WO2022215528A1 - Composition de résine et matériau élastomère comprenant ladite composition de résine - Google Patents
Composition de résine et matériau élastomère comprenant ladite composition de résine Download PDFInfo
- Publication number
- WO2022215528A1 WO2022215528A1 PCT/JP2022/013628 JP2022013628W WO2022215528A1 WO 2022215528 A1 WO2022215528 A1 WO 2022215528A1 JP 2022013628 W JP2022013628 W JP 2022013628W WO 2022215528 A1 WO2022215528 A1 WO 2022215528A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- resin composition
- silica particles
- multilayer graphene
- weight
- loss tangent
- Prior art date
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- 239000011342 resin composition Substances 0.000 title claims abstract description 91
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 69
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- LEJBBGNFPAFPKQ-UHFFFAOYSA-N 2-(2-prop-2-enoyloxyethoxy)ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOC(=O)C=C LEJBBGNFPAFPKQ-UHFFFAOYSA-N 0.000 description 6
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- 229920002595 Dielectric elastomer Polymers 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
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- MYWOJODOMFBVCB-UHFFFAOYSA-N 1,2,6-trimethylphenanthrene Chemical compound CC1=CC=C2C3=CC(C)=CC=C3C=CC2=C1C MYWOJODOMFBVCB-UHFFFAOYSA-N 0.000 description 1
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- WMYINDVYGQKYMI-UHFFFAOYSA-N 2-[2,2-bis(hydroxymethyl)butoxymethyl]-2-ethylpropane-1,3-diol Chemical compound CCC(CO)(CO)COCC(CC)(CO)CO WMYINDVYGQKYMI-UHFFFAOYSA-N 0.000 description 1
- FDSUVTROAWLVJA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OCC(CO)(CO)COCC(CO)(CO)CO FDSUVTROAWLVJA-UHFFFAOYSA-N 0.000 description 1
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- YAHUNCKQQQOYHZ-UHFFFAOYSA-N OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OCC(CO)(CO)CO.OCC(CO)(CO)CO.OCC(CO)(CO)CO.OCC(CO)(CO)CO.OCC(CO)(CO)CO Chemical compound OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OCC(CO)(CO)CO.OCC(CO)(CO)CO.OCC(CO)(CO)CO.OCC(CO)(CO)CO.OCC(CO)(CO)CO YAHUNCKQQQOYHZ-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 229910018557 Si O Inorganic materials 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 235000010724 Wisteria floribunda Nutrition 0.000 description 1
- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 description 1
- JOBBTVPTPXRUBP-UHFFFAOYSA-N [3-(3-sulfanylpropanoyloxy)-2,2-bis(3-sulfanylpropanoyloxymethyl)propyl] 3-sulfanylpropanoate Chemical compound SCCC(=O)OCC(COC(=O)CCS)(COC(=O)CCS)COC(=O)CCS JOBBTVPTPXRUBP-UHFFFAOYSA-N 0.000 description 1
- MPIAGWXWVAHQBB-UHFFFAOYSA-N [3-prop-2-enoyloxy-2-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]methyl]-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C MPIAGWXWVAHQBB-UHFFFAOYSA-N 0.000 description 1
- FHLPGTXWCFQMIU-UHFFFAOYSA-N [4-[2-(4-prop-2-enoyloxyphenyl)propan-2-yl]phenyl] prop-2-enoate Chemical class C=1C=C(OC(=O)C=C)C=CC=1C(C)(C)C1=CC=C(OC(=O)C=C)C=C1 FHLPGTXWCFQMIU-UHFFFAOYSA-N 0.000 description 1
- ANCHPZQGZBCDBK-UHFFFAOYSA-N [PH2](O)=O.C1(=CC=CC=C1)C=1C(=C(C(=O)[Li])C(=CC1C)C)C Chemical compound [PH2](O)=O.C1(=CC=CC=C1)C=1C(=C(C(=O)[Li])C(=CC1C)C)C ANCHPZQGZBCDBK-UHFFFAOYSA-N 0.000 description 1
- KYIKRXIYLAGAKQ-UHFFFAOYSA-N abcn Chemical compound C1CCCCC1(C#N)N=NC1(C#N)CCCCC1 KYIKRXIYLAGAKQ-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 239000005456 alcohol based solvent Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 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
- SNBMGLUIIGFNFE-UHFFFAOYSA-N benzyl n,n-diethylcarbamodithioate Chemical compound CCN(CC)C(=S)SCC1=CC=CC=C1 SNBMGLUIIGFNFE-UHFFFAOYSA-N 0.000 description 1
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 1
- LWMFAFLIWMPZSX-UHFFFAOYSA-N bis[2-(4,5-dihydro-1h-imidazol-2-yl)propan-2-yl]diazene Chemical compound N=1CCNC=1C(C)(C)N=NC(C)(C)C1=NCCN1 LWMFAFLIWMPZSX-UHFFFAOYSA-N 0.000 description 1
- QDVNNDYBCWZVTI-UHFFFAOYSA-N bis[4-(ethylamino)phenyl]methanone Chemical compound C1=CC(NCC)=CC=C1C(=O)C1=CC=C(NCC)C=C1 QDVNNDYBCWZVTI-UHFFFAOYSA-N 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- HDFRDWFLWVCOGP-UHFFFAOYSA-N carbonothioic O,S-acid Chemical class OC(S)=O HDFRDWFLWVCOGP-UHFFFAOYSA-N 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 150000004292 cyclic ethers Chemical group 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
- 238000011161 development Methods 0.000 description 1
- 125000004386 diacrylate group Chemical group 0.000 description 1
- 239000003989 dielectric material Substances 0.000 description 1
- PJIFJEUHCQYNHO-UHFFFAOYSA-N diethoxy-(3-isocyanatopropyl)-methylsilane Chemical compound CCO[Si](C)(OCC)CCCN=C=O PJIFJEUHCQYNHO-UHFFFAOYSA-N 0.000 description 1
- OTARVPUIYXHRRB-UHFFFAOYSA-N diethoxy-methyl-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](C)(OCC)CCCOCC1CO1 OTARVPUIYXHRRB-UHFFFAOYSA-N 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- WHGNXNCOTZPEEK-UHFFFAOYSA-N dimethoxy-methyl-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](C)(OC)CCCOCC1CO1 WHGNXNCOTZPEEK-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 150000002019 disulfides Chemical class 0.000 description 1
- 239000012990 dithiocarbamate Substances 0.000 description 1
- 150000004659 dithiocarbamates Chemical class 0.000 description 1
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 1
