WO2019112080A1 - Procédé de préparation d'un composite polyaniline pour l'utilisation antibactérienne et élimination des métaux lourds, dans lequel de l'acide organique et des ions métalliques sont dopés dans un polymère conducteur de polyaniline sous un ordre prédéterminé, et composite polyaniline préparé par l'intermédiaire du même procédé - Google Patents

Procédé de préparation d'un composite polyaniline pour l'utilisation antibactérienne et élimination des métaux lourds, dans lequel de l'acide organique et des ions métalliques sont dopés dans un polymère conducteur de polyaniline sous un ordre prédéterminé, et composite polyaniline préparé par l'intermédiaire du même procédé Download PDF

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Publication number
WO2019112080A1
WO2019112080A1 PCT/KR2017/014167 KR2017014167W WO2019112080A1 WO 2019112080 A1 WO2019112080 A1 WO 2019112080A1 KR 2017014167 W KR2017014167 W KR 2017014167W WO 2019112080 A1 WO2019112080 A1 WO 2019112080A1
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WIPO (PCT)
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polyaniline
organic acid
antibacterial
metal
polyaniline composite
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PCT/KR2017/014167
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English (en)
Korean (ko)
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윤호성
이찬우
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주식회사 파라
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Priority to PCT/KR2017/014167 priority Critical patent/WO2019112080A1/fr
Publication of WO2019112080A1 publication Critical patent/WO2019112080A1/fr

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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D53/00—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols
    • B01D53/02—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by adsorption, e.g. preparative gas chromatography
    • 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
    • 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
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/02—Polyamines
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/20—Manufacture of shaped structures of ion-exchange resins
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
    • C08L79/02—Polyamines

