KR100819676B1 - 브랜치된 멀티블록 폴리벤즈이미다졸-벤즈아마이드공중합체 및 제조방법, 이를 이용한 전해질막 및 전해질페이스트/겔 - Google Patents
브랜치된 멀티블록 폴리벤즈이미다졸-벤즈아마이드공중합체 및 제조방법, 이를 이용한 전해질막 및 전해질페이스트/겔 Download PDFInfo
- Publication number
- KR100819676B1 KR100819676B1 KR1020050108722A KR20050108722A KR100819676B1 KR 100819676 B1 KR100819676 B1 KR 100819676B1 KR 1020050108722 A KR1020050108722 A KR 1020050108722A KR 20050108722 A KR20050108722 A KR 20050108722A KR 100819676 B1 KR100819676 B1 KR 100819676B1
- Authority
- KR
- South Korea
- Prior art keywords
- acid
- aromatic
- heteroaromatic
- polybenzimidazole
- benzamide
- Prior art date
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- 239000003792 electrolyte Substances 0.000 title claims abstract description 86
- 239000012528 membrane Substances 0.000 title claims abstract description 80
- 238000000034 method Methods 0.000 title claims abstract description 48
- 238000004519 manufacturing process Methods 0.000 claims abstract description 36
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- 125000003118 aryl group Chemical group 0.000 claims description 86
- -1 aromatic carboxylic acids Chemical class 0.000 claims description 65
- 150000001875 compounds Chemical class 0.000 claims description 60
- 229920000137 polyphosphoric acid Polymers 0.000 claims description 33
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 32
- 125000001072 heteroaryl group Chemical group 0.000 claims description 31
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- 238000003756 stirring Methods 0.000 claims description 17
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- 230000008569 process Effects 0.000 claims description 12
- HEMGYNNCNNODNX-UHFFFAOYSA-N 3,4-diaminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1N HEMGYNNCNNODNX-UHFFFAOYSA-N 0.000 claims description 11
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 10
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 claims description 10
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 10
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 10
- 150000008065 acid anhydrides Chemical class 0.000 claims description 10
- 239000003054 catalyst Substances 0.000 claims description 10
- 150000003841 chloride salts Chemical class 0.000 claims description 10
- 230000007062 hydrolysis Effects 0.000 claims description 10
- 238000006460 hydrolysis reaction Methods 0.000 claims description 10
