JP2001509818A - ペルフルオロビニルイオン化合物および重合体型のイオン電導体の成分、選択膜の成分または触媒の成分としてのそれらの使用 - Google Patents
ペルフルオロビニルイオン化合物および重合体型のイオン電導体の成分、選択膜の成分または触媒の成分としてのそれらの使用Info
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Abstract
Description
Claims (1)
- 【特許請求の範囲】 1.負の電荷が高度に非局在化され、式[CF2=CF-A-]mMm+で表されるイオン化合 物。 (式中Mm+はプロトンまたはアルカリ金属、アルカリ土類金属、遷移金属また は希土類金属のイオンから選ばれる原子価mの金属陽イオン、または有機オニ ウム陽イオンまたは有機金属陽イオンであり、1≦m≦3である; A-は下記の式の1つを有する陰イオン基を示す: (I)[-(CF2)n-SO2Z]-、 (II)[-(O)n ,-Φ-SO2Z]-または (III) nおよびn'は0または1を示す; Φは縮合または非縮合芳香族基を示し、1個以上の置換基を持っていても持っ ていなくてもよく、ヘテロ原子またはポリハロゲン化基-C6H(4-x-y)FxCly-( 1≦x+y≦4)を含有してもしなくてもよい; Zは-Oまたは-NC≡N、-C(C≡N)2、-NSO2Rまたは-C[SO2R]2基を示し、 Zはnまたはn'が0である場合に-O以外のものである; Dは単一結合、酸素原子、硫黄原子、-CO-カルボニル基または-SO2-スルホニ ル基を示し; 基X1〜X4(以後Xiと表示する)は、N、C-C≡N、CR、CCOR、またはCSO2Rを示 し、ペンタ環式基においては、Xi基は同じものでもまたは異なるものでも可 能であることは理解される; RはY、YO-、YS-、Y2N-、F、RF=CqF2q+1(好ましくは0≦q≦12)、CF2=CF-、 CF2=CFCF2-、またはCF2=CF-O-を示し、もし2個のR置換基が 同じ基の上に存在するなら、それらは同じものでも異なるものでも可能である ことは理解される; YはHあるいはアルキル、アルケニル、オキサアルキル、オキサアルケニル、 アザアルキル、アザアルケニル、アリールもしくはアルキルアリール基から選 ばれる、または前述の基の鎖および/または芳香族部分においてヘテロ原子例 えばハロゲン、酸素、窒素、硫黄または燐により置換されて得られる基から選 ばれる1個から16個の炭素原子を有する1価の有機基であり、もし硫黄または 燐が存在するなら、それらは置換された窒素または酸素原子と任意に結合でき ることは理解され、Yは重合体骨格の繰り返し単位である) 2.Mm+がLi+、K+、Mg++、Ca++、Ba++、Cu++、Zn++、Fe++およびRe+++から成 る群から選ばれる金属陽イオンであることを特徴とする請求項1の化合物。 3.Mm+がアンモニウム[N(Yj)4]+、アミジニウムRC[N(Yj)2]2 +グアニジニウムC [N(Yj)2]3 +、ピリジニウム[C5N(Yj)6]+、イミダゾリウムC3N2(Yj)5 +、イミダゾ リニウムC3N2(Yj)7 +、トリアゾリウムC2N3(Yj)4 +、カルボニウムC5(Yj)5C+、NO+ (ニトロシル)、NO2 +、スルフォニウム[S(Yj)3]+、ホスホニウム[P(Yj)4]+または イオドニウム[I(Yj)2]+であり、同じ陽イオンのYj置換基は同じものでも異なる ものでも可能であり、Yについて示される置換基の1つを示すことを特徴とする 請求項1の化合物。 4.Mm+が、メタロセニウム;例えばO、S、Se、N、P、Asなどの原子により 配位され、有機分子により運ばれる金属陽イオンから選ばれる有機金属陽イオン であり、これらの陽イオンは任意に重合体の骨格の一部を形成する;またはトリ アルキルシリル、トリアルキルケルマニルもしくはトリアルキルスタンニル基で あることを特徴とする請求項1の化合物。 5.M+陽イオンが陽イオン酸化形状の共役重合体の繰り返し単位であることを 特徴とする請求項1の化合物。 6.