | 2016-04-08 | 2017-10-20 | 中国科学院大连化学物理研究所 | A kind of preparation method of bilirubin resin anion (R.A.) adsorbent |
| CN107262057B (en) * | 2016-04-08 | 2020-04-17 | 中国科学院大连化学物理研究所 | Preparation method of bilirubin anion resin adsorbent |
| CN107321199B (en) * | 2016-04-29 | 2020-11-27 | 衢州蓝然新材料有限公司 | Method for manufacturing roll type ion exchange homogeneous membrane |
| CN107321199A (en) * | 2016-04-29 | 2017-11-07 | 辽宁易辰膜科技有限公司 | A kind of manufacture method of rolling ion exchange homogeneous membrane |
| WO2018053696A1 (en) * | 2016-09-21 | 2018-03-29 | 于杰 | Nanocarrier for treating endotoxemia |
| CN108371945A (en) * | 2018-05-04 | 2018-08-07 | 南开大学 | For in removing in uremic patient body, the adsorbent of macromolecular toxins and preparation method |
| CN108371945B (en) * | 2018-05-04 | 2020-09-15 | 山东卓逸医疗科技股份有限公司 | Adsorbent for eliminating middle and large molecular toxin in body of uremia patient and preparation method thereof |
| CN109174208A (en) * | 2018-08-30 | 2019-01-11 | 深圳市纯水号水处理科技有限公司 | A kind of resin adsorption removal trace metal ion solution |
| CN109833854A (en) * | 2019-03-04 | 2019-06-04 | 蚌埠市天星树脂有限责任公司 | A kind of macroporous absorbent resin and preparation method thereof |
| CN113042113A (en) * | 2021-03-22 | 2021-06-29 | 中国科学院广州能源研究所 | Preparation method of macroporous weak base anion exchange resin special for gold extraction |
| CN113501901A (en) * | 2021-07-23 | 2021-10-15 | 核工业北京化工冶金研究院 | Preparation method of uranium-adsorbing strongly-basic resin with narrow distribution particle size |
| CN113501901B (en) * | 2021-07-23 | 2023-11-28 | 核工业北京化工冶金研究院 | Preparation method of strong alkaline resin with narrow-distribution particle size for adsorbing uranium |
| CN116586048A (en) * | 2023-07-17 | 2023-08-15 | 江苏恰瑞生物科技有限公司 | Modified polystyrene adsorption resin for blood perfusion device and preparation method thereof |
| CN116586048B (en) * | 2023-07-17 | 2023-09-08 | 江苏恰瑞生物科技有限公司 | Modified polystyrene adsorption resin for blood perfusion device and preparation method thereof |
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Application publication date: 20140813 |