JP5365075B2 - 燃料電池用接着性シリコーンゴム組成物及びセパレータシール用材料 - Google Patents
燃料電池用接着性シリコーンゴム組成物及びセパレータシール用材料 Download PDFInfo
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- JP5365075B2 JP5365075B2 JP2008161219A JP2008161219A JP5365075B2 JP 5365075 B2 JP5365075 B2 JP 5365075B2 JP 2008161219 A JP2008161219 A JP 2008161219A JP 2008161219 A JP2008161219 A JP 2008161219A JP 5365075 B2 JP5365075 B2 JP 5365075B2
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- fuel cell
- rubber composition
- silicone rubber
- adhesive silicone
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 40
- 239000000446 fuel Substances 0.000 title claims abstract description 38
- 229920002379 silicone rubber Polymers 0.000 title claims abstract description 33
- 239000004945 silicone rubber Substances 0.000 title claims abstract description 33
- 239000000853 adhesive Substances 0.000 title claims abstract description 29
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 27
- 239000000463 material Substances 0.000 title claims description 6
- 239000012528 membrane Substances 0.000 claims abstract description 29
- 239000003792 electrolyte Substances 0.000 claims abstract description 28
- 229920001296 polysiloxane Polymers 0.000 claims abstract description 12
- 239000005518 polymer electrolyte Substances 0.000 claims abstract description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 10
- 125000002723 alicyclic group Chemical group 0.000 claims abstract description 7
- 229920006136 organohydrogenpolysiloxane Polymers 0.000 claims abstract description 7
- 150000003961 organosilicon compounds Chemical class 0.000 claims abstract description 6
- 238000006459 hydrosilylation reaction Methods 0.000 claims abstract description 5
- -1 Nitrogen-containing compound Chemical class 0.000 claims description 28
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 25
- 229910052710 silicon Inorganic materials 0.000 claims description 17
- 125000003342 alkenyl group Chemical group 0.000 claims description 16
- 229920001971 elastomer Polymers 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- 239000003566 sealing material Substances 0.000 claims description 12
- 125000003700 epoxy group Chemical group 0.000 claims description 11
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 11
- 150000001875 compounds Chemical group 0.000 claims description 8
- 230000002093 peripheral effect Effects 0.000 claims description 8
- 239000011347 resin Substances 0.000 claims description 6
- 229920005989 resin Polymers 0.000 claims description 6
- 239000007809 chemical reaction catalyst Substances 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 230000006835 compression Effects 0.000 claims description 5
- 238000007906 compression Methods 0.000 claims description 5
- 229910052751 metal Inorganic materials 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 5
- 239000010703 silicon Substances 0.000 claims description 3
