WO2024113130A1 - Oligomère contenant du carbonate, son procédé de préparation et produit durci - Google Patents

Oligomère contenant du carbonate, son procédé de préparation et produit durci Download PDF

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Publication number
WO2024113130A1
WO2024113130A1 PCT/CN2022/134886 CN2022134886W WO2024113130A1 WO 2024113130 A1 WO2024113130 A1 WO 2024113130A1 CN 2022134886 W CN2022134886 W CN 2022134886W WO 2024113130 A1 WO2024113130 A1 WO 2024113130A1
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carbonate
containing oligomer
temperature
mixture
preparing
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PCT/CN2022/134886
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English (en)
Chinese (zh)
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高均其
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上纬创新育成股份有限公司
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Priority to PCT/CN2022/134886 priority Critical patent/WO2024113130A1/fr
Publication of WO2024113130A1 publication Critical patent/WO2024113130A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/14—Polycondensates modified by chemical after-treatment
    • 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
    • C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
    • C08G64/18—Block or graft polymers

Definitions

  • the present invention relates to an oligomer, a preparation method and a cured product thereof, and in particular to an oligomer containing carbonate derived from epoxy resin, a preparation method and a cured product thereof.
  • circuit boards In order to maintain the normal operation of electronic components under high temperature and high humidity environments, circuit boards must have characteristics such as heat resistance, flame retardancy and low water absorption.
  • epoxy resin is often used in the circuit board field to be cured with phenolic resin or dicyandiamide as an insulating and adhesive material.
  • this type of material has good processing characteristics and copper foil adhesion, it has the disadvantage of polar functional groups generated after curing, which leads to a decrease in electrical performance and is difficult to meet the needs of high-frequency and high-speed circuit boards.
  • some technical directions have used epoxy resin with active esters or styrene-maleic anhydride copolymers (SMA) to overcome the generation of high polar groups after curing.
  • SMA styrene-maleic anhydride copolymers
  • One object of the present invention is to provide a carbonate-containing oligomer and a preparation method thereof, utilizing the synthetic concept of the reaction of epoxy resin with active esters to introduce carbonate groups and free radical-curable functional groups into epoxy resin for modification, so that it has both the low dielectric properties of free radical curing and the nucleophilic behavior of carbonate groups towards metals and fibers.
  • Another object of the present invention is to provide a cured product, which is obtained by mixing and curing a carbonate-containing oligomer with a modified polyphenylene ether resin, so as to have low dielectric loss and sufficient high temperature cracking resistance.
  • One embodiment of the present invention provides a carbonate-containing oligomer having a structure as shown in formula (I):
  • R 1 , R 2 and X are each independently an aromatic ring group, and n is an integer from 1 to 5.
  • Another embodiment of the present invention provides a method for preparing a carbonate-containing oligomer, comprising a mixing step, a first active ester exchange step, a dilution and mixing step, a second active ester exchange step, and a filtering step.
  • the mixing step is to mix the purified bifunctional epoxy resin as shown in formula (i) with the carbonate-containing compound as shown in formula (ii), and heat to a first temperature to accelerate dissolution to obtain a first mixture:
  • the first active ester exchange step is to add a catalyst to the first mixture and maintain the reaction at a first temperature to obtain a second mixture.
  • the dilution mixing step is to add an aromatic ring solvent and an active methacrylic acid ester as shown in formula (iii) to the second mixture and mix them to obtain a third mixture:
  • the second active ester exchange step is to heat the third mixture to a second temperature and maintain the temperature at the second temperature to react, so as to obtain a fourth mixture.
  • the filtering step is to cool the fourth mixture and filter it, so as to obtain a carbonate-containing oligomer as shown in formula (I):
  • R 1 , R 2 and X are each independently an aromatic ring group, and n is an integer from 1 to 5.
  • the first temperature is not higher than 130° C.
  • the first temperature may be 80° C. to 120° C.