- 125000003438 dodecyl 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])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 description 1
- 235000019414 erythritol Nutrition 0.000 description 1
- 229940009714 erythritol Drugs 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- WRXACPLDXDLMMQ-UHFFFAOYSA-N ethene;4-(2-phenylpropan-2-yl)phenol Chemical group C=C.C=1C=C(O)C=CC=1C(C)(C)C1=CC=CC=C1 WRXACPLDXDLMMQ-UHFFFAOYSA-N 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- HOXINJBQVZWYGZ-UHFFFAOYSA-N fenbutatin oxide Chemical compound C=1C=CC=CC=1C(C)(C)C[Sn](O[Sn](CC(C)(C)C=1C=CC=CC=1)(CC(C)(C)C=1C=CC=CC=1)CC(C)(C)C=1C=CC=CC=1)(CC(C)(C)C=1C=CC=CC=1)CC(C)(C)C1=CC=CC=C1 HOXINJBQVZWYGZ-UHFFFAOYSA-N 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000007850 fluorescent dye Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 125000003827 glycol group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
- LNMQRPPRQDGUDR-UHFFFAOYSA-N hexyl prop-2-enoate Chemical compound CCCCCCOC(=O)C=C LNMQRPPRQDGUDR-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 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
- 239000012948 isocyanate Substances 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- JUYQFRXNMVWASF-UHFFFAOYSA-M lithium;phenyl-(2,4,6-trimethylbenzoyl)phosphinate Chemical compound [Li+].CC1=CC(C)=CC(C)=C1C(=O)P([O-])(=O)C1=CC=CC=C1 JUYQFRXNMVWASF-UHFFFAOYSA-M 0.000 description 1
- 125000005439 maleimidyl group Chemical group C1(C=CC(N1*)=O)=O 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- YDKNBNOOCSNPNS-UHFFFAOYSA-N methyl 1,3-benzoxazole-2-carboxylate Chemical compound C1=CC=C2OC(C(=O)OC)=NC2=C1 YDKNBNOOCSNPNS-UHFFFAOYSA-N 0.000 description 1
- ZQMHJBXHRFJKOT-UHFFFAOYSA-N methyl 2-[(1-methoxy-2-methyl-1-oxopropan-2-yl)diazenyl]-2-methylpropanoate Chemical compound COC(=O)C(C)(C)N=NC(C)(C)C(=O)OC ZQMHJBXHRFJKOT-UHFFFAOYSA-N 0.000 description 1
- PHQOGHDTIVQXHL-UHFFFAOYSA-N n'-(3-trimethoxysilylpropyl)ethane-1,2-diamine Chemical compound CO[Si](OC)(OC)CCCNCCN PHQOGHDTIVQXHL-UHFFFAOYSA-N 0.000 description 1
- MQWFLKHKWJMCEN-UHFFFAOYSA-N n'-[3-[dimethoxy(methyl)silyl]propyl]ethane-1,2-diamine Chemical compound CO[Si](C)(OC)CCCNCCN MQWFLKHKWJMCEN-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000002055 nanoplate Substances 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
- MDYPDLBFDATSCF-UHFFFAOYSA-N nonyl prop-2-enoate Chemical compound CCCCCCCCCOC(=O)C=C MDYPDLBFDATSCF-UHFFFAOYSA-N 0.000 description 1
- UCUPUEARJPTGKU-UHFFFAOYSA-N octadecyl 3-sulfanylpropanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCS UCUPUEARJPTGKU-UHFFFAOYSA-N 0.000 description 1
- ANISOHQJBAQUQP-UHFFFAOYSA-N octyl prop-2-enoate Chemical compound CCCCCCCCOC(=O)C=C ANISOHQJBAQUQP-UHFFFAOYSA-N 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- LEVJVKGPFAQPOI-UHFFFAOYSA-N phenylmethanone Chemical compound O=[C]C1=CC=CC=C1 LEVJVKGPFAQPOI-UHFFFAOYSA-N 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 239000002952 polymeric resin Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- FZYCEURIEDTWNS-UHFFFAOYSA-N prop-1-en-2-ylbenzene Chemical compound CC(=C)C1=CC=CC=C1.CC(=C)C1=CC=CC=C1 FZYCEURIEDTWNS-UHFFFAOYSA-N 0.000 description 1
- 230000001902 propagating effect Effects 0.000 description 1
- BWJUFXUULUEGMA-UHFFFAOYSA-N propan-2-yl propan-2-yloxycarbonyloxy carbonate Chemical compound CC(C)OC(=O)OOC(=O)OC(C)C BWJUFXUULUEGMA-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- KOPQZJAYZFAPBC-UHFFFAOYSA-N propanoyl propaneperoxoate Chemical compound CCC(=O)OOC(=O)CC KOPQZJAYZFAPBC-UHFFFAOYSA-N 0.000 description 1
- YPVDWEHVCUBACK-UHFFFAOYSA-N propoxycarbonyloxy propyl carbonate Chemical compound CCCOC(=O)OOC(=O)OCCC YPVDWEHVCUBACK-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000004080 punching Methods 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 125000005372 silanol group Chemical group 0.000 description 1
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Inorganic materials [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000004079 stearyl 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])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])[H] 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- NMOALOSNPWTWRH-UHFFFAOYSA-N tert-butyl 7,7-dimethyloctaneperoxoate Chemical compound CC(C)(C)CCCCCC(=O)OOC(C)(C)C NMOALOSNPWTWRH-UHFFFAOYSA-N 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 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
- WMXCDAVJEZZYLT-UHFFFAOYSA-N tert-butylthiol Chemical compound CC(C)(C)S WMXCDAVJEZZYLT-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- NBXZNTLFQLUFES-UHFFFAOYSA-N triethoxy(propyl)silane Chemical group CCC[Si](OCC)(OCC)OCC NBXZNTLFQLUFES-UHFFFAOYSA-N 0.000 description 1
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F292/00—Macromolecular compounds obtained by polymerising monomers on to inorganic materials
-
- 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
- C08K3/02—Elements
- C08K3/04—Carbon
-
- 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
- C08K3/34—Silicon-containing compounds
- C08K3/36—Silica
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/04—Homopolymers or copolymers of esters
Definitions
- the present invention comprises a resin composition that has excellent mechanical properties such as extensibility and toughness and can be suitably used as an elastomer material that exhibits excellent dielectric properties such as a high dielectric constant, and the resin composition. It relates to elastomeric materials.
