WO2022146349A1 - A polymer nanocomposite adsorbent and production method thereof - Google Patents
A polymer nanocomposite adsorbent and production method thereof Download PDFInfo
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- WO2022146349A1 WO2022146349A1 PCT/TR2021/051449 TR2021051449W WO2022146349A1 WO 2022146349 A1 WO2022146349 A1 WO 2022146349A1 TR 2021051449 W TR2021051449 W TR 2021051449W WO 2022146349 A1 WO2022146349 A1 WO 2022146349A1
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- WIPO (PCT)
- Prior art keywords
- polymer nanocomposite
- nanocomposite adsorbent
- fesc
- iron oxide
- production method
- Prior art date
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- 229920000642 polymer Polymers 0.000 title claims abstract description 23
- 239000003463 adsorbent Substances 0.000 title claims abstract description 22
- 239000002114 nanocomposite Substances 0.000 title claims abstract description 21
- 238000004519 manufacturing process Methods 0.000 title claims description 14
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 claims abstract description 26
- SZVJSHCCFOBDDC-UHFFFAOYSA-N ferrosoferric oxide Chemical compound O=[Fe]O[Fe]O[Fe]=O SZVJSHCCFOBDDC-UHFFFAOYSA-N 0.000 claims abstract description 16
- 229920002873 Polyethylenimine Polymers 0.000 claims abstract description 14
- 239000004480 active ingredient Substances 0.000 claims abstract description 5
- 239000003344 environmental pollutant Substances 0.000 claims abstract description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 36
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 14
- SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 claims description 12
- 230000015572 biosynthetic process Effects 0.000 claims description 12
- 238000003786 synthesis reaction Methods 0.000 claims description 9
- 229960000583 acetic acid Drugs 0.000 claims description 8
- 235000011054 acetic acid Nutrition 0.000 claims description 8
- 239000004094 surface-active agent Substances 0.000 claims description 8
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 7
- 229910000069 nitrogen hydride Inorganic materials 0.000 claims description 7
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims description 6
- 230000004048 modification Effects 0.000 claims description 6
- 238000012986 modification Methods 0.000 claims description 6
- 230000004913 activation Effects 0.000 claims description 5
- 239000002105 nanoparticle Substances 0.000 claims description 4
- 229910021578 Iron(III) chloride Inorganic materials 0.000 claims description 3
- 229910021529 ammonia Inorganic materials 0.000 claims description 3
- XGGLLRJQCZROSE-UHFFFAOYSA-K ammonium iron(iii) sulfate Chemical compound [NH4+].[Fe+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O XGGLLRJQCZROSE-UHFFFAOYSA-K 0.000 claims description 3
- 229920000136 polysorbate Polymers 0.000 claims 1
- 239000000463 material Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 229940079593 drug Drugs 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 238000001179 sorption measurement Methods 0.000 description 5
- 229910001868 water Inorganic materials 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 239000013543 active substance Substances 0.000 description 4
- 239000003242 anti bacterial agent Substances 0.000 description 4
- 229940088710 antibiotic agent Drugs 0.000 description 4
- 230000003115 biocidal effect Effects 0.000 description 4
- 239000002352 surface water Substances 0.000 description 4
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 230000005291 magnetic effect Effects 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000006722 reduction reaction Methods 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 239000003651 drinking water Substances 0.000 description 2
- 235000020188 drinking water Nutrition 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 239000003673 groundwater Substances 0.000 description 2
- 229960005489 paracetamol Drugs 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 239000002351 wastewater Substances 0.000 description 2
- 229910003227 N2H4 Inorganic materials 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- YBCVMFKXIKNREZ-UHFFFAOYSA-N acoh acetic acid Chemical compound CC(O)=O.CC(O)=O YBCVMFKXIKNREZ-UHFFFAOYSA-N 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 229910001567 cementite Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000005293 ferrimagnetic effect Effects 0.000 description 1
- 230000005294 ferromagnetic effect Effects 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 239000013461 intermediate chemical Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 239000000696 magnetic material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 239000013528 metallic particle Substances 0.000 description 1
- 230000006911 nucleation Effects 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000008520 organization Effects 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000005180 public health Effects 0.000 description 1
- 238000006479 redox reaction Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 229960005404 sulfamethoxazole Drugs 0.000 description 1
- JLKIGFTWXXRPMT-UHFFFAOYSA-N sulphamethoxazole Chemical compound O1C(C)=CC(NS(=O)(=O)C=2C=CC(N)=CC=2)=N1 JLKIGFTWXXRPMT-UHFFFAOYSA-N 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 238000004065 wastewater treatment Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01G—COMPOUNDS CONTAINING METALS NOT COVERED BY SUBCLASSES C01D OR C01F
- C01G49/00—Compounds of iron
- C01G49/02—Oxides; Hydroxides
- C01G49/08—Ferroso-ferric oxide (Fe3O4)
Definitions
- the present invention relates to a polymer nanocomposite adsorbent that removes micropollutant pharmaceutical active ingredients from the aquatic environment.
