JP2020534398A - フッ素化コポリマー並びにこれを含む組成物及び物品 - Google Patents
フッ素化コポリマー並びにこれを含む組成物及び物品 Download PDFInfo
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- JP2020534398A JP2020534398A JP2020515123A JP2020515123A JP2020534398A JP 2020534398 A JP2020534398 A JP 2020534398A JP 2020515123 A JP2020515123 A JP 2020515123A JP 2020515123 A JP2020515123 A JP 2020515123A JP 2020534398 A JP2020534398 A JP 2020534398A
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- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical class [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- CSJWOWRPMBXQLD-UHFFFAOYSA-N perfluoromethylvinylether group Chemical class FC(=C(C(F)(F)F)F)OC(=C(F)C(F)(F)F)F CSJWOWRPMBXQLD-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- 235000020030 perry Nutrition 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229940085991 phosphate ion Drugs 0.000 description 1
- 238000002047 photoemission electron microscopy Methods 0.000 description 1
- 229920001483 poly(ethyl methacrylate) polymer Polymers 0.000 description 1
- 229920003223 poly(pyromellitimide-1,4-diphenyl ether) Polymers 0.000 description 1
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- 125000003367 polycyclic group Chemical group 0.000 description 1
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- 229920005596 polymer binder Polymers 0.000 description 1
- 239000002491 polymer binding agent Substances 0.000 description 1
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000011698 potassium fluoride Substances 0.000 description 1
- 235000003270 potassium fluoride Nutrition 0.000 description 1
- BHZRJJOHZFYXTO-UHFFFAOYSA-L potassium sulfite Chemical compound [K+].[K+].[O-]S([O-])=O BHZRJJOHZFYXTO-UHFFFAOYSA-L 0.000 description 1
- 235000019252 potassium sulphite Nutrition 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000013074 reference sample Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- XWGJFPHUCFXLBL-UHFFFAOYSA-M rongalite Chemical compound [Na+].OCS([O-])=O XWGJFPHUCFXLBL-UHFFFAOYSA-M 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical class [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 150000003377 silicon compounds Chemical class 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 239000007784 solid electrolyte Substances 0.000 description 1
- 239000006104 solid solution Substances 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- RCYJPSGNXVLIBO-UHFFFAOYSA-N sulfanylidenetitanium Chemical compound [S].[Ti] RCYJPSGNXVLIBO-UHFFFAOYSA-N 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 150000008053 sultones Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 230000010512 thermal transition Effects 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 229910021642 ultra pure water Inorganic materials 0.000 description 1