- HSTOKWSFWGCZMH-UHFFFAOYSA-N 3,3'-diaminobenzidine Chemical group C1=C(N)C(N)=CC=C1C1=CC=C(N)C(N)=C1 HSTOKWSFWGCZMH-UHFFFAOYSA-N 0.000 claims description 9
- 239000011261 inert gas Substances 0.000 claims description 9
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- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 8
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- 239000001205 polyphosphate Substances 0.000 claims description 6
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- JLLLDVVHSNUMHE-UHFFFAOYSA-N 2-(1h-benzimidazol-2-yl)benzamide Chemical group NC(=O)C1=CC=CC=C1C1=NC2=CC=CC=C2N1 JLLLDVVHSNUMHE-UHFFFAOYSA-N 0.000 claims description 4
- FFQHUOQNSGCJMV-UHFFFAOYSA-N 2-pyridin-2-ylbenzene-1,4-diamine Chemical compound NC1=CC=C(N)C(C=2N=CC=CC=2)=C1 FFQHUOQNSGCJMV-UHFFFAOYSA-N 0.000 claims description 4
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- PIPQOFRJDBZPFR-UHFFFAOYSA-N 1h-benzimidazole-5,6-dicarboxylic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC2=C1NC=N2 PIPQOFRJDBZPFR-UHFFFAOYSA-N 0.000 claims description 2
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Abstract
Description
전해질막 | 인산도핑수준 | 걷보기 물성 | Stress at break (MPa) | Strain (%) |
시편 1 | 3.4 | 투명, 탁월한 기계적 강도 | 24.1 | 160 |
시편 2 | 4.6 | 투명, 탁월한 기계적 강도 | 26.7 | 180 |
시편 3 | 3.2 | 투명, 탁월한 기계적 강도 | 24.8 | 180 |
시편 4 | 3.9 | 투명, 우수한 기계적 강도 | 21.5 | 140 |
시편 5 | 5.4 | 투명, 우수한 기계적 강도 | 16.8 | 220 |
시편 6 | 5.1 | 투명, 우수한 기계적 강도 | 13.4 | 260 |
Claims (21)
- 하기 화학식 1로 표시되는 반복 단위로 이루어지는 것을 특징으로 하는 브랜치된 멀티블록 폴리벤즈이미다졸-벤즈아마이드 공중합체.[화학식 1]상기 화학식 1에서,AZ는 화학식 2 및 화학식 3으로 이루어지는 군으로부터 선택되는 1종 이상의 반복단위를 포함하며,AM은 화학식 4, 화학식 5, 화학식 6 및 화학식 7로 이루어지는 군으로부터 선택되는 1종 이상의 반복단위를 포함한다.[화학식 2][화학식 3][화학식 4][화학식 5][화학식 6][화학식 7]상기 화학식 1 내지 7에서,Ar, Ar2,Ar2 ′,Ar9는 동일하거나 상이하며, 각각 하나 이상의 환을 가질 수 있는 4가 방향족 또는 헤테로방향족 그룹이고,Ar1, Ar1 ′,Ar5, Ar6, Ar7, Ar7 ″은 동일하거나 상이하며, 각각 하나 이상의 환을 가질 수 있는 2가 방향족 또는 헤테로방향족 그룹이고,Ar3, Ar4 ′,Ar8은 동일하거나 상이하며, 각각 하나 이상의 환을 가질 수 있는 3가 방향족 또는 헤테로방향족 그룹이고,X는 동일하거나 상이하며, 각각 산소, 황 또는 수소 원자를 함유하는 아미노 그룹, 탄소수 1 내지 20의 그룹, 또는 아릴 그룹이고,a는 0<a<1이고, a′은 0<a′<1이고,1≤m<10,000이고, 1≤n<10,000이며 1≤k<10,000이다.
- 방향족 및 헤테로방향족 테트라아미노 화합물로부터 선택되는 1종 이상의 화합물;카르복실산 단량체 1 개당 둘 이상의 산성 그룹을 포함하는 방향족 카복실산 및 이의 에스테르로부터 선택되는 1종 이상의 화합물;방향족 및 헤테로방향족 디아미노카복실산으로부터 선택되는 1종 이상의 화합물;방향족 및 헤테로방향족 아미노카복실산 및 방향족 및 헤테로방향족 디아미노 화합물로부터 선택되는 1종 이상의 화합물; 및방향족 및 헤테로방향족 트리카복실산 및 테트라카복실산으로부터 선택되는 1종 이상의 화합물;을 불활성 가스 하에서 폴리인산에 녹여 300 ℃ 이하에서 중합하는 것을 특징으로 하는 제 1항 기재의 멀티블록 폴리벤즈이미다졸-벤즈아마이드 공중합체의 제조방법.
