KR101801294B1 - Acrylic fibrous absorbent functionalized with amines and method of manufacturing the same - Google Patents
Acrylic fibrous absorbent functionalized with amines and method of manufacturing the same Download PDFInfo
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- KR101801294B1 KR101801294B1 KR1020160030768A KR20160030768A KR101801294B1 KR 101801294 B1 KR101801294 B1 KR 101801294B1 KR 1020160030768 A KR1020160030768 A KR 1020160030768A KR 20160030768 A KR20160030768 A KR 20160030768A KR 101801294 B1 KR101801294 B1 KR 101801294B1
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- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/30—Processes for preparing, regenerating, or reactivating
- B01J20/3085—Chemical treatments not covered by groups B01J20/3007 - B01J20/3078
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- 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
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Abstract
There is provided a process for producing an acrylic fiber adsorbent comprising reacting an acrylic fiber support and an amine compound under non-metallic Lewis acid catalyst conditions to produce an acrylic fiber adsorbent.
Description
The present invention relates to amine-modified acrylic fiber adsorbents and processes for their preparation. More particularly, the present invention relates to an amine-modified acrylic fiber adsorbent having both cationic and anionic adsorptive properties and excellent adsorptivity, and a method for producing the same.
With the development of heavy chemical industries such as electronics and semiconductor industry, textile industry, food industry, steel industry and petrochemical industry, emissions of water pollution such as industrial wastewater, domestic wastewater and livestock wastewater due to population increase are increasing. However, most water pollutants contain phosphorus and nitrogen compounds of the heavy metals and anions of the cations. Therefore, in order to reduce water pollution, water pollutants such as heavy metals, phosphorus and nitrogen compounds should be removed.
Currently widely used techniques are the use of polymeric resin adsorbents (US Pat. No. 5,403,492 and US Pat. No. 5,378,802), which have small specific surface area and low adsorption capacity, and because the resin form is powder or granular, There is a problem that the installation cost and the cost of the facility and maintenance expenses increase due to the increase of the filling amount. There is also a technique for adsorbing heavy metals by collecting the strain on a silica-based carrier (KR 10-2015-003454 A1), but this requires stable operation technology of living strains and a high operating ratio. Accordingly, a variety of adsorbent technologies that can efficiently capture at low operating costs have been studied.
In recent years, fibrous adsorbents have been developed in order to solve the problems of the conventional polymer resins and adsorbents using microorganisms. The fibrous adsorbents have higher adsorbability because they have higher specific surface area and many functional groups than bead and powder forms, It can be used variously according to practical application such as module design according to facility operation condition and application method, and has many advantages that can minimize operating pressure. On the other hand, there is also a technique for producing an amine-modified fibrous chitosan adsorbent by a three-step process of fibrous chitosan (
There is also a technology for producing a PAN-based ion exchange fiber by reacting a PAN fiber structure with an amine compound under a metal chloride catalyst (KR 10-0412203 B1), which has excellent adsorption ability as compared with a conventional adsorbent, When metal chloride catalysts such as iron chloride and tin chloride are used, metal ions attributable to the catalyst may be adsorbed on the surface of the fibers to block the active site of the adsorbent to reduce the adsorption efficiency. Therefore, a second washing process using an acidic or basic solution There is a problem that is required.
Therefore, the conventional adsorbents have problems such as low adsorption ability, multi-stage production process and economical efficiency, and accordingly, there is a need to develop a new adsorbent and a manufacturing process thereof which can improve the adsorbent.
Embodiments of the present invention provide an acrylic fiber-based adsorbent having both positive adsorption characteristics of cations and anions and excellent adsorption ability.
In another embodiment of the present invention, there is provided a process for preparing the acrylic fiber-based adsorbent which can be carried out by a single process.
In one embodiment of the present invention, there is provided a process for producing an acrylic fiber adsorbent comprising reacting an acrylic fiber support and an amine compound under non-metallic Lewis acid catalyst conditions to produce an acrylic fiber adsorbent.
In an exemplary embodiment, the non-metallic Lewis acid catalyst may be a boron triflourohydrate (BF 3 .2H 2 O) catalyst.
