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Esterification of Cellulose in Protic Ionic Liquids 纤维素在质子离子液体中的酯化反应
Kobunshi Ronbunshu Pub Date : 2019-07-25 DOI: 10.1295/koron.2019-0017
M. Yoshizawa‐Fujita, Hideki Hanabusa, Y. Takeoka, M. Rikukawa
{"title":"Esterification of Cellulose in Protic Ionic Liquids","authors":"M. Yoshizawa‐Fujita, Hideki Hanabusa, Y. Takeoka, M. Rikukawa","doi":"10.1295/koron.2019-0017","DOIUrl":"https://doi.org/10.1295/koron.2019-0017","url":null,"abstract":"セルロースは天然に豊富に存在する非可食性の高分子 であり,カーボンニュートラルな材料である.機能材料 としても注目されており,セルロースの誘導体化に関す る研究が活発に行われている.たとえば,セルロースの エステル誘導体として硝酸セルロースのような無機酸エ ステルや酢酸セルロースのような有機酸エステルが報告 されている1),2).セルロースのヒドロキシ基にさまざま な官能基を導入することができ,エステル誘導体以外に も多数のセルロース誘導体が報告されている3). 一方,難溶性高分子であるセルロースを溶解するイオ ン液体 (IL)が 2002年に報告され4),多くの研究者の興味 を集めている5)~7).ILは 100°C以下に融点を有する有機 塩であり,難揮発性,難燃性などの特徴を有する8),9). ILは真空下で加熱しても飛散しないため,繰返し使用 できる環境調和型溶媒として期待され,IL中において 種々の反応が行われている8),9).たとえば,セルロース の高分子反応が IL中で行われている.Schlufterらは,1butyl-3-methylimidazolium chloride ([C4mim]Cl) 中でのセ ルロースのアセチル化およびカルボニル化を報告し た10).Hinnerらは,セルロースのビニルエステル化が 1-ethyl-3-methylimidazolium acetate ([C2mim][OAc])中で進 行すること,さらに [C2mim][OAc]がリサイクル可能で あることを報告した11). 最 近, 筆 者 ら は 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU)と酢酸 (HOAc)の中和反応により作製したプロト ン性イオン液体 (PIL)である [DBUH][OAc]が,セルロー スのエステル化反応において,溶媒兼触媒として機能す ることを報告した12).PILとは,Brønsted酸からBrønsted 塩基へのプロトン移動反応によって得られる ILであ る.酸と塩基の pKa値の差 (¦pKa)が大きいときにイオ ン性が高まるため,強酸と強塩基を組合せることが多 い.Angellらは,¦pKa値が 10以上のとき,PILは非プ ロトン性 ILと同様の挙動を示すことを見いだした13). 一方,¦pKa値が 10以下のとき,PILは蒸留により精製 できる.中和反応は可逆的であるため,真空下では逆反 応が起こり,蒸留が可能となる.[DBUH][OAc]の¦pKa 値は 8.52であり,セルロースのエステル化反応後,蒸留 により [DBUH][OAc]を精製することで繰返し使用でき る12).これは非プロトン性 ILにはない特徴である.さ らに,セルロースのエステル化反応において,PILのア ニオンがエステル交換反応によりセルロースに修飾さ れることを見いだした12).本報では,DBUと酢酸,プ ロピオン酸 (HOPr),または酪酸 (HOBu)を組合せた三 種の PIL ([DBUH][OAc], [DBUH][OPr], [DBUH][OBu]) を合成し (Figure 1),それら PIL中でセルロースのエス 公益社団法人高分子学会","PeriodicalId":17878,"journal":{"name":"Kobunshi Ronbunshu","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2019-07-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"89490100","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Fabrication and Characterization of Thick Piezoelectric Rubber Sheets 厚压电橡胶片的制备与表征
Kobunshi Ronbunshu Pub Date : 2019-05-25 DOI: 10.1295/KORON.2019-0012
Tatsuya Ota, Shogo Mamada, Ryo Nogimura
{"title":"Fabrication and Characterization of Thick Piezoelectric Rubber Sheets","authors":"Tatsuya Ota, Shogo Mamada, Ryo Nogimura","doi":"10.1295/KORON.2019-0012","DOIUrl":"https://doi.org/10.1295/KORON.2019-0012","url":null,"abstract":"","PeriodicalId":17878,"journal":{"name":"Kobunshi Ronbunshu","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2019-05-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"75201496","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Visualization of the Thermal Oxidation of Polyethylene Containing Phenolic Antioxidant 含酚类抗氧化剂聚乙烯热氧化的可视化研究
Kobunshi Ronbunshu Pub Date : 2019-05-25 DOI: 10.1295/KORON.2018-0063
Kiyomi Okada
{"title":"Visualization of the Thermal Oxidation of Polyethylene Containing Phenolic Antioxidant","authors":"Kiyomi Okada","doi":"10.1295/KORON.2018-0063","DOIUrl":"https://doi.org/10.1295/KORON.2018-0063","url":null,"abstract":"Here, we investigated the thermal oxidation process of a phenolic antioxidant in polyethylene ( PE ) by using FT - IR imaging. The peaks of the phenolic group of the antioxidant change by being oxidized with a higher sensitivity than the carbonyl group peak in the FT - IR spectra. Thus it became possible to visualize the oxidation process of PE in more detail. Samples