JP2018080318A - ブロック共重合体、イオン交換膜、及びその製造方法 - Google Patents
ブロック共重合体、イオン交換膜、及びその製造方法 Download PDFInfo
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- JP2018080318A JP2018080318A JP2017083107A JP2017083107A JP2018080318A JP 2018080318 A JP2018080318 A JP 2018080318A JP 2017083107 A JP2017083107 A JP 2017083107A JP 2017083107 A JP2017083107 A JP 2017083107A JP 2018080318 A JP2018080318 A JP 2018080318A
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Classifications
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- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
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- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08G65/4012—Other compound (II) containing a ketone group, e.g. X-Ar-C(=O)-Ar-X for polyetherketones
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G75/0204—Polyarylenethioethers
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- H—ELECTRICITY
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- H01M8/10—Fuel cells with solid electrolytes
- H01M8/1004—Fuel cells with solid electrolytes characterised by membrane-electrode assemblies [MEA]
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- H—ELECTRICITY
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- H01M8/1025—Polymeric electrolyte materials characterised by the chemical structure of the main chain of the ion-conducting polymer having only carbon and oxygen, e.g. polyethers, sulfonated polyetheretherketones [S-PEEK], sulfonated polysaccharides, sulfonated celluloses or sulfonated polyesters
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Abstract
Description
であり、(ここで、nは1ないし2であり、RaないしRdのうち少なくとも1つは高分子主鎖に連結され、残りは同一であるか又は異なり、水素、ベンゼン又はアルキルである)Aは−0−、−S−、又は−S(O2)−であり、zは0又は1であり、x及びyは、それぞれ1ないし100の整数である)
ここで、Mはアルカリ金属であり、XはOH−の陰イオンであり、nは1ないし20の有理数であり、R5ないしR7は互いに同一であるか異なり、C1ないしC6のアルキル基、シクロヘキサン又はベンジル基であり、Ar3及びAr′3は、互いに同一であるか又は異なり、1つ又は2以上のベンゼン環を含む芳香族グループであり、前記2以上のベンゼン環はそれぞれ直接連結されたり、又は−0−、−S−、−S(O2)−、−(C(O))−、−C(CH3)2−、−(CH2)n−、−C(CF3)2−、又は−(CF2)n−(ここで、nは1ないし10)に連結され、前記それぞれのベンゼン環は非置換されたり、又はハロゲン元素、又は−(CH2)nCH3(ここで、nは0ないし6)に置換され、Ar4及びAr′4は、互いに同一であるか又は異なり、
であり(ここで、nは1ないし2であり、RaないしRdのうち少なくとも1つは高分子主鎖に連結され、残りは同一であるか又は異なり、水素、ベンゼン又はアルキルである)、
Aは−0−、−S−、又は−S(O2)−であり、
zは0又は1であり、
x及びyは、それぞれ1ないし100である)
であり(ここで、nは1ないし2であり、RaないしRdのうち少なくとも1つは高分子主鎖に連結され、残りは同一であるか又は異なり、水素、ベンゼン又はアルキルである。前記アルキルはC1ないしC5のアルキルである)。
