JP6447942B2 - 重合体およびこれを含む高分子電解質膜 - Google Patents
重合体およびこれを含む高分子電解質膜 Download PDFInfo
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- JP6447942B2 JP6447942B2 JP2017526701A JP2017526701A JP6447942B2 JP 6447942 B2 JP6447942 B2 JP 6447942B2 JP 2017526701 A JP2017526701 A JP 2017526701A JP 2017526701 A JP2017526701 A JP 2017526701A JP 6447942 B2 JP6447942 B2 JP 6447942B2
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- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 1
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- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
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Description
下記化学式2で表される化合物由来のブランチャー、または下記化学式3で表されるブランチャーを含むランダム重合体を提供する。
[化学式1]
Aは、−SO3H、−SO3 −M+、−COOH、−COO−M+、−PO3H2、−PO3H−M+、−PO3 2−2M+、−O(CF2)mSO3H、−O(CF2)mSO3 −M+、−O(CF2)mCOOH、−O(CF2)mCOO−M+、−O(CF2)mPO3H2、−O(CF2)mPO3H−M+、または−O(CF2)mPO3 2−2M+であり、
mは、2〜6の整数であり、
Mは、1族元素であり、
R1およびR2は、互いに同一または異なり、それぞれ独立に、ハロゲン基であり、
nは、2〜10の整数であり、2〜10個の括弧内の構造は、互いに同一または異なり、
Xは、S;O;CO;SO;SO2;NR;炭化水素系またはフッ素系結合体であり、
lは、0〜10の整数であり、
lが2以上の場合、2以上のXは、互いに同一または異なり、
Y1およびY2は、互いに同一または異なり、それぞれ独立に、NRR;ヒドロキシ基およびハロゲン基からなる群より選択される置換基で1または2以上置換された芳香族環;またはヒドロキシ基およびハロゲン基からなる群より選択される置換基で1または2以上置換された脂肪族環であり、
Rは、ハロゲン基で置換された芳香族環;またはハロゲン基で置換された脂肪族環であり、
Zは、3価の有機基である。
[化学式1−1]
[化学式3−1]
L1〜L7は、互いに同一または異なり、それぞれ独立に、直接結合;−S−;−O−;−CO−;または−SO2−であり、
R10〜R20は、互いに同一または異なり、それぞれ独立に、水素;重水素;ハロゲン基;シアノ基;ニトリル基;ニトロ基;ヒドロキシ基;置換もしくは非置換のアルキル基;置換もしくは非置換のシクロアルキル基;置換もしくは非置換のアルコキシ基;置換もしくは非置換のアルケニル基;置換もしくは非置換のアリール基;または置換もしくは非置換のヘテロアリール基であり、
a、b、c、f、h、iおよびjは、それぞれ1〜4の整数であり、
d、eおよびgは、それぞれ1〜3の整数であり、
kは、1〜6の整数であり、
a、b、c、d、e、f、g、h、i、jおよびkがそれぞれ2以上の整数の場合、2以上の括弧内の構造は、互いに同一または異なる。
前記実施例1において、本願明細書の化学式1で表される単位の代わりに2,5−ジヒドロキシベンゼンスルホン酸(2,5−dihydroxybenzenesulfonic acid)を使用し、[1,1'−ビフェニル]−4,4'−ジオール([1,1'−biphenyl]−4,4'−diol)の代わりに4,4'−(9H−フルオレン−9,9−ジイルl)ジフェノール(4,4'−(9H−fluorene−9,9−diyl)diphenol)を使用したことを除き、炭化水素系高分子を重合した。
実施例1と同様の方法により、ベンゼン環とフッ素系スルホン酸のリンカー(linker)がSO2のモノマーを用いて重合体を製造しようと試みたが、同じ条件で高分子量の重合体を得るのに失敗した。重合体の分子量をGPCにより分子量測定して、下記表1に示した。