- 239000012498 ultrapure water Substances 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 238000004804 winding Methods 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
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Abstract
Description
本出願は、2018年9月13日に出願された米国特許仮出願第62/730,648号、並びに2017年9月14日に出願された同第62/558,655号及び同第62/558,671号の優先権を主張し、これらの開示は、参照によりその全体が本明細書に組み込まれる。
「1つの(a)」、「1つの(an)」及び「その(the)」などの用語は、単数の実体のみを指すことを意図するものではなく、具体例を例示するために用いることができる一般的な種類を含む。「1つの(a)」、「1つの(an)」及び「その(the)」などの用語は、「少なくとも1つの」という用語と互換可能に使用される。
第1の実施形態では、本開示は、
式−[CF2−CF2]−で表される二価の単位と、
独立して式
Zが水素である場合、コポリマーは最高100℃又は100℃未満のα転移温度を有し、コポリマーは300〜1400の範囲の−SO3Z当量重量を有し、−SO3Zが−SO2Fで置き換えられているコポリマーの変形体は、10分当たり最大80グラムの、265℃の温度及び5kgの支持重量で測定されるメルトフローインデックスを有する、コポリマーを提供する。
式−[CF2−CF2]−で表される二価の単位と、
独立して式
コポリマーは、300〜1400の範囲の−SO2F当量重量、並びに10分当たり最大80グラムの、265℃の温度及び5kgの支持重量で測定されるメルトフローインデックスを有し、−SO2Fが−SO3Hで置き換えられるようにコポリマーを加水分解した場合、コポリマーは最高100℃のα転移温度を有する。
25ppm未満の金属イオンを含む、かつ/又は
−SO2X末端基を含む、第34〜第47の実施形態のいずれか1つに記載のコポリマーを提供する。
固形分含有量は、分散体の試料を加熱した天秤に置き、溶媒の蒸発の前後で質量を記録することによって、重量測定により決定した。固形分含有量は、試料の初期質量と継続的な加熱によって質量が更に減少しなかった時点の試料の質量の比であった。
TFEと、スルホニルフルオリドモノマー(M2)と、ビニルエーテル又はアリルエーテルモノマー(M3)とのコポリマーのEWは、以下の式によって計算することができる。
19F−NMRスペクトルを使用して、精製したポリマーの組成を決定した。5mm広帯域プローブを有する、Bruker,Billerica,MA,USAから、商品名AVANCE II 300で入手可能なNMR分光計を使用した。約13重量%のポリマー分散体の試料を、60℃において測定した。
フーリエ変換赤外分光法(Fourier transform infrared spectroscopy、FT−IR)測定を使用して、コポリマー中のC原子106個当たりのカルボキシル末端基の数を決定することができる。測定は、FT−IRによって、透過法で実行した。測定した試料は、100μmのフィルム厚さを有する。対象のCOOHピークの波数は、1776cm−1及び1807cm−1である。C(O)Fピークの波数は、1885cm−1である。(C(O)Fはカルボキシル基に変換されることになる。)ポリマーのカルボキシル(C(O)F)末端基の量を定量するために、2つのIRスペクトルを取得した。1つはカルボキシル含有試料から取得し、1つは基準試料(カルボキシル基を有しない)から取得した。
(ピーク高さ×F1)/フィルム厚さ[mm] (1)
(ピーク高さ×F2)/フィルム厚さ[mm] (2)
(ピーク高さ×F3)/フィルム厚さ[mm] (3)
ここで、
F1:基準スペクトルに関して計算された因子であり、υ=1776cm−1
F2:基準スペクトルに関して計算された因子であり、υ=1807cm−1
F3:基準スペクトルに関して計算された因子であり、υ=1885cm−1
等式1〜3による結果の合計から、炭素原子106個当たりのカルボキシル末端基の数が得られる。
粒子サイズの決定は、ISO 13321(1996)に準拠した動的光散乱法によって実行した。分析については、532nmで動作する50mWレーザーを装備した、Malvern Instruments Ltd,Malvern,Worcestershire,UKから入手可能な、Zeta Sizer Nano ZSを使用した。1mLの体積の試料を載置するために、円形開口部及びキャップを有する、12mm平方のガラス製キュベット(PCS 8501、Malvern Instruments Ltdから入手可能)を使用した。界面活性剤の光散乱は、より大きい粒子、例えばダスト粒子の存在に対して極端に感受性が強いため、測定の前にキュベットを十分に洗浄することで、汚染物質の存在を最小化した。キュベットは、キュベット洗浄デバイス内で8時間、蒸留したばかりのアセトンを用いて洗浄した。また、実験室遠心分離機において14,500G(142,196N/kg)で10分間、測定前に界面活性剤溶液を遠心分離することによって、試料に対してダスト統制(dust discipline)を適用した。25℃において、173°後方散乱モードで測定デバイスを動作させた。研究ツール(この研究ツールは、供給業者が提供した標準的計器のソフトウェアアップグレードである)によって、t<1−6秒の低い相関時間が可能となった。試料体積の完全な散乱能力を利用するために、全ての場合において次の設定を適用した;「減衰器」、11;「測定位置」、4.65mm(セルの中心)。これらの条件の下で、純水(標準)のベースライン散乱は約250kcpsである。10回のサブランからなる各測定を、5回繰り返した。粒子サイズは、D50値として表される。