- 230000004956 cell adhesive effect Effects 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 abstract description 10
- 239000004593 Epoxy Substances 0.000 abstract description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 15
- 229920001577 copolymer Polymers 0.000 description 10
- 238000012360 testing method Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 125000005388 dimethylhydrogensiloxy group Chemical group 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 229910052697 platinum Inorganic materials 0.000 description 6
- 238000006116 polymerization reaction Methods 0.000 description 6
- 229920001843 polymethylhydrosiloxane Polymers 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 238000000465 moulding Methods 0.000 description 5
- WZJUBBHODHNQPW-UHFFFAOYSA-N 2,4,6,8-tetramethyl-1,3,5,7,2$l^{3},4$l^{3},6$l^{3},8$l^{3}-tetraoxatetrasilocane Chemical compound C[Si]1O[Si](C)O[Si](C)O[Si](C)O1 WZJUBBHODHNQPW-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 238000007259 addition reaction Methods 0.000 description 4
- 238000013329 compounding Methods 0.000 description 4
- 150000002430 hydrocarbons Chemical group 0.000 description 4
- 238000007789 sealing Methods 0.000 description 4
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 3
- 229910004283 SiO 4 Inorganic materials 0.000 description 3
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 150000002894 organic compounds Chemical class 0.000 description 3
- 238000010248 power generation Methods 0.000 description 3
- 150000003377 silicon compounds Chemical class 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 229920000557 Nafion® Polymers 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 239000004205 dimethyl polysiloxane Substances 0.000 description 2
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 2
- 239000003822 epoxy resin Substances 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000005011 phenolic resin Substances 0.000 description 2
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 2
- 229920000647 polyepoxide Polymers 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- KWEKXPWNFQBJAY-UHFFFAOYSA-N (dimethyl-$l^{3}-silanyl)oxy-dimethylsilicon Chemical compound C[Si](C)O[Si](C)C KWEKXPWNFQBJAY-UHFFFAOYSA-N 0.000 description 1
- QYLFHLNFIHBCPR-UHFFFAOYSA-N 1-ethynylcyclohexan-1-ol Chemical compound C#CC1(O)CCCCC1 QYLFHLNFIHBCPR-UHFFFAOYSA-N 0.000 description 1
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 description 1
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- PUNGSQUVTIDKNU-UHFFFAOYSA-N 2,4,6,8,10-pentamethyl-1,3,5,7,9,2$l^{3},4$l^{3},6$l^{3},8$l^{3},10$l^{3}-pentaoxapentasilecane Chemical compound C[Si]1O[Si](C)O[Si](C)O[Si](C)O[Si](C)O1 PUNGSQUVTIDKNU-UHFFFAOYSA-N 0.000 description 1
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 1
