CN114031715A - Sulfoamido-containing resin and preparation method and application thereof - Google Patents
Sulfoamido-containing resin and preparation method and application thereof Download PDFInfo
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- CN114031715A CN114031715A CN202111212779.XA CN202111212779A CN114031715A CN 114031715 A CN114031715 A CN 114031715A CN 202111212779 A CN202111212779 A CN 202111212779A CN 114031715 A CN114031715 A CN 114031715A
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/42—Nitriles
- C08F220/44—Acrylonitrile
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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
- B01J20/265—Synthetic macromolecular compounds modified or post-treated 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
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/28—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties
- B01J20/28014—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties characterised by their form
- B01J20/28026—Particles within, immobilised, dispersed, entrapped in or on a matrix, e.g. a resin
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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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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/42—Nitriles
- C08F220/50—Nitriles containing four or more carbon atoms
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/34—Introducing sulfur atoms or sulfur-containing groups
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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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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P10/00—Technologies related to metal processing
- Y02P10/20—Recycling
Abstract
The invention provides a thioamide group-containing crosslinked polymer resin, which is prepared by copolymerizing a functional monomer containing double bonds and cyano groups and a crosslinking agent containing 2 or more than 2 double bonds to obtain a cyano group-containing resin, reacting the obtained cyano group-containing crosslinked polymer resin with a compound containing sulfhydryl ions to obtain the thioamide group-containing resin, and enabling the obtained thioamide group-containing resin to have a good adsorption effect on mercury ions. The resin containing thioamide groups prepared by the invention has the advantages of high adsorption capacity to mercury ions, simple synthetic process and low cost.
Description
Technical Field
The invention relates to the field of resins for adsorbing mercury ions, in particular to a thioamide group-containing resin serving as an adsorbent for mercury ions.
Background
With the development of modern industry, some toxic and harmful substances inevitably pollute the environment, such as a large amount of waste water containing mercury ions, which is generated in the production process of certain industries, particularly mining industry. The mercury ions in the water body can be enriched in a human body through a food chain, and the mercury ions enriched in the human body are difficult to discharge out of the body through metabolism, so that cumulative irreversible damage is caused to the health of people, and symptoms such as nerve damage, movement disorder, visual deterioration, hearing loss, mood fluctuation, heart failure and the like are caused. Therefore, how to economically and effectively treat the wastewater containing the mercury ions is an urgent problem to be solved.
The method for treating the wastewater containing mercury ions mainly comprises a chemical precipitation method, an electrolysis method, an adsorption method and the like. The chemical precipitation method is a mercury treatment method which is relatively common in application, is suitable for treating wastewater with higher mercury ion concentration, and comprises a coagulation precipitation method and a sulfide precipitation method. But the method is not suitable for treating the wastewater with low concentration of mercury ions; the electrolysis method is that under the action of direct current, mercury ions are reduced into metallic mercury at a cathode, so that the concentration of the mercury ions in the wastewater is extremely low. However, the method has poor treatment effect on the wastewater containing low-concentration mercury ions, and the method has large energy consumption and high investment. In addition, the method is easy to generate mercury vapor to form secondary pollution; the adsorption method for treating mercury-containing wastewater is the most studied and widely applied method at present, and the method enriches low-concentration mercury ions through adsorption, so that the concentration of the mercury ions in the treated water is reduced to be below the concentration allowed by the emission standard. The adsorption method is suitable for treating the wastewater containing low-concentration mercury ions, particularly when the concentration of the mercury ions in the wastewater is higher, the mercury ions can be reduced to a lower concentration by adopting a chemical precipitation method, an electrolysis method and other treatment methods, and then the wastewater is treated by using the adsorption method, so that the advantages of the methods are fully exerted, the defects of the methods are overcome, and the optimal treatment effect is achieved.
