研究者詳細 - 吉田　嘉晃

論文 - 吉田　嘉晃

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自己修復およびリサイクル可能な光学用樹脂の開発招待有り

吉田　嘉晃

Material stage ( 技術情報協会 ) 24 ( 11 ) 28 - 35 2025年02月

Self-Healing and Recycling Properties of Networked Polydithiourethanes With Reversible Crosslinked Moieties via Hydrogen and Dynamic Covalent Bonding 査読有り国際誌

Yoshida Y., Suenaga R., Sakiyama T., Alem-Marchand H., Meimaroglou D.

Journal of Polymer Science, Part A: Polymer Chemistry 63 ( 16 ) 3301 - 3312 2025年01月

担当区分：筆頭著者,　責任著者記述言語：英語掲載種別：研究論文（学術雑誌）

In this study, eight types of networked Polydithiourethanes (PDTUs) were synthesized with the combinations of various dithioisocyanates, dithiols, and tetrafunctional thiols, and the self-healing behaviors of the networked PDTUs were observed. In particular, the networked PDTUs with an ether structure in the main chain (ET/ET/PE) exhibited a healing efficiency, which was estimated by the ratio of initial and healed toughness values, of up to 77% at 25°C for 24 h. Moreover, the healing efficiency of ET/ET/PE reached almost 100% under the healing conditions at 50°C for 24 h or at 25°C for 48 h. However, after four repetitions of the self-healing operation at 25°C for 24 h, the healing efficiency of ET/ET/PE decreased from 77% to 16%. Herein, the damaged ET/ET/PE was depolymerized at 150°C for 1 h, followed by repolymerization at room temperature, and the damaged ET/ET/PE was chemically recycled as the polymer that exhibited the same toughness and healing efficiency as the initial value. Since PDTUs exhibit a high refractive index and transparency, it is expected to develop applications as a self-healable and chemically recyclable optical resin.

DOI： 10.1002/pol.20250263

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The predictive machine learning model of a hydrated inverse vulcanized copolymer for effective mercury sequestration from wastewater 査読有り国際誌

Ghumman A.S.M., Shamsuddin R., Abbasi A., Ahmad M., Yoshida Y., Sami A., Almohamadi H.

Science of the Total Environment 908 2024年01月

記述言語：英語掲載種別：研究論文（学術雑誌）

Inverse vulcanized polysulfides (IVP) are promising sulfur-enriched copolymers with unconventional properties irresistible for diverse applications like Hg2+ remediation. Nevertheless, due to their inherent hydrophobic nature, these copolymers still offer low Hg2+ uptake capacity. Herein, we reported the synthesis of IVP by reacting molten sulfur with 4-vinyl benzyl chloride, followed by their functionalization using N-methyl D-glucamine (NMDG) to increase the hydration of the developed IVP. The chemical composition and structure of the functionalized IVP were proposed based on FTIR and XPS analysis. The functionalized IVP demonstrated a high mercury adsorption capacity of 608 mg/g (compared to <26 mg/g for common IVP) because of rich sulfur and hydrophilic regions. NMDG functionalized IVP removed 100 % Hg2+ from a low feed concentration (10–50 mg/l). A predictive machine learning model was also developed to predict the amount of mercury removed (%) using GPR, ANN, Decision Tree, and SVM algorithms. Hyperparameter and loss function optimization was also carried out to reduce the prediction error. The optimized GPR algorithm demonstrated high R2 (0.99 (training) and 0.98 (unseen)) and low RMSE (2.74 (training) and 2.53 (unseen)) values indicating its goodness in predicting the amount of mercury removed. The produced functionalized IVP can be regenerated and reused with constant Hg2+ uptake capacity. Sulfur is the waste of the petrochemical industry and is abundantly available, making the functionalized IVP a sustainable and cheap adsorbent that can be produced for high-volume Hg2+ remediation. Environmental implication: This research effectively addresses the removal of the global top-priority neurotoxic pollutant mercury, which is toxic even at low concentrations. We attempted to remove the Hg2+ utilizing an inexpensive adsorbent developed by NMDG functionalized copolymer of molten sulfur and VBC. A predictive machine learning model was also formulated to predict the amount of mercury removal from wastewater with only a 0.05 % error which shows the goodness of the developed model. This work is critical in utilizing this low-cost adsorbent and demonstrates its potential for large-scale industrial application.

