JP2022521145A - 散在的セルロースナノ結晶の製造方法、セルロースナノ結晶及びその使用 - Google Patents
散在的セルロースナノ結晶の製造方法、セルロースナノ結晶及びその使用 Download PDFInfo
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- JP2022521145A JP2022521145A JP2021543189A JP2021543189A JP2022521145A JP 2022521145 A JP2022521145 A JP 2022521145A JP 2021543189 A JP2021543189 A JP 2021543189A JP 2021543189 A JP2021543189 A JP 2021543189A JP 2022521145 A JP2022521145 A JP 2022521145A
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- 239000001913 cellulose Substances 0.000 title claims abstract description 58
- 229920002678 cellulose Polymers 0.000 title claims abstract description 58
- 239000002159 nanocrystal Substances 0.000 title claims abstract description 45
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 8
- 125000003118 aryl group Chemical group 0.000 claims abstract description 24
- 238000000576 coating method Methods 0.000 claims abstract description 20
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims abstract description 18
- 238000000034 method Methods 0.000 claims abstract description 18
- 239000011248 coating agent Substances 0.000 claims abstract description 17
- -1 heteroaryl compound Chemical class 0.000 claims abstract description 15
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 claims abstract description 13
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 9
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 3
- 229920000767 polyaniline Polymers 0.000 claims description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 claims description 4
- 125000005442 diisocyanate group Chemical group 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 150000003512 tertiary amines Chemical class 0.000 claims description 4
- 239000000725 suspension Substances 0.000 claims description 3
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 239000003990 capacitor Substances 0.000 claims description 2
- 239000008103 glucose Substances 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 claims description 2
- 238000006116 polymerization reaction Methods 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 2
- 238000010526 radical polymerization reaction Methods 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- 239000004964 aerogel Substances 0.000 claims 1
- 239000013078 crystal Substances 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 125000004429 atom Chemical group 0.000 abstract 1
- 125000005842 heteroatom Chemical group 0.000 abstract 1
- 230000000379 polymerizing effect Effects 0.000 abstract 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 9
- 125000003277 amino group Chemical group 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- 230000002411 adverse Effects 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 229920001940 conductive polymer Polymers 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000010793 electronic waste Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000000017 hydrogel Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000012770 industrial material Substances 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L1/00—Compositions of cellulose, modified cellulose or cellulose derivatives
- C08L1/02—Cellulose; Modified cellulose
- C08L1/04—Oxycellulose; Hydrocellulose, e.g. microcrystalline cellulose
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/24—Electrically-conducting paints
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y30/00—Nanotechnology for materials or surface science, e.g. nanocomposites
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y40/00—Manufacture or treatment of nanostructures
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
- H01B1/06—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances
- H01B1/12—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances organic substances
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- Polymers & Plastics (AREA)
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- Wood Science & Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Polyurethanes Or Polyureas (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Description
Claims (12)
- 導電性被膜を有する散在的セルロースナノ結晶を製造する方法であって、前記方法が以下の工程、
- セルロースの酸化されていないグルコース単位を、イソシアネート基を有するアリール又はヘテロアリール化合物と反応させて、前記グルコース単位のC2、C3及びC6原子のうちの少なくとも1つと前記アリール又はヘテロアリール化合物との間にカルバメート結合を形成すること、
- アリール又はヘテロアリール基を含むこれらの化合物の導電性構造が形成されるように、カルバメート基を介して前記セルロースの前記グルコース単位に結合された隣接するアリール又はヘテロアリール化合物を重合すること
を含む方法。 - 前記アリール又はヘテロアリール化合物が、フェニル基、ピロリル基、ナフチル基、アントラセニル基及び/又はフェナントレニル基を有する、請求項1に記載の方法。
