WO2023182414A1 - ペースト - Google Patents
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- WO2023182414A1 WO2023182414A1 PCT/JP2023/011447 JP2023011447W WO2023182414A1 WO 2023182414 A1 WO2023182414 A1 WO 2023182414A1 JP 2023011447 W JP2023011447 W JP 2023011447W WO 2023182414 A1 WO2023182414 A1 WO 2023182414A1
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- -1 polysiloxane Polymers 0.000 claims abstract description 69
- 229920001296 polysiloxane Polymers 0.000 claims abstract description 36
- 239000003999 initiator Substances 0.000 claims abstract description 19
- 150000001875 compounds Chemical class 0.000 claims abstract description 18
- 125000003396 thiol group Chemical group [H]S* 0.000 claims abstract description 15
- 238000010438 heat treatment Methods 0.000 claims description 67
- 125000000524 functional group Chemical group 0.000 claims description 27
- 239000011231 conductive filler Substances 0.000 claims description 5
- 238000013007 heat curing Methods 0.000 claims description 3
- 238000007493 shaping process Methods 0.000 claims description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 49
- 230000008719 thickening Effects 0.000 description 29
- 125000004432 carbon atom Chemical group C* 0.000 description 27
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 25
- 230000017525 heat dissipation Effects 0.000 description 23
- 125000000217 alkyl group Chemical group 0.000 description 15
- 229910052751 metal Inorganic materials 0.000 description 15
- 239000002184 metal Substances 0.000 description 15
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 13
- 230000000052 comparative effect Effects 0.000 description 12
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 12
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 10
- 229910052710 silicon Inorganic materials 0.000 description 10
- 125000000962 organic group Chemical group 0.000 description 9
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 description 8
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 8
- 125000003342 alkenyl group Chemical group 0.000 description 8
- 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 7
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 7
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 7
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 7
- 125000003545 alkoxy group Chemical group 0.000 description 7
- 229920001577 copolymer Polymers 0.000 description 7
- 150000002430 hydrocarbons Chemical group 0.000 description 7
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 238000000576 coating method Methods 0.000 description 6
- 229910052697 platinum Inorganic materials 0.000 description 6
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 5
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 238000010422 painting Methods 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid group Chemical group C(C=1C(C(=O)O)=CC=CC1)(=O)O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 4
- KOMNUTZXSVSERR-UHFFFAOYSA-N 1,3,5-tris(prop-2-enyl)-1,3,5-triazinane-2,4,6-trione Chemical compound C=CCN1C(=O)N(CC=C)C(=O)N(CC=C)C1=O KOMNUTZXSVSERR-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- IISBACLAFKSPIT-UHFFFAOYSA-N Bisphenol A Natural products C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 3
- PXKLMJQFEQBVLD-UHFFFAOYSA-N Bisphenol F Natural products C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- 125000004414 alkyl thio group Chemical group 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- 125000006165 cyclic alkyl group Chemical group 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000004205 dimethyl polysiloxane Substances 0.000 description 3
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 3
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 3
- 230000013011 mating Effects 0.000 description 3
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Chemical compound [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 3
- 229920002545 silicone oil Polymers 0.000 description 3
- 229960000834 vinyl ether Drugs 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- FVQMJJQUGGVLEP-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOOC(C)(C)C FVQMJJQUGGVLEP-UHFFFAOYSA-N 0.000 description 2
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- TYMYJUHDFROXOO-UHFFFAOYSA-N 1,3-bis(prop-2-enoxy)-2,2-bis(prop-2-enoxymethyl)propane Chemical compound C=CCOCC(COCC=C)(COCC=C)COCC=C TYMYJUHDFROXOO-UHFFFAOYSA-N 0.000 description 2
- AVTLBBWTUPQRAY-UHFFFAOYSA-N 2-(2-cyanobutan-2-yldiazenyl)-2-methylbutanenitrile Chemical compound CCC(C)(C#N)N=NC(C)(CC)C#N AVTLBBWTUPQRAY-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- PTJWCLYPVFJWMP-UHFFFAOYSA-N 2-[[3-hydroxy-2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)COCC(CO)(CO)CO PTJWCLYPVFJWMP-UHFFFAOYSA-N 0.000 description 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 2
- 229910004298 SiO 2 Inorganic materials 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 150000003926 acrylamides Chemical class 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 239000002199 base oil Substances 0.000 description 2
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical group O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 2
- 238000013329 compounding Methods 0.000 description 2
- 238000001723 curing Methods 0.000 description 2
- 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 2
- 230000007423 decrease Effects 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000000395 magnesium oxide Substances 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000004014 plasticizer Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 125000005372 silanol group Chemical group 0.000 description 2
- 238000007711 solidification Methods 0.000 description 2
- 230000008023 solidification Effects 0.000 description 2
- 230000001629 suppression Effects 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- WRXCBRHBHGNNQA-UHFFFAOYSA-N (2,4-dichlorobenzoyl) 2,4-dichlorobenzenecarboperoxoate Chemical compound ClC1=CC(Cl)=CC=C1C(=O)OOC(=O)C1=CC=C(Cl)C=C1Cl WRXCBRHBHGNNQA-UHFFFAOYSA-N 0.000 description 1
- KDGNCLDCOVTOCS-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy propan-2-yl carbonate Chemical compound CC(C)OC(=O)OOC(C)(C)C KDGNCLDCOVTOCS-UHFFFAOYSA-N 0.000 description 1
