CN105348462A - Triazinyl organic mesoporous polymer as well as preparation method and application thereof - Google Patents
Triazinyl organic mesoporous polymer as well as preparation method and application thereof Download PDFInfo
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- CN105348462A CN105348462A CN201510927304.7A CN201510927304A CN105348462A CN 105348462 A CN105348462 A CN 105348462A CN 201510927304 A CN201510927304 A CN 201510927304A CN 105348462 A CN105348462 A CN 105348462A
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G12/00—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
- C08G12/02—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes
- C08G12/26—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with heterocyclic compounds
- C08G12/30—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with heterocyclic compounds with substituted triazines
- C08G12/32—Melamines
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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
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/22—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material
- B01J20/26—Synthetic macromolecular compounds
- B01J20/262—Synthetic macromolecular compounds obtained otherwise than by reactions only involving carbon to carbon unsaturated bonds, e.g. obtained by polycondensation
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- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F1/00—Treatment of water, waste water, or sewage
- C02F1/28—Treatment of water, waste water, or sewage by sorption
- C02F1/285—Treatment of water, waste water, or sewage by sorption using synthetic organic sorbents
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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
- B01J2220/00—Aspects relating to sorbent materials
- B01J2220/40—Aspects relating to the composition of sorbent or filter aid materials
- B01J2220/44—Materials comprising a mixture of organic materials
- B01J2220/445—Materials comprising a mixture of organic materials comprising a mixture of polymers
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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
- B01J2220/00—Aspects relating to sorbent materials
- B01J2220/40—Aspects relating to the composition of sorbent or filter aid materials
- B01J2220/48—Sorbents characterised by the starting material used for their preparation
- B01J2220/4812—Sorbents characterised by the starting material used for their preparation the starting material being of organic character
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- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F2101/00—Nature of the contaminant
- C02F2101/10—Inorganic compounds
- C02F2101/20—Heavy metals or heavy metal compounds
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- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F2101/00—Nature of the contaminant
- C02F2101/30—Organic compounds
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- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F2101/00—Nature of the contaminant
- C02F2101/30—Organic compounds
- C02F2101/34—Organic compounds containing oxygen
Abstract
The invention discloses a triazinyl organic mesoporous polymer as well as a preparation method and application thereof, belonging to the field of synthesis and adsorption research of an organic porous material. According to the preparation method, a solvothermal method is adopted, ethylene glycol is taken as a reaction medium, tripolycyanamide and paraformaldehyde are taken as raw materials, and a reaction is performed for certain time under a high-temperature and sealed condition to prepare the triazinyl organic mesoporous polymer. The preparation method provided by the invention is cheap in price, simple in process, clean, free of foreign smell, convenient to operate and is benefit for industrial production. The prepared triazinyl organic mesoporous polymer has an open fiber framework structure, is rich in nitrogenous functional groups, can absorb various pollutants in water, and has good application prospect in the aspects of adsorption separation, water body purification and the like.
Description
Technical field
The invention belongs to synthesis and the absorption research field of organic porous polymer, be specifically related to organic mesoporous polymer of a kind of triazinyl and its preparation method and application.
Background technology
Organic pollutant and heavy metal ion are the main components of a lot of trade effluent, and the difference such as its kind, content, character are very large.In numerous water technology, absorption method because having strong adaptability, applied range, easy and simple to handle, biocompatibility is high, cost is low, be easy to the advantages such as regeneration and have broad application prospects, and therefore develops great attention and close attention that polyfunctional novel absorption material is subject to academia and industrial community always.
Porous material becomes the main solid adsorbent of a class owing to having spacious skeleton structure.Compare with metal-organic framework materials with traditional inorganic microporous material (as zeolite molecular sieve, gac etc.), organic porous polymer (POPs) is the class novel porous materials occurred in recent years.POPs is formed by connecting by covalent linkage by containing lightweight element such as C, H, O, N, B, have that preparation method is various, specific surface area is large, skeletal density is low, aperture is adjustable, modified surface and the feature (PhysicalChemistryChemicalPhysics2013 such as stability is better, 15 (15), 5430-5442; ReactiveandFunctionalPolymers2006,66 (7), 768-779; JournalofMaterialsChemistryA2013,1 (8), 2691-2718; ChemicalSocietyReviews2012,41 (6), 2083-2094).Due to the diversity of organic chemical synthesis method, the Nomenclature Composition and Structure of Complexes of POPs has designability and Scalability, can introduce different functional groups or avtive spot in skeleton, to meet the adsorption entails to varying environment pollutent.