  • the catalyst may be a pyridine derivative, an imidazole derivative or a quaternary alkylammonium salt derivative.
  • the amount of the catalyst added can be 500 ppm to 5000 ppm.
  • the aromatic ring solvent may be benzene, toluene or xylene.
  • the second temperature may be 110° C. to 130° C.
  • Another embodiment of the present invention provides a cured product, which is obtained by mixing the aforementioned carbonate-containing oligomer with a modified polyphenylene ether resin and adding a peroxide to carry out a curing reaction.
  • the solid content ratio of the carbonate-containing oligomer to the modified polyphenylene ether resin may be 50:50 to 10:90.
  • the modified polyphenylene ether resin may be methacrylate-modified polyphenylene ether.
  • the carbonate-containing oligomer of the present invention is based on the reaction mechanism of epoxy resin and active ester, and carbonate groups and free radical-curable functional groups are introduced into epoxy resin for modification, which can simultaneously retain the electrical performance advantage of free radical curing without generating polar functional groups and the good nucleophilic properties of carbonate to metal and fiber, so that the obtained cured product has low dielectric loss and high temperature cracking resistance, and is suitable for application in related fields such as glass fiber prepreg and high-frequency low-loss substrate.
  • FIG. 1 is a flow chart showing the steps of a method for preparing a carbonate-containing oligomer according to one embodiment of the present invention.
  • the structure of a compound is sometimes represented by a skeleton formula, which may omit carbon atoms, hydrogen atoms, and carbon-hydrogen bonds. If a functional group is clearly drawn in the structural formula, the one shown shall prevail.
  • a carbonate-containing oligomer having a structure as shown in formula (I) may be expressed as a carbonate-containing oligomer as shown in formula (I) or a carbonate-containing oligomer (I) for the sake of brevity and fluency, and the representation of other compounds or groups may be deduced in the same manner.
  • the group may represent a substituted or unsubstituted group.
  • alkyl may represent a substituted or unsubstituted alkyl group.
  • the present invention provides a carbonate-containing oligomer having a structure as shown in formula (I):
  • R 1 , R 2 and X are each independently an aromatic ring group, and n is an integer from 1 to 5.
  • the present invention utilizes the ester exchange reaction between epoxy resin and diaryl carbonate to introduce carbonate groups and free radical-curable functional groups into the epoxy resin for modification, while retaining the electrical performance advantage of free radical curing without generating polar functional groups, and satisfying the good nucleophilic properties of the carbonate structure to metals and fibers. Therefore, it has great potential for application in the field of glass fiber prepregs and high-frequency low-loss substrates.
  • the method 100 for preparing a carbonate-containing oligomer comprises steps 110 , 120 , 130 , 140 , and 150 .
  • Step 110 is a mixing step, which is to mix the purified bifunctional epoxy resin shown in formula (i) with the carbonate-containing compound shown in formula (ii), and heat it to a first temperature to accelerate dissolution, so as to obtain a first mixture:
  • the first temperature of the present invention is to accelerate the complete dissolution of the bifunctional epoxy resin and the carbonate-containing compound, wherein the first temperature is not higher than 130°C to prevent the bifunctional epoxy resin from self-polymerizing and causing the viscosity to increase. If the first temperature is too low, the reaction rate is low and the reaction time is prolonged. Therefore, in the present invention, the first temperature is preferably 80°C to 120°C, but is not limited thereto.
  • the "purified" in the purified bifunctional epoxy resin of the present invention means that the bifunctional epoxy resin does not contain an OH functional group, and can be any type of epoxy resin known in the art.
  • the commonly used bifunctional epoxy resin can be, but is not limited to, commercially available epoxy resin products such as bisphenol A epoxy resin, bisphenol F epoxy resin, biphenyl epoxy resin or naphthol epoxy resin.