of PE containing a phenolic antioxidant were being kept in air at 60 ° C for up to 11300 hours, and the following results were obtained. ( i ) The antioxidant inside PE was not oxidized. ( ii ) The antioxidant di ff used from the inside of PE to the surface, where it was oxidized. ( iii ) The oxidation started at the surface of PE and the speed of oxidation inside PE was very high because of the low concentration of the antioxidant.","PeriodicalId":17878,"journal":{"name":"Kobunshi Ronbunshu","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2019-05-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"86708690","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Living Cationic Cyclopolymerization of Divinyl Ether with Bulky Substituents: Synthesis of High-Molecular-Weight Cyclopolymers and Star-Shaped Cyclopolymers 含大体积取代基的二乙烯基醚活性阳离子环聚合:高分子量环聚合物和星形环聚合物的合成
Kobunshi Ronbunshu Pub Date : 2019-05-25 DOI: 10.1295/KORON.2019-0002
T. Niwa, Takafumi Yamamoto, T. Hashimoto, Michio Urushisaki, T. Sakaguchi
{"title":"Living Cationic Cyclopolymerization of Divinyl Ether with Bulky Substituents: Synthesis of High-Molecular-Weight Cyclopolymers and Star-Shaped Cyclopolymers","authors":"T. Niwa, Takafumi Yamamoto, T. Hashimoto, Michio Urushisaki, T. Sakaguchi","doi":"10.1295/KORON.2019-0002","DOIUrl":"https://doi.org/10.1295/KORON.2019-0002","url":null,"abstract":"synthesis of star - shaped cyclopolymers. Living cationic cyclopolymerization of 1,2 - bis ( 2 - vinyloxyethoxy )- 3,5 - di - tert - butylbenzene ( 1 ) was investigated with the CH 3 CH ( O i Bu )-OCOCH 3 / Et 1.5 AlCl 1.5 / CH 3 COOEt initiating system in toluene at 0 ° C. All the reactions proceeded quantitatively to give gel - free polymers, soluble in organic solvents. The number - average molecular weight ( M n ) of the polymers increased in direct proportion to monomer conversion and further increased on addition of a fresh monomer feed to the almost completely polymerized reaction mixture, indicating that living cyclopolymerization of 1 occurred. The content of unreacted vinyl groups in the produced soluble polymers was less than ³ 2mol%, and therefore, the degree of cyclization of the polymers was determined to be over ³ 98%. Preparation of high - molecular - weight cyclopoly ( 1 ) was achieved by sequential monomer addition to the living polymerization system and polymer linking reaction of living cyclopoly ( 1 ) leading to star - shaped polymers. Glass transition temperature ( T g ) of linear cyclopoly ( 1 ) ( M n = 18,500 ) was 134 ° C and T g of star - shaped cyclopoly ( 1 ) ( M n = 95,900 ) was 132 ° C, and thermal decomposition temperatures ( T d s ) of these cyclopoly ( 1 ) were over 350 ° C, indicating their high thermal stability.","PeriodicalId":17878,"journal":{"name":"Kobunshi Ronbunshu","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2019-05-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"90519029","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Impact of Particle Softness on Segregation of Binary Colloidal Suspensions Flowing in a Microchannel 颗粒柔软度对微通道中二元胶体悬浮液偏析的影响
Kobunshi Ronbunshu Pub Date : 2019-05-25 DOI: 10.1295/KORON.2019-0003
Shun Oura, Takumi Watanabe, Haruka Minato, D. Suzuki