- QYXVDGZUXHFXTO-UHFFFAOYSA-L 3-oxobutanoate;platinum(2+) Chemical compound [Pt+2].CC(=O)CC([O-])=O.CC(=O)CC([O-])=O QYXVDGZUXHFXTO-UHFFFAOYSA-L 0.000 description 1
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 1
- 229910002012 Aerosil® Inorganic materials 0.000 description 1
- 229910002016 Aerosil® 200 Inorganic materials 0.000 description 1
- LYJHVEDILOKZCG-UHFFFAOYSA-N Allyl benzoate Chemical compound C=CCOC(=O)C1=CC=CC=C1 LYJHVEDILOKZCG-UHFFFAOYSA-N 0.000 description 1
- 229920002799 BoPET Polymers 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- MOVRNJGDXREIBM-UHFFFAOYSA-N aid-1 Chemical compound O=C1NC(=O)C(C)=CN1C1OC(COP(O)(=O)OC2C(OC(C2)N2C3=C(C(NC(N)=N3)=O)N=C2)COP(O)(=O)OC2C(OC(C2)N2C3=C(C(NC(N)=N3)=O)N=C2)COP(O)(=O)OC2C(OC(C2)N2C3=C(C(NC(N)=N3)=O)N=C2)COP(O)(=O)OC2C(OC(C2)N2C(NC(=O)C(C)=C2)=O)COP(O)(=O)OC2C(OC(C2)N2C3=C(C(NC(N)=N3)=O)N=C2)COP(O)(=O)OC2C(OC(C2)N2C3=C(C(NC(N)=N3)=O)N=C2)COP(O)(=O)OC2C(OC(C2)N2C3=C(C(NC(N)=N3)=O)N=C2)COP(O)(=O)OC2C(OC(C2)N2C(NC(=O)C(C)=C2)=O)COP(O)(=O)OC2C(OC(C2)N2C3=C(C(NC(N)=N3)=O)N=C2)COP(O)(=O)OC2C(OC(C2)N2C3=C(C(NC(N)=N3)=O)N=C2)COP(O)(=O)OC2C(OC(C2)N2C3=C(C(NC(N)=N3)=O)N=C2)COP(O)(=O)OC2C(OC(C2)N2C(NC(=O)C(C)=C2)=O)COP(O)(=O)OC2C(OC(C2)N2C3=C(C(NC(N)=N3)=O)N=C2)COP(O)(=O)OC2C(OC(C2)N2C3=C(C(NC(N)=N3)=O)N=C2)COP(O)(=O)OC2C(OC(C2)N2C3=C(C(NC(N)=N3)=O)N=C2)CO)C(O)C1 MOVRNJGDXREIBM-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- VHOLOZYRMQVHBK-UHFFFAOYSA-N benzotriazol-1-yl(trimethyl)silane Chemical compound C1=CC=C2N([Si](C)(C)C)N=NC2=C1 VHOLOZYRMQVHBK-UHFFFAOYSA-N 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000005998 bromoethyl group Chemical group 0.000 description 1
- PVEOYINWKBTPIZ-UHFFFAOYSA-N but-3-enoic acid Chemical compound OC(=O)CC=C PVEOYINWKBTPIZ-UHFFFAOYSA-N 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical compound [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 239000002803 fossil fuel Substances 0.000 description 1
- 229910021485 fumed silica Inorganic materials 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- NYMPGSQKHIOWIO-UHFFFAOYSA-N hydroxy(diphenyl)silicon Chemical class C=1C=CC=CC=1[Si](O)C1=CC=CC=C1 NYMPGSQKHIOWIO-UHFFFAOYSA-N 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- UIUXUFNYAYAMOE-UHFFFAOYSA-N methylsilane Chemical compound [SiH3]C UIUXUFNYAYAMOE-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 150000001282 organosilanes Chemical class 0.000 description 1
- 125000005375 organosiloxane group Chemical group 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- PARWUHTVGZSQPD-UHFFFAOYSA-N phenylsilane Chemical group [SiH3]C1=CC=CC=C1 PARWUHTVGZSQPD-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- CLSUSRZJUQMOHH-UHFFFAOYSA-L platinum dichloride Chemical compound Cl[Pt]Cl CLSUSRZJUQMOHH-UHFFFAOYSA-L 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 239000009719 polyimide resin Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- QTECDUFMBMSHKR-UHFFFAOYSA-N prop-2-enyl prop-2-enoate Chemical compound C=CCOC(=O)C=C QTECDUFMBMSHKR-UHFFFAOYSA-N 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 239000012495 reaction gas Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000003014 reinforcing effect Effects 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000000725 trifluoropropyl group Chemical group [H]C([H])(*)C([H])([H])C(F)(F)F 0.000 description 1