- 제 2항에 있어서,(a) 방향족 및 헤테로방향족 테트라아미노 화합물과 방향족 및 헤테로방향족 카복실산에 방향족 및 헤테로방향족 트리카복실산 및 테트라카복실산에서 선택되는 1종 이상의 화합물을 브랜처로 사용하되, 브랜처는 브랜치된 AZ 블록 제조 시 사용되는 테트라아미노 화합물의 함량을 기준으로 0.01 내지 30 몰%의 함량으로 사용하여 아졸계 AZ 블록을 먼저 제조하는 단계;(b) 상기 AZ 블록을 구성하는 화합물을 불활성 가스 하에서 폴리인산에 녹여 300 ℃ 이하의 온도에서 8 시간 이하 교반한 후, 방향족 및 헤테로방향족 디아미노카복실산을 AZ 블록을 구성하는 테트라아미노 화합물의 함량을 기준으로 0.01 내지 99.99 몰%의 함량으로 사용하여 브랜치된 AZ 블록과 블록이 교대로 화학적으로 결합된 공중합체 를 제조하는 단계; 및(c) 상기 공중합체 용액에 방향족 및 헤테로방향족 디아미노카복실산을 가하여 48 시간 교반한 후, 방향족 및 헤테로방향족 아미노카복실산 및 방향족 및 헤테로방향족 디아미노 화합물로부터 선택되는 1종 이상의 화합물, 방향족 및 헤테로방향족 카복실산으로부터 선택되는 1종 이상의 화합물과 방향족 및 헤테로방향족 트리카복실산 및 테트라카복실산 등을 AZ 블록을 구성하는 테트라아미노 화합물의 함량을 기준으로 0.01 내지 49.99 몰%의 함량으로 사용하여 상기 화학식 1로 표시되는 반복단위로 이루어지는 브랜치된 멀티블록 공중합체를 제조하는 단계;를 포함하여 이루어지는 것을 특징으로 하는 브랜치된 멀티블록 폴리벤즈이미다졸-벤즈아미이드 공중합체의 제조방법.
- 제 2항에 있어서,(b′) 방향족 및 헤테로방향족 아미노카복실산 및 방향족 및 헤테로방향족 디아미노 화합물로부터 선택되는 1종 이상의 화합물, 방향족 및 헤테로방향족 카복실산으로부터 선택되는 1종 이상의 화합물과 방향족 및 헤테로방향족 트리카복실산 및 테트라카복실산을 블록을 구성하는 방향족 및 헤테로방향족 디아미노카복실산 화합물의 함량을 기준으로 0.01 내지 99.99 몰%의 함량으로 사용하여 220 ℃ 이하의 온도에서 48 시간 이하 교반하여 반복단위 로 이루어지는 멀티블록 공중합체를 제조하는 단계; 및(c′) 방향족 및 헤테로방향족 테트라아미노 화합물과 방향족 및 헤테로방향족 카복실산에 방향족 및 헤테로방향족 트리카복실산 및 테트라카복실산을 브랜처 로 사용하되, 블록을 구성하는 방향족 및 헤테로방향족 디아미노카복실산 화합물의 함량을 기준으로 10 내지 1000 몰%의 함량으로 사용하여 220 ℃ 이하의 온도에서 48 시간 이하 교반하여 상기 화학식 1로 표시되는 반복단위로 이루어지는 브랜치된 멀티블록 공중합체를 제조하는 단계;를 포함하여 이루어지는 것을 특징으로 하는 브랜치된 멀티블록 폴리벤즈이미다졸-벤즈아미이드 공중합체의 제조방법.
- 제 2항에 있어서,상기 방향족 및 헤테로방향족 테트라아미노 화합물은 3,3′,4,4′-테트라아미노비페닐, 2,3,5,6-테트라아미노피리딘, 1,2,4,5-테트라아미노벤젠, 비스(3,4-디아미노페닐)설폰, 비스(3,4-디아미노페닐)에테르, 3,3′,4,4′-테트라아미노벤조페논, 또는 3,3′,4,4′-테트라아미노디페닐메탄 및 3,3′,4,4′-테트라아미노디페닐디메틸메탄과 이들의 염, 및 이들의 모노-, 디-, 트리- 및 테트라하이드로클로라이드 유도체로 이루어진 군으로부터 1종 이상 선택하여 사용하는 것을 특징으로 하는 브랜치된 멀티블록 폴리벤즈이미다졸-벤즈아마이드 공중합체의 제조방법.