DOI： 10.1016/j.scitotenv.2023.168034

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Synthesis, properties, and chemical recyclability of aromatic polyesters using alkylamide diphenolic acid 査読有り国際誌

Omura S., Fukushima S., Sakiyama T., Morita T., Takase M., Yoshida Y., Suzuki T., Mawatari Y.

European Polymer Journal 235 2025年07月

記述言語：英語掲載種別：研究論文（学術雑誌）

This study explores sustainable polymers by synthesizing and characterizing a novel, chemically recyclable, fully aromatic polyester derived from the bio-based compound diphenolic acid (DPA). The new polyester, PDPANHC18, was synthesized via the polycondensation of a DPA monomer modified with a long-chain alkylamide group (DPANHC18) and terephthaloyl chloride. Its properties and chemical recyclability were compared with those of PDPAOC18, an analogous polyester containing a long-chain alkyl ester linkage. The amide linkages in PDPANHC18 significantly enhanced its material properties compared to the ester-linked PDPAOC18. PDPANHC18 exhibited a higher glass transition temperature (Tg) due to strong intermolecular hydrogen bonding between amide groups, which restricted chain mobility and improved thermal stability. Furthermore, PDPANHC18 films demonstrated lower gas permeability, which was attributed to a decrease in free volume and restricted chain mobility caused by hydrogen bonding. Notably, PDPANHC18 exhibited exceptional chemical recyclability via mechanochemical depolymerization under dry, basic conditions. Unlike the ester linkages in PDPAOC18, the amide linkages in PDPANHC18 were resistant to hydrolysis, allowing for the near-quantitative recovery of the DPANHC18 monomer without side-chain degradation. The recovered DPANHC18 monomer mixture could be directly repolymerized into PDPANHC18 without purification, demonstrating a closed-loop recycling process. This research highlights the potential of amide-modified DPA for the development of sustainable, high-performance polymers with efficient chemical recyclability. Strategically modifying bio-based monomers with functional groups such as amides enhances material properties and enables closed-loop recycling, contributing to a circular economy for plastics.

DOI： 10.1016/j.eurpolymj.2025.114048

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易解体およびリサイクルを志向したサスティナブル接着剤の創生招待有り

吉田　嘉晃

明専会報 ( 明専会 ) ( 2025-07 ) 4 - 7 令和７年７・８月号 2025年07月

Aminolysis of five-membered cyclic carbonate catalyzed by guanidines: Solvent effects on the formation of guanidine dimers 査読有り国際誌

Dong W., Sun Y., Yoshida Y., Endo T.

Journal of Molecular Structure 1321 2025年02月

担当区分：責任著者記述言語：英語掲載種別：研究論文（学術雑誌）

This paper presents an experimental and computational investigation on the aminolysis reactions of five-membered cyclic carbonate (5CC) catalyzed by mono- or bi-cyclic guanidines in various solvents. For both liquid and solid 5CC substrate employed, higher polar solvent favors the monomeric active guanidine responsible for the catalytic aminolysis reactions. The formation of the dimeric state of the guanidine catalyst, which is seemingly inert to catalytic activity, is prevented by the bulkier substituents connecting to the guanidine moiety. Extensive DFT calculations further confirm that the relative stabilities of dimeric guanidine is depended on both the polarities of the solvents and the bulkiness of the substituents connected to the guanidine moiety, which is consistent with the experimental kinetic results.

DOI： 10.1016/j.molstruc.2024.140299

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ポリジチオウレタンフィルムの光学物性，熱物性，機械物性およびケミカルリサイクル査読有り

吉田　嘉晃, 末永　龍一, 渡邉　ほのか, 遠藤　剛

ネットワークポリマー論文集 ( 合成樹脂工業協会 ) 45 ( 6 ) 270 - 279 2024年11月

担当区分：筆頭著者,　責任著者記述言語：日本語掲載種別：研究論文（学術雑誌）

<p>異なる炭素数のメチレン鎖を有するジイソチオシアネートおよびジチオールをモノマーとして合成した脂肪族ポリジチオウレタン（PDTU）フィルムの光学物性，熱物性および機械物性を評価し，メチレン鎖長が生成ポリマーの物性に与える影響について検討した。さらに，三官能性イソチオシアネートあるいは三官能性チオールを架橋剤として合成したネットワークPDTU フィルムと鎖状ポリマーから成形したフィルムとの物性を比較し，それらのケミカルリサイクル挙動について検討した。</p>