In an exemplary embodiment, the acrylic fiber support is made from a monomer comprising at least one selected from the group consisting of acrylonitrile, vinyl alcohol, vinyl acetate, vinyl chloride, methyl acrylate, butyl acrylate and vinyl acetic acid Based acrylic fiber.
In an exemplary embodiment, the amine compound is selected from the group consisting of ethylenediamine (EDA), diethylenetriamine (DETA), tris (2-aminoethylamine), propane- Propane-1,3-diamine, methane triamine, 3- (2-aminoethyl) pentane-1 , 5-diamine, melamine, diaminofurazan, diaminopyridine, and diaminopyrimidine. The term " pharmaceutically acceptable salt thereof "
In an exemplary embodiment, the non-metallic Lewis acid catalyst may be added in a proportion of 0.5-10 wt% based on the weight of the mixture of acrylic fiber support and amine compound.
In an exemplary embodiment, the step of reacting the acrylic fiber support with an amine compound can be carried out at a temperature of from 50 to 150 DEG C for a time ranging from 30 to 120 minutes.
In an exemplary embodiment, the acrylic fiber adsorbent is capable of adsorbing cations and anions.
In an exemplary embodiment, the acrylic fiber adsorbent may exhibit an adsorptive capacity in the range of 0.5 to 30 mmol / g.
In another embodiment of the present invention, an acrylic-based adsorbent that adsorbs cations and anions is provided as an acrylic-based adsorptive fiber that is a reaction product of an acrylic fiber support and an amine compound.
In an exemplary embodiment, the acrylic adsorbent fiber can be prepared by reacting the acrylic fiber support with the amine compound under non-metallic Lewis acid catalyst conditions.
In an exemplary embodiment, the non-metallic Lewis acid catalyst may be a boron triflourohydrate (BF 3 .2H 2 O) catalyst.
In an exemplary embodiment, the acrylic fiber adsorbent may exhibit an adsorptive capacity in the range of 0.5 to 30 mmol / g.
The acrylic fiber-based adsorbent according to an embodiment of the present invention contains a large number of amine groups and can have multifunctional properties and can have both cationic and anionic characteristics, so that it can adsorb both cations and anions which are water pollutants. Accordingly, the acrylic fiber-based adsorbent can exhibit excellent adsorption ability. Therefore, the acrylic fiber-based adsorbent can be widely used as various filter materials such as noxious gas and air purifying device, automobile air purifying filter, air conditioning filter for building, water purifying device, separating and recovering various rare metals and heavy metals .
According to the method for producing an acrylic fiber-based adsorbent according to an embodiment of the present invention, the acrylic fiber-based adsorbent can be prepared through a single polymerization process using only an amine compound and an acrylic fiber support under non-metallic Lewis acid catalyst conditions. Accordingly, an acrylic fiber-based adsorbent having a high specific surface area and excellent adsorptivity can be produced only by a single process, thereby lowering the manufacturing cost.
1 is a view showing a reaction for producing an acrylic fiber adsorbent according to an embodiment of the present invention.
2 is a view for comparing the active region of the acrylic fiber adsorbent produced under the nonmetallic Lewis acid catalyst conditions (top of FIG. 2) and the metal Lewis acid catalyst conditions (bottom of FIG. 2).
3 is an ATR FT-IR spectrum of the acrylic fiber adsorbent prepared according to Example 1 and Comparative Example 1. Fig.
4 is a graph showing the results of an experiment for measuring PO4 anion of the acrylic fiber adsorbent prepared according to Example 1 and Comparative Example 1. Fig.
5A to 5D are graphs showing results of heavy metal adsorption experiments of the acrylic fiber adsorbent prepared according to Example 1 and Comparative Example 1. FIG. 5B is a graph showing the results of the iron adsorption test of the acrylic fiber adsorbents, FIG. 5C is a graph showing the zinc adsorption test of the acrylic fiber adsorbents, and FIG. FIG. 5D is a graph showing the results of the lead adsorption test of the acrylic fiber adsorbents. FIG.
6A to 6C are photographs showing the results of observation of the surface of an acrylic fiber adsorbent produced according to Example 1 and an acrylic fiber adsorbent prepared according to Comparative Examples 1 and 2, respectively. 6B is a photograph showing the result of observing the surface of an acrylic fiber adsorbent produced under an AlCl 3 catalyst, and FIG. 6C is a photograph showing the result of observation of the surface of acrylic fiber of
In the present specification, the term " acrylic fiber support " means an acrylic fiber that serves as a support during the polymerization reaction.