{"title":"Impact of Particle Softness on Segregation of Binary Colloidal Suspensions Flowing in a Microchannel","authors":"Shun Oura, Takumi Watanabe, Haruka Minato, D. Suzuki","doi":"10.1295/KORON.2019-0003","DOIUrl":"https://doi.org/10.1295/KORON.2019-0003","url":null,"abstract":"In order to realize drug delivery systems, deeper understanding of the relationship between the position of colloidal particles, fl owing in a microchannel, and particle characteristics, such as size and softness, is crucial. However, the in fl uence of the softness of the particles on the fl owing position ( or segregation ) in colloidal mixtures containing polymeric microspheres is still not clear. In this study, we investigated the particle position of binary mixtures in microchannels, observed by an optical microscope equipped with a high - speed camera, and clari fi ed the e ff ect of microgel softness on the segregation. These fi ndings help designing carrier microspheres, for some applications, including drug delivery systems and as arti fi cial blood cells.","PeriodicalId":17878,"journal":{"name":"Kobunshi Ronbunshu","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2019-05-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"75441854","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 1
Direct Arylation Polycondensation of Fluoroarenes with Dibromoarenes 氟芳烃与二溴芳烃的直接芳基化缩聚
Kobunshi Ronbunshu Pub Date : 2019-05-25 DOI: 10.1295/KORON.2019-0005
Yuki Togawa, Shin-ichi Yamamoto, S. Hayashi, T. Koizumi
{"title":"Direct Arylation Polycondensation of Fluoroarenes with Dibromoarenes","authors":"Yuki Togawa, Shin-ichi Yamamoto, S. Hayashi, T. Koizumi","doi":"10.1295/KORON.2019-0005","DOIUrl":"https://doi.org/10.1295/KORON.2019-0005","url":null,"abstract":"[Notes] Here, we demonstrate that the direct arylation polycondensation of fl uoroarenes with dibromoarenes proceeds e ffi ciently under the conditions that we have previously reported for the synthesis of other polymers. The polycondensation of 1.2.4.5 - tetra fl uorobenzene, 1,2,3,5 - tetra fl uorobenzene or 2,2 B ,3,3 B ,5,5 B ,6,6 B - octa fl uorobiphenyl with 5,5 B - dibromo - 3,3 B - dihexyl - 2,2 B - bitiophene, 3,6 - dibromo - N - octylcarbazole or 4,4 B - dibromo - N -( 2 - ethyl hexyl ) diphenylamine in the presence of palladium acetate ( 2.5mol% ) , di - tert - butylmethylphosphonium tetra fl uoroborate ( 5.0mol% ) , acetic acid ( 2eq. ) , and potassium carbonate ( 6eq. ) in toluene ( 0.5mL ) at 120 ° C for 24h gave the corresponding alternating polymers.","PeriodicalId":17878,"journal":{"name":"Kobunshi Ronbunshu","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2019-05-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"75249054","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Influence on Particle Double-Network Gels by Gamma Irradiation and Improvement of Radiation Tolerance γ辐照对颗粒双网凝胶的影响及辐射耐受性的提高
Kobunshi Ronbunshu Pub Date : 2019-05-25 DOI: 10.1295/KORON.2019-0007
K. Kikuchi, Hirano Katsuhiko, Kouichi Kurosawa, M. Kawakami, H. Furukawa
{"title":"Influence on Particle Double-Network Gels by Gamma Irradiation and Improvement of Radiation Tolerance","authors":"K. Kikuchi, Hirano Katsuhiko, Kouichi Kurosawa, M. Kawakami, H. Furukawa","doi":"10.1295/KORON.2019-0007","DOIUrl":"https://doi.org/10.1295/KORON.2019-0007","url":null,"abstract":"","PeriodicalId":17878,"journal":{"name":"Kobunshi Ronbunshu","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2019-05-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"74380111","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Analysis of Crack Initiation Sites of Fuel Cell Catalyst Layers 燃料电池催化剂层裂纹起裂部位分析
Kobunshi Ronbunshu Pub Date : 2019-05-25 DOI: 10.1295/KORON.2018-0053
Y. Higuchi, Naomi Kumano, M. Harada, K. Kudo, M. Ishi, Hiroshi Nakamura
