JP2016079044A - 層状物質含有液及びその製造方法 - Google Patents
層状物質含有液及びその製造方法 Download PDFInfo
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- JP2016079044A JP2016079044A JP2014208570A JP2014208570A JP2016079044A JP 2016079044 A JP2016079044 A JP 2016079044A JP 2014208570 A JP2014208570 A JP 2014208570A JP 2014208570 A JP2014208570 A JP 2014208570A JP 2016079044 A JP2016079044 A JP 2016079044A
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- 150000004679 hydroxides Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052622 kaolinite Inorganic materials 0.000 description 1
- 229910001416 lithium ion Inorganic materials 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229910001425 magnesium ion Inorganic materials 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- QPJSUIGXIBEQAC-UHFFFAOYSA-N n-(2,4-dichloro-5-propan-2-yloxyphenyl)acetamide Chemical compound CC(C)OC1=CC(NC(C)=O)=C(Cl)C=C1Cl QPJSUIGXIBEQAC-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910052758 niobium Inorganic materials 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- UHGIMQLJWRAPLT-UHFFFAOYSA-N octadecyl dihydrogen phosphate Chemical compound CCCCCCCCCCCCCCCCCCOP(O)(O)=O UHGIMQLJWRAPLT-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- SOQBVABWOPYFQZ-UHFFFAOYSA-N oxygen(2-);titanium(4+) Chemical class [O-2].[O-2].[Ti+4] SOQBVABWOPYFQZ-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N p-toluenesulfonic acid Substances CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 125000005489 p-toluenesulfonic acid group Chemical group 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Chemical compound [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- CMPQUABWPXYYSH-UHFFFAOYSA-N phenyl phosphate Chemical compound OP(O)(=O)OC1=CC=CC=C1 CMPQUABWPXYYSH-UHFFFAOYSA-N 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 229910000275 saponite Inorganic materials 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- SZWHXXNVLACKBV-UHFFFAOYSA-N tetraethylphosphanium Chemical compound CC[P+](CC)(CC)CC SZWHXXNVLACKBV-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- BXYHVFRRNNWPMB-UHFFFAOYSA-N tetramethylphosphanium Chemical compound C[P+](C)(C)C BXYHVFRRNNWPMB-UHFFFAOYSA-N 0.000 description 1
- USFPINLPPFWTJW-UHFFFAOYSA-N tetraphenylphosphonium Chemical compound C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 USFPINLPPFWTJW-UHFFFAOYSA-N 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
- JFZKOODUSFUFIZ-UHFFFAOYSA-N trifluoro phosphate Chemical compound FOP(=O)(OF)OF JFZKOODUSFUFIZ-UHFFFAOYSA-N 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- ZFEAYIKULRXTAR-UHFFFAOYSA-M triphenylsulfanium;chloride Chemical compound [Cl-].C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 ZFEAYIKULRXTAR-UHFFFAOYSA-M 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
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Abstract
Description
1.層状物質含有液
1−1.イオン液体
1−1−1.カチオン
1−1−2.アニオン
1−2.層状物質
1−3.他の材料
2.層状物質含有液の製造方法
2−1.層状物質含有液の調整
2−2.層状物質含有液の精製
3.作用及び効果
まず、層状物質含有液の構成に関して説明する。
イオン液体は、液体の塩であり、カチオン及びアニオンを含んでいる。
カチオンは、任意の陽イオンのうちのいずれか1種類又は2種類以上を含んでいる。この陽イオンの種類及び価数は、特に限定されない。後述するように、アニオンが非E−F結合含有イオンを含んでいれば、カチオンの種類に依存せずに、安全性等に関する利点が得られるからである。
アニオンは、任意の陰イオンのうちのいずれか1種類又は2種類以上を含んでいる。この陰イオンの価数は、特に限定されない。
層状物質は、上記したように、層状の薄い物質であり、いわゆるナノシートである。
尚、層状物質含有液は、上記したイオン液体及び層状物質と一緒に、他の材料のうちのいずれか1種類又は2種類以上を含有していてもよい。
次に、上記した層状物質含有液の製造方法に関して説明する。尚、以下では、複数の層状物質の積層物を「層状積層物」という。
層状物質含有液を調製する場合には、最初に、例えば、任意の合成手順により、非E−F結合含有イオンのうちのいずれか1種類又は2種類以上をアニオンとして含むイオン液体を準備する。尚、カチオンの種類は、任意でよい。
層状物質含有液を調整した後、必要に応じて、その層状物質含有液を精製してもよい。
上記した層状物質含有液及びその製造方法によれば、アニオンとして非E−F結合含有イオンを含むイオン液体に層状積層物を含有させて、その層状積層物を含有するイオン液体に音波等を照射している。
1.イオン液体の合成
2.層状物質含有液の製造
3.層状物質含有液の評価
3−1.層数分布
3−2.安全性