The most widely used adsorbents in adsorption processes are chelating resins, and many groups containing sulfur, nitrogen and oxygen, particularly sulfur-containing groups, can form stable complexes with heavy metal ions such as mercury ions, and thus many chelating resins containing these groups have been developed for adsorbing heavy metal ions such as mercury ions. However, the chelating resins containing sulfur groups reported in the literature often have the disadvantages of complicated preparation process, high preparation cost, low adsorption capacity and the like, and limit the practical application of the chelating resins in the treatment of wastewater containing mercury ions.
Disclosure of Invention
The invention provides a method for preparing a thioamide group-containing polymer resin as an adsorbent of mercury ions, aiming at overcoming the defects of the sulfur-containing chelating resin reported in the above documents. The invented thioamido mercury ion adsorbent is obtained by the reaction of resin containing cyano and hydrogen sulfide ions, and the reaction formula can be represented by the following formula:
the cyano-containing resin is obtained by carrying out conventional suspension free radical polymerization on a double bond and cyano-containing functional group monomer and a cross-linking agent containing 2 or more than 2 double bonds, and the cyano-containing resin obtained by polymerization can be gel resin or macroporous resin. I.e. if no porogen is added during the polymerization, a gel-type resin is obtained. If a pore-forming agent is added in the polymerization process, the macroporous resin is obtained. Porogens are inert compounds which are insoluble or sparingly soluble in water and do not participate in free radical polymerization.
The functional group monomers containing double bonds and cyano groups include, but are not limited to, acrylonitrile, methacrylonitrile, and 2-butenenitrile; crosslinking agents containing 2 or more than 2 double bonds include, but are not limited to, divinylbenzene, ethylene glycol dimethacrylate, triallyl cyanurate, triallyl isocyanurate, and the like. The cross-linking agents can be used singly, or 2 or more than 2 cross-linking agents can be used as the cross-linking agents in a mixture of any proportion; the pore-forming agent includes toluene, ethylbenzene, n-hexane, cyclohexane, heptane, liquid paraffin, solvent oil, butanol, hexanol, cyclohexanol, etc. The pore-forming agent can be used alone, or 2 or more than 2 pore-forming agents can be used in combination in any proportion.
The cyano-containing resin is reacted with the hydrogen sulfide group-containing compound to obtain the thioamide group-containing resin. The hydrosulfide-containing compounds used include sodium hydrosulfide, potassium hydrosulfide and ammonium hydrosulfide. The reaction can use water, methanol, ethanol, dimethylformamide, dimethyl sulfoxide and the like as solvents, and can use a single solvent or a mixed solvent. The reaction temperature was from room temperature to reflux temperature. The particle size of the resulting crosslinked polymer resin is controlled to be 0.05 to 1.5mm, preferably 0.2 to 1.2 mm.
The invention further provides application of the thioamide group-containing resin as an adsorbent, in particular to adsorption of mercury ions in water.
The invention has the advantages and beneficial effects that:
the resin containing thioamide groups has the advantages of simple preparation process, low cost and large mercury ion adsorption capacity.
Detailed Description
The invention is further illustrated by the following examples, which are intended only for a better understanding of the contents of the invention. It is to be understood that the scope of the invention is not to be limited by the embodiments, but is to be determined by the scope of the appended claims.
Example 1
34.8g of acrylonitrile and 5.2g of divinylbenzene (content: 63%) were mixed uniformly, 0.2g of azobisisobutyronitrile was added and stirred to dissolve, and referred to as an oil phase. 1.5g of polyvinyl alcohol (model 1788) and 15g of sodium chloride were dissolved in 300mL of deionized water and referred to as the aqueous phase. Adding the oil phase into the water phase, starting mechanical stirring, adjusting the stirring speed to disperse the oil phase into small oil droplets, enabling the peak value of the diameter distribution of the oil droplets to be about 0.4mm, heating to enable the temperature of the system to reach 65 ℃ and keeping for 6 hours, and then heating to 75 ℃ and keeping for 4 hours. The heating was stopped, the system was allowed to cool, the resulting resin was collected by filtration, washed with hot water several times, and air-dried, and the resulting resin was referred to as white ball PCN-1.