Definitions

  • the present invention relates to a method for preparing a polyaniline composite for removing antimicrobial and heavy metals in which a polyaniline conductive polymer is doped with an organic acid and a metal ion in a predetermined order, and a polyaniline composite prepared by the method. More particularly, the present invention relates to a polyaniline composite comprising porous nonconductive polyaniline emulsion The present invention relates to a method for producing a polyaniline composite for removing insoluble antibacterial and heavy metals in which metal ions are attached to the surface of a conductive polymer by doping an organic acid into a lanthanum base to thereby impart conductivity and then doping metal ions and a polyaniline composite prepared by the method .
  • an antibacterial filter capable of removing bacteria and microorganisms is installed, and an antibacterial material capable of adsorbing and removing pollutants such as various viruses (microorganisms) .
  • antibacterial functional materials have been developed as antibacterial filter materials using a material in which metallic powder materials such as silver, copper, gold, zinc, alumina and titanium dioxide are dispersed and adhered in an aqueous solution to a porous material.
  • a porous material a wide variety of porous resins such as activated carbon, silica gel, polyurethane, zeolite, activated carbon, charcoal, and phenol resin can be used, and Korean Patent Publication Nos.
  • Korean Patent Laid-Open Publication No. 2003-0080769 discloses a patent for an antibacterial filter in which an antibacterial metal or metal salt is adsorbed on a carbon ball composed of a hollow core portion and a porous carbon shell portion.
  • the metal or metal salt used in the antibacterial filter is simply adsorbed on the porous activated carbon substrate, there is a high possibility that the metal or the metal salt will be eluted according to changes in the environment such as moisture and heat. When a certain amount of contaminants are adsorbed, Resulting in a drawback.
  • the present invention has been made to solve the problems of the conventional antibacterial filter material as described above, and it has an antibacterial and antimicrobial effect which is excellent in adsorption or elimination efficiency of bacteria and microorganisms and can be applied to air filters as well as antibacterial And a method for producing a polyaniline composite for removing heavy metals and a polyaniline composite prepared by the method.
  • the present invention provides a composite material obtained by preparing a composite obtained by doping an organic acid into a basic polyaniline conductive polymer based on a porous polyaniline conductive polymer, and then adsorbing the metal and the metal salt to the composite material, A conductive polymer-metal complex is produced, and an excellent antibacterial function and a filter material for heavy metal removal are provided.
  • the basic polyaniline conductive polymer used in the composite filter for removing antibacterial and heavy metals according to the present invention has a nano-sized fiber structure and has a fine pore structure so that bacteria and microorganisms can be easily adsorbed.
  • the basic polyaniline conductive polymer has a basic amine structure in the monomolecular chain, so that heavy metals can be easily adsorbed due to strong interaction with heavy metal ions.
  • non-conductive polyaniline emeraldine base has conductivity with various organic acids through acid-base reaction when it is doped. The molecular state at this time is called emeraldine salt, and the bacteria and microorganisms 52 (No. 4, 2016) reported that it can be adsorbed onto the surface of polymers by interaction with molecules.
  • Sulfonic acid derivatives having high acidity such as camphorsulfonic acid are typically used for improving electrical conductivity.
  • carboxylic acid derivatives which are weakly acidic and toxic, are used in the present invention as compared with derivatives having sulfonic acid functional groups It is preferred that the organic acid of the carboxylic acid type is used as the dopant of the present invention freely.
  • organic acids having carboxylic acid functional groups ethylenediaminetetracarboxylic acid (EDTA) is a molecule having two amine functional groups and four carboxylic acid functional groups simultaneously in the molecule. This molecule is a chelate compound due to strong interaction with various heavy metal ions It is a widely known substance.
  • carboxylic acid derivatives used in the present invention are not limited to EDTA molecules, as they can form not only EDTA but also polyaniline emeraldine salt complexes having two carboxylic acid functional groups and also insoluble in glutaric acid and acetic acid.
  • Ag is a strong antimicrobial and antimicrobial agent against -SH, -CO 2 H, -OH, , which is known to destroy bacterial cell membranes or disturb cell functions. It is assumed that the antimicrobial metal ions (Ag + , Zn 2+ , Cu 2+, etc.) dissociated from the inorganic carrier in the antimicrobial agent using other inorganic carriers inhibit the energy metabolism of the cells by binding with proteins such as cell membranes and enzymes At this time, the metal ion used in the inorganic carrier is called an antimicrobial metal.
  • the polyaniline emeraldine salt complex prepared by doping polyaniline emeraldine base with an organic acid such as EDTA, glutaric acid, or acetic acid is further doped with the above-
  • the metal ions are adsorbed on the polyaniline emeraldine salt complex, so that the basic polyaniline conductive polymer inherently has a function of adsorbing bacteria and microorganisms, and is designed to add microbial killing capability of the antimicrobial metal.
  • silver (Ag) ions in the antimicrobial metal ions used in the present invention react with polyaniline emeraldine salt to be reduced to silver nanomaterial particles to form a basic polyaniline conductive polymer and a polyaniline emeraldine salt complex have.
  • silver nano-metal solids are used instead of silver ions, insoluble complexes are formed in various solvents, and thus they have a continuous antibacterial function, which is advantageous for long-term antimicrobial function.
  • a nanoporous polyaniline emeraldine base represented by the following formula (1) is synthesized using a conventional interfacial polymerization method.
  • the porous nanofiber obtained by interfacial polymerization has a diameter of 10 to 500 nm, It is preferable that the diameter of the formed pores is 1 to 50 nm.
  • any of the conductive polymer complexes represented by the following formula (2) may be used, and organic acid used as a dopant in the following formula (2) may include ethylene diamine tetracarboxylic acid (EDTA), glutaric acid, May be used, or may be a polyaniline emeraldine salt complex doped with two or more organic acids. Accordingly, the polyaniline emeraldine salt complex containing an organic acid according to the present invention may be combined and configured in various compositions depending on the application such as antimicrobial activity and removal of heavy metals.
  • EDTA ethylene diamine tetracarboxylic acid
  • glutaric acid May be used
  • polyaniline emeraldine salt complex doped with two or more organic acids may be combined and configured in various compositions depending on the application such as antimicrobial activity and removal of heavy metals.