As used herein, the term "acrylic fiber adsorbent" refers to an adsorbent prepared by using an acrylic fiber (that is, an acrylic fiber support).
Hereinafter, embodiments of the present invention will be described in detail with reference to the accompanying drawings. Although the embodiments of the present invention have been described with reference to the accompanying drawings, it is to be understood that the same is by way of illustration and example only and is not to be construed as limiting the scope of the present invention.
In one embodiment of the present invention, there is provided a process for producing an acrylic fiber adsorbent comprising reacting an acrylic fiber support and an amine compound under non-metallic Lewis acid catalyst conditions to produce an acrylic fiber adsorbent. 1 is a view illustrating a method of producing an acrylic fiber adsorbent according to an embodiment of the present invention.
The acrylic fiber adsorbent of the present invention is prepared by reacting an acrylic fiber support with an amine compound under non-metallic Lewis acid catalyst conditions.
In the amine-modified acrylic fiber adsorbent, the ability to utilize amine functional groups can be maximized and the adsorption capacity can be improved.
In general, metal-based Lewis acid catalysts are used in the production of acrylic fiber adsorbents. If metal-based Lewis acid catalysts other than the non-metallic Lewis acid catalysts are used in preparing the acrylic fiber adsorbents, And coordination bonds with the amine functional group of the amine compound to block the active site related to the adsorption ability (the bottom of FIG. 2).
On the other hand, the acrylic fiber adsorbent of the present invention may be free of metal cations which may reduce the active sites ability by utilizing a non-metal-based Lewis acid catalyst in the production thereof (the top of FIG. 2). Accordingly, the adsorption capability of the acrylic fiber adsorbent can be further improved. Hereinafter, the configuration thereof will be described in detail.
In an exemplary embodiment, the acrylic fiber support is made from a monomer comprising at least one selected from the group consisting of acrylonitrile, vinyl alcohol, vinyl acetate, vinyl chloride, methyl acrylate, butyl acrylate and vinyl acetic acid Based acrylic fiber.
In one embodiment, the acrylic fiber support may have a molecular weight of 10,000 to 100,000 (Mw) or more. If the molecular weight of the acrylic fiber support is 100,000 or less, the acrylic fiber support has excellent strength as a support for retaining the fibrous phase, and the processing according to the processing method can be performed flexibly. When the molecular weight of the acrylic fiber support is less than 10,000, the solubility in water may increase due to the influence of amine groups after the reaction, which may be unsuitable as a water treatment agent.
In an exemplary embodiment, the acrylic fiber support may have a diameter between 100 and 100 nm. Generally, the smaller the diameter, the larger the specific surface area and thus the greater the adsorption amount per g. Therefore, theoretically, the smaller the diameter, the better the adsorption capacity. However, when the fiber having the diameter of 100 nm or less is used as the support, And there may be economic problems in the production process.
In one embodiment, the acrylic fiber support may be spun through a wet process, and may be a long fiber or a short fiber, depending on the application, and may be a fibrous structure composed of a nonwoven fabric or a woven fabric.
In an exemplary embodiment, the amine compound may be a substance capable of binding with the acrylic fiber support to serve as a ligand, and may be a primary or higher amine compound having an alkyl group, Type structure.
In one embodiment, the amine compound is selected from the group consisting of ethylenediamine (EDA), diethylenetriamine (DETA), tris (2-aminoethylamine), propane- Propane-1,3-diamine, methane triamine, 3- (2-aminoethyl) pentane-1, 5-diamine, melamine, diaminofurazan, diaminopyridine, and diaminopyrimidine. The term " pharmaceutically acceptable salt thereof "
In an exemplary embodiment, the non-metallic Lewis acid catalyst may be a boron triflourohydrate (BF 3 .2H 2 O) catalyst. In the case of using the conventional metal chloride catalyst, the metal ions attributed to the catalyst are adsorbed on the surface of the finally formed fibrous adsorbent, blocking the active site of the adsorbent to reduce the adsorption efficiency. In order to remove the acidic or basic solution, The second fiber washing step of the fiber adsorbent used is required. However, since the non-metal-based Lewis acid catalyst is used in the present invention, the problem that metal ions are adsorbed on the fibers may not occur. As a result, the acrylic fiber adsorbent finally produced can be excellent in adsorbability.