3フラスコにメカニカル攪拌機を連結して窒素パージをした。2、5−Dichlorobenzophenone(1.40mmol、0.3511g)、4−chlorophenol(0.11mmol、0.0138g)、そして、bipyridine(3.64mmol、0.5678g)を入れてNMPを溶媒として用いた。反応溶液を80℃で2時間攪拌した後、Ni(COD)2(3.64mmol、1.0000g)を触媒として入れて3時間攪拌した。常温に温度を低くして反応溶液を塩酸水溶液に沈殿させた後、沈殿したオリゴマーは水とメタノールを用いて数回洗浄した。最終オリゴマーは80℃真空状態で乾燥して取得した。
3フラスコにメカニカル攪拌機を連結して窒素パージをした。2、5−Dichloro−p−xylene(0.26mmol、0.0463g)、2、4−dichlorotoluene(1.06mmol、0.1703g)、4−chlorophenol(0.11mmol、0.0138g)、そして、bipyridine(3.64mmol、0.5678g)を入れてNMPを溶媒として用いる。反応溶液を80℃で2時間攪拌した。
3口フラスコに冷却水が連結されたコンデンサとメカニカル攪拌機とを連結して窒素パージをした。合成例1、2で合成された親水性及び疎水性前駆体オリゴマーと高分子鎖延長環、そして、触媒であるpotassium carbonateを入れてDMAcを溶媒として用いた。120℃で攪拌して1時間単位でGPCを用いてモニタリングしながら所望する分子量になるまで同じ状態を維持して反応を終了した。高分子溶液を常温に下げてDMAcを用いて粘度を低くした。高分子溶液は、メタノールに沈殿させて高分子を取得して水を用いて数回洗浄した。高分子は、100℃真空状態で乾燥して回収した後、回収された高分子はメチルグループの選択的ブロム化によってイオン交換作用器(Fg、(CF2)SO3H)を導入してブロック共重合体を製造した。製造されたブロック共重合体の分子量及び分散度を測定して表1に示す。
高分子鎖延長環を導入しないこと以外は実施形態と同じ方法でイオン伝導性ブロック共重合体を製造した。製造されたブロック共重合体の分子量及び分散度を測定して表1に示した。
Claims (20)
- 下記の化学式1に表示される疎水性反復単位と、
下記の化学式2に表示される親水性反復単位と、
を含むブロック共重合体。
Ar2は、−COR2又は−(CH2)nCH3(ここで、nは0ないし6)に置換されたベンゼン環であり、前記R2は非置換されたり、又は−(CH2)nCH3(ここで、nは0ないし6)に置換された1つ以上のベンゼン環を含む芳香族グループであり、
Ar3及びAr′3は、1つ又は2以上のベンゼン環を含む芳香族グループであり、前記2以上のベンゼン環はそれぞれ直接連結されたり、又は−0−、−S−、−S(O2)−、−(C(O))−、−C(CH3)2−、−(CH2)n−、−C(CF3)2−、又は−(CF2)n−(ここで、nは1ないし10)に連結され、前記それぞれのベンゼン環は非置換されたり、又はハロゲン元素、ヒドロキシ、アセチレン又は−(CH2)nCH3(ここで、nは0ないし6)に置換され、
Ar4及びAr′4は、Ar1及びAr2と同一であるか又は異なり、
であり、
(ここで、nは1ないし2であり、RaないしRdのうち少なくとも1つは高分子主鎖に連結され、残りは同一であるか又は異なり、水素、ベンゼン又はアルキルである)
Aは−0−、−S−、又は−S(O2)−であり、
zは0又は1であり、
x及びyは、それぞれ1ないし100の整数である) - 前記ブロック共重合体の重合体鎖に含まれる全体反復単位のうち化学式1に表示される反復単位は50ないし95モル%の比率であり、化学式2に表示される反復単位は5ないし50モル%の比率である、請求項1に記載のブロック共重合体。
- 下記の化学式1に表示される疎水性反復単位と、
下記の化学式3に表示される親水性反復単位と、
を含むイオン伝導性ブロック共重合体。
Ar′2は、−COR4、R4又はこの2つに置換された1つ又は2以上のベンゼン環を含む芳香族グループであり、前記R4は下記の化学式に表示される高密度化作用器(Fg)で選択され、
ここで、Mはアルカリ金属であり、XはOH−の陰イオンであり、nは1ないし20の有理数であり、R5ないしR7は互いに同一であるか異なり、C1ないしC6のアルキル基、シクロヘキサン又はベンジル基であり、
Ar3及びAr′3は、互いに同一であるか又は異なり、1つ又は2以上のベンゼン環を含む芳香族グループであり、前記2以上のベンゼン環はそれぞれ直接連結されたり、又は−0−、−S−、−S(O2)−、−(C(O))−、−C(CH3)2−、−(CH2)n−、−C(CF3)2−、又は−(CF2)n−(ここで、nは1ないし10)に連結され、前記それぞれのベンゼン環は非置換されたり、又はハロゲン元素、又は−(CH2)nCH3(ここで、nは0ないし6)に置換され、
Ar4及びAr′4は、互いに同一であるか又は異なり、
であり(ここで、nは1ないし2であり、RaないしRdのうち少なくとも1つは高分子主鎖に連結され、残りは同一であるか又は異なり、水素、ベンゼン又はアルキルである)、
Aは−0−、−S−、又は−S(O2)−であり、
zは0又は1であり、
x及びyは、それぞれ1ないし100である) - 活性成分として請求項11のイオン伝導性ブロック共重合体を含む、ポリマー電解質。
- 請求項12のポリマー電解質を含む、イオン交換膜。
- 請求項1のブロック共重合体を含む、アイオノマーバインダー。
- アノード層と、
カソード層と、
前記アノード層とカソード層との間に請求項13のイオン交換膜と、
を含む、燃料電池。 - 前記アノード層、前記カソード層又はこの2つは、請求項14のアイオノマーバインダーをさらに含む、請求項15に記載の燃料電池。
- 前記化学式4及び化学式5に表示されるオリゴマーの分散度(PD:polydispersity)は3以下である、請求項17に記載の製造方法。
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