- the size of the communication device can be further reduced by increasing the dielectric constant of the antenna substrate incorporated in the communication device.
- the dielectric constant indicates the degree of polarization inside the dielectric. The higher the dielectric constant of the antenna substrate, the shorter the wavelength of the signal propagating through the circuit formed on the substrate, and the higher the frequency of the signal. In other words, by using a substrate with a high dielectric constant, it is possible to reduce the size of the circuit and the size of the communication device by increasing the frequency.
- a high dielectric ceramic substrate is known as a substrate with a high dielectric constant.
- ceramics are not suitable for complex-shaped antennas because they have very poor workability.
- Elastomer materials typified by rubber, are used in automobiles, industrial products, and living materials because of their excellent flexibility and toughness, their ability to conform to complex shapes, and their durability against large deformations, in addition to their workability. It is widely used as a component of many products.
- Patent Document 1 discloses a highly dielectric elastomer composition obtained by blending an elastomer with a highly dielectric ceramic powder. Since most of the constituent components of the highly dielectric elastomer composition are inorganic substances, it is difficult to utilize the excellent mechanical properties such as flexibility of the elastomer.
- the present invention solves the above problems, and in particular, has excellent mechanical properties such as elongation and toughness, and has excellent properties such as a sufficiently high relative permittivity and a sufficiently low dielectric loss tangent.
- An object of the present invention is to provide a resin composition that can be suitably used as an elastomer material exhibiting dielectric properties, and an elastomer material comprising the resin composition.
- the present inventors have achieved the above object by providing a resin composition containing a polyacrylate resin, silica particles and multilayer graphene, wherein the total amount of the polyacrylate resin, silica particles and multilayer graphene is: The content of the silica particles is 8 to 62% by weight, The content of the multilayer graphene is 1 to 8% by weight, The total content of the silica particles and the multilayer graphene is 15 to 62% by weight, The inventors have found that the above resin composition can achieve the above-described characteristics, and have reached the present invention.
- the present invention provides a novel resin composition.
- the resin composition of the invention is particularly suitable as an elastomer material.
- Elastomer materials made from the resin composition of the present invention are excellent in dielectric properties such as a high dielectric constant and a low rate of change in dielectric loss tangent, and are excellent in mechanical properties such as extensibility and toughness.
- FIG. 1 is a stress/strain curve of the resin composition obtained in Example 1; 4 is a stress/strain curve of the resin composition obtained in Example 2.
- FIG. 4 is a stress/strain curve of the resin composition obtained in Example 3.
- 4 is a stress/strain curve of the resin composition obtained in Comparative Example 1.
- the resin composition of the present invention contains at least a polyacrylate resin, silica particles and multilayer graphene.
- the polyacrylate resin contained in the resin composition will be described.
- the polyacrylate resin preferably contains an acrylate monomer (A) represented by the following general formula (1) as a monomer unit.
- R 0 represents a hydrogen atom, a methyl group or an ethyl group, preferably a hydrogen atom or a methyl group, more preferably a methyl group.
- R 1 represents a hydrogen atom or a methyl group, preferably a methyl group.
- n represents an integer of 1-9, preferably 1-5, more preferably 1-3, even more preferably 1-2, most preferably 2;
- the acrylate monomer (A) represented by the general formula (1) can be made into an acrylate resin by thermal polymerization or photopolymerization.
- acrylate monomers represented by formula (1) include 2-methoxyethyl acrylate, 2-methoxyethyl methacrylate, diethylene glycol monomethyl ether acrylate, diethylene glycol monomethyl ether methacrylate, triethylene glycol monomethyl ether acrylate, and triethylene glycol monomethyl.
- 2-methoxyethyl acrylate, 2-methoxyethyl methacrylate, and diethylene glycol monomethyl are preferred from the viewpoint of the dispersibility of silica particles and the physical properties of the resulting resin composition (especially the viewpoint of further improvement in mechanical properties and dielectric properties).
- Ether acrylate diethylene glycol monomethyl ether methacrylate, triethylene glycol monomethyl ether acrylate, triethylene glycol monomethyl ether methacrylate, more preferably 2-methoxyethyl acrylate, diethylene glycol monomethyl ether acrylate, diethylene glycol monomethyl ether methacrylate, triethylene glycol monomethyl ether methacrylate, and more More preferred are 2-methoxyethyl acrylate and diethylene glycol monomethyl ether methacrylate. Most preferred is diethylene glycol monomethyl ether methacrylate.
- the acrylate monomer represented by formula (1) may be used alone or in combination as long as the effects of the present invention are not impaired.
- the content of the acrylate monomer (A) is not particularly limited. or more), and from the viewpoint of further improving mechanical properties and dielectric properties, it is preferably 50 mol% or more, more preferably 70 mol% or more, still more preferably 90 mol% or more, and fully preferably 99 mol% Above, more preferably 100 mol %.
- the content of 100 mol % means that the polyacrylate resin contains the acrylate monomer (A) alone as a monomer unit.
- bifunctional or higher functional acrylate monomer may be used as a monomer unit as a cross-linking agent.