- OXYKVVLTXXXVRT-UHFFFAOYSA-N (4-chlorobenzoyl) 4-chlorobenzenecarboperoxoate Chemical compound C1=CC(Cl)=CC=C1C(=O)OOC(=O)C1=CC=C(Cl)C=C1 OXYKVVLTXXXVRT-UHFFFAOYSA-N 0.000 description 1
- RIPYNJLMMFGZSX-UHFFFAOYSA-N (5-benzoylperoxy-2,5-dimethylhexan-2-yl) benzenecarboperoxoate Chemical compound C=1C=CC=CC=1C(=O)OOC(C)(C)CCC(C)(C)OOC(=O)C1=CC=CC=C1 RIPYNJLMMFGZSX-UHFFFAOYSA-N 0.000 description 1
- GPHWXFINOWXMDN-UHFFFAOYSA-N 1,1-bis(ethenoxy)hexane Chemical compound CCCCCC(OC=C)OC=C GPHWXFINOWXMDN-UHFFFAOYSA-N 0.000 description 1
- BEQKKZICTDFVMG-UHFFFAOYSA-N 1,2,3,4,6-pentaoxepane-5,7-dione Chemical compound O=C1OOOOC(=O)O1 BEQKKZICTDFVMG-UHFFFAOYSA-N 0.000 description 1
- CGXVUIBINWTLNT-UHFFFAOYSA-N 1,2,3-tris(ethenoxy)propane Chemical compound C=COCC(OC=C)COC=C CGXVUIBINWTLNT-UHFFFAOYSA-N 0.000 description 1
- ZXHDVRATSGZISC-UHFFFAOYSA-N 1,2-bis(ethenoxy)ethane Chemical compound C=COCCOC=C ZXHDVRATSGZISC-UHFFFAOYSA-N 0.000 description 1
- LXSVCBDMOGLGFA-UHFFFAOYSA-N 1,2-bis(ethenoxy)propane Chemical compound C=COC(C)COC=C LXSVCBDMOGLGFA-UHFFFAOYSA-N 0.000 description 1
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 1
- XDWRKTULOHXYGN-UHFFFAOYSA-N 1,3-bis(ethenoxy)-2,2-bis(ethenoxymethyl)propane Chemical compound C=COCC(COC=C)(COC=C)COC=C XDWRKTULOHXYGN-UHFFFAOYSA-N 0.000 description 1
- VDCVMQLEPHJYHI-UHFFFAOYSA-N 1,3-bis(ethenoxy)-2,2-bis(ethenoxymethyl)propane;oxirane Chemical compound C1CO1.C=COCC(COC=C)(COC=C)COC=C VDCVMQLEPHJYHI-UHFFFAOYSA-N 0.000 description 1
- MWZJGRDWJVHRDV-UHFFFAOYSA-N 1,4-bis(ethenoxy)butane Chemical compound C=COCCCCOC=C MWZJGRDWJVHRDV-UHFFFAOYSA-N 0.000 description 1
- IPJGAEWUPXWFPL-UHFFFAOYSA-N 1-[3-(2,5-dioxopyrrol-1-yl)phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC(N2C(C=CC2=O)=O)=C1 IPJGAEWUPXWFPL-UHFFFAOYSA-N 0.000 description 1
- CZAVRNDQSIORTH-UHFFFAOYSA-N 1-ethenoxy-2,2-bis(ethenoxymethyl)butane Chemical compound C=COCC(CC)(COC=C)COC=C CZAVRNDQSIORTH-UHFFFAOYSA-N 0.000 description 1
- SAMJGBVVQUEMGC-UHFFFAOYSA-N 1-ethenoxy-2-(2-ethenoxyethoxy)ethane Chemical compound C=COCCOCCOC=C SAMJGBVVQUEMGC-UHFFFAOYSA-N 0.000 description 1
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 1
- BJELTSYBAHKXRW-UHFFFAOYSA-N 2,4,6-triallyloxy-1,3,5-triazine Chemical compound C=CCOC1=NC(OCC=C)=NC(OCC=C)=N1 BJELTSYBAHKXRW-UHFFFAOYSA-N 0.000 description 1
- DMWVYCCGCQPJEA-UHFFFAOYSA-N 2,5-bis(tert-butylperoxy)-2,5-dimethylhexane Chemical compound CC(C)(C)OOC(C)(C)CCC(C)(C)OOC(C)(C)C DMWVYCCGCQPJEA-UHFFFAOYSA-N 0.000 description 1
- 150000003923 2,5-pyrrolediones Chemical class 0.000 description 1
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 1
- MTLWTRLYHAQCAM-UHFFFAOYSA-N 2-[(1-cyano-2-methylpropyl)diazenyl]-3-methylbutanenitrile Chemical compound CC(C)C(C#N)N=NC(C#N)C(C)C MTLWTRLYHAQCAM-UHFFFAOYSA-N 0.000 description 1
- PYZCOYROAJKRSK-UHFFFAOYSA-N 2-[(2-carboxy-3-methylbutan-2-yl)diazenyl]-2,3-dimethylbutanoic acid Chemical compound CC(C)C(C)(C(O)=O)N=NC(C)(C(C)C)C(O)=O PYZCOYROAJKRSK-UHFFFAOYSA-N 0.000 description 1
- WYGWHHGCAGTUCH-UHFFFAOYSA-N 2-[(2-cyano-4-methylpentan-2-yl)diazenyl]-2,4-dimethylpentanenitrile Chemical compound CC(C)CC(C)(C#N)N=NC(C)(C#N)CC(C)C WYGWHHGCAGTUCH-UHFFFAOYSA-N 0.000 description 1
- RSROEZYGRKHVMN-UHFFFAOYSA-N 2-ethyl-2-(hydroxymethyl)propane-1,3-diol;oxirane Chemical compound C1CO1.CCC(CO)(CO)CO RSROEZYGRKHVMN-UHFFFAOYSA-N 0.000 description 1
- YCCGYQHYCAMQKT-UHFFFAOYSA-N 2-ethyl-2-(hydroxymethyl)propane-1,3-diol;oxirane Chemical compound C1CO1.CCC(CO)(CO)CO.CCC(CO)(CO)CO YCCGYQHYCAMQKT-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- 125000000094 2-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
- CARNFEUGBMWTON-UHFFFAOYSA-N 3-(2-prop-2-enoxyethoxy)prop-1-ene Chemical compound C=CCOCCOCC=C CARNFEUGBMWTON-UHFFFAOYSA-N 0.000 description 1
- XSSOJMFOKGTAFU-UHFFFAOYSA-N 3-[2-(2-prop-2-enoxyethoxy)ethoxy]prop-1-ene Chemical compound C=CCOCCOCCOCC=C XSSOJMFOKGTAFU-UHFFFAOYSA-N 0.000 description 1
- VFXXTYGQYWRHJP-UHFFFAOYSA-N 4,4'-azobis(4-cyanopentanoic acid) Chemical compound OC(=O)CCC(C)(C#N)N=NC(C)(CCC(O)=O)C#N VFXXTYGQYWRHJP-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 1
- PIGFYZPCRLYGLF-UHFFFAOYSA-N Aluminum nitride Chemical compound [Al]#N PIGFYZPCRLYGLF-UHFFFAOYSA-N 0.000 description 1
- 229910052582 BN Inorganic materials 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- LTPBRCUWZOMYOC-UHFFFAOYSA-N Beryllium oxide Chemical compound O=[Be] LTPBRCUWZOMYOC-UHFFFAOYSA-N 0.000 description 1
- PZNSFCLAULLKQX-UHFFFAOYSA-N Boron nitride Chemical compound N#B PZNSFCLAULLKQX-UHFFFAOYSA-N 0.000 description 1
- 102100026735 Coagulation factor VIII Human genes 0.000 description 1
- 239000004641 Diallyl-phthalate Substances 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- 101000911390 Homo sapiens Coagulation factor VIII Proteins 0.000 description 1
- 239000005058 Isophorone diisocyanate Substances 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical class CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- 229910052581 Si3N4 Inorganic materials 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- OKKRPWIIYQTPQF-UHFFFAOYSA-N Trimethylolpropane trimethacrylate Chemical compound CC(=C)C(=O)OCC(CC)(COC(=O)C(C)=C)COC(=O)C(C)=C OKKRPWIIYQTPQF-UHFFFAOYSA-N 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- ORLQHILJRHBSAY-UHFFFAOYSA-N [1-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1(CO)CCCCC1 ORLQHILJRHBSAY-UHFFFAOYSA-N 0.000 description 1
- LXEKPEMOWBOYRF-UHFFFAOYSA-N [2-[(1-azaniumyl-1-imino-2-methylpropan-2-yl)diazenyl]-2-methylpropanimidoyl]azanium;dichloride Chemical compound Cl.Cl.NC(=N)C(C)(C)N=NC(C)(C)C(N)=N LXEKPEMOWBOYRF-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
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 229920006397 acrylic thermoplastic Polymers 0.000 description 1
- 125000005336 allyloxy group Chemical group 0.000 description 1
- 230000003712 anti-aging effect Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 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
- HZTNYDWTDTYXQC-UHFFFAOYSA-N bis(prop-2-ynyl) benzene-1,4-dicarboxylate Chemical compound C#CCOC(=O)C1=CC=C(C(=O)OCC#C)C=C1 HZTNYDWTDTYXQC-UHFFFAOYSA-N 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 239000002041 carbon nanotube Substances 0.000 description 1
- 229910021393 carbon nanotube Inorganic materials 0.000 description 1