- XMMPIRNYESGWOO-UHFFFAOYSA-N trimethyl-[methyl-[methyl-[methyl-[methyl(trimethylsilyloxy)silyl]oxysilyl]oxysilyl]oxysilyl]oxysilane Chemical compound C[Si](C)(C)O[SiH](C)O[SiH](C)O[SiH](C)O[SiH](C)O[Si](C)(C)C XMMPIRNYESGWOO-UHFFFAOYSA-N 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
Images
Classifications
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M8/00—Fuel cells; Manufacture thereof
- H01M8/02—Details
- H01M8/0271—Sealing or supporting means around electrodes, matrices or membranes
- H01M8/028—Sealing means characterised by their material
- H01M8/0284—Organic resins; Organic polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/10—Metal compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/54—Silicon-containing compounds
- C08K5/541—Silicon-containing compounds containing oxygen
- C08K5/5435—Silicon-containing compounds containing oxygen containing oxygen in a ring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J183/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Adhesives based on derivatives of such polymers
- C09J183/04—Polysiloxanes
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
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Description
請求項1:
固体高分子型燃料電池の電解質膜又は電解質膜及びその周縁部に接着するための材料であって、
(A)一分子中に珪素原子に結合したアルケニル基を2個以上含有するオルガノポリシロキサン 100質量部、
(B)一分子中に珪素原子に結合した水素原子を少なくとも2個含有し、エポキシ基を含有しないオルガノハイドロジェンポリシロキサン 0.5〜20質量部、
(C)ヒドロシリル化反応触媒 有効量、
(D)一分子中に、フェニル骨格を少なくとも1個有すると共に、反応性基として少なくとも1個の脂環式エポキシ基及び少なくとも1個の珪素原子に結合した水素原子のみを有する有機珪素化合物 0.1〜50質量部
を含有することを特徴とする燃料電池用接着性シリコーンゴム組成物。
請求項2:
(A)成分中の珪素原子結合アルケニル基に対する(B)成分中の珪素原子に結合した水素原子(Si−H基)のモル比が、Si−H基/アルケニル基=0.8〜3.0の範囲であることを特徴とする請求項1記載の燃料電池用接着性シリコーンゴム組成物。
請求項3:
(D)成分が、下記化合物群から選ばれるものであることを特徴とする請求項1又は2記載の燃料電池用接着性シリコーンゴム組成物。
更に、圧縮永久歪改良剤として、
(E)窒素含有化合物 0.1〜50質量部
を添加することを特徴とする請求項1乃至3のいずれか1項記載の燃料電池用接着性シリコーンゴム組成物。
請求項5:
(E)窒素含有化合物が、トリアゾール化合物及びイミダゾール化合物からなる群より選ばれる少なくとも1種の窒素含有化合物であることを特徴とする請求項4記載の燃料電池用接着性シリコーンゴム組成物。
請求項6:
周縁部が金属製又は有機樹脂製のセパレータ部材である請求項1乃至5のいずれか1項記載の燃料電池用接着性シリコーンゴム組成物。
請求項7:
請求項1乃至6のいずれか1項記載の燃料電池用接着性シリコーンゴム組成物からなる固体高分子型燃料電池のセパレータシール用材料。
この場合、セパレータとしては、金属製あるいはカーボン等の導電性粉末をエポキシ樹脂、フェノール樹脂、ポリイミド樹脂などのバインダー樹脂により一体成型された有機樹脂製の基板とするものなどが好適に使用される。
本発明の(A)成分の一分子中に平均2個以上のアルケニル基を有するオルガノポリシロキサンとしては、下記平均組成式(1)で示されるものを用いることができる。
R1 aSiO(4-a)/2 (1)
R2 bHcSiO(4-b-c)/2 (2)
(式中、R2は炭素数1〜10の置換又は非置換の一価炭化水素基である。またbは0.7〜2.1、cは0.001〜1.0で、かつb+cは0.8〜3.0を満足する正数である。)