DOI： 10.11364/networkedpolymer.45.6_270

その他リンク： http://id.ndl.go.jp/bib/033829212

Systematic studies on polyacrylates containing side-chain hydrogen bonding units: Significant effects of the pendant functions on thermal behaviors and solubility of polymers 査読有り国際誌

Hirose Y., Yoshida Y., Furusho Y., Tomita I., Endo T.

Journal of Polymer Science 62 ( 10 ) 2116 - 2128 2024年05月

記述言語：英語掲載種別：研究論文（学術雑誌）

The synthesis of polyacrylates containing various pendant hydrogen bonding or non-hydrogen bonding functions and the effects of side-chain functions on their physical properties are described. The polyacrylates possessing urea, urethane, N-substituted urea, or carbonate groups are prepared by the free radical polymerization of acrylate monomers possessing the corresponding functional groups. The presence of stronger hydrogen bonding interactions both in bulk and solutions of a highly polar solvent such as dimethyl sulfoxide (DMSO) is supported by the infrared (IR) spectra, whereas the urethane-based polyacrylate does not exhibit the interaction in the solution. The presence of the stronger hydrogen bonding interactions of the urea unit is discussed by the IR and nuclear magnetic resonance spectra and the density functional theory calculations of the corresponding model compounds. The solubility in organic solvents and the glass transition temperature (Tg) of polymers are also dependent on the structure of the pendant groups. Polar aprotic solvents such as DMSO can only dissolve the urea-based polyacrylate, while the other polymers are soluble in a much wider range of solvents such as tetrahydrofuran. The urea-based polyacrylate shows the highest Tg among the polymers studied owing to the presence of plural hydrogen bonding sites in the urea groups.

DOI： 10.1002/pol.20230893

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Synthesis of water-soluble tetrafunctional urethane acrylate bearing a pentaerythritol core and its radical polymerization behaviors in an aqueous solution 査読有り

Okamoto S., Watanabe Y., Yoshida Y., Endo T.

Polymer 286 2023年11月

担当区分：責任著者記述言語：英語掲載種別：研究論文（学術雑誌）

A novel water-soluble tetrafunctional urethane acrylate (TUA) was successfully synthesized by addition reaction of pentaerythritol to 2-isocyanatoethyl acrylate. TUA efficiently underwent radical polymerization and its copolymerization with monofunctional acrylate monomers exhibiting hydrophilicity in an ethanol aqueous solution, affording corresponding networked polymers in high yields. Notably, TUA exhibited much lower volume shrinkage during the radical polymerization compared to a comparative pentaerythritol core based tetrafunctional acrylate containing no urethane bonds. The thermal decomposition temperature of the networked homopolymer, synthesized from TUA, was much higher than those of the linear polymers, synthesized from monofunctional urethane acrylate monomers. TUA is expected to be applied to the development of environmentally sustainable polymer materials.

DOI： 10.1016/j.polymer.2023.126402

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Bivalent monomer bearing styryl and five-membered cyclic dithiocarbonate moieties for orthogonal radical and cationic ring-opening polymerizations 査読有り国際誌

Yoshida Y., Krishnamurthy S., Asakura N., Endo T.

Journal of Polymer Science 61 ( 15 ) 1651 - 1659 2023年08月

担当区分：筆頭著者記述言語：英語掲載種別：研究論文（学術雑誌）

We synthesized a novel bivalent monomer 1 bearing 4-vinylbenzyl group and five-membered cyclic dithiocarbonate. This monomer 1 was polymerized orthogonally by free radical polymerization to afford polystyrene 1a bearing a five-membered cyclic dithiocarbonate moiety in the side chain. On the other hand, cationic ring-opening polymerization of five-membered cyclic dithiocarbonate in the monomer 1 successfully proceeded, resulting in a narrow molecular weight distribution of polydithiocarbonate 1b bearing a 4-vinylbenzyl group in the side chain. Furthermore, post-polymerizations of 1a and 1b maintaining the polymerizable functionality were carried out respectively by suitable polymerization methods. The five-membered cyclic dithiocarbonate of 1a underwent cationic ring-opening polymerization with a high molar ratio of methyl trifluoromethanesulfonate at a high temperature compared to the case of monomer 1, whereas radical polymerization of the 4-vinylbenzyl group of 1b successfully proceeded under the almost same conditions as the case of monomer 1. These post-polymerizations achieved the synthesis of corresponding networked polymers 2a and 2b.