- bifunctional acrylate monomers include ethylene glycol diacrylate, EO-modified bisphenol A diacrylate, 1,4-butanediol diacrylate, diethylene glycol diacrylate, 1,6-hexanediol diacrylate, neopentyl glycol diacrylate, and trimethylol.
- Trifunctional acrylate monomers such as propane diacrylate and polyethylene glycol diacrylate (polyethylene glycol chain molecular weight of 100 to 10000), trimethylolpropane triacrylate, pentaerythritol triacrylate and the like, and pentaerythritol tetraacrylate as tetrafunctional or higher acrylate monomers , dipentaerythritol pentaacrylate, dipentaerythritol hexaacrylate, tripentaerythritol octaacrylate, tetrapentaerythritol decaacrylate, pentapentaerythritol dodecaacrylate and the like.
- a bifunctional acrylate monomer more preferably ethylene glycol diacrylate, 1,4-butanediol diacrylate, diethylene glycol diacrylate, more preferably diethylene glycol diacrylate.
- Bifunctional or higher functional acrylates may be used alone or in combination as long as the effects of the present invention are not impaired.
- the resulting acrylate resin when using an acrylate monomer in which R 1 is a hydrogen atom, the resulting acrylate resin has a glass transition point that is significantly below zero and has high viscosity, making handling difficult. It is preferred to use a difunctional or higher acrylate monomer as a cross-linking agent.
- the difunctional or higher acrylate monomer is less than 5 mol%, preferably less than 2 mol%, more preferably less than 1 mol%, even more preferably less than 0.6 mol%, relative to 100 mol% of all monomer units.
- a range of amounts may be included in the resin composition.
- the content of the above bifunctional or higher acrylates is 5 mol % or more, the tensile elongation at break of the elastomer material is remarkably lowered.
- the polyacrylate resin contained in the resin composition of the present invention may contain a silane coupling agent represented by the following general formula (2) as a monomer unit.
- R2 represents a hydrogen atom or a methyl group, preferably a methyl group.
- R 3 represents a methoxy or ethoxy group, preferably a methoxy group.
- R 4 represents a methyl, methoxy or ethoxy group, preferably a methyl or methoxy group.
- silane coupling agent represented by formula (2) examples include 3-methacryloxypropylmethyldimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-methacryloxypropylmethyldiethoxysilane, 3-methacryloxypropylmethyldiethoxysilane, and 3-methacryloxypropylmethyldimethoxysilane. roxypropyltriethoxysilane, 3-acryloxypropyltrimethoxysilane and the like. 3-methacryloxypropylmethyldimethoxysilane or 3-methacryloxypropyltrimethoxysilane is preferred, and 3-methacryloxypropyltrimethoxysilane is more preferred, because of high improvement in mechanical properties.
- the silane coupling agent represented by formula (2) may be used alone or in combination as long as the effects of the present invention are not impaired.
- the surface coverage ratio of the silane coupling agent to silica particles is 0.005-0.080, preferably 0.006-0.076, more preferably 0.007-0. 080, and more preferably in the range of 0.010 to 0.075.
- the surface coverage ratio is a value obtained by the following formula.
- [Surface coverage ratio] [amount of silane coupling agent contained in resin composition (g)] ⁇ [minimum coating area of silane coupling agent ( m / g)] ⁇ [silica particles contained in the resin composition The sum of the surface areas (m 2 ) of
- the “minimum coating area of the silane coupling agent (m 2 /g)” means that when 1 g of the silane coupling agent reacts, adsorbs, etc. on the surface of a material such as silica, the run coupling agent covers the surface.
- the minimum coverage area of each silane coupling agent can be calculated as follows.
- Si(O) 3 obtained by hydrolysis of trialkoxysilane has one spherical Si atom with a radius of 2.10 ⁇ , three spherical O atoms with a radius of 1.52 ⁇ , and the Si—O bond distance Assuming 1.51 ⁇ and a tetrahedral angle of 109.5°, and further assuming that all three O atoms in the model react with the silanol groups on the silica surface, the minimum that three O atoms can cover Calculate circular area.
- the coverage area per molecule is 1.3 ⁇ 10 ⁇ 19 m 2 /molecule, which is multiplied by Avogadro’s constant of 6.0 ⁇ 10 23 molecules/mol to convert to 7.8 ⁇ 10 4 m per mole. 2 /mol.
- the minimum coverage area of each coupling agent is the value obtained by dividing the coverage area value per mole by the molecular weight of each silane coupling agent.
- silane coupling agents For commercially available silane coupling agents, the characteristic values are indicated and described, and in the present invention, the values indicated and described by the distributor may be used.
- the sum of the surface area (m 2 ) of the silica particles is “the surface area (m 2 ) of the silica particles obtained from the average particle diameter” ⁇ "addition amount of silica particles (g) ⁇ “density of silica particles (g /cm 3 )” ⁇ “Volume of silica particles (m 3 ) obtained from the average particle diameter”.
- the polyacrylate resin is a resin containing an acrylate monomer component as a monomer unit, such as the compounds represented by the above formulas (1) and (2).
- a compound containing a group is meant.
- the polyacrylate resin in the resin composition of the present invention is a different acrylate monomer than the acrylate monomer components represented by the general formulas (1) and (2), as long as it does not impair the effects of the present invention.
- alkyl acrylates such as butyl acrylate, n-hexyl acrylate, 2-ethylhexyl acrylate, n-octyl acrylate, n-nonyl acrylate and isononyl acrylate; methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate , n-butyl (meth)acrylate, isobutyl (meth)acrylate, t-butyl (meth)acrylate, pentyl (meth)acrylate, hexyl (meth)acrylate, heptyl (meth)acrylate, n-octyl (meth)acrylate, isooctyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, nonyl (meth)acrylate, isononyl (meth)acrylate, n-decyl
- maleimide group such as (meth) acrylolyloxyethylhe
- N-hydroxyalkyl (meth)acrylamide such as N-hydroxyethyl (meth)acrylamide; N,N-dimethylaminoethyl (meth)acrylamide, N,N-dimethylaminopropyl (meth)acrylamide, N,N- Dimethyl (meth)acrylamide, N,N-diethyl (meth)acrylamide, N,N-di-n-propyl (meth)acrylamide, N,N-diisopropyl (meth)acrylamide, N,N-di-n-butyl ( N,N-dialkyl (meth)acrylamide of meth)acrylamide and N,N-dihexyl (meth)acrylamide may be combined, and a different silane other than the silane coupling agent (B) represented by the general formula (2) may be used.