- 239000003575 carbonaceous material Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 230000003247 decreasing effect Effects 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
- 239000000412 dendrimer Substances 0.000 description 1
- 229920000736 dendritic polymer Polymers 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- 229910003460 diamond Inorganic materials 0.000 description 1
- 239000010432 diamond Substances 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- GKCPCPKXFGQXGS-UHFFFAOYSA-N ditert-butyldiazene Chemical compound CC(C)(C)N=NC(C)(C)C GKCPCPKXFGQXGS-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 239000004519 grease Substances 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
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 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
- 150000002513 isocyanates Chemical class 0.000 description 1
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 238000007561 laser diffraction method Methods 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 125000005439 maleimidyl group Chemical group C1(C=CC(N1*)=O)=O 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- 125000002801 octanoyl group Chemical group C(CCCCCCC)(=O)* 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
- 125000005375 organosiloxane group Chemical group 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000000790 scattering method Methods 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000003746 surface roughness Effects 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- MHSKRLJMQQNJNC-UHFFFAOYSA-N terephthalamide Chemical compound NC(=O)C1=CC=C(C(N)=O)C=C1 MHSKRLJMQQNJNC-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
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- GRPURDFRFHUDSP-UHFFFAOYSA-N tris(prop-2-enyl) benzene-1,2,4-tricarboxylate Chemical compound C=CCOC(=O)C1=CC=C(C(=O)OCC=C)C(C(=O)OCC=C)=C1 GRPURDFRFHUDSP-UHFFFAOYSA-N 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
- C08G75/02—Polythioethers
- C08G75/04—Polythioethers from mercapto compounds or metallic derivatives thereof
- C08G75/045—Polythioethers from mercapto compounds or metallic derivatives thereof from mercapto compounds and unsaturated 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
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
-
- 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
- C08K5/04—Oxygen-containing compounds
- C08K5/14—Peroxides
-
- 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
- C08L83/04—Polysiloxanes
-
- 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
- C08L83/04—Polysiloxanes
- C08L83/08—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K5/00—Heat-transfer, heat-exchange or heat-storage materials, e.g. refrigerants; Materials for the production of heat or cold by chemical reactions other than by combustion
- C09K5/08—Materials not undergoing a change of physical state when used
- C09K5/14—Solid materials, e.g. powdery or granular
Definitions
- One embodiment of the present invention relates to a paste.
- Paste also called grease
- a heat radiating (thermally conductive) material is used between a heat generating element and a heat radiating part in an electronic component or the like in order to efficiently transfer heat from the heat generating element to the heat radiating part.
- heat dissipation materials There are mainly two types of heat dissipation materials: sheet type and paste type. Sheet types have poor compatibility with other surfaces such as heating elements and heat dissipation parts, and require a certain amount of thickness for the sheet itself. Because of this, the contact thermal resistance increases. For this reason, a paste type is used as a heat dissipation material because it can be made into a thin film during coating, has good compatibility with the mating surface, and has excellent heat dissipation performance.
- the paste has a low viscosity during painting, workability such as paintability and productivity will improve, and it will be easier to place a predetermined amount, especially a small amount of paste, in a predetermined place. Since it is possible to reduce the thickness of the paste layer and improve heat dissipation performance, it is required that the viscosity at the time of coating be low.
- the paste is also required to remain in place in order to achieve its required purpose.
- a silicone paste using a silicone compound as a base oil is known (Patent Documents 1 and 2).
- JP2013-227374A Japanese Patent Application Publication No. 2017-165791
- paste formed at a predetermined location may be heated and thickened before use in order to prevent it from flowing out from that location.
- pastes with low viscosity during coating have problems such as being easy to pump out even after being heated and thickened in this way, making it difficult to maintain desired performance over a long period of time.
- An embodiment of the present invention provides a paste that does not solidify even after heating and thickening, and can suppress pump-out even when heating and thickening at a relatively low heating temperature, despite having a low initial viscosity. do.
- the initial viscosity here refers to the viscosity at the time of paste preparation, the viscosity before the paste is heated and thickened, and is usually the viscosity at the time of coating.
- a configuration example of the present invention is as follows.
- the paste does not solidify even after heating and thickening (does not solidify, remains paste-like), and although the initial viscosity is low, the heating temperature is relatively low (e.g. It is possible to provide a paste that can suppress pump-out even when heated and thickened due to the 1-minute half-life temperature of the radical initiator. Further, according to an embodiment of the present invention, it is possible to provide a paste having heat resistance (e.g., heat resistance of 150°C or higher), and for example, if stored at room temperature, the pot life is almost negligible. (extremely long) paste. Since the paste according to one embodiment of the present invention does not solidify even at high temperatures and is in a paste form, it is possible to maintain the performance required of the member in which the paste is used for a long period of time even at high temperatures.