In an exemplary embodiment, the non-metallic Lewis acid catalyst may be added in a proportion of 0.1 to 20 wt%, more preferably 0.5 to 10 wt%, based on the weight of the mixture of the acrylic fiber support and the amine compound Can be injected. When the non-metallic Lewis acid catalyst is added in an amount of less than 0.1 wt% based on the mixture, the reaction between the acrylic fiber support and the amine compound may not proceed. When the non-metallic Lewis acid catalyst is contained in an amount exceeding 20 wt% It is not suitable for the surface modification of the acrylic fiber support and is economically undesirable.
In an exemplary embodiment, the reaction of the acrylic fiber adsorbent may be conducted at a temperature ranging from 50 to 150 < 0 > C. If the reaction temperature is lower than 50 ° C, the reaction between the acrylic fiber support and the amine compound may not be smooth. If the reaction temperature is higher than 150 ° C, the acrylic fiber support is dissolved in the amine solution, It may not have mechanical characteristics of fibrous structure.
In an exemplary embodiment, the reaction of the acrylic fiber adsorbent can proceed for a time in the range of 30 minutes to 120 minutes. When the reaction proceeds for less than 30 minutes, the yield of the acrylic fiber adsorbent is low because the yield of the reaction is low, and if the reaction proceeds for more than 120 minutes, the final adsorbent may not have the characteristics of the fiber .
As described above, the acrylic fiber adsorbent may be a product of reaction between an acrylic fiber support and an amine compound under a non-metallic Lewis acid catalyst. Accordingly, both the cation and the anion can be adsorbed, and the adsorbing ability thereof can be also excellent.
The acrylic fiber adsorbent prepared in one embodiment may exhibit an adsorption capacity in the range of 0.5 to 30 mmol / g. The above ranges are related to the number and degree of amines in the monomers, the degree of amine modification of the acrylic fiber support, and the affinity of the adsorbent and the adsorbate depending on the kind of the amine compound. Also, the above range may be influenced by the type of fiber support selected in accordance with the acrylic fiber adsorbent production process, the amine compound, the reaction conditions, and the properties of the adsorbate present in the application site.
Hereinafter, the present invention will be described in more detail with reference to Examples. It is to be understood by those skilled in the art that these embodiments are only for illustrating the present invention and that the scope of the present invention is not construed as being limited by these embodiments.
Example
Example 1: Boron trifluoride hydrate (BF 3 ㆍ 2H 2 O) Catalysts for the Synthesis of Diethylenetriamine (DETA) and Acrylic Copolymer Fibers
Acrylonitrile 90% used as acrylic fiber. 5 g of a 10% polyvinyl acetate copolymer fiber is placed in a 500 ml volumetric round bottom flask with 250 ml of diethylenetriamine (DETA) and dispersed evenly at room temperature for 30 minutes. Boron trifluoride hydrate (BF 3 .2H 2 O) used as a catalyst is diluted with deionized water to 10 wt%, 2 ml is added, and the mixture is stirred at room temperature for about 30 minutes. After the catalyst was evenly dispersed, a reflux condenser was installed and the reaction time was terminated at 120 ° C for 90 minutes. After cooling to room temperature, the reaction product was washed with water and dried to prepare an acrylic adsorbent fiber.
Example 2: Boron trifluoride hydrate (BF 3 ㆍ 2H 2 O) Catalysts for the Synthesis of Ethylenetriamine (EDA) and Acrylic Copolymer Fibers
The procedure of Example 1 was repeated except that ethylenediamine was used instead of diethylenetriamine.
Example 3: Boron trifluoride Hydrate BF 3 ㆍ 2 H 2 O ) Catalyst tris Synthesis of 2-aminoethylamine and Acrylic Copolymer Fibers
The procedure of Example 1 was repeated except that tris-2-aminoethylamine was used instead of ethylenetriamine.
Comparative Example 1
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An acrylic fiber adsorbent was prepared in the same manner as in Example 1 except that boron trifluoride hydrate (BF 3 .2H 2 O) was used as a catalyst, but the reaction was carried out under an AlCl 3 catalyst.