- the present invention relates to a polymer nanocomposite adsorbent containing iron oxide (FesO ⁇ doped polyethyleneimine and the production method thereof.
- the present invention relates to polymer nanocomposite adsorbent which fulfills the abovementioned requirements, eliminates all disadvantages and brings some additional advantages.
- the main aim of the invention is to remove micro-polluting pharmaceutical active substances from aquatic environments such as wastewater, drinking water, surface waters (lakes, rivers, etc.), and groundwater.
- the aim of the invention is to develop a polymer nanocomposite material that can be easily separated from the water after completing the treatment process.
- Another aim of the invention is to synthesize a modified ferrimagnetic polymer nanocomposite adsorbent whose production method is innovative and easy.
- the inventive polymer nanocomposite adsorbent contains polyethyleneimine (PEI) polymer doped with iron oxide (FesC ).
- the inventive polymer nanocomposite adsorbent production method comprises the following process steps:
- inventive polymer nanocomposite adsorbent is described only for clarifying the subject matter in a manner such that no limiting effect is created.
- the present invention is a polymer nanocomposite adsorbent containing iron oxide (Fe3O4) added polyethyleneimine which removes micro-pollutant pharmaceutical active ingredients from the aquatic environment and production method thereof.
- Fe3O4 iron oxide
- the inventive polymer nanocomposite adsorbent contains in its composition; the weight average Fe 3 O4:PEI ratio between 1 :2 and 1 :4. Preferably the weight average FesC PEI ratio is 1 :2. According to a preferred embodiment of the invention, the polymer nanocomposite adsorbent further containsTween-85 surfactant.
- the inventive polymer nanocomposite adsorbent production method comprises the following process steps:
- inventive polymer nanocomposite adsorbent production method is described in detail in the following.
- This method is based on the reduction of metal ions to metallic particles in the presence of strong reducing agent reagents (such as NH 3 , NaBH 4 , N2H4.H2O, CeHsOe etc). Reduction can be carried out in both aqueous and organic solvent-containing environments. Particles gain their final condition as a result of nucleation and subsequent growth of particles. The formed metallic powders are separated from the system by precipitation.
- strong reducing agent reagents such as NH 3 , NaBH 4 , N2H4.H2O, CeHsOe etc.
- Strong reducing NH 3 reagent was used for iron oxide synthesis.
- the basis of the method used in the synthesis stage comprises the chemical reduction procedure within the scope of ferromagnetic adsorbent synthesis.
- 0.2 M FeCI 3 and 0.1 M NH 4 Fe(SC>4) were used.
- Component 3 NH 3 (25% Dilute solution); (Redox Reaction Strong Oxidizing Reagent) 1 part product + 3 parts ionized water
- Component 4 Tween-85 (surfactant that reduces surface tension with its hydrophilic head part -hydrophobic tail part, and attracts the drug active substance to the surface with ester bonds)
- Component 1 Fe 3 O4 (1 g) (Skeleton, magnetic material)
- Component 2 PEI (2g) (Polycation adding polymer)
- Component 3 Glutaraldehyde (GA) (20 ml 50% dilute GA solution) (Crosslink agent in modification)
- Component 4 Ethanoic acid (0.5% wt) (Provides surface activation to prepare GA for binding.)
- ethanoic acid acetic acid
- acetic acid 50% dilute GA (10 ml) for surface activation and it is mixed in a magnetic stirrer for 4 hours.