18g of sodium hydrosulfide was added to 50mL of water, 10g of white ball PCN-1 was then added thereto, and the reaction was heated under reflux for 4 hours. Cooling, filtering, and washing the obtained resin with water to obtain the thioamide resin PCNS-1.
Example 2
71.6g of acrylonitrile, 5.2g of divinylbenzene (content: 63%), 3.2g of triallyl isocyanurate and 40g of toluene were mixed uniformly, 0.4g of azobisisobutyronitrile was added thereto and dissolved by stirring, and the mixture was referred to as an oil phase. 2.5g of polyvinyl alcohol (model 1788) and 25g of sodium chloride were dissolved in 500mL of deionized water and referred to as the aqueous phase. Adding the oil phase into the water phase, starting mechanical stirring, adjusting the stirring speed to disperse the oil phase into small oil droplets, enabling the peak value of the diameter distribution of the oil droplets to be about 0.4mm, heating to enable the temperature of the system to reach 65 ℃ and keeping for 6 hours, and then heating to 75 ℃ and keeping for 4 hours. The heating was stopped, the system was allowed to cool, the resulting resin was collected by filtration, washed with hot water several times, air dried, extracted with acetone for 8 hours with a soxhlet extractor, and air dried, and the resulting resin was named white ball PCN-2.
18g of sodium hydrosulfide was added to 50mL of water, 10g of white ball PCN-2 was then added thereto, and the reaction was heated under reflux for 4 hours. Cooling, filtering, and washing the obtained resin with water to obtain the thioamide resin PCNS-2-1.
20g of potassium hydrosulfide was added to 50mL of water, 10g of white ball PCN-2 was then added thereto, and the reaction was heated under reflux for 4 hours. Cooling, filtering, and washing the obtained resin with water to obtain the thioamide resin PCNS-2-2.
Example 3
71.6g of acrylonitrile, 5.2g of divinylbenzene (content: 63%), 3.2g of triallyl cyanurate, 20g of toluene and 20g of cyclohexanol were mixed uniformly, and 0.4g of azobisisobutyronitrile was added and stirred to dissolve it, which was referred to as an oil phase. 2.5g of polyvinyl alcohol (model 1788) and 25g of sodium chloride were dissolved in 500mL of deionized water and referred to as the aqueous phase. Adding the oil phase into the water phase, starting mechanical stirring, adjusting the stirring speed to disperse the oil phase into small oil droplets, enabling the peak value of the diameter distribution of the oil droplets to be about 0.4mm, heating to enable the temperature of the system to reach 65 ℃ and keeping for 6 hours, and then heating to 75 ℃ and keeping for 4 hours. The heating was stopped, the system was allowed to cool, the resulting resin was collected by filtration, washed with hot water several times, air dried, extracted with acetone for 8 hours with a soxhlet extractor, and air dried, and the resulting resin was named white ball PCN-3.
18g of ammonium bisulfide was added to a mixed solvent of 25mL of water and 25mL of ethanol, and then 10g of white ball PCN-3 was added, followed by heating and refluxing for reaction for 8 hours. Cooling, filtering, and washing the obtained resin with water to obtain the thioamide resin PCNS-3-1.
18g of ammonium bisulfide was added to 50mL of ethanol, 10g of white ball PCN-3 was then added, and the reaction was heated under reflux for 15 hours. Cooling, filtering, and washing the obtained resin with water to obtain the thioamide resin PCNS-3-2.
Example 4
90.6g of 2-butenenitrile, 5.2g of divinylbenzene (content: 63%), 6.1g of ethylene glycol dimethacrylate and 40g of toluene were homogenized, 0.4g of azobisisobutyronitrile was added thereto and dissolved by stirring, and the mixture was referred to as an oil phase. 5g of gelatin 50g of sodium chloride are dissolved in 500mL of deionized water, referred to as the aqueous phase. Adding the oil phase into the water phase, starting mechanical stirring, adjusting the stirring speed to disperse the oil phase into small oil droplets, enabling the peak value of the diameter distribution of the oil droplets to be about 0.4mm, heating to enable the temperature of the system to reach 65 ℃ and keeping for 6 hours, and then heating to 75 ℃ and keeping for 4 hours. The heating was stopped, the system was allowed to cool, the resulting resin was collected by filtration, washed with hot water several times, air dried, extracted with acetone for 8 hours with a soxhlet extractor, and air dried, and the resulting resin was named white ball PCN-4.