Comparative Example 2
The non-amine-modified acrylic fiber itself was used as the adsorbent.
Experimental Example 1: Synthesis of amine-modified acrylic fiber adsorbent
The structure of the adsorbent prepared according to Example 1 and Comparative Example 1 was observed, and its ATR FT-IR spectrum was shown in Fig. 3 (a) shows the adsorbent according to Comparative Example 1, and FIG. 3 (b) shows the reaction spectrum of the amine-modified acrylic fiber adsorbent prepared according to Example 1. FIG. Nitrile group is as shown in Figure 3 (C≡N; 2243㎝ -1) is reduced and the amine group (3500-2000㎝ -1), (NH 2 ; 1600㎝ -1), (NH; 1574㎝ -1) , And amidine (N-C = N; 1650 cm <" 1 &
Experimental Example 2: Determination of anion adsorption ability of an amine-modified acrylic fiber adsorbent
The PO 4 anion measurement experiment was carried out using the acrylic fiber adsorbent prepared according to Example 1 and Comparative Example 1.
At this time, a fiber adsorbent having a diameter of 40 μm was used, and adsorption experiments were carried out in 100 ml of the prepared adsorbent of 0.1 g. The prepared solution was prepared at a concentration of 100 mM and a concentration suitable for deriving the maximum adsorption capacity of the adsorbent was prepared. The adsorption was then analyzed using ICP-OES. The results are shown in Fig.
Referring to FIG. 4, the adsorbent prepared under the catalyst of AlCl 3 of Comparative Example 1 had an adsorption capacity of 4.7 mmol / g, whereas the adsorbent prepared under the BF 3 catalyst of Example 1 exhibited adsorbability of 9.7 mmol / g . Thus, it was confirmed that the adsorbent fiber prepared under the nonmetal catalyst exhibited about twice the anion adsorbing ability than the metal catalyst.
Experimental Example 3: Amine Reformed The metal ion of the acrylic fiber adsorbent Adsorption capacity Confirm
The experiment of measuring the metal ion (cation) using the acrylic fiber adsorbent prepared according to Example 1 and Comparative Example 1 was carried out
At this time, a fiber adsorbent having a diameter of 40 μm was used, and adsorption experiments were carried out in 100 ml of the prepared adsorbent of 0.1 g. The prepared solution was prepared at a concentration of 100 mM and a concentration suitable for deriving the maximum adsorption capacity of the adsorbent was prepared. To evaluate the adsorptivity according to the properties of the adsorbent and the adsorbate, the pH of the solution was adjusted with dilute hydrochloric acid Respectively. And proceeded in the maximum adsorbable state through the adsorption experiment time of 24 hours. The adsorption was then analyzed using ICP-OES. Thereafter, the results are shown in Figs. 5A to 5D.
5A to 5D, it was confirmed that when the acrylic fiber adsorbent prepared according to Example 1 was used, the amount of cation adsorption tended to be better in Example 1 than in Comparative Example 1 over the entire pH analysis range.
Specifically, it was confirmed that the maximum adsorption amount of copper cation was 4.49 mmol / g in Comparative Example 1, and the maximum amount of adsorption was 5.99 mmol / g in Example 1 (FIG. 5A) The maximum adsorption amount of Example 1 was 3.69 mmol / g, the adsorption amount of Example 1 was 5.72 mmol / g (FIG. 5b), and the adsorption amount of zinc cation was 3 mmol / g (Fig. 5C). The amount of lead cation adsorption in Comparative Example 1 was 1.07 mmol / g, and the adsorption amount in Example 1 was 3.65 mmol / g / g. < / RTI >
Experimental Example 4: Surface analysis of acrylic fiber adsorbent
The surfaces of the acrylic fiber adsorbent prepared according to Example 1 and the acrylic fiber adsorbent prepared according to Comparative Examples 1 and 2 were observed and shown in Figs. 6A to 6C. Specifically, Figure 6a shows the result of observing the surface of the acrylic fibers of the raw materials, Figure 6b shows the result of observing the surface of the acrylic fiber adsorbents produced in the AlCl 3 catalyst, Figure 6c is produced in the BF 3 catalyst And the surface of the adsorbed fiber is observed.