- 제 2항에 있어서,상기 방향족 카복실산은 2,3-비스(4-카복실페닐)퀸옥살린, 1,4-페닐렌-비스-[3-(4′-카복실페닐)티오우레아], p-페닐렌-2,2′-비스[5(6)-카복실벤즈이미다졸], 비스(4-카복실페닐)포스피닉산, 비스(4-카복실페닐)페닐메탄올, 비스(4-카복실페닐)페닐포스핀옥사이드, 5-포스포노이소프탈산, 이소프탈산, 테레프탈산, 프탈산, 5-하이드록시이소프탈산, 4-하이드록시이소프탈산, 2-하이드록시이소프탈산, 2,5-디하이드록시테레프탈산, 2,6-디하이드록시이소프탈산, 4,6-디하이드록시이소프탈산, 2,3-디하이드록시프탈산, 2,4-디하이드록시프탈산, 3,4-디하이드록시프탈산, 3-플루오로프탈산, 5-플루오로이소프탈산, 2-플루오로테레프탈산, 테트라플루오로프탈산, 테트라플루오로이소프탈산, 테트라플루오로테레프탈산, 1,4-나프탈렌디카복실산, 1,5-나프탈렌디카복실산, 2,6-나프탈렌디카복실산, 2,7-나프탈렌디카복실산, 디펜산, 1,8-디하이드록시나프탈렌-3,6-디카복실산, 비스(4-카복시페닐)에테르, 벤조페논-4,4′-디카복실산, 비스(4-카복시페닐)설폰, 비페닐-4,4′-디카복실산, 4-트리플루오로메틸프탈산, 2,2-비스(4-카복시페닐)헥사플루오로프로판, 4,4′-스틸벤디카복실산, 4-카복시신남산으로 이루어지는 방향족 디카복실산; 이들의 C1-C20-알킬에스테르, C5-C12-아릴에스테르; 이들의 산 무수물 및 이들의 산 클로라이드로 이루어지는 군으로부터 1종 이상 선택하여 사용하는 것을 특징으로 하는 브랜치된 멀티블록 폴리벤즈이미다졸-벤즈아마이드 공중합체의 제조방법.
- 제 2항에 있어서,상기 헤테로방향족 카복실산은 피리딘-2,5-디카복실산, 피리딘-3,5-디카복실산, 피리딘-2,6-디카복실산, 피리딘-2,4-디카복실산, 4-페닐-2,5-피리딘디카복실산, 3,5-피라졸디카복실산, 2,6-피리미딘디카복실산, 2,5-피리미진디카복실산, 벤 즈이미다졸-5,6-디카복실산; 이들의 C1-C20-알킬에스테르, C5-C12-아릴에스테르; 이들의 산 무수물 및 이들의 산 클로라이드로 이루어지는 군으로부터 1종 이상 선택하여 사용하는 것을 특징으로 하는 브랜치된 멀티블록 폴리벤즈이미다졸-벤즈아마이드 공중합체의 제조방법.
- 제 2항에 있어서,상기 브랜처로 사용되는 방향족 트리카복실산; 이들의 C1-C20-알킬에스테르, C5-C12-아릴에스테르; 이들의 산 무수물 및 이들의 산 클로라이드는 1,3,5-벤젠트리카복실산(트리메스산), 1,2,4- 벤젠트리카복실산(트리멜리트산), 3,5,3′-비페닐트리카복실산, 및 3,5,4′- 비페닐트리카복실산으로 이루어진 군으로부터 1종 이상 선택하여 사용하고,상기 브랜처로 사용되는 방향족 테트라카복실산 또는 테트라카복실산; 이들의 C1-C20-알킬에스테르, C5-C12-아릴에스테르; 이들의 산 무수물 및 산 클로라이드는 3,5,3′,5′-비페닐테트라카복실산, 1,2,4,5-벤젠테트라카복실산, 벤조페논테트라카복실산, 3,3′,4,4′-비페닐테트라카복실산, 2,2′,3,3′-비페닐테트라카복실산, 1,2,5,6-나프탈렌테트라카복실산, 및 1,4,5,8-나프탈렌테트라카복실산으로 이루어진 군으로부터 1종 이상 선택하여 사용하고,상기 브랜처로 사용되는 헤테로방향족 트리카복실산 및 테트라카복실산; 이들의 C1-C20-알킬에스테르, C5-C12-아릴에스테르; 및 이들의 산 무수물은 2,4,6-피리딘트리카복실산을 사용하는 것을 특징으로 하는 브랜치된 멀티블록 폴리벤즈이미 다졸-벤즈아마이드 공중합체의 제조방법.