- the PEI-Fe 3 O4 mixture is added to the solution and mixed in a shaker at 300 rpm in a flask for 2 hours.
- the mixture is treated in an ultrasonic bath at 60 'C for 15 minutes.
Abstract
The present invention relates to a polymer nanocomposite adsorbent containing iron oxide (Fe3O4) added polyethyleneimine which removes micro-pollutant pharmaceutical active ingredients from the aquatic environment.
Description
A POLYMER NANOCOMPOSITE ADSORBENT AND PRODUCTION METHOD THEREOF
Field of the Invention
The present invention relates to a polymer nanocomposite adsorbent that removes micropollutant pharmaceutical active ingredients from the aquatic environment.
In particular, the present invention relates to a polymer nanocomposite adsorbent containing iron oxide (FesO^ doped polyethyleneimine and the production method thereof.
State of the Art
Today, the annual drug consumption globally varies between 100,000-200,000 tons. The countries that have the largest share in this consumption are developing countries such as Brazil, Russia, China, India and South African countries. Turkey ranks 1 st among the countries in the European continent in the use of antibiotics and uses 2-3 times more antibiotics compared to these countries. It has been determined according to the 2014 World Health Organization (WHO) report that 43 out of every thousand people in Turkey use antibiotics per day. In a study published in the journal Environmental Sciences, the estimates for the total global antibiotic consumption in 2030 from the antibiotic consumption between 2000 and 2015 in 76 countries around the world are predicted as 200%. According to the Center for Disease Dynamics, Economics and Policy (CDDEP) research, it has been determined that Turkey is the country that consumes the most antibiotics in the animal food sector and reducing global antibiotic consumption is of critical importance to reduce the threat of antibiotic resistance and local/global resistance patterns should be considered.
Environmental impact analysis and the results to be obtained will have a very high unique value in the process that starts in the discharge areas of the effluent of biological wastewater treatment plant wastewaters to surface water resources and ends with the production, use, and disposal stages of drug-active micro-pollutants that are added to the ecosystem in various ways (such as groundwater, surface water resources, etc.). The most important reason for this is the trace amount of micro-polluting compounds in the aquatic environment and the limitation of the measurement and removal methods of the intermediate chemicals
that are not fully mineralized. The presence of active pharmaceutical ingredients in mains waters and drinking water treatment plants coming without being treated has just noticed. There is a need for innovative studies that will solve this very daily problem concerning public health.
One of the studies carried out in the state of the art regarding this is the adsorption method. Many methods such as acetaminophen, sulfamethoxazole, paracetamol drug active ingredients, activated carbon and nanomembrane hybrid system, adsorption of activated carbon treated with NH4CI, adsorption with (HSZSM-5) brand high silica zeolite have been studied in drug active substance removal studies by adsorption method. A contribution has been made to the literature on maximum removal capacities (mg/g), adsorption kinetics (such as langmuir, freundlich, etc.) and optimum operating conditions, however the desired efficiency could not be obtained.
The problems identified in the state of the art are listed as follows:
Low removal efficiency,
- The production stages are difficult and costly,
- After completing the material treatment, it requires a separate step so as to separate the same from the water,
It is not capable of holding ng or pg drug active substances due to the weight of the material, high surface tension, and low active surface area.
As a result, due to the abovementioned disadvantages, and the insufficiency of the current solutions regarding the subject matter, a development is required to be made in the relevant technical field.
Brief Description of the Invention
The present invention relates to polymer nanocomposite adsorbent which fulfills the abovementioned requirements, eliminates all disadvantages and brings some additional advantages.
The main aim of the invention is to remove micro-polluting pharmaceutical active substances from aquatic environments such as wastewater, drinking water, surface waters (lakes, rivers, etc.), and groundwater.
The aim of the invention is to develop a polymer nanocomposite material that can be easily separated from the water after completing the treatment process.
Another aim of the invention is to synthesize a modified ferrimagnetic polymer nanocomposite adsorbent whose production method is innovative and easy.
In order to fulfill the above-described aims, the inventive polymer nanocomposite adsorbent contains polyethyleneimine (PEI) polymer doped with iron oxide (FesC ).