- heat resistance e.g., heat resistance of 150°C or higher
- the paste according to an embodiment of the present invention has a thickness of 200 ⁇ m or less when 0.2 g of the paste is made into 5 mm squares and compressed at 23° C. with a pressure of 1.0 MPa. defined. Since the paste according to one embodiment of the present invention is a paste that does not solidify even after heating and thickening, it is heated and cured for 10 minutes at a temperature corresponding to the 1-minute half-life of the radical initiator (C). It is preferable that the paste has a thickness of 200 ⁇ m or less when 0.2 g of the paste is made into a 5 mm square and then compressed at 23° C. and a pressure of 1.0 MPa. The method for measuring the thickness is specifically as described in the Examples below.
- the paste according to one embodiment of the present invention (hereinafter also referred to as “this paste”) is a polysiloxane (A) having a mercapto group [hereinafter also referred to as “component (A)”].
- component (A) a mercapto group
- a compound (B) containing a group having two or more ethylenically unsaturated bonds in one molecule and a radical initiator (C).
- Component (A) is not particularly limited as long as it is a polysiloxane having a mercapto group (-SH).
- the paste has excellent heat resistance and does not solidify even after heating and thickening, and although the initial viscosity is low, it can be heated and thickened at a relatively low heating temperature. It is also possible to easily obtain a paste that can suppress pump-out.
- the number of components (A) used in this paste may be one or two or more.
- the bonding position of the mercapto group is not particularly limited, and it may be a so-called side chain type, a terminal type (including one terminal type and a double terminal type), or a side chain both terminal type.
- a side chain type or both terminal type is preferable, and a side chain type is more preferable.
- Component (A) is an organopolysiloxane in which an organic group is bonded to a silicon atom, and is preferably a polysiloxane having a mercapto group in at least a portion of the organopolysiloxane.
- Examples of the organic group bonded to a silicon atom include a linear alkyl group, a branched alkyl group, a cyclic alkyl group, an aryl group, an aralkyl group, a halogenated alkyl group, and an alkoxy group.
- Examples of the straight-chain alkyl group include groups having 1 to 20 carbon atoms, preferably 1 to 6 carbon atoms, such as methyl, ethyl, propyl, hexyl, octyl, and decyl.
- Examples of the branched alkyl group include groups having 1 to 20 carbon atoms, preferably 1 to 6 carbon atoms, such as isopropyl group, isobutyl group, t-butyl group, and 2-ethylhexyl group.
- Examples of the cyclic alkyl group include groups having 3 to 20 carbon atoms such as a cyclopentyl group and a cyclohexyl group.
- Examples of the aryl group include groups having 6 to 20 carbon atoms such as phenyl group and tolyl group.
- Examples of the aralkyl group include groups having 7 to 20 carbon atoms, such as benzyl group, 2-phenylethyl group, and 2-methyl-2-phenylethyl group.
- halogenated alkyl group examples include a 3,3,3-trifluoropropyl group, a 2-(nonafluorobutyl)ethyl group, and a 2-(heptadecafluorooctyl)ethyl group having 1 to 20 carbon atoms, preferably Examples include groups having 1 to 6 carbon atoms.
- alkoxy group examples include groups having 1 to 20 carbon atoms, preferably 1 to 6 carbon atoms, such as methoxy and ethoxy groups.
- the organic group bonded to the silicon atom is preferably a linear alkyl group or an aryl group, more preferably a linear alkyl group or aryl group having 1 to 6 carbon atoms, and particularly preferably a methyl group or a phenyl group. That is, the organopolysiloxane other than the mercapto group-containing structure preferably has at least one polysiloxane structure selected from dimethylpolysiloxane, methylphenylpolysiloxane, and diphenylpolysiloxane. is more preferable.
- the mercapto group may be bonded directly to the silicon atom, or may be bonded to the silicon atom via an organic group bonded to the silicon atom.
- component (A) is not particularly limited, and examples thereof include linear, branched, partially branched linear, and dendritic (dendrimer), preferably linear and partially branched. It has a straight chain shape.
- Component (A) may be a single polymer having these molecular structures, a copolymer having these molecular structures, or a mixture of two or more of these polymers. You can.
- component (A) include polysiloxane represented by the following formula (2).
- R 1 and R 2 are each independently an unsubstituted or substituted monovalent hydrocarbon group, a mercapto group, an alkoxy group, or an alkylmercapto group having 1 to 6 carbon atoms, and a and b The sum is an integer from 2 to 500. However, at least one of R 1 and R 2 in formula (2) contains a mercapto group or an alkylmercapto group having 1 to 6 carbon atoms, and each of the plurality of R 1s present in formula (2) is the same. However, they may be different, and the plurality of R 2s present in formula (2) may be the same or different. ]
- the unsubstituted or substituted monovalent hydrocarbon group in R 1 and R 2 is preferably an unsubstituted or substituted monovalent hydrocarbon group having 1 to 20 carbon atoms.
- Examples of the bonded organic group include the same groups as those exemplified (other than alkoxy groups). Among these, monovalent hydrocarbon groups having 1 to 6 carbon atoms are preferred, and alkyl groups and aryl groups having 1 to 6 carbon atoms are more preferred.
- Examples of the alkoxy group in R 1 and R 2 include the same groups as the alkoxy group exemplified as the organic group bonded to the silicon atom.
- the alkylmercapto group having 1 to 6 carbon atoms in R 1 and R 2 is a group represented by -R-SH (R is an alkylene group having 1 to 6 carbon atoms), and as R, the above-mentioned Examples of the organic group bonded to a silicon atom include groups obtained by removing one hydrogen atom from the exemplified groups (groups other than halogenated alkyl groups and alkoxy groups).
- component (A) those synthesized by conventionally known methods may be used, or commercially available products may be used.
- the shear viscosity of component (A) at 23°C measured with a cone-plate viscometer is preferably 0.005 Pa ⁇ s or more, more preferably 0.01 Pa ⁇ s or more, and preferably 60.00 Pa ⁇ s or less, More preferably, it is 5.00 Pa ⁇ s or less.
- a paste with low initial viscosity and excellent coating properties can be easily obtained.
- a paste with a low initial viscosity is a heat dissipation paste, it is possible to easily form a thin paste layer at a predetermined location, such as between a heating element and a heat dissipation part, for example. Since it is possible to easily form a paste layer that is compatible with a mating surface such as a part, the thermal resistance due to the paste layer can be reduced, and electronic components and the like having excellent heat dissipation characteristics can be easily obtained.