  • the purified bifunctional epoxy resin of the present invention can be a bisphenol A epoxy resin having a structure as shown in formula (i-1):
  • R1 can be, but is not limited to, phenyl, monofluorophenyl, perfluorophenyl or 4-tert-butylphenyl.
  • R1 of the present invention is phenyl, which has a structure as shown in formula (ii-1):
  • Step 120 is a first active transesterification step, which is to add a catalyst to the first mixture and maintain the reaction at a first temperature to obtain a second mixture.
  • the catalyst is preferably a pyridine derivative, an imidazole derivative, or a quaternary alkylammonium salt derivative, which may be, but not limited to, 4-dimethylaminopyridine (DMAP), 1-alkylimidazole, 1-acetylimidazole, 1-benzylimidazole, 2-alkylimidazole, 2-ethyl-4-methylimidazole, 2,4-dimethylimidazole, 2-phenylimidazole, and n-tetrabutylammonium bromide or its derivatives, and the amount of the catalyst added may be 500 ppm to 5000 ppm.
  • DMAP 4-dimethylaminopyridine
  • Step 130 is a dilution and mixing step, which is to add the aromatic ring solvent and the active methacrylic acid ester represented by formula (iii) into the second mixture and mix them to obtain a third mixture:
  • R2 is an aromatic ring group, which may be but is not limited to phenyl, 1-naphthyl, 2-naphthyl or perfluorophenyl.
  • R2 of the present invention is phenyl, which has a structure as shown in formula (iii-1):
  • aromatic ring solvent may be, but is not limited to, benzene, toluene or xylene.
  • Step 140 is a second active ester exchange step, which is to heat the third mixture to a second temperature and maintain the reaction at the second temperature to obtain a fourth mixture.
  • the second temperature is not higher than 130°C to avoid self-polymerization of the bifunctional epoxy resin. If the second temperature is too low, the reaction rate is low and the reaction time is prolonged. Therefore, in the present invention, the second temperature is preferably 110°C to 130°C and maintained at the second temperature for 2 hours to 6 hours.
  • the process can be monitored by an infrared spectrometer (Fourier Transform infrared spectrometer, FTIR) to monitor the epoxy group until the epoxy group completely disappears, which means the reaction is complete.
  • FTIR Fast Transform infrared spectrometer
  • Step 150 is a filtering step, which is to cool the fourth mixture and filter it to obtain a carbonate-containing oligomer as shown in formula (I):
  • R 1 , R 2 and X are each independently an aromatic ring group, and n is an integer from 1 to 5.
  • n value of the product of formula (I) produced in step 150 is normally distributed, so n may be an integer of 0, 1, 2, 3, 4 or 5.
  • n of the present invention is limited to an integer from 1 to 5.
  • the preparation method of carbonate-containing oligomers of the present invention uses the first stage of the active ester reaction mechanism of the diaryl carbonate and the epoxy resin to carry out ester exchange and chain extension of the epoxy resin, and the molecular weight can be adjusted according to the molecular structure and the impregnation requirements of the fiber. Furthermore, the free radical curable functional group is modified on the main structure through the second stage of the active ester reaction mechanism, so that it can be introduced and used without a special purification step, providing the feasibility of commercial mass production.
  • the present invention further provides a cured product, which is obtained by mixing the carbonate-containing oligomer represented by the aforementioned formula (I) with a modified polyphenylene ether resin, and adding a peroxide to carry out a curing reaction.
  • the solid content ratio of the carbonate-containing oligomer represented by formula (I) to the modified polyphenylene ether resin can be 50:50 to 10:90, and the curing reaction can be carried out by a step-by-step heating method, but is not limited to this heating method.
  • the modified polyphenylene ether resin can be a methacrylate-modified polyphenylene ether or a vinylbenzyl-modified polyphenylene ether, but is not limited thereto.
  • the specific preparation method of the carbonate-containing oligomer of the present invention is as follows: Synthesis Example 1 and Synthesis Example 2.