DOI： 10.1002/pol.20230173

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Stereospecific radical polymerization of methacrylate bearing oxazolidone structure and improvement of glass transition temperature of urethane methacrylate copolymers 査読有り国際誌

Yoshinaga Y., Yoshida Y.

Journal of Polymer Science 2023年01月

担当区分：責任著者記述言語：英語掲載種別：研究論文（学術雑誌）

We synthesized the novel methacrylate monomer bearing an oxazolidone structure (M1) and performed radical polymerization of M1 by traditional procedures. The glass transition temperature (Tg) of the obtained polymer (P1) was a significantly high value compared to that of poly(methyl methacrylate) and typical poly(urethane methacrylate)s. The copolymers of M1 and monofunctional urethane methacrylate derived from 2-hydroxyethyl methacrylate and phenyl isocyanate (M2) exhibited a linear rise of the Tg values depending on the composition ratio of M1. The NMR analysis and the estimation of monomer reactivity ratio and Q–e values suggested that the improvement of glass transition temperature resulted from a stereoregularity, meaning a syndiotacticity of the copolymers improved with increasing the composition ratio of M1. Furthermore, the thermal curing reaction of M1 or M2 with bifunctional urethane acrylate successfully proceeded, then the Tg value of the cured product from M1 was much higher than that from M2.

DOI： 10.1002/pol.20230210

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Special structures and thermal stabilities of polyurethanes derived from diol and triol having oxazolidone moieties 査読有り国際誌

Yoshida Y., Yoshinaga Y., Endo T.

Journal of Polymer Science 2023年01月

担当区分：筆頭著者記述言語：英語掲載種別：研究論文（学術雑誌）

We synthesized regular polyurethanes from the diol having oxazolidone structure (Diol-1) and the aliphatic diisocyanate by typical polyaddition. The results of the structural analysis suggested that the polyurethane having a cyclic urethane structure such as oxazolidone formed a rod-like structure, although the control polyurethane having a chain urethane structure formed a linear structure. The polyaddition of Diol-1 and aliphatic diisocyanate with triol having oxazolidone structure (Triol-1) as a crosslinker also proceeded successfully to achieve corresponding polyurethanes. However, the polyurethanes containing a molar ratio of Triol-1 less than or equal 50% were soluble in high polar organic solvents nevertheless those polyurethanes contained some trifunctional units in the polymer chain. On the other hand, the polyurethanes containing a molar ratio of Triol-1 more than 50% were insoluble in any organic solvents. We hypothesized that the soluble polyurethanes containing Triol-1 formed multi-branched structure and the insoluble polyurethanes formed cross-linking structure. Such structures of polymer chain affected significantly to the thermal properties of the obtained polyurethanes.

DOI： 10.1002/pol.20230187

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Cationic ring-opening polymerization of a five membered cyclic dithiocarbonate having a tertiary amine moiety 査読有り国際誌

Krishnamurthy S., Yoshida Y., Endo T.

Polymer Chemistry 13 ( 2 ) 267 - 274 2022年01月

記述言語：英語掲載種別：研究論文（学術雑誌）

In this work, a facile route for the cationic ring-opening polymerization (CROP) of a cyclic dithiocarbonate derived from N,N-dibenzyl glycidylamine (DBGA) and carbon disulfide has been developed. The cyclic dithiocarbonate monomer, 5-((dibenzylamino)methyl)-1,3-oxathiolane-2-thione (1), can be obtained economically and easily in three steps from commercially available N,N-dibenzylamine. The cationic polymerization of 5-((dibenzylamino)methyl)-1,3-oxathiolane-2-thione (1) was achieved using methyl triflate or ethyl triflate as an initiator. The polymerization proceeded smoothly in chlorobenzene with high monomer conversion (>90%). The polymers exhibited a high molar mass with narrow dispersity. The structure of the polymers was confirmed by NMR and IR analyses. Investigation of the mechanism of this polymerization by NMR studies on the stoichiometric reaction of 1 with MeOTf indicates the higher reactivity of sulfur than that of nitrogen for the initiator (methyl cation, S > N). A strong possibility of formation of a transient aziridinium ion by neighboring group participation of the tertiary amine moiety is also seen. Finally evidence from DFT calculation also clarifies the presence of more negative charge on the sulfur atom of the thiocarbonyl group compared to nitrogen.