Tan etc. first with trimeric cyanamide and paraformaldehyde for raw material, with dimethyl sulfoxide (DMSO) (DMSO) for solvent, a kind of novel organic mesoporous polymer (referred to as mPMF) (GreenChemistry2013 has been synthesized react 72h at 170 DEG C after, 15 (5), 1127-1132 and ChemSusChem2013,6 (7), 1186-1190).MPMF introduces nitrogen-atoms as Adsorption in polymer backbone, can be used for selective adsorption and remove heavy metal ion (Energy & EnvironmentalScience2013 in sewage, 6 (11), 3254-3259).But when finding to synthesize mPMF in actual mechanical process in DMSO, at least there is following problem: 1, the reaction times longer (3d); 2, product washing process is complicated, separation recovery efficiencies is low (as product needs to use DMSO, acetone (3 ×), tetrahydrofuran (THF) (3 ×) and methylene dichloride four kinds of organic solvent washings successively; And sample is a monoblock rigid solid when driving still, wash to make sample and more thoroughly need grinding, but the sample after grinding is easily dispersed in washings when centrifugation, causes loss of product larger); 3, DMSO at high temperature easily decomposes as solvent, produce the sulfocompound with fetor taste, not only can introduce sulphur impurity (content reaches 5%) in the product, and have a strong impact on Working environment and healthy, bring very big inconvenience to the cleaning of product, separation and recovery.
Except DMSO, also once attempted synthesis mPMF in other polar solvent (as dimethyl formamide, N-Methyl pyrrolidone) in the literature, but the little (4.6m of the specific surface area of products therefrom
2/ g), the low (0.005cm of porosity
3/ g), show that DMSO plays an important role to forming the polymkeric substance with vesicular structure, these may owing to the hydrogen bond action of DMSO between initial reaction stage and reactant (ChemSusChem2013,6 (7), 1186-1190).
Therefore, for promoting performance study and the application and development of nitrogenous organic porous polymer further, be necessary to explore more clean, environmental protection and easy production technique.
Summary of the invention
The object of this invention is to provide organic mesoporous polymer of a kind of triazinyl and its preparation method and application, the raw material related to is cheap and easy to get, technique is simple, easy to operate, be conducive to suitability for industrialized production, the organic mesoporous polymer of gained triazinyl can multiple pollutant in planar water, has good application prospect in the field such as fractionation by adsorption, water body purification.
For achieving the above object, the technical solution used in the present invention is:
A preparation method for the organic mesoporous polymer of triazinyl, comprises the following steps:
1) with trimeric cyanamide and paraformaldehyde for raw material, the two is added in ethylene glycol, heats and the white suspension that stirs to obtain;
2) by step 1) by gained white suspension liquid sealing, heating is reacted, and then successively through annealing cooling, washing, centrifugation, drying, obtains the organic mesoporous polymer of described triazinyl.
In such scheme, the mol ratio of described paraformaldehyde and trimeric cyanamide is 1.5 ~ 3.0.
Preferably, the mol ratio of described paraformaldehyde and trimeric cyanamide is 1.8 ~ 2.3.
In such scheme, in ethylene glycol, total starting point concentration of trimeric cyanamide and paraformaldehyde is 2.0 ~ 5.0mol/L.
In such scheme, step 1) described in Heating temperature be 100-140 DEG C, the time is 1-2h.
In such scheme, step 2) described in temperature of reaction be 120 ~ 185 DEG C, the reaction times is 2 ~ 72h.
Preferably, step 2) described in temperature of reaction be 150 ~ 170 DEG C, the reaction times is 48 ~ 56h.
According to the organic mesoporous polymer of triazinyl prepared by such scheme, it is the organic mesoporous polymer based on trimeric cyanamide and paraformaldehyde condensation reaction.
The application of the organic mesoporous polymer of triazinyl in fractionation by adsorption and water body purification field according to prepared by such scheme: can be used for the pollutents such as the cupric ion in adsorbed water body, Ibuprofen BP/EP, tsiklomitsin, Ciprofloxacin, F ion and orange G, the adsorptive capacity of the organic mesoporous polymer of wherein said triazinyl to cupric ion reaches 24.6mg/g, 42.6mg/g is reached to the adsorptive capacity of Ibuprofen BP/EP, 2.5mg/g is reached to the adsorptive capacity of tsiklomitsin, 3.3mg/g is reached to the adsorptive capacity of Ciprofloxacin, 13.7mg/g is reached to the adsorptive capacity of fluorion, 65% is reached to the percent of decolourization of orange G solution.