- 前記イソシアネート基を有するアリール又はヘテロアリール化合物が、ジイソシアネート基を有するものである、請求項1に記載の方法。
- 反応及び前記カルバメート結合の形成の後に第2のイソシアネート基を加水分解する工程を含む、請求項3に記載の方法。
- 前記重合がラジカル重合である、請求項1~4のいずれか一項に記載の方法。
- 前記導電性被膜がポリアニリンに類似の被膜である、請求項1~5のいずれか一項に記載の方法。
- 前記セルロースのC6原子で酸化されていないグルコース単位を、イソシアネート基を有するアリール又はヘテロアリール化合物と反応させて、前記グルコース単位の前記C6原子と前記アリール又はヘテロアリール化合物との間にカルバメート結合を形成する、請求項1~6のいずれか一項に記載の方法。
- 前記グルコースと前記イソシアネート基を有するアリール又はヘテロアリール化合物の反応が、第三級アミン(TEA)を有するトルエン、アセトン、ジメチルスルホキシド、テトラヒドロフラン、クロロメタン又はピリジン中で行われる、請求項1~7のいずれか一項に記載の方法。
- 導電性被膜を有する散在的セルロースナノ結晶であって、これらのセルロースナノ結晶が棒状に形成されており、50nm~500nmの長さ及び/又は3nm~20nmの幅若しくは直径を有する、散在的セルロースナノ結晶。
- 請求項1~8のいずれか一項に記載の方法で得られる散在的セルロースナノ結晶。
- これらのセルロースナノ結晶が棒状に形成されており、50nm~500nmの長さ及び/又は3nm~20nmの幅若しくは直径を有する、請求項10に記載のセルロースナノ結晶。
- 生物学的に分解可能な導電性構成部材として、エアロゲルとして、印刷された電気若しくは電子回路として、付加的に製造された3次元構造体として、センサとして、コンデンサとして、ヒューズとして、バッテリとして、導電性懸濁液として、表面被膜として、紙として、コイル及び/又はナノケーブルとしての、請求項9~11のいずれか一項に記載された、又は請求項1~7のいずれか一項に記載の方法に従って製造された、導電性被膜を有するセルロースナノ結晶の使用。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102019103717.4A DE102019103717A1 (de) | 2019-02-14 | 2019-02-14 | Verfahren zur Herstellung vereinzelter Cellulose-Nanokristalle sowie Cellulose-Nanokristalle und deren Verwendung |
DE102019103717.4 | 2019-02-14 | ||
PCT/EP2020/051880 WO2020164893A1 (de) | 2019-02-14 | 2020-01-27 | Verfahren zur herstellung vereinzelter cellulose-nanokristalle sowie cellulose-nanokristalle und deren verwendung |
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JP2022521145A true JP2022521145A (ja) | 2022-04-06 |
JP7518840B2 JP7518840B2 (ja) | 2024-07-18 |
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JP2021543189A Active JP7518840B2 (ja) | 2019-02-14 | 2020-01-27 | 散在的セルロースナノ結晶の製造方法、セルロースナノ結晶及びその使用 |
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US (1) | US20220135775A1 (ja) |
EP (1) | EP3924416B1 (ja) |
JP (1) | JP7518840B2 (ja) |
CA (1) | CA3126442A1 (ja) |
DE (1) | DE102019103717A1 (ja) |
FI (1) | FI3924416T3 (ja) |
WO (1) | WO2020164893A1 (ja) |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20070143932A1 (en) * | 2003-12-23 | 2007-06-28 | Johanna Buchert | Process for producing a fibre compositions |
US20160148715A1 (en) * | 2013-06-18 | 2016-05-26 | Celluforce Inc. | Conductive cellulose nanocrystals, method of producing same and uses thereof |
JP2018055866A (ja) * | 2016-09-27 | 2018-04-05 | 東レ株式会社 | 導電性ファイバー、導電性組成物、導電性材料ならびに導電性ファイバーおよび導電性材料の製造方法 |
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GB0916031D0 (en) | 2009-09-14 | 2009-10-28 | Univ Nottingham | Cellulose nanoparticle aerogels,hydrogels and organogels |
CA2796988A1 (en) * | 2010-05-12 | 2011-11-17 | The Governing Council Of The University Of Toronto | Method of producing electrically conductive polymer and cellulose nanocomposites |
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2019
- 2019-02-14 DE DE102019103717.4A patent/DE102019103717A1/de active Pending
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2020
- 2020-01-27 EP EP20702438.1A patent/EP3924416B1/de active Active
- 2020-01-27 JP JP2021543189A patent/JP7518840B2/ja active Active
- 2020-01-27 CA CA3126442A patent/CA3126442A1/en active Pending
- 2020-01-27 FI FIEP20702438.1T patent/FI3924416T3/fi active
- 2020-01-27 US US17/430,513 patent/US20220135775A1/en active Pending
- 2020-01-27 WO PCT/EP2020/051880 patent/WO2020164893A1/de unknown
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20070143932A1 (en) * | 2003-12-23 | 2007-06-28 | Johanna Buchert | Process for producing a fibre compositions |
US20160148715A1 (en) * | 2013-06-18 | 2016-05-26 | Celluforce Inc. | Conductive cellulose nanocrystals, method of producing same and uses thereof |
JP2018055866A (ja) * | 2016-09-27 | 2018-04-05 | 東レ株式会社 | 導電性ファイバー、導電性組成物、導電性材料ならびに導電性ファイバーおよび導電性材料の製造方法 |
Non-Patent Citations (3)
Title |
---|
"ポリアニリン", ウィキペディア, JPN6023050336, 8 November 2023 (2023-11-08), ISSN: 0005216994 * |
佐藤俊彦,ほか3名: "イソシアナート基を有する反応性セルロースの合成とアミノ酸との反応", 高分子論文集, vol. 39, no. 11, JPN6023050337, 1982, pages 699 - 704, ISSN: 0005216995 * |
倉本憲幸: "導電性高分子ポリアニリンの基礎と応用", 色材, vol. 76, no. 9, JPN6023050335, 2003, pages 352 - 359, ISSN: 0005216993 * |
Also Published As
Publication number | Publication date |
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WO2020164893A1 (de) | 2020-08-20 |
US20220135775A1 (en) | 2022-05-05 |
DE102019103717A1 (de) | 2020-08-20 |
FI3924416T3 (fi) | 2023-03-08 |
EP3924416B1 (de) | 2023-01-04 |
EP3924416A1 (de) | 2021-12-22 |
JP7518840B2 (ja) | 2024-07-18 |
CA3126442A1 (en) | 2020-08-20 |
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