  • Synthesis Example 1 136 parts by weight of purified bisphenol A epoxy resin (epoxy equivalent of 170 g/eq to 172 g/eq) and 43 parts by weight of diphenyl carbonate are placed in a reaction kettle equipped with a stirrer, a thermometer and an air duct, and dry air is passed through, heated to 90°C and maintained for 1 hour. After that, 1.25 parts by weight of 4-dimethylaminopyridine is added as a catalyst and maintained at 90°C for 2 hours, and the process is monitored by an infrared spectrometer.
  • the reaction equation of Synthesis Example 1 is shown in Table 1 below.
  • Synthesis Example 2 136 parts by weight of purified bisphenol A epoxy resin (epoxy equivalent of 170 g/eq to 172 g/eq) and 57 parts by weight of diphenyl carbonate were placed in a reaction kettle equipped with a stirrer, a thermometer and an air duct, and dry air was passed through, and the mixture was heated to 110°C and maintained for 1 hour. After that, 1.16 parts by weight of 1-methylimidazole was added as a catalyst and maintained at 110°C for 2 hours, and the process was monitored by an infrared spectrometer.
  • the reaction equation of Synthesis Example 2 is shown in Table 2 below.
  • the preparation method of the carbonate-containing oligomer of the present invention is applicable to esters having an epoxy structure, such as glycidyl methacrylate (GMA), which has both epoxy and methacrylate functional groups.
  • GMA glycidyl methacrylate
  • Comparative Synthesis Example 1 142 parts by weight of glycidyl methacrylate and 107 parts by weight of diphenyl carbonate were placed in a reaction kettle equipped with a stirrer, a thermometer and an air duct, and dry air was passed through, heated to 120°C, and 0.5 parts by weight of n-tetrabutylammonium bromide was added as a catalyst and kept at the temperature for 6 hours. The process was monitored by an infrared spectrometer. When the signal with a wave number of 915 cm -1 completely disappeared, it indicated that the reaction was complete. The temperature was lowered and filtered to obtain the carbonate-containing compound of Comparative Synthesis Example 1.
  • the reaction equation for Comparative Synthesis Example 1 is shown in Table 3 below.
  • Example 1 8 parts by weight of methacrylate-modified polyphenylene ether resin (model SA9000, purchased from Sabic) was mixed with 3.3 parts by weight of Synthesis Example 1 (solid content 60%), and 0.2 parts by weight of dicumyl peroxide was added. Then, an appropriate amount of butanone was added to adjust the viscosity to an appropriate level, and an appropriate amount was poured into an aluminum tray with a release treatment, and cured in a nitrogen oven to form a film. The curing temperature was increased in stages to obtain a sheet-like cured product of Example 1.
  • methacrylate-modified polyphenylene ether resin model SA9000, purchased from Sabic
  • Example 2 5 parts by weight of methacrylate-modified polyphenylene ether resin was mixed with 8.3 parts by weight of Synthesis Example 1 (solid content 60%), and 0.2 parts by weight of dicumyl peroxide was added. Then, an appropriate amount of butanone was added to adjust the viscosity to an appropriate level, and an appropriate amount was poured into an aluminum tray treated with a release agent, and cured in a nitrogen oven to form a film. The curing temperature was increased in stages to obtain a sheet-like cured product of Example 2.
  • Example 3 8 parts by weight of methacrylate-modified polyphenylene ether resin was mixed with 3.6 parts by weight of Synthesis Example 2 (solid content 55%), and 0.2 parts by weight of dicumyl peroxide was added. Then, an appropriate amount of butanone was added to adjust the viscosity to an appropriate level, and an appropriate amount was poured into an aluminum tray treated with a release agent, and cured in a nitrogen oven to form a film. The curing temperature was increased in stages to obtain a sheet-like cured product of Example 3.