- the functional group (mercapto group) equivalent of component (A) has a viscosity sufficient to suppress pump-out after heating and thickening, but it does not solidify even after heating and thickening, and it is easy to obtain a paste that remains in the form of a paste. From the viewpoint of the ability to produce the desired amount, it is preferably 1,000 g/mol or more, more preferably 1,500 g/mol or more, and preferably 50,000 g/mol or less, more preferably 35,000 g/mol or less.
- the component (A) has a viscosity sufficient to suppress pump-out after heating and thickening, but it does not solidify even after heating and thickening, and it is possible to easily obtain a paste that remains in the form of a paste.
- polysiloxane (A1) having a functional group equivalent of preferably 1000 to 5000 g/mol, more preferably 1500 to 5000 g/mol and a functional group equivalent of preferably 15000 g/mol or more, more preferably 20000 g/mol It is desirable to use polysiloxane (A2) having a mol or more, preferably 50,000 g/mol or less, more preferably 35,000 g/mol or less.
- the proportion of polysiloxane (A2) relative to the total of 100% by mass is preferably 50.0% by mass or more, more preferably 75.0% by mass. % or more, preferably 99.5% by mass or less, more preferably 99.0% by mass or less.
- the number average molecular weight (Mn) of component (A) measured by gel permeation chromatography (GPC) shows that, despite its low initial viscosity, pump-out is suppressed even when the viscosity is increased by heating at a relatively low heating temperature. It is preferably 3,000 or more, more preferably 15,000 or more, and preferably 50,000 or less, more preferably 25,000 or less, from the viewpoint of easily obtaining a paste.
- the content of component (A) in this paste is determined from the viewpoint that it is possible to easily obtain a paste that is excellent in heat resistance, low initial viscosity, and pump-out suppressing property in a well-balanced manner. It is preferably 40.0% by mass or more, more preferably 70.0% by mass or more, even more preferably 85.0% by mass or more, and preferably 99.0% by mass or more, based on the total 100% by mass of (A) and (B). It is 0% by mass or less, more preferably 98.5% by mass or less.
- the components in the present paste may be The content of (A) is preferably 40.0% by mass or more, more preferably 60.0% by mass or more, and preferably 95.0% by mass or less, more preferably 90% by mass, based on 100% by mass of the present paste. .0% by mass or less.
- the content of component (A) in this paste is preferably 5.0% by mass or more, more preferably 5.0% by mass or more based on 100% by mass of this paste. is 10.0% by mass or more, preferably 30.0% by mass or less, more preferably 20.0% by mass or less.
- Component (B) is not particularly limited as long as it is a compound containing a group having two or more ethylenically unsaturated bonds in one molecule other than the component (A), and may be a conventionally known compound (co-crosslinking agent). can be used.
- component (B) it is possible to easily obtain a paste that is excellent in suppressing pump-out after heating and thickening.
- the number of components (B) used in this paste may be one or two or more.
- the number of groups having an ethylenically unsaturated bond in component (B) may be two, but from the viewpoint of being able to further suppress pump-out, etc., it is preferably three or more, and more preferably There are 3 to 6 pieces.
- the groups having two or more ethylenically unsaturated bonds contained in the component (B) may be the same or different. That is, component (B) may contain a group having two or more types of ethylenically unsaturated bonds.
- Examples of the group having an ethylenically unsaturated bond include a group having 2 to 8 carbon atoms such as a vinyl group, a methylvinyl group, an allyl group, a propenyl group, an isopropenyl group, a butenyl group, a pentenyl group, a hexenyl group, and a heptenyl group.
- Examples include alkenyl group, vinylphenyl group, (meth)acryloyl group, allyloxy group, styryl group, propargyl group, and maleimide group.
- alkenyl groups having 2 to 8 carbon atoms and (meth)acryloyl groups are preferred, alkenyl groups having 2 to 4 carbon atoms and (meth)acryloyl groups are more preferred, and vinyl groups, allyl groups, and (meth)acryloyl groups are preferred. is particularly preferred.
- component (B) for example, a polysiloxane containing a group having two or more ethylenically unsaturated bonds in one molecule; Ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, polyethylene glycol di(meth)acrylate, propylene glycol di(meth)acrylate, butylene glycol di(meth)acrylate, hexanediol di(meth)acrylate, cyclohexanedimethanol Di(meth)acrylate, Bisphenol A alkylene oxide di(meth)acrylate, Bisphenol F alkylene oxide di(meth)acrylate, Trimethylolpropane tri(meth)acrylate, Ditrimethylolpropane tetra(meth)acrylate, Glycerin tri(meth)acrylate , pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dip
- Acid esters Ethylene glycol diallyl ether, diethylene glycol diallyl ether, polyethylene glycol diallyl ether, propylene glycol diallyl ether, butylene glycol diallyl ether, hexanediol diallyl ether, bisphenol A alkylene oxide diallyl ether, bisphenol F alkylene oxide diallyl ether, trimethylolpropane triallyl ether, Ditrimethylolpropane tetraallyl ether, diallyl phthalate, glycerin triallyl ether, pentaerythritol tetraallyl ether, dipentaerythritol pentaallyl ether, dipentaerythritol hexaallyl ether, ethylene oxide added trimethylolpropane triallyl ether, ethylene oxide added ditrimethylolpropane tetraallyl ether Polyfunctional allyl compounds such as allyl ether, ethylene oxide-
- Allyl group-containing (meth)acrylic esters such as allyl (meth)acrylate; Polyfunctional (meth)acrylamide compounds such as N,N-ethylenebis(meth)acrylamide; Polyfunctional propargyl compounds such as dipropargyl terephthalate; Polyfunctional maleimide compounds such as N,N'-m-phenylene bismaleimide; Reaction of polyfunctional isocyanates such as tolylene diisocyanate, isophorone diisocyanate, and xylylene diisocyanate with hydroxyl group-containing (meth)acrylic acid esters such as 2-hydroxyethyl (meth)acrylate and 2-hydroxypropyl (meth)acrylate.
- Polyfunctional urethane (meth)acrylates obtained from; Polyfunctional aromatic vinyls such as divinylbenzene; can be mentioned.
- polyfunctional (meth)acrylate compounds polyfunctional allyl compounds, and polyfunctional (meth)acrylamide compounds are preferred because they have excellent reactivity and can easily produce a paste with excellent heat resistance.