二価の基Φは置換がオルト位、メタ位およびパラ位に対応するフェニルC6H4 または芳香族基、すなわち置換されるフェニルおよび/またはヘテロ原子を含有 してもまたは含有しなくてもよい縮合核を有するフェニルであることを特徴 とする請求項1の化合物。 7.下記の式の1つに対応する請求項1の化合物: 8.下記の式の1つに対応する請求項1の化合物: 9.有機金属化合物(OM1)を化学量論的割合でイオン化合物(IC1)と触媒の存在下 で反応させることを特徴とする請求項1のイオン化合物の調製方法。 有機金属化合物(OM1)は式[CF2=CF-(CF2)n]e-Eに対応し、 (式中EはLi、MgL1、ZnL1、CdL1、Cu、Mg、Zn、Cd、Hgまたはトリアルキルシ リル、トリアルキルゲルマニルまたはトリアルキルスタンニル基を示し; nは0または1であり; eはEの原子価を示し; L1はハロゲン、疑似ハロゲン、スルホン酸塩、イミダゾルまたは1,2,4-トリ アゾル環を有する基およびその同族体で1個以上の炭素原子が置換基を有する ものおよびその置換基が環を形成するもの、ペルフルオロアルキルスルホニル オキシ基およびアリールスルホニルオキシ基から選ばれる離脱基を示し); イオン化合物(IC1)は式[(LA1)-]m'M'm'+[sic]に対応し、 (式中M'm'+はプロトンまたはアルカリ金属イオン、アルカリ土類金属イオン 、遷移金属イオンもしくは希土類金属イオンから選ばれる原子価mの金属陽イ オン、または有機オニウム金属陽イオンまたは有機金属陽イオンを示し、1≦ m≦3であり、M'は生成反応と干渉しないように選ばれる; LはL1と同じ意味を有し、反応中に使用される反応体のL基とL1基は同じも のでも異なるものでも可能である; A1は下記式の1つに対応する陰イオン基を示す: [-(CF2)n-SO2Z1]-、[-(O)n'-Φ-SO2Z1]-または (式中nおよびn’は0または1を示す; Dは単一結合、酸素原子、硫黄原子、-CO-カルボニル基または-SO2-スルホニ ル基を示し; Z1は-O酸素(nまたはn’が零である場合以外)または-NC≡N、-C(C≡N)2、 -NSO2R1および-C[SO2R1]2基の1つを示し; 基X'1〜X'4(以後X'iと表示する)は、N、C-C≡N、CR1、CCOR1、また はCSO2R1を示し、ペンタ環式基においては、X'i基は同じものでもまたは異な るものでも可能であることは理解される; R1はY、YO-、YS-、Y2N-、F、CF2=CF-、CF2=CFCF2-、CF2=CF-O-またはRF=CqF2q+1(0≦q≦12)、またはハロゲン、疑似ハロゲン、スルホン酸塩、イミダゾル または1,2,4-トリアゾル環を有する基およびその同族体、ペルフルオロアルキ ルスルホニルオキシ基およびアリールスルホニルオキシ基から選ばれる脱離基 を示し、もし2個のR1置換基が同じ基の上に存在するなら、それらは同じも のでも異なるものでも可能であり、また多くて2個のR1置換基は脱離基であ ることは理解される; Yは請求項1と同じ意味を有する) 10.M'陽イオンが陽イオン交換によりM陽イオンと置き換えられることを特 徴とする請求項9の方法。 11.触媒がアミンまたはホスフィン型の塩基と配位結合されるニッケルまたは パラジウムの誘導体から選ばれることを特徴とする請求項9の方法。 12.触媒がニッケルビス(2,2'-ビピリジル)、ニッケルテトラキス(トリフェ ニルホスフィン)およびそのスルホン化誘導体、酢酸パラジウム、トリスベンジ リデンケトンジパラジウム、パラジウムテトラキス(トリフェニルホスフィン) およびそのスルホン化誘導体、および2つのトリフェニルホスフィン分子を[(C6 H5)2PCH2]2または[(C6H5)2PCH2]2CH2で置換することにより得られる化合物から 選ばれることを特徴とする請求項11の方法。 13.