  • the doping level is preferably 0.1 to 50 wt% based on the total weight of the conductive polymer.
  • A represents a kind of organic acid and a dopant which is used independently of each other.
  • the antimicrobial and heavy metal removal filter material according to the present invention may be a conductive polyaniline / metal complex represented by the following general formula (3).
  • Antimicrobial metals or metal salts used in the following general formula (3) Alumina, and the like, or a polyaniline / metal composite doped with two or more kinds of metal ions.
  • the polyaniline / metal composite containing the metal ion according to the present invention may be combined and configured in various compositions depending on applications such as antimicrobial activity and removal of heavy metals.
  • the adsorption amount of the antibacterial metal or metal salt is preferably 0.1 to 30% by weight based on the total weight of the conductive polymer.
  • M represents a metal ion which is used independently of each other.
  • the polyaniline composite for antibacterial and heavy metal removal of the present invention is excellent in antibacterial and antifungal properties such as purifier filter, automobile or domestic air filter, air conditioner, gas mask, water purifier, It can be applied variously for the purpose of heavy metal removal.
  • 1 is an electron micrograph showing that the polyaniline emeraldine base of the present invention is composed of nanofiber type and numerous pores.
  • FIG. 3 is an electron micrograph showing an image formed by adsorption of silver (Ag) nanoparticles on the surface of a polyaniline emeraldine salt complex, which is an organic acid, EDTA-doped polyaniline / metal complex to be.
  • a polyaniline emeraldine salt complex which is an organic acid, EDTA-doped polyaniline / metal complex to be.
  • Fig. 4 is a photograph showing the results of the virus-removing activity of the polyaniline complex for removing the antibacterial and heavy metals according to the present invention.
  • FIG. 5 is a photograph showing the antibacterial activity of the polyaniline composite for removing the antibacterial and heavy metals according to the present invention.
  • the method for producing the polyaniline composite for removing antibacterial and heavy metals according to the present invention is as follows.
  • the polyaniline emeraldine base of the present invention has a structure composed of numerous nano-sized fiber shapes and numerous pores.
  • EDTA 1 g was dissolved in 2 L of water in order to dope the synthesized polyaniline emeraldine base with an organic acid. Then, 2 g of the polyaniline emeraldine base was added to the EDTA aqueous solution, Treated for 1 hour and then treated with a 12-hour agitator. The polyaniline emeraldine salt complex doped with EDTA was filtered through filter paper, and unreacted EDTA molecules were washed and dried several times using distilled water.
  • the structure of the polyaniline emeraldine salt complex was still maintained in the form of nanofiber and numerous pores, despite the fact that EDTA, which is an organic acid, was doped.
  • the organic acid-EDTA-doped polyaniline emeraldine salt complex with a 1 L aqueous solution of 5% silver nitrate (AgNO 3 )
  • the EDTA-doped polyaniline emeraldine salt complex complex was slowly immersed in the solution for 2 days and the silver (Ag) ion attached to the surface of the polymer was slowly reduced to form silver (Ag) nanoparticles on the surface of the polymer.
  • the polyaniline / metal complex The composite was washed several times with distilled water to remove unreacted silver nitrate and dried.
  • nano-sized silver (Ag) particles were uniformly grown on the insoluble polyaniline / metal complex surface.
  • the polyaniline composite for antibacterial and heavy metal removal of the present invention was prepared in the same manner as in Example 1 except that glutaric acid (HOOCCH 2 CH 2 CH 2 COOH) was used as an organic acid and copper chloride (CuCl) .
  • a polyaniline composite of the present invention for removing antimicrobial and heavy metals was prepared in the same manner as in Example 1 except that acetic acid (CH 3 COOH) was used as an organic acid and zinc chloride (ZnCl 2) was used as a metal ion.
  • a polyaniline composite of the present invention for removing antibacterial and heavy metals was prepared in the same manner as in Example 1 except that camphorsulfonic acid was used as an organic acid and aluminum oxide (Al 2 O 3 ) was used as a metal ion.
  • a polyaniline / metal complex doped with antimicrobial metal ion silver nitrate (polyaniline / metal complex) was prepared by doping polyaniline emeraldine base with antimicrobial metal ion silver nitrate (AgNO 3 ) to prepare polyaniline / metal complex.
  • the preparation of polyaniline complex for antibacterial and heavy metal removal was carried out in the same manner as in Example 1 except that polyaniline emeraldine salt complex was prepared by doping.
  • Example 2 2 g of the polyaniline composite for antibacterial and heavy metal removal of Example 1 was filled in a 16 x 12 urethane hose to prepare a filter for a water purifier.
  • a filter for a water purifier was prepared as described above, except that the antibacterial and heavy metal removal polyaniline composite of the comparative example was used as a control.
  • the virus used was MS2 Virus and the virus removal rate was judged according to VF international standard.
  • the initial input log value of the polyaniline composite for antibacterial and heavy metal removal of the present invention was 6.1, and the output log value remained at 5.7 after 4 days, It was found that it was removed.
  • the initial input log value was 6.3, and after one day, the output log value decreased to 3.8, .
  • the bacteria used was E. coli and the bacterial clearance was determined according to the VF international standard.
  • the Log value was determined for the bacterial reference value shown in FIG.
  • the bacterial removal test of the polyaniline composite for antibacterial and heavy metal removal of the present invention showed that the output log value remained unchanged at 8.0 after 1 day from the initial input log value of 8.0, By keeping the log value at about 7.5, it was found that the bacteria were continuously removed by 90% or more.
  • Example 2 g of the polyaniline composite for antibacterial and heavy metal removal of Example 1 was filled in a 16x12 urethane hose to prepare a filter for removing heavy metals and then passed through a 2 L aqueous solution containing 1000 ppm of heavy metal ions to finally measure The TDS value was calculated to determine the removal rate.
  • test was carried out in the same manner as above except that a polyaniline complex for removing antimicrobial and heavy metals of the comparative example was used as a control group.
  • the order of doping of metal ions and organic acids was nickel (85%), lead (95), cadmium (90%), chromium (77%), , Zinc (89%), copper (93%) and mercury (95%), respectively.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
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  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Analytical Chemistry (AREA)
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  • Oil, Petroleum & Natural Gas (AREA)
  • General Chemical & Material Sciences (AREA)
  • Materials Engineering (AREA)
  • Solid-Sorbent Or Filter-Aiding Compositions (AREA)
  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)