実施例1と同様の方法により、本願明細書の化学式1の単位である2,4−ジフルオロ(2,4−difluoro)部分フッ素系モノマーの代わりに2,5−ジフルオロ(2,5−difluoro)部分フッ素系モノマーを用いて重合体を製造しようと試みたが、同じ条件で高分子量の重合体を得るのに失敗した。重合体の分子量をゲル透過クロマトグラフィー(GPC:Gel Permeation Chromatography)により分子量測定して、下記表1に示した。
200a:アノード
200b:カソード
10、20:タンク
11、21:ポンプ
31:電解質膜
32:正極セル
33:負極セル
41:正極電解液
42:負極電解液
60:スタック
70:酸化剤供給部
80:燃料供給部
81:燃料タンク
82:ポンプ
Claims (16)
- 下記の化学式1で表される単位;および
下記の化学式1以外の化学式で表される化合物由来の単位;および
ブランチャーとして機能する下記の化学式3で表されるブランチャー単位を含む
ランダム重合体:
[化学式1]
Aは、−SO3H、−SO3 −M+、−COOH、−COO−M+、−PO3H2、−PO3H−M+、−PO3 2−2M+、−O(CF2)mSO3H、−O(CF2)mSO3 −M+、−O(CF2)mCOOH、−O(CF2)mCOO−M+、−O(CF2)mPO3H2、−O(CF2)mPO3H−M+、または−O(CF2)mPO3 2−2M+であり、
mは、2から6の整数であり、
Mは、1族元素であり、
R1およびR2は、互いに同一または異なり、それぞれ独立に、ハロゲン基であり、
nは、2から10の整数であり、2から10個の括弧内の構造は、互いに同一または異なり、
Xは、S;O;CO;SO;SO2;NR;炭化水素系またはフッ素系結合体であり、
lは、0から10の整数であり、
lが2以上の場合、2以上のXは、互いに同一または異なり、
Y1およびY2は、互いに同一または異なり、それぞれ独立に、NRR;ヒドロキシ基およびハロゲン基からなる群より選択される置換基で1または2以上置換された芳香族環;またはヒドロキシ基およびハロゲン基からなる群より選択される置換基で1または2以上置換された脂肪族環であり、
Rは、ハロゲン基で置換された芳香族環;またはハロゲン基で置換された脂肪族環であり、
Zは、3価の有機基である。 - Aは、−SO3Hまたは−SO3 −M+である、
請求項1に記載のランダム重合体。 - nは、2から6の整数である、
請求項1または2に記載のランダム重合体。 - 前記化学式1で表される単位は、下記の化学式1−1から1−9のうちのいずれか1つで表されるものである、
請求項1に記載のランダム重合体:
[化学式1−1]
- ブランチャーとして機能する前記化学式3で表されるブランチャー単位は、下記の構造のうちのいずれか1つである、
請求項1から4のいずれか1項に記載のランダム重合体:
- 前記ランダム重合体の重量平均分子量は、500g/molから5,000,000g/molである、
請求項1から5のいずれか1項に記載のランダム重合体。 - 請求項1から6のいずれか1項に記載のランダム重合体を含む
高分子電解質膜。 - 基材と、
請求項1から6のいずれか1項に記載のランダム重合体と
を含む
強化膜。 - 前記高分子電解質膜のイオン伝導度は、0.01S/cmから0.5S/cmである、
請求項7に記載の高分子電解質膜。 - 前記高分子電解質膜のイオン交換容量(IEC)値は、0.01mmol/gから5mmol/gである、
請求項7または9に記載の高分子電解質膜。 - アノードと、
カソードと、
前記アノードと前記カソードとの間に備えられた、請求項7、9または10のいずれか1項に記載の高分子電解質膜と
を含む
膜−電極接合体。 - 2以上の、請求項11に記載の膜−電極接合体と、
前記膜−電極接合体の間に備えられるバイポーラプレートを含むスタックと、
前記スタックに燃料を供給する燃料供給部と、
前記スタックに酸化剤を供給する酸化剤供給部と
を含む
高分子電解質型燃料電池。 - 正極および正極電解液を含む正極セルと、
負極および負極電解液を含む負極セルと、
前記正極セルと前記負極セルとの間に備えられる、請求項7、9または10のいずれか1項に記載の高分子電解質膜と
を含む
レドックスフロー電池。 - アノードと、
カソードと、
前記アノードと前記カソードとの間に備えられた、請求項8に記載の強化膜と
を含む
膜−電極接合体。 - 2以上の、請求項11または14に記載の膜−電極接合体と、
前記膜−電極接合体の間に備えられるバイポーラプレートを含むスタックと、
前記スタックに燃料を供給する燃料供給部と、
前記スタックに酸化剤を供給する酸化剤供給部と
を含む高分子電解質型燃料電池。 - 正極および正極電解液を含む正極セルと、
負極および負極電解液を含む負極セルと、
前記正極セルと前記負極セルとの間に備えられる、請求項8に記載の強化膜と
を含む
レドックスフロー電池。
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