DOI： 10.1039/d1py01230d

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Rate Control of Helix Oscillation of Poly(arylacetylene)s Achieved by Design of Side-Group Structures 査読有り

Mawatari Y., Oouchi M., Yoshida Y., Hiraoki T., Tabata M.

Macromolecules 54 ( 16 ) 7400 - 7408 2021年08月

記述言語：英語掲載種別：研究論文（学術雑誌）

Poly(2-ethynylnaphthalene)s with different alkylester moieties at the 6-position (PNRs) were synthesized to observe the first helix oscillation (HELIOS) of helical poly(arylacetylene)s, a transition between stretched and contracted helices in solution unique to helical structures. Variable-temperature (VT) 1H NMR spectra of PNRs were measured to analyze the microstructures of the two helices. The size of the aromatic ring and the structures of the alkyl chain in the side group on the PNRs strongly affected the rate of the HELIOS mode. The temperature dependencies of the relative ratio of populations between stretched and contracted helices were estimated. The differences in microstructures between stretched and contracted helices were also discussed based on the results of molecular mechanics calculations and 1H-13C heteronuclear single-quantum correlation spectroscopy (1H-13C HSQC). Consequently, we successfully changed the rate of HELIOS of PNRs and obtained detailed information on the molecular conformation of the stretched and contracted helices.

DOI： 10.1021/acs.macromol.1c00790

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Synthesis of multifunctional 4-hydroxymethyl 2-oxazolidinones from glycidyl carbamate derivatives catalyzed by bicyclic guanidine 査読有り

Yoshida Y., Endo T.

Tetrahedron Letters 72 2021年05月

担当区分：筆頭著者記述言語：英語掲載種別：研究論文（学術雑誌）

4-Hydroxymethyl 2-oxazolidinones have been successfully synthesized under mild conditions by the intramolecular cyclization of glycidyl carbamate derivatives with a bicyclic guanidine as the efficient catalyst. This reaction system, which is also applicable to the multifunctional compounds, can provide bi- and tri-functional alcohols having oxazolidinone moieties.

DOI： 10.1016/j.tetlet.2021.153086

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Synthesis of poly(hydroxyurethane) from 5-membered cyclic carbonate under mild conditions in the presence of bicyclic guanidine and their reaction process 査読有り

Dong W., Yoshida Y., Endo T.

Journal of Polymer Science 59 ( 6 ) 502 - 509 2021年03月

記述言語：英語掲載種別：研究論文（学術雑誌）

A series of amines are applied as catalysts in the aminolysis reactions of five-membered cyclic carbonate (5CC). Kinetic results display that TBD, which has a guanidine structure, exhibits the best catalytic efficacy and the reaction rate constant is about 100 times higher than the blank system without catalyst. The reaction medium, NMP is found to be as both solvent and promoter in the aminolysis of 5CC. Finally, with TBD and NMP as catalyst and solvent, respectively, the polymerization of bis-functional 5CC (B5CC) and 1, 6-diaminohexane can proceed almost 100% at room temperature in less than 4 h to obtain poly(hydroxyurethane)s (PHUs) with moderate molecular weight.

DOI： 10.1002/pol.20200825

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Synthesis and Thermal Properties of Polyamic Acids and Its Six-Membered Cyclic Polyimides from Ethylenediaminetetraacetic Acid 査読有り

CHENNAPURAM Madhu, YOSHIDA Yoshiaki, ENDO Takeshi

ネットワークポリマー論文集 ( 合成樹脂工業協会 ) 42 ( 3 ) 90 - 97 2021年01月

担当区分：筆頭著者記述言語：英語掲載種別：研究論文（学術雑誌）

<p>This article represents the synthesis and characterization of polyamic acids and polyimides derived from several bifunctional amines with ethylenediaminetetraacetic acid (EDTA) anhydride using polyaddition followed by chemical/thermal imidization methods. The structural and thermal properties of the obtained polyamic acids and their six-membered cyclic polyimides were determined in detail by using FT-IR, TGA, and DSC analysis. Additionally, this method was also extended to synthesis of networked polyamic acid and polyimide using trifunctional amine and EDTA anhydride.</p>