18g of sodium hydrosulfide was added to 50mL of water, 10g of white ball PCN-4 was then added thereto, and the reaction was heated under reflux for 4 hours. Cooling, filtering, and washing the obtained resin with water to obtain the thioamide resin PCNS-4.
Example 5
34.8g of methacrylonitrile, 5.2g of divinylbenzene (content: 63%), 10g of toluene and 10g of n-heptane were mixed uniformly, 0.3g of benzoyl peroxide was added thereto and dissolved by stirring, and referred to as an oil phase. 1.25g of gelatin and 15g of sodium chloride were dissolved in 250mL of deionized water, referred to as the aqueous phase. Adding the oil phase into the water phase, starting mechanical stirring, adjusting the stirring speed until the oil phase is dispersed into oil beads with proper size, heating to enable the temperature of the system to reach 70 ℃ and keeping for 6 hours, and then heating to 75 ℃ and keeping for 4 hours. The heating was stopped, the system was allowed to cool, the resulting resin was collected by filtration, washed with hot water several times, air dried, extracted with acetone for 8 hours with a soxhlet extractor, and air dried, and the resulting resin was named white ball PCN-5.
18g of sodium hydrosulfide was added to 50mL of methanol, 10g of white ball PCN-5 was then added, and the reaction was heated under reflux for 15 hours. Cooling, filtering, and washing the obtained resin with water to obtain the thioamide resin PCNS-5.
Application examples
Approximately 0.06g of the thioamide group containing resin was dispersed in 25mL of mercury sulfate solution having an initial mercury ion concentration of 150mg/L and shaken at room temperature for 24 hours. The supernatant was taken and the concentration of mercury ions was measured by ICP method, and then the amount of mercury ions adsorbed was calculated as shown in the table below.
Table 1: adsorption capacity of mercuric ions of thioamide-based resin
| Resin composition | Adsorption Capacity (mg/g) | Resin composition | Adsorption Capacity (mg/g) |
| PCNS-1 | 28.7 | PCNS-3-2 | 32.8 |
| PCNS-2-1 | 30.5 | PCNS-4 | 26.7 |
| PCNS-2-2 | 31.2 | PCNS-5 | 29.2 |
| PCNS-3-1 | 29.6 |
Description of the drawings: the above embodiments are only used to illustrate the present invention and do not limit the technical solutions described in the present invention; thus, while the present invention has been described in detail with reference to the foregoing embodiments, it will be understood by those skilled in the art that various changes may be made and equivalents may be substituted; all such modifications and variations are intended to be included herein within the scope of this disclosure and the present invention and protected by the following claims.
Claims (10)
1. A crosslinked polymer resin containing thioamide groups, the thioamide groups being functional groups of said crosslinked polymer resin and represented by the following structural formula:
2. the method for preparing a thioamide group-containing crosslinked polymer resin according to claim 1, wherein: the thioamide group-containing crosslinked polymer resin is obtained by reacting a cyano group-containing crosslinked polymer resin with a compound containing a hydrogensulfate ion.
3. The method for preparing a thioamide group-containing crosslinked polymer resin according to claim 2, wherein: the cyano-containing crosslinked polymer resin is obtained by copolymerizing a functional monomer containing double bonds and cyano groups and a crosslinking agent containing 2 or more than 2 double bonds.
4. The method for preparing a thioamide group-containing crosslinked polymer resin according to claims 2 and 3, wherein: the monomer containing double bonds and cyano is one or a composition of more than two of acrylonitrile, methacrylonitrile and 2-butenenitrile.