- 제 2항에 있어서,상기 방향족 및 헤테로방향족 디아미노카복실산은 3,4-디아미노벤조산, 이의 모노- 및 다이히드로클로라이드 유도체로 이루어진 군으로부터 1종 이상 선택하여 사용하는 것을 특징으로 하는 브랜치된 멀티블록 폴리벤즈이미다졸-벤즈아마이드 공중합체의 제조방법.
- 제 2항에 있어서,상기 방향족 및 헤테레로방향족 아미노카복실산은 4-아미노벤조산, 3-아미노벤조산, 4-아미노-2-술포벤조산, 4-아미노-3-술포벤조산, 4-아미노-2-술포벤조산, 2-아미노피리미딘-5-카복실산, 6-아미노피리딘-3-카복실산, 5-아미노피리딘-2-카복실산, 5-아미노피라진-2-카복실산, 5-아미노피리미딘-2-카복실산, 2-(페닐)-p-아미노벤조산, 및 3-(페닐)-p-아미노벤조산으로 이루어진 군으로부터 1종 이상 선택하여 사용하는 것을 특징으로 하는 브랜치된 멀티블록 폴리벤즈이미다졸-벤즈아마이드 공중합체의 제조방법.
- 제 2항에 있어서,상기 방향족 및 헤테로방향족 디아미노 화합물은 벤젠-1,4-디아민, 2,5-디아미노벤젠술폰산, 피라진-2,5-디아민, 피리딘-2,5-디아민, 2-(페닐)벤젠-1,4-디아 민, 피리미딘-2,5-디아민, 2-(피리딘-3-일)벤젠-1,4-디아민, 2-(피리딘-2-일)벤젠-1,4-디아민, 2-(피리딘-2-일)벤젠-1,4-디아민, 2-(피리딘-5-일)벤젠-1,4-디아민, 4,4′-디아미노비페닐, 3,3′-디아미노비페닐, 3,4′-디아미노비페닐, 5-아미노-2-(p-아미노페닐)벤젠술폰산, 2-아미노-5-(p-아미노페닐)벤젠술폰산, 및 4,4´-디아미노-2-페닐비페닐로 이루어진 군으로부터 1종 이상 선택하여 사용하는 것을 특징으로 하는 브랜치된 멀티블록 폴리벤즈이미다졸-벤즈아마이드 공중합체의 제조방법.
- 제 2항에 있어서,상기 브랜치된 멀티블록 폴리벤즈이미다졸-벤즈아마이드 공중합체는 아졸계 AZ 반복단위의 수가 10개 이상이고, 아마이드계 AM 반복단위의 수가 1 이상인 것을 특징으로 하는 브랜치된 멀티블록 폴리벤즈이미다졸-벤즈아마이드 공중합체의 제조방법.
- 제 1항 기재의 멀티블록 폴리벤즈이미다졸-벤즈아마이드 공중합체로부터 제조되는 것을 특징으로 하는 멀티블록 폴리벤즈이미다졸-벤즈아마이드 공중합체 전해질막.
- 제 1항 기재의 멀티블록 폴리벤즈이미다졸-벤즈아마이드 공중합체의 폴리인산 용액을 지지체 상에 직접 도포한 후, 도포된 용액으로부터 막이 형성될 때까지 폴리인산 용매의 가수분해를 유도하여 제조하는 것을 특징으로 하는 멀티블록 폴리벤즈이미다졸-벤즈아마이드 공중합체 전해질막의 제조방법.