- B silane coupling agent represented by the general formula (2)
- Coupling agents such as 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldiethoxy Silane coupling agents having an epoxy group such as silane and 3-glycidoxypropyltriethoxysilane; 3-isocyanatopropylmethyldimethoxysilane, 3-isocyanatopropyltrimethoxysilane, 3-isocyanatopropylmethyldiethoxysilane, 3-isocyanate Silane carbons with isocyanate groups such as propyltriethoxysilane Pulling agent; having an amino group such as N-2-(aminoethyl)-3-aminopropylmethyldimethoxysilane, N-2-(aminoethyl)-3-aminopropyltrimethoxysilane,
- silica particles are an important component for enabling the resin composition of the present invention to be used as an elastomer material and for improving the toughness of the resin composition.
- the absence of silica particles results in a brittle material that cannot withstand large deformations.
- the coexistence of silica particles and multi-layer graphene improves the dispersibility of multi-layer graphene in the acrylate monomer, making it possible to add more multi-layer graphene.
- coexistence of silica particles and multilayer graphene makes it possible to suppress an increase in dielectric loss tangent due to an increase in multilayer graphene.
- the shape of the silica particles used in the present invention is not particularly limited as long as it does not impair the effects of the present invention, but from the viewpoint of dispersibility in acrylate monomers (especially from the viewpoint of further improving mechanical properties and dielectric properties) It is preferably "spherical".
- spherical refers to a true sphere, a substantially spherical shape, or a spheroid, excluding rod-like and plate-like shapes, and may have uneven surfaces.
- Spherical silica particles are silica particles having such a “spherical” shape.
- spherical silica particles known ones such as powdered spherical silica particles, colloidal silica (silica sol), etc. can be used, and various known ones having different average particle sizes are known. and is commercially available.
- the silica particles used in the present invention have an average particle size of less than 10 ⁇ m, and from the viewpoint of further improving mechanical properties and dielectric properties, are preferably less than 5 ⁇ m, more preferably less than 1 ⁇ m, even more preferably less than 500 nm, and most preferably less than 500 nm. Preferably less than 200 nm, most preferably less than 150 nm.
- the silica particles may generally have an average particle size of 10 nm or more. In the present invention, the average particle size is represented by a mode size measured with a centrifugal sedimentation particle size distribution analyzer.
- the content of the silica particles is (usually 8 to 62% by weight) relative to the total amount of the polyacrylate resin, silica particles and multilayer graphene, and from the viewpoint of further improving mechanical properties and dielectric properties, preferably 9-60% by weight, more preferably 10-58% by weight, even more preferably 11-56% by weight, fully preferably 12-54% by weight, more preferably 15-50% by weight, most preferably 15% by weight
- the lower the silica particle content the smaller the reinforcement effect of the polymer material due to the silica particle filling, resulting in an elastomer material inferior in tensile rupture stress and tensile rupture strain.
- the silica particle content is too high. In this case, it becomes difficult to uniformly disperse the silica particles in the acrylate monomer.
- the multilayer graphene used in the present invention is a plate-like filler in which about 2 to 20 pieces of graphene are stacked to form a layer, and has a thickness of several nanometers to several tens of nanometers and a width of several microns to several tens of microns.
- the thickness may be, for example, 1-90 nm, especially 1-20 nm.
- the width may be, for example, 1-80 ⁇ m, especially 10-50 ⁇ m.
- Such multilayer graphene is commercially available, for example, from Fujifilm Wako Pure Chemical Industries, Ltd., Tokyo Kasei Co., Ltd., and the like. They can be appropriately used in the present invention.
- the content of the multilayer graphene is usually 1 to 8% by weight with respect to the total amount of the polyacrylate resin, silica particles and multilayer graphene, and from the viewpoint of further improving mechanical properties and dielectric properties, preferably 1 .5 to 8 wt%, more preferably 2 to 8 wt%, even more preferably 2 to 7.5 wt%, fully preferably 2.5 to 7.5 wt%, more fully preferably 3 to 7 .5% by weight.
- the content of multilayer graphene decreases, the effect of increasing the dielectric constant due to multilayer graphene decreases. If the content of multi-layer graphene is too high, the dispersion containing acrylate monomers, silica particles and multi-layer graphene becomes too viscous and loses fluidity, making processing difficult.
- the resin composition of the present invention is obtained by polymerizing a dispersion containing at least the acrylate monomer (A) represented by general formula (1), silica particles, and multilayer graphene.
- the total content of silica particles and multi-layer graphene is usually 15 to 62% by weight based on the total amount of polyacrylate resin, silica particles and multi-layer graphene, further improving mechanical properties and dielectric properties. From the viewpoint of, preferably 15 to 60% by weight, more preferably 20 to 59% by weight, even more preferably 24 to 58% by weight, even more preferably 25 to 58% by weight, fully preferably 25 to 50% by weight, More preferably, a content of 25-40% by weight is used. If the amount is too large, the fluidity will be lost, making it difficult to obtain a sheet. If the amount is too small, the fluidity will increase, making it difficult to form a sheet. If the total amount is too small, the mechanical properties (especially tensile breaking stress) may deteriorate.
- the acrylate monomer (A) is usually 38 to 85% by weight with respect to the total amount of the polyacrylate resin, silica particles and multilayer graphene, and from the viewpoint of further improving mechanical properties and dielectric properties, preferably 40 to 85 wt%, more preferably 41 to 80 wt%, even more preferably 42 to 76 wt%, even more preferably 42 to 75 wt%, fully preferably 50 to 75 wt%, more fully preferably 60 to A content of 75% by weight is used.