  • Example 4 5 parts by weight of methacrylate-modified polyphenylene ether resin was mixed with 9.1 parts by weight of Synthesis Example 2 (solid content 55%), and 0.2 parts by weight of dicumyl peroxide was added. Then, an appropriate amount of butanone was added to adjust the viscosity to an appropriate level, and an appropriate amount was poured into an aluminum tray with a release treatment, and cured in a nitrogen oven to form a film. The curing temperature was increased in stages to obtain a sheet-like cured product of Example 4. As the addition ratio of Synthesis Example 2 increased, the surface of the cured product showed slight phase separation.
  • Example 5 60 parts by weight of methacrylate-modified polyphenylene ether resin, 16.7 parts by weight of Synthesis Example 1 (solid content 60%), 10 parts by weight of butadiene-styrene copolymer (model Ricon100, purchased from Total Cray Valley) and 20 parts by weight of triallyl isocyanurate (TAIC) were mixed, and 2 parts by weight of diisopropylbenzene peroxide were added. After that, a proper amount of butanone was added to adjust to a proper viscosity, and a proper amount was poured into an aluminum tray with release treatment, and cured in a nitrogen oven to form a film, and the curing temperature was raised in stages to obtain a sheet-like cured product of Example 5.
  • Synthesis Example 1 solid content 60%
  • 10 parts by weight of butadiene-styrene copolymer model Ricon100, purchased from Total Cray Valley
  • TAIC triallyl isocyanurate
  • Comparative Example 1 8 parts by weight of methacrylate-modified polyphenylene ether resin was mixed with 2 parts by weight of Synthetic Comparative Example 1, and 0.2 parts by weight of dicumyl peroxide was added. Then, an appropriate amount of butanone was added to adjust the viscosity to an appropriate level, and an appropriate amount was poured into an aluminum pan treated with a release agent, and cured in a nitrogen oven to form a film. The curing temperature was increased in stages to obtain a sheet-like cured product of Comparative Example 1.
  • Comparative Example 2 5 parts by weight of methacrylate-modified polyphenylene ether resin was mixed with 5 parts by weight of Comparative Example 1, and 0.2 parts by weight of dicumyl peroxide was added. Then, an appropriate amount of butanone was added to adjust the viscosity to an appropriate level, and an appropriate amount was poured into an aluminum tray with a release treatment, and cured in a nitrogen oven to form a film. The curing temperature was increased in stages, and finally, due to excessive curing shrinkage, a complete cured film could not be produced.
  • Comparative Example 3 10 parts by weight of methacrylate-modified polyphenylene ether resin was dissolved in toluene, and 0.2 parts by weight of dicumyl peroxide was added. Then, an appropriate amount of butanone was added to adjust the viscosity to an appropriate level, and an appropriate amount was poured into an aluminum pan, and cured in a nitrogen oven to form a film. The curing temperature was increased in stages to obtain a sheet-like cured product of Comparative Example 3.
  • the propagation delay of signals depends on the dielectric constant (D k ).
  • D k dielectric constant
  • D f dielectric loss
  • the glass transition temperature (T g ), 5% thermogravimetric loss temperature (T d5 ), 800°C char yield, dielectric constant (D k ) and dielectric loss (D f ) of the cured products of Examples 1 to 5 and Comparative Examples 1 to 3 were measured.
  • Dielectric analysis method The dielectric constant (D k ) and dielectric loss (D f ) of the cured product were measured at 10 GHz.
  • Glass transition temperature (T g ) Differential scanning calorimetry (DSC) was used to measure the glass transition temperature of the cured product at a heating rate of 10° C./min.
  • thermogravimetric loss temperature T d5
  • char yield Thermo-Gravimetric Analysis (TGA) was used to measure the 5% thermogravimetric loss temperature of the cured product and the char yield at 800°C. The test was performed under a nitrogen atmosphere at a heating rate of 10°C/min.
  • the glue of Example 5 is homogeneous before curing, indicating that the compatibility between Synthesis Example 1 of the present invention and the commonly used components SA9000, Ricon 100 and TAIC in the industry is high, and there is no phase separation phenomenon after curing.