The present invention is solvent with ethylene glycol first, provides organic mesoporous polymer of a kind of novel triazinyl and its preparation method and application.Ethylene glycol is a kind of conventional protic polar solvent, use it for and prepare the organic mesoporous polymer tool of triazinyl and have the following advantages: 1) high boiling point, strong polarity and solvability preferably, solubilized trimeric cyanamide and paraformaldehyde under high temperature, thus promote polycondensation between the two; 2) not easily decompose under high temperature, no foul smell by product is formed, and DMSO pyrolytic decomposition effectively can be avoided to produce the sulfocompound problem with fetor taste, belong to the more eco-friendly high-temperature solvent of one; 3) containing two end position hydroxyls, abundant intermolecular hydrogen bonding network structure can be formed with reactant, be conducive to the formation promoting vesicular structure.
The present invention makes spent glycol replace DMSO as reaction medium, and not only simply, whole technological process cleans free from extraneous odour, environmental friendliness, convenient operation and amplification and produces for preparation technology and reaction conditions; And change the pattern of products therefrom, elementary composition and porous, synthesize the organic mesoporous polymer of a kind of novel triazinyl.The organic mesoporous polymer of gained triazinyl can multiple pollutant in planar water, has good application prospect in the field such as fractionation by adsorption, water body purification.
Beneficial effect of the present invention is:
1) make employing ethylene glycol prepare the organic mesoporous polymer of triazinyl as solvent first, the raw materials cost related to be low, preparation technology and reaction conditions are simple, clean free from extraneous odour, convenient operation and amplifying is produced; And products therefrom not sulfur-containing impurities, aftertreatment is simple, simply washs, centrifugation, environmental friendliness.
2) ethylene glycol is a kind of high boiling organic solvent of no color or smell, solubilized trimeric cyanamide and paraformaldehyde under high temperature, promotes polycondensation between the two; High temperature not easily decomposes, and no foul smell by product is formed, and is the more friendly pyroreaction medium of a kind of environment; Containing two end position hydroxyls, abundant hydrogen bond network structure can be formed with reactant molecule, thus promote the formation of porous structure polymer.
3) the organic mesoporous polymer of gained triazinyl can be used as Multifunction Water body cleansing agent, and multiple noxious pollutant in planar water, has good application prospect in the field such as fractionation by adsorption and water body purification.
Accompanying drawing explanation
Fig. 1 is the infrared spectrogram of the organic mesoporous polymer of triazinyl of preparation in embodiment 1.
Fig. 2 is the X-ray diffractogram of the organic mesoporous polymer of triazinyl of preparation in embodiment 1.
Fig. 3 is the scanning electron microscope (SEM) photograph of the organic mesoporous polymer of triazinyl of preparation in embodiment 1.
Fig. 4 is the N of the organic mesoporous polymer of triazinyl of preparation in embodiment 1
2adsorption-desorption isothermal.
Embodiment
In order to understand the present invention better, illustrate content of the present invention further below in conjunction with embodiment, but the present invention is not only confined to the following examples.
As no specific instructions, the reagent of employing is commercially available chemical reagent or Industrial products to following examples.
Embodiment 1
A preparation method for the organic mesoporous polymer of triazinyl, comprises the following steps:
Be added in 6.8mL ethylene glycol by trimeric cyanamide (6mmol) and paraformaldehyde (10.8mmol), stir to obtain heat 1h at 120 DEG C after white suspension; Gained white suspension is sealed in isothermal reaction 48h in 170 DEG C of baking ovens, then carries out annealing cooling, use water and washing with alcohol, centrifugation, drying respectively, obtain final product.
The infrared spectrogram of the present embodiment products therefrom is shown in Fig. 1.812cm in figure
-1for triazine ring out-of-plane deformation vibration absorption peak, 1000-1564cm
-1interval is the absorption band of asymmetric stretching vibration and NH flexural vibration in triazine anchor ring, 3409cm
-1for NH stretching vibration peak; 2950cm
-1and 2872cm
-1be respectively CH
2unsymmetrically and symmetrical stretching vibration peak.Result shows that products therefrom contains triazine ring structure, and passes through-NHCH
2nH-is connected to form polymkeric substance.
The X-ray diffractogram of the present embodiment products therefrom is shown in Fig. 2, shows that this polymkeric substance is unformed.