- the content of the acrylate monomer (A) may also represent the content of the polyacrylate resin in the resulting polyacrylate resin composition.
- thermal polymerization with a thermal polymerization initiator thermal polymerization initiator
- photopolymerization with active energy ray irradiation such as ultraviolet rays with a photopolymerization initiator, etc.
- other methods can be used as long as the effects of the present invention are not impaired.
- Polymerization methods may also be used.
- the thermal polymerization initiator is not particularly limited in structure as long as it generates radicals by heating and is used to initiate polymerization of the polymerizable functional groups in the resin composition.
- the thermal polymerization initiator is not particularly limited in structure as long as it generates radicals by heating and is used to initiate polymerization of the polymerizable functional groups in the resin composition.
- the amount of the thermal polymerization initiator to be added is 0.001 parts by mass or more, preferably 0.01 parts by mass or more, more preferably 0.1 parts by mass or more with respect to 100 parts by weight of the acrylic monomer component. It is no more than 5 parts by mass, more preferably no more than 3 parts by mass.
- thermal polymerization initiators may be used alone or in combination of two or more.
- the "acryloyl monomer component” means a compound containing an acryloyl group or a methacryloyl group, and in addition to the component represented by the above formula (1), other appropriately used acryloyl groups and methacryloyl groups Contains a compound component containing
- the photopolymerization initiator is not particularly limited in its structure as long as it generates radicals upon irradiation with ultraviolet rays and is used to initiate polymerization of the polymerizable functional groups in the resin composition.
- the photopolymerization initiator it is preferable to use an initiator that absorbs light at a wavelength of 360 nm to 470 nm. is mentioned. By using these initiators, polymerization efficiently progresses to the inside of the resin composition, so that the mechanical strength is improved and the amount of residual components such as initiators and monomers is reduced.
- Photopolymerization initiators such as 2,4,6-trimethylbenzoyl-diphenyl-phosphine oxide, ethyl(2,4,6-trimethylbenzoyl)phenylphosphine oxide, bis(2,4,6-trimethylbenzoyl) -phenylphosphine oxide, 2,4-diethylthioxanthone, 2-isopropylthioxanthone, oligo(2-hydroxy-2-methyl-1-(4-(1-methylvinyl)phenyl)propanone), 2-benzyl-2-dimethyl amino-1-(4-morpholinophenyl)-butanone-1,2-dimethylamino-2-(4-methyl-benzyl)-1-(4-morpholin-4-yl-phenyl)-butan-1-one, 2-[4-(methylthiobenzoyl)]-2-(4-morpholinyl)propane, 2-hydroxy-1- ⁇ 4-[4-(2-hydroxy-2-methyl-propion
- the amount of the photopolymerization initiator added is 0.001 parts by mass or more, preferably 0.01 parts by mass or more, more preferably 0.1 parts by mass or more with respect to 100 parts by weight of the acrylic monomer component. It is no more than 5 parts by mass, more preferably no more than 3 parts by mass. These photopolymerization initiators may be used alone or in combination of two or more.
- a chain transfer agent may also be used in the polymerization reaction.
- Chain transfer agents include, for example, mercaptocarboxylic acids such as mercaptoacetic acid and 3-mercaptopropionic acid; , methoxybutyl 3-mercaptopropionate, stearyl 3-mercaptopropionate, trimethylolpropane tris (3-mercaptopropionate), pentaerythritol tetrakis (3-mercaptopropionate), dipentaerythritol hexakis (3-mercapto mercaptocarboxylic acid esters such as propionate); alkyl mercaptans such as ethyl mercaptan, t-butyl mercaptan, n-dodecyl mercaptan, and 1,2-dimercaptoethane; 2-mercaptoethanol, 4-mercapto-1-butanol mercapto alcohols such as; benzenethiol, m
- the amount of the chain transfer agent to be added is 0.001 parts by mass or more, preferably 0.01 parts by mass or more, more preferably 0.1 parts by mass or more with respect to 100 parts by weight of the acrylic monomer component. parts or less, preferably 5 parts by mass or less, more preferably 3 parts by mass or less. These may be used alone or in combination of two or more.
- the silica particles When powdered silica particles are used as the silica particles, it is preferable to first disperse the silica particles in the acrylate monomer (A).
- the method for dispersing the silica particles in the acrylate monomer (A) is not particularly limited as long as it does not impair the effects of the present invention.
- colloidal silica silica (silica sol) is used as the silica particles
- an organic solvent that is compatible with the acrylic monomer component, such as alcohols, ketones, esters, and glycol ethers.
- Alcohol-based solvents such as methanol, ethanol, isopropyl alcohol, butyl alcohol, and n-propyl alcohol
- ketone-based organic solvents such as methyl ethyl ketone and methyl isobutyl ketone, are exemplified for ease of solvent removal.
- Colloidal silica (silica sol) dispersed in isopropyl alcohol or methyl ethyl ketone is preferred.
- a preferred method for producing the resin composition of the present invention is to prepare a dispersion by mixing and dispersing predetermined amounts of silica particles and multilayer graphene in an acrylate monomer (A) represented by general formula (1), and If necessary, a polymerization initiator, other acrylic monomers and desired additives are mixed and dispersed, and the resulting dispersion is polymerized.
- the desired additives include plasticizers, surfactants, dispersants, antioxidants, ultraviolet absorbers, fluorescent agents, cross-linking agents, organic solvents, etc.
- the effect of the present invention can be obtained. It can be added and used as long as it does not damage it.
- the content of the acrylate monomer (A) in the dispersion liquid is the content of the acrylate monomer (A) with respect to the above-mentioned "total amount of polyacrylate resin, silica particles and multilayer graphene". It may be applied as the content of the acrylate monomer (A) with respect to the "total amount of graphene”.
- the acrylate monomer corresponds to the above-mentioned "acrylate monomer component".
- the content of silica particles in the dispersion liquid is the content of silica particles relative to the above-mentioned "total amount of polyacrylate resin, silica particles and multilayer graphene" relative to “total amount of acrylate monomer, silica particles and multilayer graphene". It may be applied as a content of silica particles.