  • Comparative Example 1 is cured using Synthetic Comparative Example 1.
  • the molecular weight of the structure of Synthetic Comparative Example 1 is relatively small, and the glass transition temperature decreases slightly after curing, but it lacks rigid structures such as aromatic rings, resulting in a significant decrease in the 5% thermogravimetric loss temperature, and the electrical performance also shows a significant decrease.
  • Comparative Example 2 the addition ratio of Synthetic Comparative Example 1 is increased, and even curing shrinkage is caused, resulting in an inability to form a film. Therefore, it can be proved that the carbonate-containing oligomer of the present invention has great development potential in the production of high-frequency and low-loss substrates.
  • the carbonate-containing oligomer of the present invention can be used without special purification through the reaction mechanism of epoxy resin and active ester, and can be used in combination with commercially available modified polyphenylene ether resin to create a more balanced formulation application value.

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  • Chemical Kinetics & Catalysis (AREA)
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Abstract

La présente invention concerne un oligomère contenant du carbonate, son procédé de préparation et un produit durci. L'oligomère contenant du carbonate a une structure telle que représentée par la formule (I), et les symboles dans la formule (I) sont tels que définis dans la description. Par conséquent, au moyen du concept de synthèse de la réaction entre une résine époxy et un ester actif, un groupe carbonate et un groupe fonctionnel durcissable par radicaux libres sont introduits dans la résine époxy pour modification, de telle sorte que la résine époxy présente de faibles propriétés diélectriques de durcissement par radicaux libres et de comportements nucléophiles du groupe carbonate sur des métaux et des fibres.
PCT/CN2022/134886 2022-11-29 2022-11-29 Oligomère contenant du carbonate, son procédé de préparation et produit durci WO2024113130A1 (fr)

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005015309A2 (fr) * 2003-07-17 2005-02-17 Cytec Surface Specialties, S.A. Composition durcissable au rayonnement, a developpement alcalin
JP2010059317A (ja) * 2008-09-04 2010-03-18 Dic Corp エポキシ樹脂組成物、その硬化物、硬化物の製造方法、光半導体封止用樹脂組成物、及び光半導体装置
TW201833197A (zh) * 2017-03-08 2018-09-16 國立中興大學 固化物及其製備方法
CN109970519A (zh) * 2018-06-05 2019-07-05 台湾中油股份有限公司 含双环戊二烯之官能化聚(2,6-二甲基苯醚)寡聚物、其制造方法及其用途
CN112262178A (zh) * 2018-06-08 2021-01-22 三菱化学株式会社 聚碳酸酯树脂组合物、成型品、层叠体

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005015309A2 (fr) * 2003-07-17 2005-02-17 Cytec Surface Specialties, S.A. Composition durcissable au rayonnement, a developpement alcalin
JP2010059317A (ja) * 2008-09-04 2010-03-18 Dic Corp エポキシ樹脂組成物、その硬化物、硬化物の製造方法、光半導体封止用樹脂組成物、及び光半導体装置
TW201833197A (zh) * 2017-03-08 2018-09-16 國立中興大學 固化物及其製備方法
CN109970519A (zh) * 2018-06-05 2019-07-05 台湾中油股份有限公司 含双环戊二烯之官能化聚(2,6-二甲基苯醚)寡聚物、其制造方法及其用途
CN112262178A (zh) * 2018-06-08 2021-01-22 三菱化学株式会社 聚碳酸酯树脂组合物、成型品、层叠体

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
YE, RENYU ET AL.: "Preparation and Degradation of Waste Polycarbonate-Derived Epoxy Thermosets and Composites", ACS APPLIED POLYMER MATERIALS, vol. 4, no. 1, 14 January 2022 (2022-01-14), XP093012965, DOI: 10.1021/acsapm.1c01336 *

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