保護フルオロビニル基CF2L3CFL4-(CF2)nE1を含有する化合物と陰イオン基 Aの形成を可能とする反応体[(L5)aA2]m'M'm'+とを化学量論的割合で反応させ、 次にその保護基が化学または電気化学還元によりまたは脱ハロゲン化水素化によ り除去されること、および M'm'+はプロトンまたはアルカリ金属イオン、アルカリ土類金属イオン、遷移金 属イオンまたは希土類金属イオンから選ばれる原子価mの金属陽イオン、または 有機オニウム金属陽イオンまたは有機金属陽イオンを示し、1≦m≦3であり、 M'm'+は生成反応と干渉しないように選ばれる; ことを特徴とする請求項1のイオン化合物[CF2=CF-A-]mMm+の調製方法。 L3とL4はHまたはハロゲンを示し、そのうちの1個だけが任意にHである; E1はLi、MgL1、ZnL1、CdL1、Cu、Mg、Zn、Cd、Hgまたはトリアルキルシリル 、トリアルキルゲルマニルまたはトリアルキルスタンニル基を示し; L5はハロゲン、疑似ハロゲン、スルホン酸塩、イミダゾルまたは1,2,4-トリ アゾル環を有する基およびその同族体で1個以上の炭素原子が置換基を有する ものおよびその置換基が環を形成するもの、ペルフルオロアルキルスルホニル オキシ基およびアリールスルホニルオキシ基から選ばれる脱離基を示し; aは陰イオン基A2の原子価であり; A2は下記の式の1つに対応する基を示す: [-(CF2)n-SO2Z2]-、[-(O)n ,-ΦSO2Z2]-または (式中Z2は-O酸素(nまたはn’が零である場合以外)または-NC≡N、-C(C ≡N)2、-NSO2R2または-C[SO2R2]2基の1つを示し; 基X"1〜X"4(以後X"iと表示する)は、N、C-C≡N、CR2、CCOR2またはCSO2 R2を示し、ペンタ環式基においては、X"i基は同じものでもまたは異なるもの でも可能であることは理解される; R2は-OH、-SH、Y、YO-、YS-、Y2N-、F、CF2=CF-、CF2=CFCF2-CF2=CF-O-また はRF=CqF2q+1(0≦q≦12)、もし2個のR2置換基が同じ基の上に存在するなら 、それらは同じものでも異なるものでも可能であり、また多くて2個のR2置 換基は-OHまたは-SHを示すことは理解される; 14.基L3L4が亜鉛、銅・亜鉛カップル、Ti3+、V2+、Cr3+またはSm2+の塩、お よびテトラキス(ジメチルアミノエチレン){[(CH3)2N]2C=}2から選ばれる還元 剤を使用して還元により除去されることを特徴とする請求項13の方法。 15.化合物CF2=CFL2(L2はCl、Br、またはFを示す)が化学量論的割合でイオ ン化合物[(HQA3)-]m'(M')m'+と反応すること、および得られた添加生成物が強塩 基Bで処理されること; を特徴とする請求項1の化合物を調製する方法。 M'm'+はプロトンまたはアルカリ金属イオン、アルカリ土類金属イオン、遷移 金属イオンまたは希土類金属イオンから選ばれる原子価mの金属陽イオン、ま たは有機オニウム金属陽イオンまたは有機金属陽イオンを示し、1≦m≦3で あり、M'm'+は形成反応と干渉しないように選ばれる; QがOまたはSを示し; A3が下記の式の1つに対応する陰イオン基を示し: [-(CF2)n-SO2Z3]-、[-ΦSO2Z3]-または Z3は-O酸素(nが零である場合以外)または-NC≡N、-C(C≡N)2、-NSO2R3ま たは-C[SO2R3]2基の1つを示し; 基X"'1〜X"'4(以後X"'iと表示する)は、N、C-C≡N、CR3、CCOR3またはC SO2R3を示し、ペンタ環式基においては、X"'i基は同じものでもまたは異なる ものでも可能であることは理解される: R3は-HO、-HS、Y、YO-、YS-、Y2N-、F、CF2=CF-、CF2=CFCF2-CF2=CF-O-ま たはRF=CqF2q+1(0≦q≦12)、もし2個のR3置換基が同じ基の上に存在するな ら、それらは同じものでも異なるものでも可能であることおよび多くて2個の R3置換基は-OHまたは-SH基であることは理解される 16.強塩基BがNaH(任意にホスファゼン型の燐酸含有塩基の存在下で使用され る)、(CH3)3CONa、(CH3)3COK、LDA(リチウムジイソプロピルアミド)、[(CH3)2CH ]2NLiまたはヘキサアルキルジシラザン誘導体であること; を特徴とする請求項15の方法。 17.