5. The method for preparing a thioamide group-containing crosslinked polymer resin according to claims 2 and 3, wherein: the crosslinking agent containing 2 or more than 2 double bonds is one or a composition of more than two of divinylbenzene, ethylene glycol dimethacrylate, triallyl cyanurate and triallyl isocyanurate.
6. The method for preparing a thioamide group-containing crosslinked polymer resin according to claims 2 and 3, wherein: the functional monomer containing double bonds and cyano groups is copolymerized with a cross-linking agent containing 2 or more than 2 double bonds with or without adding a pore-foaming agent, and the cross-linked polymer resin containing cyano groups obtained correspondingly is macroporous or gel.
7. The method for preparing a thioamide group-containing crosslinked polymer resin according to claims 2 and 3, wherein: the particle size of the obtained crosslinked polymer resin is controlled to be 0.05-1.5 mm.
8. The method for preparing a thioamide group-containing crosslinked polymer resin according to claim 2, wherein: the compound containing the hydrogen sulfide ions is one or a composition of more than two of sodium hydrogen sulfide, potassium hydrogen sulfide and ammonium hydrogen sulfide.
9. Use of the thioamide group-containing crosslinked polymer resin as defined in claim 1 as an adsorbent.
10. Use of the thioamide group-containing crosslinked polymer resin as defined in claim 1 as an adsorbent for adsorbing mercury ions from an aqueous solution.
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Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3423336A (en) * | 1965-10-18 | 1969-01-21 | Diamond Shamrock Corp | Weak base anion exchange resin and process of preparing same |
| GB1377880A (en) * | 1971-12-01 | 1974-12-18 | Akzo Nv | Removal of mercury ions from solutions which contain mercury in the form of soluble salts |
| US3998797A (en) * | 1974-10-24 | 1976-12-21 | Labofina S.A. | Posttreatment of copolymer of styrene and acrylonitrile |
| CN102140705A (en) * | 2010-12-24 | 2011-08-03 | 吉林大学 | Method for preparing thioamide-based chelating nanofiber for adsorbing heavy metal ions |
| CN105837742A (en) * | 2016-05-17 | 2016-08-10 | 张国华 | Preparation method of polyamide adsorption resin |
| CN109289807A (en) * | 2018-10-31 | 2019-02-01 | 扬州金珠树脂有限公司 | A kind of preparation method of mercury ion absorption resin |
-
2021
- 2021-10-18 CN CN202111212779.XA patent/CN114031715B/en active Active
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3423336A (en) * | 1965-10-18 | 1969-01-21 | Diamond Shamrock Corp | Weak base anion exchange resin and process of preparing same |
| GB1377880A (en) * | 1971-12-01 | 1974-12-18 | Akzo Nv | Removal of mercury ions from solutions which contain mercury in the form of soluble salts |
| US3998797A (en) * | 1974-10-24 | 1976-12-21 | Labofina S.A. | Posttreatment of copolymer of styrene and acrylonitrile |
| CN102140705A (en) * | 2010-12-24 | 2011-08-03 | 吉林大学 | Method for preparing thioamide-based chelating nanofiber for adsorbing heavy metal ions |
| CN105837742A (en) * | 2016-05-17 | 2016-08-10 | 张国华 | Preparation method of polyamide adsorption resin |
| CN109289807A (en) * | 2018-10-31 | 2019-02-01 | 扬州金珠树脂有限公司 | A kind of preparation method of mercury ion absorption resin |
Non-Patent Citations (2)
| Title |
|---|
| 周俊杰;唐志珂;张超;王洞天;张开;孙宏滨;: "连续流微反应器中CuCN-TsOH催化合成2-芳基-4, 5-二氢-1H-咪唑啉", 有机化学, no. 11, pages 161 - 168 * |
| 崔振峰;杨华;王永芝;: "聚丙烯腈螯合纳米纤维的制备及其吸附性能研究", 长春工程学院学报(自然科学版), no. 03, pages 165 - 168 * |
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