で示され、一分子中に少なくとも2個(通常、2〜300個)、好ましくは3個以上(例えば、3〜200個)、より好ましくは3〜100個、更に好ましくは4〜50個の珪素原子結合水素原子を有するものが好適に用いられる。ここでR2の一価炭化水素基としては、R1で例示したものと同様のものを挙げることができるが、脂肪族不飽和基を有しないものが好ましい。更に、エポキシ基も含有しない。また、bは好ましくは0.8〜2.0、cは好ましくは0.01〜1.0、b+cは好ましくは1.0〜2.5であり、オルガノハイドロジェンポリシロキサンの分子構造は、直鎖状、環状、分岐状、三次元網目状のいずれの構造であってもよい。この場合、一分子中の珪素原子の数(又は重合度)は2〜300個、特に4〜150個程度の室温(25℃)で液状のものが好適に用いられる。なお、珪素原子に結合する水素原子は分子鎖末端、分子鎖の途中のいずれに位置していてもよく、両方に位置するものであってもよい。
1,3,5,7−テトラメチルシクロテトラシロキサン1モルに対してα−メチルスチレン、セロキサイド2000(ダイセル化学工業社製)を、白金触媒を用いてそれぞれ1モル滴下付加させて接着助剤1を得た。
1,1,1,3,5,7,9,11,11,11−デカメチルヘキサシロキサン1モルに対してα−メチルスチレンを1モル、セロキサイド2000(ダイセル化学工業社製)を2モル、白金触媒を用いて滴下付加させて接着助剤2を得た。
1,3,5,7−テトラメチルシクロテトラシロキサン1モルに対してα−メチルスチレンのみ、あるいはセロキサイド2000(ダイセル化学工業社製)のみを、白金触媒を用いてそれぞれ1モル滴下付加させて接着助剤3,4を得た。
両末端がジメチルビニルシロキシ基で封鎖された平均重合度が500のジメチルポリシロキサン(1)68部、比表面積が200m2/gであるヒュームドシリカ(日本アエロジル社製、アエロジル200)32部、ヘキサメチルジシラザン5部、水2.0部を室温で30分混合後、150℃に昇温し、3時間撹拌を続けて冷却し、シリコーンゴムベースを得た。このシリコーンゴムベース100部に、両末端がジメチルビニルシロキシ基で封鎖された平均重合度が250のジメチルシロキサン40部を入れ、30分撹拌を続けた。ここに架橋剤として、両末端及び側鎖にSi−H基を有するメチルハイドロジェンポリシロキサン(重合度17、Si−H基量0.0060mol/g)を2.2部[Si−H基/アルケニル基=1.5]、反応制御剤としてエチニルシクロヘキサノール0.05部を添加し、15分撹拌を続けてシリコーンゴムベース1を得た。
実施例1において接着助剤1を接着助剤5に換えたものを作製し、同様な試験を行った。
2 ゴム
Claims (7)
- 固体高分子型燃料電池の電解質膜又は電解質膜及びその周縁部に接着するための材料であって、
(A)一分子中に珪素原子に結合したアルケニル基を2個以上含有するオルガノポリシロキサン 100質量部、
(B)一分子中に珪素原子に結合した水素原子を少なくとも2個含有し、エポキシ基を含有しないオルガノハイドロジェンポリシロキサン 0.5〜20質量部、
(C)ヒドロシリル化反応触媒 有効量、
(D)一分子中に、フェニル骨格を少なくとも1個有すると共に、反応性基として少なくとも1個の脂環式エポキシ基及び少なくとも1個の珪素原子に結合した水素原子のみを有する有機珪素化合物 0.1〜50質量部
を含有することを特徴とする燃料電池用接着性シリコーンゴム組成物。 - (A)成分中の珪素原子結合アルケニル基に対する(B)成分中の珪素原子に結合した水素原子(Si−H基)のモル比が、Si−H基/アルケニル基=0.8〜3.0の範囲であることを特徴とする請求項1記載の燃料電池用接着性シリコーンゴム組成物。
- 更に、圧縮永久歪改良剤として、
(E)窒素含有化合物 0.1〜50質量部
を添加することを特徴とする請求項1乃至3のいずれか1項記載の燃料電池用接着性シリコーンゴム組成物。 - (E)窒素含有化合物が、トリアゾール化合物及びイミダゾール化合物からなる群より選ばれる少なくとも1種の窒素含有化合物であることを特徴とする請求項4記載の燃料電池用接着性シリコーンゴム組成物。
- 周縁部が金属製又は有機樹脂製のセパレータ部材である請求項1乃至5のいずれか1項記載の燃料電池用接着性シリコーンゴム組成物。
- 請求項1乃至6のいずれか1項記載の燃料電池用接着性シリコーンゴム組成物からなる固体高分子型燃料電池のセパレータシール用材料。
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EP3113271A1 (en) | 2015-06-30 | 2017-01-04 | Shin-Etsu Chemical Co., Ltd. | Sealing material for solid polymer fuel cell separator, separator seal and separator |
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US7695840B2 (en) | 2006-12-08 | 2010-04-13 | Eveready Battery Co., Inc. | Electrochemical cell having a deposited gas electrode |
JP4513987B2 (ja) * | 2007-12-07 | 2010-07-28 | 本田技研工業株式会社 | 固体高分子型燃料電池セパレータ用シール材料、セパレータシール、及びセパレータ |
JP5091890B2 (ja) * | 2009-03-02 | 2012-12-05 | 本田技研工業株式会社 | 燃料電池用接着剤及びこれを用いて作製した膜電極構造体 |
US8722277B2 (en) | 2009-08-07 | 2014-05-13 | Nissan Motor Co., Ltd. | Fuel cell and method for manufacturing same |
JP5387517B2 (ja) * | 2010-06-18 | 2014-01-15 | 信越化学工業株式会社 | 熱硬化性フルオロポリエーテル系接着剤組成物及びその接着方法 |
CN102532900B (zh) * | 2010-12-20 | 2014-04-30 | 常州化学研究所 | 功率型led封装用有机硅透镜材料 |
JP5748512B2 (ja) * | 2011-03-07 | 2015-07-15 | 信越化学工業株式会社 | 付加硬化型自己接着性シリコーンゴム組成物 |
DE102012213260A1 (de) * | 2012-07-27 | 2014-01-30 | Wacker Chemie Ag | Additionsvernetzende Siliconzusammensetzung mit niedrigem Druckverformungsrest |