Abstract

La présente invention concerne un procédé de préparation d'un composite polyaniline insoluble pour l'utilisation antibactérienne et l'élimination de métaux lourds, un acide organique étant dopé dans une base polyaniline éméraldine non conductrice poreuse pour lui donner une conductivité et ensuite les ions métalliques étant dopés à l'intérieur de sorte que les ions métalliques sont fixés sur une surface polymère conductrice, et sur un composite polyaniline préparé grâce au procédé. Le composite polyaniline présente d'excellents effets d'adsorption ou d'élimination de bactéries et de microbes et d'élimination des métaux lourds, et ainsi peut être appliqué de manière diverse, pour l'utilisation antibactérienne et l'élimination des métaux lourds, à un filtre purificateur d'eau, un filtre de conditionnement d'air automobile ou domestique, un conditionneur d'air, un masque à gaz, un dispositif de traitement d'eau potable et d'égout, un purificateur d'air, une salle blanche, et similaires.
PCT/KR2017/014167 2017-12-05 2017-12-05 Procédé de préparation d'un composite polyaniline pour l'utilisation antibactérienne et élimination des métaux lourds, dans lequel de l'acide organique et des ions métalliques sont dopés dans un polymère conducteur de polyaniline sous un ordre prédéterminé, et composite polyaniline préparé par l'intermédiaire du même procédé WO2019112080A1 (fr)

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PCT/KR2017/014167 WO2019112080A1 (fr) 2017-12-05 2017-12-05 Procédé de préparation d'un composite polyaniline pour l'utilisation antibactérienne et élimination des métaux lourds, dans lequel de l'acide organique et des ions métalliques sont dopés dans un polymère conducteur de polyaniline sous un ordre prédéterminé, et composite polyaniline préparé par l'intermédiaire du même procédé

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PCT/KR2017/014167 WO2019112080A1 (fr) 2017-12-05 2017-12-05 Procédé de préparation d'un composite polyaniline pour l'utilisation antibactérienne et élimination des métaux lourds, dans lequel de l'acide organique et des ions métalliques sont dopés dans un polymère conducteur de polyaniline sous un ordre prédéterminé, et composite polyaniline préparé par l'intermédiaire du même procédé

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CN114292475A (zh) * 2021-12-30 2022-04-08 深圳恒方大高分子材料科技有限公司 一种具有表面抗菌功能的双离子型医用pvc材料

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Publication number Priority date Publication date Assignee Title
CN114292475A (zh) * 2021-12-30 2022-04-08 深圳恒方大高分子材料科技有限公司 一种具有表面抗菌功能的双离子型医用pvc材料

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