化合物L6CF2CF2L6をイオン化合物[(HQA3)-]m'(M')m'+と化学量論的に反 応させること;得られた置換化合物を化学的にまたは電気化学的に還元すること ;および M'm'+はプロトンまたはアルカリ金属イオンであり、アルカリ土類金属イオン、 遷移金属イオンまたは希土類金属イオンから選ばれる原子価mの金属陽イオン、 または有機オニウム金属陽イオンまたは有機金属陽イオンを示し、1≦m≦3で あり、M'm'+は形成反応と干渉しないように選ばれ、; QがOまたはSを示し; A3が下記の式の1つに対応する陰イオン基を示すことを特徴とする請求項1の 化合物を調製する方法。 [-(CF2)n-SO2Z3]-、[-ΦSO2Z3]-または 式中Z3は-O酸素(nが零である場合以外)または-NC≡N、-C(C≡N)2、-NSO 2R3または-C[SO2R3]2基の1つを示し; 基X"'1〜X"'4(以後X"'iと表示する)は、N、C-C≡N、CR3、CCOR3また はCSO2R3を示し、ペンタ環式基においては、X"'i基は同じものでもまたは 異なるものでも可能であることは理解される; R3は-HO、-HS、Y、YO-、YS-、Y2N-、F、CF2=CF-、CF2=CFCF2-CF2=CF-O-ま たはRF=CqF2q+1(0≦q≦12)を示し、もし2個のR3置換基が同じ基の上に 存在するなら、それらは同じものでも異なるものでも可能であることおよび 多くて2個のR3置換基は-OHまたは-SH基であることは理解される; L6はハロゲン、疑似ハロゲンまたはスルホン酸塩を示す 18.還元を行う場合に、亜鉛、銅・亜鉛カップル、Ti3+、V2+、Cr3+またはSm2+ の塩類、およびテトラキス(ジメチルアミノエチレン){[(CH3)2N]2C=}2から 選ばれる触媒を使用することを特徴とする請求項17の方法。 19.重合体の電子的中性を確保するのに充分な数の陽イオンと結合するポリ陰 イオン部分を有し、ポリ陰イオン部分は下記の繰り返し単位: (式中Aは請求項1に示される意味を有する) を有することを特徴とするポリ陰イオン部分を有する重合体。 20.重合体の電子的中性を確保するのに充分な数の陽イオンと結合するポリ陰 イオン部分を有し、ポリ陰イオン部分は下記式: (式中A'-は請求項1に定義された式(I),(II)または(III)の1つに対応する陰 イオンを示し、ZまたはXiの置換基はペルフルオロビニル基を含有する) に対応する繰り返し単位を有することを特徴とするポリ陰イオン分を有する重合 体。 21.少なくとも2つのCF2=CF-基を有する請求項1に記載の化合物を重合また は共重合することにより得られる橋かけ結合された高分子材料。 22.請求項19および20のいずれかに記載の重合体または請求項21に記載 の橋かけ結合高分子材料から主として成るイオン伝導性材料。 23.極性溶媒に請求項1の化合物を溶解することからなる電解質。 24.少なくとも1つの極性溶媒と請求項1の単官能化合物を重合することによ り得られた重合体または共重合体から成る電解質。 25.請求項1に記載の少なくとも1つの化合物と1個以上の溶媒和ポリエーテ ルの前駆体との共重合体を含有することを特徴とする固体電解質。 26.請求項1に記載の少なくとも1つの化合物と前記化合物のペルフルオロビ ニル基と反応できる反応性官能基を有する溶媒和ポリエーテルとの共橋かけ結合 により得られる高分子材料を含有することを特徴とする固体電解質。 27.ポリエーテルと請求項1に記載の少なくとも1つの化合物から得られる単 独重合体または共重合体の混合物を含有し、前記混合物は任意に橋かけ結合され て相互貫入網目構造を形成することが可能であることを特徴とする固体電解質。 28.請求項1に記載の少なくとも1つの化合物と1個以上の溶媒和ポリエーテ ルの前駆体との共重合体、または請求項1に記載の少なくとも1つの化合物と本 発明の化合物のペルフルオロビニル基と反応できる反応性官能基を有する溶媒和 ポリエーテルとの共橋かけ結合により得られる高分子材料のいずれかを含有する ことを特徴とする固体電解質。 29.