JP6059472B2 (ja) * | 2012-09-07 | 2017-01-11 | 東レ・ダウコーニング株式会社 | 硬化性シリコーン組成物および光半導体装置 |
JP5867383B2 (ja) * | 2012-12-21 | 2016-02-24 | 信越化学工業株式会社 | 付加硬化型自己接着性シリコーンゴム組成物 |
EP2832812A1 (en) * | 2013-07-29 | 2015-02-04 | Nitto Shinko Corporation | Sealant |
CN103483372B (zh) * | 2013-09-02 | 2015-10-14 | 上海硅普化学品有限公司 | 3,4-环氧环己基乙基甲基环硅氧烷及其制备方法 |
WO2016138660A1 (en) * | 2015-03-05 | 2016-09-09 | Dow Corning Toray Co., Ltd. | Curable organopolysiloxane composition, a use thereof, and a laminate prepared from the composition |
KR101664740B1 (ko) | 2015-09-07 | 2016-10-12 | 현대자동차주식회사 | 연료전지용 가스켓 |
US10138258B2 (en) * | 2015-11-19 | 2018-11-27 | Milliken & Company | Cyclic siloxane compounds and compositions comprising the same |
WO2017154777A1 (ja) * | 2016-03-09 | 2017-09-14 | 株式会社スリーボンド | 硬化性樹脂組成物、燃料電池およびシール方法 |
CN107652689A (zh) * | 2017-10-17 | 2018-02-02 | 成都瑞琦科技实业股份有限公司 | 一种传感膜、制备方法及其应用 |
DE102018217291A1 (de) * | 2018-10-10 | 2020-04-16 | Robert Bosch Gmbh | Verfahren zum Abdichten einer Brennstoffzelle |
CN110951411A (zh) * | 2019-12-31 | 2020-04-03 | 广州机械科学研究院有限公司 | 一种单组分加成型有机硅密封粘接剂及其制备方法 |
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JPS5224258A (en) * | 1975-08-19 | 1977-02-23 | Toray Silicone Co Ltd | Curable organopolysiloxane composition |
US5536803A (en) | 1994-06-06 | 1996-07-16 | Shin-Etsu Chemical Co., Ltd. | Adhesive silicone compositions |
JP3317092B2 (ja) | 1994-06-06 | 2002-08-19 | 信越化学工業株式会社 | シリコーン接着剤組成物及びシリコーン硬化物と有機樹脂との複合体 |
JP4221545B2 (ja) * | 2001-01-05 | 2009-02-12 | 信越化学工業株式会社 | シリコーンゴム接着剤組成物並びにシリコーンゴムと熱可塑性樹脂との一体成形体及びその製造方法 |
JP3998438B2 (ja) * | 2001-06-22 | 2007-10-24 | 信越化学工業株式会社 | 固体高分子型燃料電池用接着剤 |
DE10204893A1 (de) * | 2002-02-06 | 2003-08-14 | Ge Bayer Silicones Gmbh & Co | Selbsthaftende additionsvernetzende Silikonkautschukmischungen, ein Verfahren zu deren Herstellung, Verfahren zur Herstellung von Verbund-Formteilen und deren Verwendung |
JP2004331820A (ja) * | 2003-05-08 | 2004-11-25 | Shin Etsu Chem Co Ltd | 移動体用シリコーンゴム接着剤組成物 |
JP4404205B2 (ja) | 2004-12-24 | 2010-01-27 | 本田技研工業株式会社 | ポリフェニレンスルフィド樹脂−シリコーンゴム複合材料、並びに燃料電池用セパレータ及びそれを用いた燃料電池 |
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EP3113271A1 (en) | 2015-06-30 | 2017-01-04 | Shin-Etsu Chemical Co., Ltd. | Sealing material for solid polymer fuel cell separator, separator seal and separator |
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ATE507275T1 (de) | 2011-05-15 |
US8158738B2 (en) | 2012-04-17 |
CN101679833A (zh) | 2010-03-24 |
WO2008156218A2 (en) | 2008-12-24 |
CA2691521C (en) | 2015-10-13 |
EP2158285B1 (en) | 2011-04-27 |
CN101679833B (zh) | 2012-07-25 |
DE602008006549D1 (de) | 2011-06-09 |
US20100216920A1 (en) | 2010-08-26 |
WO2008156218A3 (en) | 2009-06-04 |
JP2009026752A (ja) | 2009-02-05 |
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EP2158285A2 (en) | 2010-03-03 |
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