- Trifunctional or higher polyfunctional (meth)acrylate compounds and trifunctional or higher functional allyl compounds are more preferred, and triallylisocyanurate and trimethylolpropane tri(meth)acrylate are particularly preferred.
- Examples of the polysiloxane containing a group having two or more ethylenically unsaturated bonds in one molecule include dimethylpolysiloxane with dimethylvinylsiloxy groups blocked at both ends of the molecular chain, and dimethyl blocked with methylphenylvinylsiloxy groups at both ends of the molecular chain.
- a specific example of the polysiloxane containing a group having two or more ethylenically unsaturated bonds in one molecule includes a compound represented by the following formula (3).
- R 3 is each independently an unsubstituted or substituted monovalent hydrocarbon group
- R 4 is each independently an alkyl group, an alkoxyalkyl group, an alkenyl group, or an acyl group
- the sum of c and d is an integer from 2 to 1000
- e is an integer from 1 to 3.
- at least two of R 3 and R 4 in formula (3) contain the group having the ethylenically unsaturated bond, and each of the plurality of R 3s present in formula (3) may be the same or different.
- the plurality of R 4s present in formula (3) may be the same or different.
- R 3 is each independently an unsubstituted or substituted monovalent hydrocarbon group having 1 to 10 carbon atoms, and examples thereof include the same groups as the organic group bonded to the silicon atom. and alkenyl groups. Among these, monovalent hydrocarbon groups having 1 to 6 carbon atoms are preferred, and alkenyl groups, aryl groups, and alkyl groups having 1 to 3 carbon atoms are more preferred.
- Examples of the alkyl group for R 4 include linear alkyl groups, branched alkyl groups, and cyclic alkyl groups similar to those exemplified as the organic group bonded to the silicon atom.
- Examples of the alkoxyalkyl group for R 4 include groups having 2 to 10 carbon atoms such as methoxyethyl group and methoxypropyl group.
- Examples of the alkenyl group in R 3 and R 4 include the same alkenyl groups as those exemplified as the ethylenically unsaturated bond-containing group.
- Examples of the acyl group for R 4 include groups having 2 to 10 carbon atoms such as an acetyl group and an octanoyl group. The sum of c and d is preferably an integer of 10 to 50, and e is preferably 1.
- the functional group (ethylenically unsaturated bond) equivalent of component (B) has a viscosity sufficient to suppress pump-out after heating and thickening, but it does not solidify even after heating and thickening and maintains a paste-like paste. From the standpoint of being easily obtainable, it is preferably 4 g/mol or more, more preferably 50 g/mol or more, even more preferably 75 g/mol or more, and preferably 25000 g/mol or less, more preferably 130 g/mol or less. It is.
- Component (B) has a viscosity sufficient to suppress pump-out after heating and thickening, but it does not solidify even after heating and thickening, and it is possible to easily obtain a paste that remains in the form of a paste.
- the functional group ratio represented by the following formula (1) is preferably 3 or less, more preferably 2 or less, even more preferably 1 or less, particularly preferably 0.45 or less, more preferably 0.01 or more, even more preferably It is preferable to use it so that it is 0.015 or more, particularly preferably 0.02 or more.
- Functional group ratio (amount of component (A) blended/functional group equivalent of component (A))/(amount of component (B) blended/functional group equivalent of component (B))...(1)
- component (A) for example, when component (A) with a functional group equivalent ag/mol is used in a blending amount x 1% by mass, and component (A) with a functional group equivalent bg/mol is used in a blending amount x 2% by mass.
- the numerator of the formula (1) is "(x1/a+x2/b)". The same applies when two or more types of components (A) and (B) are used.
- the content of component (B) based on 100% by mass of this paste is preferably such that it satisfies the above formula (1), but it is preferable that the content of component (B) in this paste is as small as possible. From this point and the fact that it is possible to easily obtain a paste that has a viscosity sufficient to suppress pump-out after heating and thickening, but does not solidify and remains paste-like even after heating and thickening, etc. Preferably 0.2% by mass or more, more preferably 0.3% by mass or more, even more preferably 0.5% by mass or more, preferably 50% by mass or less, more preferably 15% by mass or less, still more preferably 5% by mass or less. .5% by mass or less.
- Component (C) is not particularly limited as long as it is a radical initiator, and conventionally known radical initiators can be used.
- a paste with suppressed pump-out can be created without using the platinum catalyst used in conventional pastes. For example, if stored at room temperature, a paste with almost no (extremely long) pot life can be easily obtained.
- the number of component (C) used in this paste may be one or two or more.
- Component (C) includes, for example, 2,5-dimethyl-2,5-di(t-butylperoxy)hexane, dicumyl peroxide, 2,4-dichlorobenzoyl peroxide, di-t-butyl peroxide.
- t-butyl dicumyl peroxide t-butylperoxy-2-ethylhexanoate
- benzoyl peroxide 2,5-dimethyl-2,5-(t-butylperoxy)hexyne-3,2,5 -dimethyl-2,5-di(benzoylperoxy)hexane, ⁇ , ⁇ '-bis(t-butylperoxy-m-isopropyl)benzene, t-butylperoxyisopropyl carbonate, di-(4-t-butyl) Peroxides such as cyclohexyl) peroxydicarbonate, p-chlorobenzoyl peroxide, t-butyl peroxy-2-ethylhexanoate, t-butyl perbenzoate, 2,2'-azobis(2-methylpropyl) nitrile), 2,2'-azobisisobutyronitrile, 2,2'-azobis(2-
- the content of component (C) in this paste is such that it has a viscosity sufficient to suppress pump-out after heating and thickening, but it does not solidify even after heating and thickening, and it is possible to easily obtain a paste that remains paste-like. From the point of view that it is possible to produce
- the amount is at least 30 parts by mass, preferably 30 parts by mass or less, more preferably 20 parts by mass or less, particularly preferably 10 parts by mass or less.
- the content of component (C) is preferable for the content of component (C) to be as low as possible based on 100% by mass of this paste, so in this respect, it has a viscosity sufficient to suppress pump-out after heating and thickening, but it does not solidify even after heating and thickening.
- the content of component (C) in 100% by mass of the present paste is preferably 0.4% by mass or more, more preferably 0.5%, from the viewpoint of easily obtaining a paste that remains pasty. It is at least 1% by mass, more preferably at least 1% by mass, preferably at most 15% by mass, more preferably at most 9% by mass, even more preferably at most 7.5% by mass.
- the present paste preferably contains component (D).
- component (D) is used in the present paste, the number of components (D) used may be one or two or more.
- two or more types of components (D) with different materials may be used, or two or more types of components (D) with different shapes, average particle diameters, etc. may be used. .