6A to 6C, the surface photograph of Example 1 maintains a very clean surface as the surface of acrylic fiber as raw material, but the surface photograph of Comparative Example 1 shows a rough surface by adsorption of aluminum metal ion as a catalyst . As a result, it was confirmed that the acrylic fiber adsorbent of Comparative Example 1 had lower adsorption capacity than the acrylic fiber adsorbent of Example 1.
The embodiments of the present invention described above should not be construed as limiting the technical idea of the present invention. The scope of protection of the present invention is limited only by the matters described in the claims, and those skilled in the art will be able to modify the technical idea of the present invention in various forms. Accordingly, such improvements and modifications will fall within the scope of protection of the present invention as long as it is obvious to those skilled in the art.
Claims (12)
The acrylic fiber support is an acrylic fiber prepared from a monomer containing at least one selected from the group consisting of acrylonitrile, vinyl alcohol, vinyl acetate, vinyl chloride, methyl acrylate, butyl acrylate and vinyl acetic acid By weight based on the total weight of the acrylic fiber adsorbent.
Wherein the non-metallic Lewis acid catalyst is a boron triflourohydrate (BF 3 .2H 2 O) catalyst.
The acrylic fiber support has a molecular weight of 10,000 to 100,000 (Mw)
Wherein the acrylic fiber support has a diameter between 100 nm and 100 mu m.
The amine compound may be selected from the group consisting of ethylenediamine (EDA), diethylenetriamine (DETA), tris (2-aminoethylamine), propane-1,3-diamine 1,3-diamine, methane triamine, 3- (2-aminoethyl) pentane-1,5-diamine, A method for producing an acrylic fiber adsorbent, which comprises at least one selected from the group consisting of melamine, diaminofurazan, diaminopyridine, and diaminopyrimidine.
Wherein the non-metallic Lewis acid catalyst is added in an amount of 0.5-10 wt% based on the weight of the mixture of the acrylic fiber support and the amine compound.
Wherein the step of reacting the acrylic fiber support and the amine compound is performed at a temperature of 50 to 150 ° C for a time ranging from 30 to 120 minutes.
Wherein the acrylic fiber adsorbent adsorbs cations and anions.
Wherein the acrylic fiber adsorbent exhibits an adsorption capacity in the range of 0.5 to 30 mmol / g with respect to cations and anions.
The acrylic fiber adsorbent adsorbs cations and anions,
Wherein the acrylic fiber adsorbent is prepared by reaction of the acrylic fiber support with the amine compound under non-metallic Lewis acid catalyst conditions,
The acrylic fiber support is an acrylic fiber prepared from a monomer containing at least one selected from the group consisting of acrylonitrile, vinyl alcohol, vinyl acetate, vinyl chloride, methyl acrylate, butyl acrylate and vinyl acetic acid Acrylic fiber adsorbent.
The acrylic fiber support has a molecular weight of 10,000 to 100,000 (Mw)
Wherein the acrylic fiber support has a diameter of between 100 nm and 100 μm.
Wherein the non-metallic Lewis acid catalyst is a boron triflouride hydrate (BF 3 .2H 2 O) catalyst.
Wherein the acrylic fiber adsorbent exhibits an adsorption capacity in the range of 0.5 to 30 mmol / g with respect to the cation and the anion.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20190101311A (en) | 2018-02-22 | 2019-08-30 | 공성욱 | Ion exchange powder |
| KR20230149454A (en) | 2022-04-20 | 2023-10-27 | 한국과학기술연구원 | Self-regenerable fibrous adsorbent for heavy metal adsorption |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5629434A (en) | 1992-12-17 | 1997-05-13 | Exxon Chemical Patents Inc | Functionalization of polymers based on Koch chemistry and derivatives thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5629434A (en) | 1992-12-17 | 1997-05-13 | Exxon Chemical Patents Inc | Functionalization of polymers based on Koch chemistry and derivatives thereof |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20190101311A (en) | 2018-02-22 | 2019-08-30 | 공성욱 | Ion exchange powder |
| KR20230149454A (en) | 2022-04-20 | 2023-10-27 | 한국과학기술연구원 | Self-regenerable fibrous adsorbent for heavy metal adsorption |
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