- the content of multi-layer graphene in the dispersion liquid is the content of multi-layer graphene relative to the above-mentioned "total amount of polyacrylate resin, silica particles and multi-layer graphene" relative to “total amount of acrylate monomer, silica particles and multi-layer graphene". It may be applied as content of multilayer graphene.
- the total content of silica particles and multi-layer graphene in the dispersion liquid is the total content of silica particles and multi-layer graphene with respect to the above-mentioned "total amount of polyacrylate resin, silica particles and multi-layer graphene", and "acrylate monomer, silica particles and the total amount of multilayer graphene".
- the resin composition of the present invention can be suitably used as an elastomer material.
- the term "elastomer material” means a polymer material or polymer resin composition having such rubber elasticity that it undergoes a large change in shape under a relatively small external force and quickly returns to its original shape when the external force is removed. and is a material that can be used as a constituent material for members that require rubber elasticity.
- the polyacrylate resin contained in the resin composition of the present invention generally exhibits rubber elasticity.
- Elastomer materials made of the resin composition of the present invention are excellent in dielectric properties, particularly high relative permittivity and low rate of change in dielectric loss tangent, and are excellent in elongation and toughness, especially tensile breaking stress, Excellent mechanical properties such as tensile breaking strain.
- the terms "relative permittivity” and “dielectric loss tangent” refer to characteristics evaluated by relative permittivity and dielectric loss tangent obtained using a 1 mm thick sheet made of the resin composition of the present invention.
- the value obtained by the method described in the following examples is used for the dielectric constant.
- a higher dielectric constant indicates a higher degree of polarization inside the dielectric.
- the elastomer comprising the composition of the present invention usually has a dielectric constant of 7 or more, preferably 7.5 or more, more preferably 7.8 or more, even more preferably 8.0 or more, and fully preferably 10.0 or greater.
- the rate of change in the dielectric loss tangent obtained by the following formula is usually 60% or less, preferably 45% or less, more preferably 30% or less, and still more preferably 25% or less. preferably 20% or less, more preferably 15% or less, most preferably 10% or less.
- [Change rate of dielectric loss tangent] [[Dielectric loss tangent of resin composition] ⁇ [Dielectric loss tangent of polyacrylate resin] -1] ⁇ 100
- the elastomer material made of the resin composition of the present invention is also excellent in elongation, toughness, etc., and is excellent in mechanical properties such as tensile breaking stress and tensile breaking strain.
- mechanical properties such as tensile breaking stress and tensile breaking strain mean the tensile breaking stress and tensile breaking strain obtained based on the stress/strain curve obtained according to JIS K7161-2. More specifically, it is described in the examples below.
- the elastomer material made of the resin composition of the present invention has a tensile breaking stress of 2.0 MPa or more, preferably 2.3 MPa or more, and more preferably 2.5 MPa or more.
- the elastomer material made of the resin composition of the present invention has a tensile strain at break of 350% or more, preferably 400% or more, more preferably 450% or more.
- the resin composition of the present invention can be suitably used as an elastomer material with a high dielectric constant.
- the resin composition of the present invention is molded or processed into films, sheets, coating agents, adhesives, adhesives, etc., and can be suitably used, for example, as the following materials: (i) Materials for antenna substrates adapted to automobiles, railways, aircraft, home appliances/OA equipment, construction machinery, wearable devices, etc.; (ii) encapsulating materials for packages that require miniaturization and thinning, including optical transceivers; and (iii) printed wiring board materials.
- the resin composition of the present invention when used as a package sealing material, it can be applied to applications such as Wifi modules, optical communication modules, millimeter wave radars, and electromagnetic wave shields.
- the package may be a package for electronic/electrical equipment.
- the resin composition of the present invention when used as a printed wiring board material, it can be applied to smartphones, car navigation systems, power devices, and the like.
- mechanical properties are used as a concept including extensibility and toughness.
- Extensibility is the property of exhibiting a sufficiently large tensile strain at break. The higher the tensile strain at break, the better the extensibility.
- Toughness is a property that simultaneously exhibits a sufficiently large tensile stress at break and tensile strain at break. The higher the tensile stress at break and the tensile strain at break, the better the toughness.
- Dielectric properties are properties that exhibit a sufficiently high dielectric constant and a sufficiently low dielectric loss tangent. Note that the dielectric loss tangent value varies greatly depending on the monomer composition of the polyacrylate resin.
- the dielectric loss tangent of a given resin composition is the dielectric loss tangent of a resin composition (for example, a simple “polyacrylate resin”) having the same composition as the resin composition except that it does not contain silica particles and multilayer graphene. is significant. Therefore, in the present invention, the dielectric loss tangent of the resin composition is represented by the rate of change from the dielectric loss tangent of the polyacrylate resin, as described above. Therefore, the lower the dielectric loss tangent of the resin composition, the smaller the change rate of the dielectric loss tangent of the resin composition. The lower the dielectric loss tangent of the resin composition, the better, and the smaller the change rate of the dielectric loss tangent of the resin composition, the better.
- a No. 7 dumbbell test piece (JISK7161-2) was prepared from a resin composition sheet with a thickness of 1 mm using a punching die.
- a tensile tester (EZ-LX) manufactured by Shimadzu Corporation, under a standard environment (temperature 23 ⁇ 2 ° C, air, humidity (50 ⁇ 10%)
- strain 0.1 mm / up to 0.3% After the strain was 0.3%, the tensile speed was 50 mm/min.
- Tensile breaking stress was evaluated according to the following criteria. ⁇ : 2.5 MPa ⁇ tensile breaking stress (excellent); ⁇ : 2.0 MPa ⁇ tensile breaking stress ⁇ 2.5 MPa (good: practically no problem); x: Tensile breaking stress ⁇ 2.0 MPa (practically problematic).