- component (D) it is preferable to use a filler having a thermal conductivity of 1 W/m ⁇ K or more.
- component (D) include metal powder, metal oxide powder, metal nitride powder, metal hydroxide powder, metal oxynitride powder, metal carbide powder, and carbon materials.
- metal powder metal oxide powder, metal oxide powder, metal nitride powder, metal hydroxide powder, metal oxynitride powder, metal carbide powder, and carbon materials.
- Al 2 O 3 aluminum oxide
- magnesium oxide MgO
- BeO beryllium oxide
- ZnO zinc oxide
- boron nitride e.g. Examples include hexagonal BN and cubic BN), aluminum nitride (AlN), silicon carbide (SiC), graphite, diamond, and carbon nanotubes.
- the shape of component (D) is not particularly limited, and examples thereof include granular, scaly, and acicular shapes, but granular is preferable because it allows for higher density packing.
- the average particle diameter of the granular component (D) is, for example, 0.1 ⁇ m or more, preferably 0.5 ⁇ m or more, and, for example, 100 ⁇ m or less, preferably 50 ⁇ m or less.
- the average particle size is the value of d50 in the particle size distribution obtained by laser diffraction/scattering method (Microtrack method).
- the content of the component (D) is determined by the volume of 100 volumes of the present paste, from the viewpoints that a paste with low initial viscosity and excellent heat dissipation properties can be easily obtained.
- % preferably 30 volume % or more, more preferably 50 volume % or more, and preferably 80 volume % or less, more preferably 70 volume % or less.
- the amount of component (D) when the amount of component (D) was increased, the initial viscosity increased and workability decreased (difficult to form a paste in a predetermined place by painting or pouring). In this case, it was not possible to blend a large amount of component (D).
- the present paste since the present paste has a low initial viscosity, the workability is unlikely to deteriorate even if the amount of component (D) is increased.
- component (D) is preferably added to 40% by volume or more, more preferably 50% by volume, based on 100% by volume of the present paste. Even if the amount is at least 80% by volume, more preferably at most 70% by volume, a paste with low initial viscosity and excellent workability can be obtained.
- This paste may contain plasticizers such as fluorine-based or silicone oils; silane coupling agents; surfactants; crosslinking accelerators; solvents; dispersants; anti-aging agents, as long as they do not impair the effects of the present invention. It may contain other components other than the above-mentioned components (A) to (D), such as; an antioxidant; a flame retardant; and a pigment. These other components may be used alone or in combination of two or more.
- the present paste preferably does not contain a platinum-based catalyst, since it is possible to obtain a paste with almost no (extremely long) pot life if stored at room temperature, for example.
- Conventional pastes use platinum-based catalysts, but when platinum-based catalysts are used, the pot life is short and the paste cannot be stored for a long time.
- not containing a platinum-based catalyst means that the content of the platinum-based catalyst is, for example, 0.0001 parts by mass or less with respect to a total of 100 parts by mass of components (A) and (B), and the lower limit is preferably It is 0 parts by mass.
- the present paste can be prepared by mixing the components (A) to (C), the component (D) used as necessary, and the other components, and kneading and dispersing the mixture using a mixer, rolls, or the like.
- the initial shear viscosity (this viscosity refers to the initial viscosity) of this paste at 23°C measured with a cone-plate viscometer is preferably low, and specifically, preferably 500 Pa ⁇ s or less, or more. It is preferably 300 Pa ⁇ s or less, particularly preferably 250 Pa ⁇ s or less, and preferably 1 Pa ⁇ s or more.
- the initial viscosity of the present paste is within the above range, it is possible to easily obtain a paste that has excellent workability (the paste can be easily formed in a predetermined location by painting, pouring, etc.).
- a paste with a low initial viscosity is a heat dissipation paste
- pastes with low initial viscosity tend to pump out even when heated and thickened, but according to the present paste, even if the initial viscosity is low, pumping out can be suppressed after heating and thickening.
- viscosity after heating/initial viscosity is preferably 3 times or more, more preferably 4 times or more, still more preferably 5 times or more.
- the viscosity after heating is preferably such that the ratio of the viscosity after heating to the initial viscosity is within the above range, but from the viewpoint of suppressing pump-out, it is preferably 40 Pa ⁇ s or more, more preferably 50 Pa. s or more, and when this paste is used for applications where suppression of pump-out is extremely important, examples of specific numerical values of the viscosity after heating are preferably 500 Pa-s or more, more preferably 1000 Pa-s or more, Particularly preferably, it is 1500 Pa ⁇ s or more. When the viscosity after heating is within the above range, pump-out can be easily suppressed after heating and thickening due to flow resistance.
- This paste can be used without restriction in applications for which conventional pastes have been used, but it may be exposed to high temperatures (e.g. 200°C or higher) in order to better demonstrate the effects of the present invention.
- the present paste containing the component (D) may be used as a heat dissipation paste used between a heat generating element and a heat dissipation part in electronic components and the like. Examples of applications in which suppression of pump-out is extremely important include the heat dissipation paste.
- the present paste containing the component (D) has a low initial viscosity, and after heating, it is a paste that suppresses pump-out, base oil removal, solidification, dripping, etc., and has good heat dissipation (thermal conductivity). ) can be maintained for a long period of time, so it can be suitably used for devices, equipment, parts, etc. that have heating elements. By using this paste in these, devices, equipment, parts, etc. that have excellent long-term reliability can be manufactured. Obtainable.
- the paste has a low initial viscosity and is compatible with the heating element and the heat radiation part, so a thin paste layer can be formed between the heating element and the heat radiation part, reducing thermal resistance due to the paste layer.
- thermoelectric paste provided between a heating element and a heat dissipation part.Furthermore, it does not solidify, is difficult to crack, and can absorb (suppress) vibrations, so it can be used for semiconductor devices such as power modules. It is suitably used as a heat dissipation paste for cars, vehicles such as automobiles, and particularly suitably used as a heat dissipation paste for power modules.
- Examples of methods for forming the paste at a predetermined location include applying the paste to a predetermined location using a conventionally known coating method and pouring the paste into a predetermined location.
- pressure may be applied while heating as described below if necessary.
- the thinner the thickness of the formed present paste (layer) is, the better, in consideration of thermal resistance. Therefore, in this case, it is preferable to form the present paste between the heating element and the heat radiating section and then apply pressure to spread the present paste.
- the heating temperature at this time may be appropriately set according to each component used in the preparation of the present paste, and in particular, may be appropriately set according to the type of component (C) used, but preferably 80°C or higher, more preferably 80°C or higher.