The inventive polymer nanocomposite adsorbent production method comprises the following process steps:
Synthesis of iron (III) chloride (FeCI8), ammonium iron (III) sulfate (NH4Fe(SO4)) and ammonia (NH3) and iron oxide (FesC ),
- Formation of iron oxide (FesC ) nanoparticles by adding Tween-85 surfactant,
- Surface activation of glutaraldehyde (C5H8O2) with ethanoic acid (CH3COOH),
- Making Fe8C>4 modification with polyethyleneimine in glutaraldehyde (C5H8O2) and ethanoic acid (CH3COOH) solution.
The structural and characteristic features of the present invention will be understood clearly by the following detailed description and therefore the evaluation shall be made by taking the detailed description into consideration.
Detailed Description of the Invention
In this detailed description, the inventive polymer nanocomposite adsorbent is described only for clarifying the subject matter in a manner such that no limiting effect is created.
The present invention is a polymer nanocomposite adsorbent containing iron oxide (Fe3O4) added polyethyleneimine which removes micro-pollutant pharmaceutical active ingredients from the aquatic environment and production method thereof.
The inventive polymer nanocomposite adsorbent contains in its composition; the weight average Fe3O4:PEI ratio between 1 :2 and 1 :4. Preferably the weight average FesC PEI ratio is 1 :2.
According to a preferred embodiment of the invention, the polymer nanocomposite adsorbent further containsTween-85 surfactant.
The inventive polymer nanocomposite adsorbent production method comprises the following process steps:
Synthesis of iron (III) chloride (FeCI3), ammonium iron (III) sulfate (NH4Fe(SO4)) and ammonia (NH3) and iron oxide (FesC ),
- Formation of iron oxide (FesC ) nanoparticles by adding Tween-85 surfactant,
- Surface activation of glutaraldehyde (C5H8O2) with ethanoic acid (CH3COOH),
- Making Fe3O4 modification with polyethyleneimine in glutaraldehyde (C5H8O2) and ethanoic acid (CH3COOH) solution.
The inventive polymer nanocomposite adsorbent production method is described in detail in the following.
Magnetic Tween-85 Surfactant Iron Oxide (Fe3O4) Nanoparticle Synthesis:
This method is based on the reduction of metal ions to metallic particles in the presence of strong reducing agent reagents (such as NH3, NaBH4, N2H4.H2O, CeHsOe etc). Reduction can be carried out in both aqueous and organic solvent-containing environments. Particles gain their final condition as a result of nucleation and subsequent growth of particles. The formed metallic powders are separated from the system by precipitation.
Strong reducing NH3 reagent was used for iron oxide synthesis. The basis of the method used in the synthesis stage comprises the chemical reduction procedure within the scope of ferromagnetic adsorbent synthesis. In the magnetic Fe3C>4 synthesis procedure, 0.2 M FeCI3 and 0.1 M NH4 Fe(SC>4) were used.
Component 1 : FeCI3; Fw=162.5 g/mol m=3.25 gr is weighed and completed up to 100 ml.
Component 2: NH4Fe(SC>4); Fw=170 g/mol m=1.7 gr is weighed and completed up to 100 ml.
Component 3: NH3 (25% Dilute solution); (Redox Reaction Strong Oxidizing Reagent) 1 part product + 3 parts ionized water
Component 4: Tween-85 (surfactant that reduces surface tension with its hydrophilic head part -hydrophobic tail part, and attracts the drug active substance to the surface with ester bonds)
Production steps are explained below:
- The FeCI3, NH4Fe(SC>4) mixture is treated at 90 O for 45 minutes.
- Then NH3 is added and the brown color suddenly turns black and precipitates are formed.
- While the mixing process continues, tween-85 surfactant is added.
- After the precipitation of the formed iron occurs, the supernatant thereon is withdrawn by means of a micropipette.
- Afterwards, it is kept for 48 hours in the oven to dry, the dried material is ground.
Innovative Adsorbent Synthesis and Modification:
Component 1 : Fe3O4 (1 g) (Skeleton, magnetic material)
Component 2: PEI (2g) (Polycation adding polymer)
Component 3: Glutaraldehyde (GA) (20 ml 50% dilute GA solution) (Crosslink agent in modification)
Component 4: Ethanoic acid (0.5% wt) (Provides surface activation to prepare GA for binding.)