- ⁇ Change rate of dielectric loss tangent ⁇ 10% (excellent); ⁇ : 10% ⁇ change rate of dielectric loss tangent ⁇ 25% (good); ⁇ : 25% ⁇ change rate of dielectric loss tangent ⁇ 60% (no practical problem) x: 60% ⁇ change rate of dielectric loss tangent (problematic in practice).
- Example 1 Diethylene glycol monomethyl ether methacrylate (MEO2MA, manufactured by Aldrich) 3386 parts by mass, spherical silica particles with an average particle size of 110 nm (Silbol 110, manufactured by Fuji Chemical Co., Ltd.) 1056 parts by mass, thickness 6-8 nm, width 25 ⁇ m multilayer graphene (graphene nanoplates 360 parts by mass of Rett, manufactured by Tokyo Chemical Industry Co., Ltd.) was placed in a test tube and dispersed with an ultrasonic homogenizer (UP200St, manufactured by Hielscher) at 5° C. for 20 minutes.
- MEO2MA Diethylene glycol monomethyl ether methacrylate
- FIG. 1 shows the results of values close to the average value in the stress/strain curve chart obtained from the five test pieces.
- the fluidity of the dispersion before polymerization the mechanical properties (tensile breaking stress, tensile breaking strain) obtained from the stress/strain curve, the relative permittivity, the dielectric loss tangent and the rate of change of the dielectric loss tangent are measured and evaluated. It is shown in Table 1 collectively.
- Examples 2-5, Comparative Examples 1-10 A sheet was produced and evaluated in the same manner as in Example 1, except that the filling amounts of silica particles and multilayer graphene were changed to those shown in Table 1.
- the resin compositions obtained in Examples 1 to 5 had excellent mechanical properties such as high tensile breaking stress and tensile breaking strain and high toughness. Moreover, the relative permittivity was 7.0 or more, and the rate of change of the dielectric loss tangent showed a small value or a negative value, indicating excellent dielectric properties.
- the resin composition of Comparative Example 3 did not contain silica particles, had a very low content of multilayer graphene, and was a fragile material with low tensile breaking stress and tensile breaking strain. Moreover, it was a material with a low dielectric constant and poor dielectric properties.
- the resin compositions of Comparative Examples 4 to 6 had a small amount of multi-layered graphene filled, and were materials with low dielectric constant values and poor dielectric properties.
- the resin composition of Comparative Example 7 was a fragile material with a low total content of silica particles and multilayer graphene and a low tensile breaking stress.
- the resin composition of the present invention is useful for applications such as antenna substrate materials, packaging sealing materials for electronic and electrical equipment, and printed wiring board materials.
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Abstract
La présente invention concerne une composition de résine qui peut être utilisée de manière appropriée en tant que matériau élastomère qui présente d'excellentes propriétés mécaniques par rapport à l'aptitude à l'étirage et à la ténacité et présente également d'excellentes propriétés diélectriques par rapport à une constante diélectrique suffisamment grande, une tangente diélectrique suffisamment petite et équivalents. La présente invention concerne une composition de résine comprenant une résine polyacrylate, des particules de silice et du graphène multicouche, dans laquelle la teneur en particules de silice est de 8 à 62 % en poids, la teneur en graphène multicouche est de 1 à 8 % en poids et la teneur totale en particules de silice et en graphène multicouche est de 15 à 62 % en poids par rapport à la quantité totale de la résine de polyacrylate, des particules de silice et du graphène multicouche.
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Citations (6)
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WO2006082902A1 (fr) * | 2005-02-03 | 2006-08-10 | Asahi Kasei Chemicals Corporation | Composition de resine pour des composants electroniques et electriques destines a des applications haute frequence et ses produits moules |
KR20090115517A (ko) * | 2008-05-02 | 2009-11-05 | 엘에스엠트론 주식회사 | 탄성 회복 특성이 조절된 이방도전필름 및 이를 이용한회로접속구조체 |
CN108659237A (zh) * | 2018-05-22 | 2018-10-16 | 中南林业科技大学 | 一种导电性能随温度调谐的纳米纤维复合水凝胶及其制备方法和应用 |
WO2020020334A1 (fr) * | 2018-07-27 | 2020-01-30 | 杭州蓉阳电子科技有限公司 | Adhésif conducteur, composition de matière première, élément électronique et procédé de préparation et application |
CN110938894A (zh) * | 2019-11-05 | 2020-03-31 | 东华大学 | 一种抗冻、自修复导电纳米复合水凝胶纤维及其制备方法 |
JP2021031660A (ja) * | 2019-08-29 | 2021-03-01 | Eneos株式会社 | アクチュエータ用エラストマー組成物、アクチュエータ部材、およびアクチュエータ素子 |
-
2022
- 2022-03-23 WO PCT/JP2022/013628 patent/WO2022215528A1/fr active Application Filing
- 2022-03-23 JP JP2023512926A patent/JPWO2022215528A1/ja active Pending
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2006082902A1 (fr) * | 2005-02-03 | 2006-08-10 | Asahi Kasei Chemicals Corporation | Composition de resine pour des composants electroniques et electriques destines a des applications haute frequence et ses produits moules |
KR20090115517A (ko) * | 2008-05-02 | 2009-11-05 | 엘에스엠트론 주식회사 | 탄성 회복 특성이 조절된 이방도전필름 및 이를 이용한회로접속구조체 |
CN108659237A (zh) * | 2018-05-22 | 2018-10-16 | 中南林业科技大学 | 一种导电性能随温度调谐的纳米纤维复合水凝胶及其制备方法和应用 |
WO2020020334A1 (fr) * | 2018-07-27 | 2020-01-30 | 杭州蓉阳电子科技有限公司 | Adhésif conducteur, composition de matière première, élément électronique et procédé de préparation et application |
JP2021031660A (ja) * | 2019-08-29 | 2021-03-01 | Eneos株式会社 | アクチュエータ用エラストマー組成物、アクチュエータ部材、およびアクチュエータ素子 |
CN110938894A (zh) * | 2019-11-05 | 2020-03-31 | 东华大学 | 一种抗冻、自修复导电纳米复合水凝胶纤维及其制备方法 |
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