以下の手順により、イオン液体として化合物1〜3を合成した。
以下の手順により、層状物質含有液を製造した。
最初に、層状積層物(グラファイト)100mgと、表1に示したイオン液体1ml(=1cm3 )とを混合した。
実験例4:BMIm・BF4 (1-buthyl-3-methylimidazolium tetrafluoroborate)
実験例5:BMIm・TFSI(1-butyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide )
実験例6:BMIm・AcO(1-buthyl-3-methylimidazolium acetate)
実験例7:BMIm・CH3 SO3 (1-buthyl-3-methylimidazolium mesylate )
実験例8:BMIm・I(1-butyl-3-methylimidazolium iodide)
実験例9:Bpy・TFSI(1-butylpyridinium bis(trifluoromethylsulfonyl)imide )
実験例10:Ph3 T・TFSI(Trihexyltetradecylphosphonium bis(trifluoromethylsulfonyl)amide )
実験例11:BMIm・PF6 (1-buthyl-3-methylimidazolium hexafluorophosphate)
実験例12:BMIm・FAP(1-buthyl-3-methylimidazolium tris(pentafluoroethyl)trifluorophosphate )
以下の手順により、層状物質含有液を評価した。
Nature Materials(”Wetting transparency of graphene”,Javad Rafiee 等,vol.11 ,217 頁〜222 頁,2012年)に記載されている方法を用いて、層状物質含有液中に分散されている層状物質(グラフェン)の層数分布を調べたところ、図1に示した結果が得られた。この場合には、層状物質含有液のラマンスペクトル(横軸:波数(cm-1),縦軸:スペクトル強度)を測定した。このラマンスペクトルに基づいて、波数=約2600cm-1〜約2800cm-1の範囲内に検出される2Dバンドのラマンピークを判定して、層状物質の層数分布を調べた。
遠心分離機(株式会社久保田製作所製マイクロ冷却遠心機3740)を用いて層状物質含有液を遠心分離(遠心力=20000G)して、その層状物質含有液中に残存している層状積層物を沈降させた。続いて、遠心分離後の層状物質含有液の液相(上澄み液)をPTFEタイプメンブレンフィルタ(ADVANTEC製T010A025A )に通して、濾液を得た。最後に、NMR(19F−NMR)法を用いて濾液0.05ml(=0.05cm3 )を分析して、その濾液中におけるフッ化水素酸の濃度(重量%)を求めたところ、表1に示した結果が得られた。
Claims (9)
- 長周期型周期表の15族元素(E)とフッ素(F)との結合を有していない第1アニオン、を含むイオン液体と、
層状物質と
を含有する、層状物質含有液。 - 前記15族元素は、リン(P)及びヒ素(As)を含む、
請求項1記載の層状物質含有液。 - 前記第1アニオンは、フッ素を構成元素として含んでいない、
請求項1又は請求項2に記載の層状物質含有液。 - 前記イオン液体は、前記15族元素とフッ素との結合を有している第2アニオン、を含み、
前記イオン液体中における前記第1アニオンの含有量Cは、50mol%<C<100mol%を満たす、
請求項1ないし請求項3のいずれか1項に記載の層状物質含有液。 - 長周期型周期表の15族元素(E)とフッ素(F)との結合を有していない第1アニオン、を含むイオン液体に、層状物質の積層物を含有させて、
その層状物質の積層物を含有する前記イオン液体に、音波及び電波のうちの少なくとも一方を照射する、
層状物質含有液の製造方法。 - 前記イオン液体は、前記15族元素とフッ素との結合を有している第2アニオン、を含み、
前記イオン液体中における前記第1アニオンの含有量Cは、50mol%<C<100mol%を満たす、
請求項5記載の層状物質含有液の製造方法。 - 前記音波として超音波を用いると共に、前記電波としてマイクロ波を用いる、
請求項5又は請求項6に記載の層状物質含有液の製造方法。 - 前記音波及び電波のうちの少なくとも一方が照射された前記イオン液体を遠心分離する、
請求項5ないし請求項7のいずれか1項に記載の層状物質含有液の製造方法。 - 前記遠心分離された前記イオン液体から液相を回収する、
請求項8記載の層状物質含有液の製造方法。
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Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2008291231A (ja) * | 2007-04-23 | 2008-12-04 | Nippon Synthetic Chem Ind Co Ltd:The | イオン液体組成物およびそれを用いてなる合成潤滑油 |
WO2010065346A1 (en) * | 2008-11-25 | 2010-06-10 | The University Of Alabama | Exfoliation of graphite using ionic liquids |
JP2013514963A (ja) * | 2009-12-22 | 2013-05-02 | スー・クワンスック | グラフェン分散液およびグラフェン−イオン性液体高分子複合物 |
WO2013132261A1 (en) * | 2012-03-09 | 2013-09-12 | The University Of Manchester | Production of graphene |
WO2013172350A1 (ja) * | 2012-05-14 | 2013-11-21 | 国立大学法人 東京大学 | 新規グラフェンナノ分散液及びその調製方法 |
CN103681000A (zh) * | 2012-09-25 | 2014-03-26 | 海洋王照明科技股份有限公司 | 一种石墨烯纸的制备方法 |
CN104008894A (zh) * | 2013-02-21 | 2014-08-27 | 海洋王照明科技股份有限公司 | 掺氮石墨烯材料及其制备方法、掺氮石墨烯电极和电化学电容器 |
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Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2008291231A (ja) * | 2007-04-23 | 2008-12-04 | Nippon Synthetic Chem Ind Co Ltd:The | イオン液体組成物およびそれを用いてなる合成潤滑油 |
WO2010065346A1 (en) * | 2008-11-25 | 2010-06-10 | The University Of Alabama | Exfoliation of graphite using ionic liquids |
JP2013514963A (ja) * | 2009-12-22 | 2013-05-02 | スー・クワンスック | グラフェン分散液およびグラフェン−イオン性液体高分子複合物 |
WO2013132261A1 (en) * | 2012-03-09 | 2013-09-12 | The University Of Manchester | Production of graphene |
WO2013172350A1 (ja) * | 2012-05-14 | 2013-11-21 | 国立大学法人 東京大学 | 新規グラフェンナノ分散液及びその調製方法 |
CN103681000A (zh) * | 2012-09-25 | 2014-03-26 | 海洋王照明科技股份有限公司 | 一种石墨烯纸的制备方法 |
CN104008894A (zh) * | 2013-02-21 | 2014-08-27 | 海洋王照明科技股份有限公司 | 掺氮石墨烯材料及其制备方法、掺氮石墨烯电极和电化学电容器 |
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