- 제 1항 기재의 멀티블록 폴리벤즈이미다졸-벤즈아마이드 공중합체로부터 제조되는 것을 특징으로 하는 멀티블록 폴리벤즈이미다졸-벤즈아마이드 공중합체 경점성 전해질 페이스트.
- 제 1항 기재의 멀티블록 폴리벤즈이미다졸-벤즈아마이드 공중합체의 폴리인산 용액에 소량의 물을 첨가하고 교반하여 폴리인산의 가수분해를 유도함과 동시에 남아있는 물을 제거하여 제조하는 것을 특징으로 하는 멀티블록 폴리벤즈이미다졸-벤즈아마이드 공중합체 경점성 전해질 페이스트의 제조방법.
- 제 17항에 있어서,상기 멀티블록 폴리벤즈이미다졸-벤즈아마이드 공중합체 경점성 전해질 페이스트는 인산 함유량이 50 내지 200 중량%인 것을 특징으로 하는 멀티블록 폴리벤즈이미다졸-벤즈아마이드 공중합체 경점성 전해질 페이스트의 제조방법.
- 제 14항 기재의 멀티블록 폴리벤즈이미다졸-벤즈아마이드 공중합체 전해질막및 제 16항 기재의 멀티블록 폴리벤즈이미다졸-벤즈아마이드 공중합체 경점성 전해질 페이스트로부터 제조되는 것을 특징으로 하는 막-전극 접합체.
- 제 14항 기재의 멀티블록 폴리벤즈이미다졸-벤즈아마이드 공중합체 전해질막에 제 16항 기재의 멀티블록 폴리벤즈이미다졸-벤즈아마이드 공중합체 경점성 전해질 페이스트 및 귀금속에 기초하는 촉매를 함유하는 전극을 피복하는 것을 특징으로 하는 막-전극 접합체의 제조방법.
- 제 19항 기재의 막-전극 접합체로부터 제조되는 것을 특징으로 하는 연료전지.
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KR1020050108722A KR100819676B1 (ko) | 2005-11-14 | 2005-11-14 | 브랜치된 멀티블록 폴리벤즈이미다졸-벤즈아마이드공중합체 및 제조방법, 이를 이용한 전해질막 및 전해질페이스트/겔 |
JP2007544285A JP4445553B2 (ja) | 2005-11-14 | 2006-08-22 | 分岐マルチブロックポリベンゾイミダゾール−ベンズアミド共重合体及びこれの製造方法、それから製造された電解質膜、硬粘性電解質ペースト/ゲル |
PCT/KR2006/003287 WO2007055459A1 (en) | 2005-11-14 | 2006-08-22 | Branched multiblock polybenzimidazole-benzamide copolymer and method for preparing the same, electrolyte membrane and paste/gel prepared therefrom |
DE112006000037T DE112006000037B4 (de) | 2005-11-14 | 2006-08-22 | Verzweigtes Multiblock-Polybenzimidazol-Benzamidcopolymer und Verfahren zur Herstellung desselben, Elektrolytmembran und daraus hergestellte Paste/Gel |
TW095131243A TWI316522B (en) | 2005-11-14 | 2006-08-25 | Branched multiblock polybenzimidazole-benzamide copolymer and method for preparing the same, electrolyte membrane and paste/gel prepared therefrom |
US11/593,471 US7632591B2 (en) | 2005-11-14 | 2006-11-07 | Branched multiblock polybenzimidazole-benzamide copolymer and method for preparing the same, electrolyte membrane and paste/gel prepared therefrom |
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WO2015088579A1 (en) | 2013-12-09 | 2015-06-18 | General Electric Company | Polymeric-metal composite electrode-based electrochemical device for generating oxidants |
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US7632591B2 (en) | 2009-12-15 |
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