少なくとも1つの極性溶剤、請求項1に記載のイオン単量体化合物および 極性重合体の混合物または少なくとも1つの極性溶媒および請求項1に記載の単 官能化合物の重合により得られる重合体または共重合体の混合物から成ることを 特徴とする可塑化電解質またはゲル状の電解質。 30.請求項1に記載の化合物の陽イオンがアルカリ金属陽イオンであることを 特徴とする請求項23から請求項29までのいずれか1項に記載の電解質。 31.電解質が請求項1に記載のイオン化合物または請求項1に記載のイオン化 合物から得られる高分子材料を含有することを特徴とする負の電極、正の電極お よび電解質を有する一次または二次バッテリー。 32.電解質が請求項23から請求項30までのいずれか1項に記載の電解質である ことを特徴とする負の電極、正の電極および電解質を含有する一次または二次バ ッテリー。 33.電解質が請求項1に記載のイオン化合物または請求項1に記載のイオン化 合物から得られた高分子材料を含有することを特徴とする電解質と電極を有する 光を変性するシステム。 34.電解質が請求項1に記載のイオン化合物または請求項1に記載のイオン化 合物から得られる高分子材料を含有することを特徴とする電解質および電極から 成るスーパーキャパシター。 35.カルボカチオンを生成するために前記重合体を部分的に酸化することから 成り、その電荷はイオン化合物の陰イオンにより埋め合わされ、該イオン化合物 が請求項1に記載の化合物であることを特徴とする重合体をドーピングする方法 。 36.イオン化合物が、Zが-C(C≡N)2、-NSO2Rまたは-C(SO2R)2であるものから 選ばれることを特徴とする請求項35に記載の重合体をドーピングする方法。 37.膜の調製において請求項1に記載のイオン化合物の使用。 38.CF2=CF-基を有する請求項1に記載の少なくとも1つの化合物と少なく とも2つのCF2=CF-基を有する請求項1に記載の少なくとも1つの化合物の共重 合体から成る膜。 39.反応に触媒作用を及ぼす酸の源である光開始剤として請求項1に記載の化 合物を使用することを特徴とするカチオン法により反応することのできる単量体 またはプレポリマーの重合または橋かけ結合を行う方法。 40.重合反応、縮合反応、添加または脱離反応、酸化または還元反応、加溶媒 分解、フリーデル・クラフツ反応およびジールス・アルダー反応における請求項 19および請求項20に記載のイオン重合体の触媒としての使用。
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Also Published As
Publication number | Publication date |
---|---|
WO1999005126A1 (fr) | 1999-02-04 |
CA2266660C (fr) | 2012-07-17 |
US20020193540A1 (en) | 2002-12-19 |
US20040023092A1 (en) | 2004-02-05 |
US6593019B2 (en) | 2003-07-15 |
JP4657390B2 (ja) | 2011-03-23 |
WO1999005126A8 (fr) | 1999-04-15 |
US6288187B1 (en) | 2001-09-11 |
US6426397B1 (en) | 2002-07-30 |
DE69827239D1 (de) | 2004-12-02 |
US7271228B2 (en) | 2007-09-18 |
EP0968196A1 (fr) | 2000-01-05 |
CA2266660A1 (fr) | 1999-02-04 |
US20020026021A1 (en) | 2002-02-28 |
EP0968196B1 (fr) | 2004-10-27 |
DE69827239T2 (de) | 2005-12-01 |
US6858691B2 (en) | 2005-02-22 |
US20050266289A1 (en) | 2005-12-01 |
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