The present embodiment products therefrom is carried out SEM observation (see Fig. 3), result shows that products therefrom has spacious fiber reinforcement structure.Contrast therewith, the mPMF synthesized in DMSO is become by many framboid combinate forms.
The N of the present embodiment products therefrom
2adsorption-desorption isothermal is shown in Fig. 4.By the N in Fig. 4
2the BET specific surface area that adsorpting data calculates product is 334.5m
2/ g, pore volume is 1.06cm
3/ g, mean pore size is 12.6nm.
The above results shows that gained final product is the organic mesoporous polymer of triazinyl of the present invention, and ultimate analysis shows that its C, H, N content are respectively 36.53%, 5.05% and 50.28%, sulphur impurity do not detected.
Embodiment 2
A preparation method for the organic mesoporous polymer of triazinyl, comprises the following steps:
Add in 3.4mL ethylene glycol by trimeric cyanamide (3mmol) and paraformaldehyde (9.0mmol), stir to obtain heat 1h at 120 DEG C after white suspension; Gained white suspension to be sealed in 170 DEG C of baking ovens after isothermal reaction 72h, to carry out annealing cooling, use ethanol and water washing, centrifugation, drying successively, obtain the organic mesoporous polymer of described triazinyl.
Embodiment 3
A preparation method for the organic mesoporous polymer of triazinyl, comprises the following steps:
Add in 3.4mL ethylene glycol by trimeric cyanamide (3mmol) and paraformaldehyde (4.5mmol), stir to obtain heat 1h at 120 DEG C after white suspension; Gained white suspension to be sealed in 170 DEG C of baking ovens after isothermal reaction 6h, to carry out annealing cooling, use ethanol and water washing, centrifugation, drying successively, obtain the organic mesoporous polymer of described triazinyl.
Embodiment 4
A preparation method for the organic mesoporous polymer of triazinyl, comprises the following steps:
Add in 3.4mL ethylene glycol by trimeric cyanamide (3mmol) and paraformaldehyde (5.4mmol), stir to obtain heat 1h at 120 DEG C after white suspension; Gained white suspension to be sealed in 120 DEG C of baking ovens after isothermal reaction 72h, to carry out annealing cooling, use ethanol and water washing, centrifugation, drying successively, obtain the organic mesoporous polymer of described triazinyl.
Embodiment 5
A preparation method for the organic mesoporous polymer of triazinyl, comprises the following steps:
Add in 3.4mL ethylene glycol by trimeric cyanamide (6mmol) and paraformaldehyde (10.8mmol), stir to obtain heat 1h at 120 DEG C after white suspension; Gained white suspension to be sealed in 170 DEG C of baking ovens after isothermal reaction 48h, to carry out annealing cooling, use ethanol and water washing, centrifugation, drying successively, obtain the organic mesoporous polymer of described triazinyl.
Application examples 1
The organic mesoporous polymer of triazinyl embodiment 1 prepared is applied to absorbing copper ion, and concrete steps are as follows:
The organic mesoporous polymer of triazinyl of preparation in 0.2g embodiment 1 is added 40mLCuCl
2solution (0.1wt% (in copper), pH value is 4.28) in, respectively after room temperature and 80 DEG C of lower magnetic forces stir 3-4h, adopt the copper content in solution before and after iodimetry,iodometry indirect measurement absorption, inhaling copper amount under calculating room temperature is 14.3mg/g, and the suction copper amount at 80 DEG C is 24.6mg/g.
Application examples 2
Organic for triazinyl after absorbing copper ion mesoporous polymer is applied to absorption Ibuprofen BP/EP, and concrete steps are as follows:
The organic mesoporous polymer of the triazinyl absorbing copper ion under 80 DEG C of temperature condition according to step described in application examples 1 prepared by embodiment 1, after distilled water wash and 100 DEG C of dryings, (concentration is 0.487g/L to add 40mL Ibuprofen BP/EP solution, pH value is 7.51) in, and 4h is adsorbed in room temperature shaker.
Ultraviolet spectrophotometry is adopted to measure the concentration (λ of the Ibuprofen BP/EP before and after absorption in solution respectively
maxfor 264nm), the adsorptive capacity calculating Ibuprofen BP/EP is 42.6mg/g.
Application examples 3
The organic mesoporous polymer of triazinyl embodiment 1 prepared is applied to tetracycline adsorption, and concrete steps are as follows:
The organic mesoporous polymer of triazinyl 0.2g embodiment 1 prepared adds in 40mL tetracycline hydrochloride solution (concentration is 20mg/L, and pH value is 6.51), then in room temperature shaker, adsorbs 4h.