DOI： 10.11364/networkedpolymer.42.3_90

その他リンク： https://ci.nii.ac.jp/naid/130008073107

Curing behavior and properties of epoxy monomers with ethylenediaminetetraacetic dianhydride 査読有り

Chennapuram M., Yoshida Y., Endo T.

Journal of Applied Polymer Science 2021年01月

担当区分：筆頭著者記述言語：英語掲載種別：研究論文（学術雑誌）

Ethylenediaminetetraacetic acid dianhydride (EDTADA) is a six-membered cyclic anhydride that contains two tertiary amino groups in the structure. In this work, we have demonstrated that a curing reaction of diglycidyl ether of bisphenol A (DGEBA) and EDTADA proceeded efficiently without any accelerant such as tertiary amine and imidazole. This result proves that EDTADA can act as a self-sustaining accelerant for the curing reaction of the epoxy monomers. On the other hand, the curing reaction of glycidol with EDTADA proceed successfully via an initiation step owing to the esterification of primary alcohol and anhydride moieties. In this case, we demonstrate that EDTADA also works as an amine catalyst for esterification. Moreover, we have studied the adhesive properties of two types of epoxy resin derived from DGEBA and glycidol with EDTADA.

DOI： 10.1002/app.51626

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Phosgene-free and Chemoselective Synthesis of Novel Polyureas from Activated l -Lysine with Diphenyl Carbonate 査読有り

Yakeya D., Yoshida Y., Endo T.

Macromolecules 53 ( 16 ) 6809 - 6815 2020年08月

記述言語：英語掲載種別：研究論文（学術雑誌）

© 2020 American Chemical Society. Nα,Nϵ-(Phenoxycarbonyl)-l-lysine methyl ester 1a can be expected to behave as a difunctional blocked diisocyanate monomer derived from l-lysine with diphenyl carbonate. In this report, we examined a reaction of the obtained compound 1a and 1 equiv of n-butylamine as a model reaction to find that the Nα position of compound 1a reacted selectively with an amine. This means that the reactivity of Nα- and Nϵ-phenoxycarbonyl groups is different because the Nα-phenoxycarbonyl moiety has an adjacent ester group. From this result, synthesis of the corresponding polyureas was evaluated by a stepwise reaction of compound 1a with various diamines. The structure analysis and the study of thermal properties of the synthesized polyureas suggested that the carbodiimide moieties were partly constructed in the main chain because of the dehydration triggered by heat treatment of the polyureas.

DOI： 10.1021/acs.macromol.0c01039

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Synthesis and fundamental properties of methacrylate polymer containing five-membered cyclic trithiocarbonate group 査読有り

Nishi M., Komeda M., Aoyagi N., Yoshida Y., Endo T.

Journal of Polymer Science 58 ( 15 ) 2126 - 2133 2020年08月

記述言語：英語掲載種別：研究論文（学術雑誌）

© 2020 Wiley Periodicals LLC. 4-(1,3-Dithia-2-thioxocyclopenthyl)methacrylate (TCMA), containing the five-membered trithiocarbonate moiety, was prepared from glycidyl methacrylate (GMA) through 2,3-epithiopropyl methacrylate (ETMA). At first step, GMA was converted to ETMA by the reaction using thiourea. At second step, ETMA was reacted efficiently with carbon disulfide in the presence of a catalytic amount of 1,2-dimethyltetrahydropyrimidine to give TCMA. The polymerization of TCMA proceeded under standard radical conditions to give the polymeric TCMA in 94% yield. The copolymerizations of TCMA with ethyl acrylate (EA) or acrylonitrile (AN) were conducted by changing the feed molar ratios of the monomers, in which the corresponding copolymers were obtained in over 83% yields. In addition, the obtained polymers showed the high values of refractive index over ca. 1.6 due to the presence of the cyclic trithiocarbonate structure.

DOI： 10.1002/pol.20200201

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