5.0kgの支持重量及び265℃の温度において、DIN EN ISO1133−1に記載される手順と同様の手順に従って、Goettfert MPD、MI−Robo、MI4メルトインデクサ(Buchen,Germany)を用いて、g/10分で報告するメルトフローインデックス(MFI)を測定した。直径2.1mm及び長さ8.0mmの標準化された押出成形ダイによって、MFIを得た。
TA Instruments AR2000 EXレオメータを使用して、ポリマー試料のT(α)を測定した。−100℃から約125℃まで2℃/分の温度傾斜で、試料を加熱した。測定は、1ヘルツの周波数で行った。
TA Instruments Q2000 DSCを使用して、ポリマー試料のガラス転移温度(Tg)を測定した。−50℃から約200℃まで10℃/分の温度傾斜で、試料を加熱した。転移温度は、第2の加熱に関して分析した。
タイムラグ法を使用して、各膜について、温度の関数として酸素透過性を決定した。1cm2の作用面積を有する膜を、透過セルに配置した。続いて、セルの両方のチャンバを6時間排気した。試験について、時間ゼロは、課題のガス(酸素)による、上部チャンバの760cmHgへの加圧と一致した。排気した下部チャンバ内の圧力の変動を、時間の関数として、10−3cmHgの感度を有する圧力センサ(Baratron(登録商標),MKS,MA,USA)を使用して測定した。
テトラフルオロエチレン(TFE)、F2C=CF−O−CF2CF2CF2CF2SO2F(MV4S)、及びCF2=CF−O−(CF2)3−OCF3(MV31)のポリマーを調製した。
テトラフルオロエチレン(TFE)、F2C=CF−O−CF2CF2CF2CF2SO2F(MV4S)、及びCF2=CF−O−(CF2)3−OCF3(MV31)のポリマーを調製した。
テトラフルオロエチレン(TFE)、F2C=CF−O−CF2CF2CF2CF2SO2F(MV4S)、及びCF2=CF−O−(CF2)2−CF3(PPVE−1)のポリマーを調製した。
テトラフルオロエチレン(TFE)、及びF2C=CF−O−CF2CF2CF2CF2SO2F(MV4S)のポリマーを調製した。
Claims (15)
- 式−[CF2−CF2]−で表される二価の単位と、
独立して式
独立して式
Zが水素である場合、前記コポリマーは最高100℃のα転移温度を有し、前記コポリマーは300〜1400の範囲の−SO3Z当量重量を有し、−SO3Zが−SO2Fで置き換えられている前記コポリマーの変形体は、10分当たり最大80グラムの、265℃の温度及び5kgの支持重量で測定されるメルトフローインデックスを有する、コポリマー。 - bが2又は3であり、cが0又は1であり、eが4である、請求項1に記載のコポリマー。
- zが1又は2であり、nが1、2又は3である、請求項1又は2に記載のコポリマー。
- a及びcが0である場合、eが3〜8である、請求項1〜3のいずれか一項に記載のコポリマー。
- −SO3Zが−SO2Fで置き換えられている前記コポリマーの前記変形体が、最高20℃のガラス転移温度を有する、請求項1〜4のいずれか一項に記載のコポリマー。
- 前記コポリマーが、クロロトリフルオロエチレンに由来する二価の単位、又はヘキサフルオロプロピレンに由来する二価の単位のうちの少なくとも1つを更に含む、請求項1〜5のいずれか一項に記載のコポリマー。
- Zが水素である場合、前記コポリマーが少なくとも60℃のT(α)を有する、請求項1〜6のいずれか一項に記載のコポリマー。
- Zが水素である場合、前記コポリマーが少なくとも95℃のT(α)を有する、請求項1〜7のいずれか一項に記載のコポリマー。
- 前記コポリマーが300〜1200の範囲の−SO3Z当量重量を有する、請求項1〜8のいずれか一項に記載のコポリマー。
- −SO3Zが−SO2Fで置き換えられている前記コポリマーの変形体が、10分当たり最大40グラムの、265℃の温度及び5kgの支持重量で測定されるメルトフローインデックスを有する、請求項1〜9のいずれか一項に記載のコポリマー。
- 請求項1〜12のいずれか一項に記載のコポリマーを含む、触媒インク。
- 請求項1〜12のいずれか一項に記載のコポリマーから調製される、ポリマー電解質膜。
- 請求項13に記載の触媒インク、又は請求項14に記載のポリマー電解質膜のうちの少なくとも1つを含む、膜電極接合体。
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EP3681948A1 (en) | 2020-07-22 |
CN111133015B (zh) | 2022-09-06 |
JP2020534400A (ja) | 2020-11-26 |
EP3681949A1 (en) | 2020-07-22 |
CN111094439B (zh) | 2022-11-08 |
CN111094438B (zh) | 2022-11-08 |
US20200277420A1 (en) | 2020-09-03 |
KR20200054213A (ko) | 2020-05-19 |
WO2019055791A1 (en) | 2019-03-21 |
US20200303755A1 (en) | 2020-09-24 |
JP2020534402A (ja) | 2020-11-26 |
US20200199259A1 (en) | 2020-06-25 |
KR102601806B1 (ko) | 2023-11-14 |
CN111094438A (zh) | 2020-05-01 |
WO2019055793A1 (en) | 2019-03-21 |
CN111094439A (zh) | 2020-05-01 |
US11492431B2 (en) | 2022-11-08 |
KR20200052896A (ko) | 2020-05-15 |
US11377510B2 (en) | 2022-07-05 |
KR20200052897A (ko) | 2020-05-15 |
CN111133015A (zh) | 2020-05-08 |
EP3681948A4 (en) | 2021-07-14 |
EP3681949A4 (en) | 2021-07-14 |
WO2019055799A1 (en) | 2019-03-21 |
EP3681917A1 (en) | 2020-07-22 |
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