Production steps are explained below:
Before the PEI-Fe3O4 mixture is modified, it is exposed to sunlight for 48 hours at room temperature.
- 0.5% by weight ethanoic acid (acetic acid) is added to a 20ml solution of 50% dilute GA (10 ml) for surface activation and it is mixed in a magnetic stirrer for 4 hours.
- The PEI-Fe3O4 mixture is added to the solution and mixed in a shaker at 300 rpm in a flask for 2 hours.
- Then, the mixture is treated in an ultrasonic bath at 60 'C for 15 minutes.
In order to remove excess GA and acetic acid from the surface of the material, (the part that does not participate in the modification) is washed repeatedly with deionized water (approximately 15 times) so as to remove the surface water with a micropipette and dried in a vacuum oven at 50 'C fo r 2 days.
The waste removal efficiency of the inventive product is quite high compared to its counterparts. The production method is innovative, easy, industrially applicable and cost- effective. The inventive product lost 95% of its weight after the material was modified. After completing the material treatment, it can be easily separated from the water.
Claims
1. A polymer nanocomposite adsorbent containing iron oxide (Fe3O4) added polyethyleneimine (PEI) which removes micro-pollutant pharmaceutical active ingredients from the aquatic environment.
2. A polymer nanocomposite adsorbent according to claim 1 , characterized in that; weight average of FesC PEI ratio is between 1 :2 and 1 :4.
3. A polymer nanocomposite adsorbent according to claim 1 , characterized in that; weight average FesC :P E I ratio is 1 :2.
4. A polymer nanocomposite adsorbent according to claim 1 , characterized in that; it comprises Tween®85 surfactant.
5. A polymer nanocomposite adsorbent production method, characterized in that; it comprises the following process steps:
Synthesis of iron (III) chloride (FeCI8), ammonium iron (III) sulfate (NH4Fe(SO4)) and ammonia (NH3) and iron oxide (FesC ),
- Formation of iron oxide (FesC ) nanoparticles by adding Tween-85 surfactant,
- Surface activation of glutaraldehyde (C5H8O2) with ethanoic acid (CH3COOH),
- Making Fe8C>4 modification with polyethyleneimine in glutaraldehyde (C5H8O2) and ethanoic acid (CH3COOH) solution.
7
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| TR2020/22560 | 2020-12-30 | ||
| TR2020/22560A TR202022560A2 (en) | 2020-12-30 | 2020-12-30 | A POLYMER NANOCOMPOSIDE ADSORBAN AND PRODUCTION METHOD |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2022146349A1 true WO2022146349A1 (en) | 2022-07-07 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/TR2021/051449 WO2022146349A1 (en) | 2020-12-30 | 2021-12-21 | A polymer nanocomposite adsorbent and production method thereof |
Country Status (2)
| Country | Link |
|---|---|
| TR (1) | TR202022560A2 (en) |
| WO (1) | WO2022146349A1 (en) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102502879A (en) * | 2011-11-02 | 2012-06-20 | 华东师范大学 | Fe3O4 nano-microsphere and preparation method thereof |
-
2020
- 2020-12-30 TR TR2020/22560A patent/TR202022560A2/en unknown
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2021
- 2021-12-21 WO PCT/TR2021/051449 patent/WO2022146349A1/en active Application Filing
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102502879A (en) * | 2011-11-02 | 2012-06-20 | 华东师范大学 | Fe3O4 nano-microsphere and preparation method thereof |
Non-Patent Citations (2)
| Title |
|---|
| REN LU: "Effectors of selectivity in laccase catalyzed reactions PhD thesis Sciences Chimiques ED250", 17 December 2019 (2019-12-17), pages 1 - 271, XP055954528, Retrieved from the Internet <URL:https://tel.archives-ouvertes.fr/tel-03080959/document> * |
| SOLODOV, A. N. ET AL.: "Polyethyleneimine- modified iron oxide nanoparticles: their synthesis and state in water and in solutions of ligands", COLLOID AND POLYMER SCIENCE, 2018, XP036641984, DOI: 10.1007/s00396-018-4425-5 * |
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| TR202022560A2 (en) | 2022-07-21 |
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