Employing ultraviolet spectrophotometry measures the tetracycline concentration (λ before and after absorption in solution respectively
maxfor 264nm), the adsorptive capacity calculating tsiklomitsin is 2.5mg/g (absorption percentage 62%).
Application examples 4
The organic mesoporous polymer of triazinyl embodiment 1 prepared is applied to absorption Ciprofloxacin, and concrete steps are as follows:
The organic mesoporous polymer of triazinyl 0.2g embodiment 1 prepared adds in 33mL ciprofloxacin lactate solution (concentration is 40mg/L, and pH value is 6.22), then in room temperature shaker, adsorbs 4h.
Employing ultraviolet spectrophotometry measures the Ciprofloxacin Concentration (λ before and after absorption in solution respectively
maxfor 264nm), the adsorptive capacity calculating Ciprofloxacin is 3.3mg/g (absorption percentage 50%).
Application examples 5
The organic mesoporous polymer of triazinyl embodiment 1 prepared is applied to Adsorption of fluoride ion, and concrete steps are as follows:
The organic mesoporous polymer of triazinyl 0.2g embodiment 1 prepared adds in 50mLNaF solution (concentration is 0.1mol/L, and pH value is adjusted to 5.56), then at room temperature magnetic agitation 3h.
Adopt Fluoride ion selective electrode method to measure fluorinion concentration in the solution of absorption front and back respectively, calculating fluorion adsorptive capacity is 13.7mg/g.
Application examples 6
The organic mesoporous polymer of triazinyl embodiment 1 prepared is applied to absorption orange G, and concrete steps are as follows:
The organic mesoporous polymer of triazinyl 0.2g embodiment 1 prepared adds in 50mL orange G solution (concentration is 0.05mmol/L, and pH value is 7.05), and then at room temperature magnetic agitation 0.5h reaches adsorption equilibrium.
Employing ultraviolet-visible spectrophotometry measures the orange G concentration (λ before and after absorption in solution respectively
maxfor 478nm), the percent of decolourization calculating orange G solution is 65%.
Above embodiment just understands method of the present invention and core concept thereof for helping.It should be pointed out that for those skilled in the art, under the premise without departing from the principles of the invention, can also carry out some improvement and modification to the present invention, these improve and modify and also fall in the protection domain of the claims in the present invention.
Claims (10)
1. a preparation method for the organic mesoporous polymer of triazinyl, is characterized in that, comprise the following steps:
1) with trimeric cyanamide and paraformaldehyde for raw material, the two is added in ethylene glycol, heats and the white suspension that stirs to obtain;
2) by step 1) by gained white suspension liquid sealing, heating is reacted, and then through annealing cooling, washing, centrifugation, drying, obtains the organic mesoporous polymer of described triazinyl.
2. preparation method according to claim 1, is characterized in that, the mol ratio of described paraformaldehyde and trimeric cyanamide is 1.5 ~ 3.0.
3. preparation method according to claim 1, is characterized in that, the mol ratio of described paraformaldehyde and trimeric cyanamide is 1.8 ~ 2.3.
4. preparation method according to claim 1, is characterized in that, in ethylene glycol, the total concn of trimeric cyanamide and paraformaldehyde is 2.0 ~ 5.0mol/L.
5. preparation method according to claim 1, is characterized in that, step 1) described in Heating temperature be 100-140 DEG C, the time is 1-2h.
6. preparation method according to claim 1, is characterized in that, step 2) described in temperature of reaction be 120 ~ 185 DEG C, the reaction times is 2 ~ 72h.
7. preparation method according to claim 1, is characterized in that, step 2) described in temperature of reaction be 150 ~ 170 DEG C, the reaction times is 48 ~ 56h.
8. the organic mesoporous polymer of triazinyl that described in any one of claim 1 ~ 7 prepared by preparation method.
9. the application of the organic mesoporous polymer of triazinyl described in claim 8 in fractionation by adsorption and water body purification field.
10. application according to claim 9, it is characterized in that, the adsorptive capacity of the organic mesoporous polymer of described triazinyl to cupric ion reaches 24.6mg/g, 42.6mg/g is reached to the adsorptive capacity of Ibuprofen BP/EP, 2.5mg/g is reached to the adsorptive capacity of tsiklomitsin, 3.3mg/g is reached to the adsorptive capacity of Ciprofloxacin, 13.7mg/g is reached to the adsorptive capacity of fluorion, 65% is reached to the percent of decolourization of orange G solution.
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