{"title":"Analysis of Crack Initiation Sites of Fuel Cell Catalyst Layers","authors":"Y. Higuchi, Naomi Kumano, M. Harada, K. Kudo, M. Ishi, Hiroshi Nakamura","doi":"10.1295/KORON.2018-0053","DOIUrl":"https://doi.org/10.1295/KORON.2018-0053","url":null,"abstract":"The catalyst layers in fuel cells are manufactured by drying slurries called catalyst inks. Since cracks which often appear in the catalyst layer a ff ect the performance of fuel cell, it is important to control the formation of the cracks in the manufacturing processes. Understanding the formation mechanisms of cracks helps to control the crack formation. However, the mechanisms are not su ffi ciently clari fi ed because catalyst inks are complex slurries. In this paper, we investigated the density structures during the drying processes of catalyst layers in a fuel cell by radiography observations using synchrotron X - rays at the SPring - 8 BL33XU beam line in order to clarify the crack formations. The results reveal that the cracks are generated at lower density areas than the surroundings as well as at clumps in the drying fi lm. We conclude that controlling both the density distribution during the drying process and the clumps in the catalyst ink is e ff ective for controlling the size and concentration of the cracks.","PeriodicalId":17878,"journal":{"name":"Kobunshi Ronbunshu","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2019-05-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"81179191","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Halogenation of Propagating Terminal in Anionic Polymerization of Isoprene for the Synthesis of Block Copolymers 异戊二烯阴离子聚合中扩展端卤化反应合成嵌段共聚物
Kobunshi Ronbunshu Pub Date : 2019-05-25 DOI: 10.1295/KORON.2019-0004
K. Satoh, Y. Mori, M. Kamigaito
{"title":"Halogenation of Propagating Terminal in Anionic Polymerization of Isoprene for the Synthesis of Block Copolymers","authors":"K. Satoh, Y. Mori, M. Kamigaito","doi":"10.1295/KORON.2019-0004","DOIUrl":"https://doi.org/10.1295/KORON.2019-0004","url":null,"abstract":"","PeriodicalId":17878,"journal":{"name":"Kobunshi Ronbunshu","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2019-05-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"89227392","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Crosslinking Reaction of Polybutadiene Using Urethane Acrylate Derived from Castor Oil 蓖麻油丙烯酸氨基甲酸酯与聚丁二烯的交联反应
Kobunshi Ronbunshu Pub Date : 2019-05-25 DOI: 10.1295/KORON.2016-0008
N. Uchida, Kousuke Shimomura, H. Kouzai
{"title":"Crosslinking Reaction of Polybutadiene Using Urethane Acrylate Derived from Castor Oil","authors":"N. Uchida, Kousuke Shimomura, H. Kouzai","doi":"10.1295/KORON.2016-0008","DOIUrl":"https://doi.org/10.1295/KORON.2016-0008","url":null,"abstract":"[Notes] A urethane acrylate derived from castor oil was synthesized using castor oil with 2 - acryloyloxyethyl isocyanate and obtained in high yield. Furthermore, the obtained urethane acrylate was subjected to a UV cure reaction with polybutadiene. The UV cured fi lm was characterized by thermal and mechanical measurements. The thermal stability of the obtained fi lm was measured by TGA, and 20% thermal weight loss temperature at 425 ° C was observed. The glass transition temperature of the product was ¹ 60 ° C as revealed by DMA. The Young ’ s modulus of the product was 2.00MPa, taken from the stress - strain curve.","PeriodicalId":17878,"journal":{"name":"Kobunshi Ronbunshu","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2019-05-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"85819571","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
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