- the temperature is preferably 100°C or higher, preferably 200°C or lower, and more preferably 170°C or lower.
- Examples 1 to 21 and Comparative Examples 1 to 6 A paste was prepared by mixing each compounding component in Table 1 or 2 at the compounding ratio shown in Table 1 or 2 (the unit of numerical value is parts by mass). Each component in Tables 1 and 2 is as follows.
- ⁇ Polysiloxane A-1 "KF-2001” manufactured by Shin-Etsu Chemical Co., Ltd. (polysiloxane having a mercapto group, functional group equivalent: 1900 g/mol)
- ⁇ Polysiloxane A-2 “KF-2004” manufactured by Shin-Etsu Chemical Co., Ltd. (polysiloxane having a mercapto group, functional group equivalent: 30000 g/mol)
- ⁇ Polysiloxane A-3 "X-22-167C” manufactured by Shin-Etsu Chemical Co., Ltd.
- Compound B-1 “DMS-V25” manufactured by Gelest (polysiloxane containing a group having two ethylenically unsaturated bonds in one molecule, functional group equivalent: 8600 g/mol)
- Compound B-2 “DMS-V35” manufactured by Gelest (polysiloxane containing a group having two ethylenically unsaturated bonds in one molecule, functional group equivalent: 24,750 g/mol)
- Compound B-3 “KE-1950-10A” manufactured by Shin-Etsu Chemical Co., Ltd.
- the sample was compressed to 1.0 MPa by stretching 0.2 g of the sample into a 5 mm square on a metal disc with a threaded part, sandwiching it between another metal disc, and tightening the screw into the threaded part with a torque wrench. This was done by applying a load of
- the thickness was measured as follows. The length of both ends of the two metal disks under a load of 1 MPa (length without sample) after 3 minutes have elapsed since 1 MPa was applied by stacking two metal disks in advance and tightening the screws (length without sample) ) was measured. Next, 0.2 g of the sample was stretched into a 5 mm square on a metal disk, and then sandwiched between another metal disk, a screw was tightened, and a load of 1.0 MPa was applied to the sample. Thereafter, to unclog the screw, the screw was loosened and the sample was removed from the metal disk. One cycle consisted of the steps from stretching 0.2 g of the sample onto the metal disk into a 5 mm square to removing the sample from the metal disk.
- the length of both ends of the two metal discs under a load of 1 MPa (sample The length of the dovetail) was measured.
- the thickness of the sample was calculated by subtracting the length without the sample from the length with the sample, and the paste properties were evaluated based on the thickness of the sample. The reason why the thickness was measured at the 5th cycle as described above is that due to the characteristics of the measuring jig, a part of the fluid sample that should be discharged remains (clogged) in the threaded part, and the thickness is not properly measured. This is to prevent the condition from becoming impossible to measure.
- the metal disk used was made of SUS304 and had a diameter of 14 mm, a thickness of 3 mm, and a surface roughness Ra of 0.2.
- the pastes obtained in Examples 1 to 21 remained pastes without solidifying even after heating and thickening, and despite their low initial viscosity, they did not pump out even when heating and thickening at relatively low heating temperatures. It was a paste that could be suppressed.
- the paste obtained in Comparative Example 2 could not suppress pump-out even after heating and thickening, and the pastes obtained in Comparative Examples 1 and 3 to 6 could not be called pastes after heating and curing ( There was no liquidity).
- the present paste contains the components (A) to (C) described above, it exhibits the above effects.
- the following can be considered as an example of the reason why such an effect is produced.
- the component (A) reacts during heat curing (heat thickening), and plays the role of promoting crosslinking while acting as an appropriate plasticizer.
- heat thickening since it is difficult to bleed out, it is thought that the viscosity can be increased while maintaining the paste state.
- Comparative Examples 3 to 6 when polysiloxane containing a group having an ethylenically unsaturated bond or general silicone oil is used without component (A), appropriate thickening cannot be achieved. (Thickening does not proceed) or silicone oil bleeds out, making it impossible to maintain paste properties after heating and curing.
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Abstract
Description
また、電子部品等における発熱体と放熱部との間には、発熱体からの熱を効率よく放熱部に伝達するために、放熱(熱伝導性)材料が使用されている。この放熱材料としては、主に、シートタイプとペーストタイプの2種類の形態があるが、シートタイプは、発熱体や放熱部などの相手面との馴染みの悪さやシート自体にある程度の厚みが必要である等の点から、接触熱抵抗が大きくなる。このため、塗工時に薄膜化でき、相手面との馴染みもよく、放熱性能に優れる等の点から、放熱材料としては、ペーストタイプが用いられている。
このようなペーストとして、例えば、シリコーン系の化合物を基油としたシリコーン系ペーストが知られている(特許文献1および2)。
しかしながら、塗装時の粘度が低いペーストは、このように加熱増粘させた後であってもポンプアウトしやすく、長期にわたる所定の性能の維持が困難であるなどの問題があった。
なお、ここで初期粘度とは、ペースト調製時の粘度であり、ペーストを加熱増粘する前の粘度であり、通常、塗装時の粘度である。
官能基比=(前記ポリシロキサン(A)の配合量/前記ポリシロキサン(A)の官能基当量)/(前記化合物(B)の配合量/前記化合物(B)の官能基当量) ・・・(1)
要件(I):前記ラジカル開始剤(C)の1分間半減期の温度で、10分間加熱硬化を行い、該加熱硬化後のペースト0.2gを5mm角にした後、23℃、1.0MPaの圧力で圧縮した際の厚みが200μm以下である
[7] 熱伝導性フィラー(D)の含有量が、ペースト100体積%に対し、30~80体積%である、[6]に記載のペースト。
また、本発明の一実施形態によれば、耐熱性(例:150℃以上の耐熱性)を有するペーストを提供することができ、例えば、常温下での保管環境であれば、ポットライフがほとんどない(極めて長い)ペーストを提供することができる。
このような本発明の一実施形態に係るペーストは、高温下でも固化せず、ペースト状であるため、高温下でも、ペーストが用いられる部材に要求される性能を長期にわたって維持することができる。
本発明の一実施形態に係るペーストは、加熱増粘後においても固化しないペーストであるため、前記ラジカル開始剤(C)の1分間半減期の温度で、10分間加熱硬化を行い、該加熱硬化後のペースト0.2gを5mm角にした後、23℃、1.0MPaの圧力で圧縮した際の厚みが200μm以下のペーストであることが好ましい。
前記厚みの測定方法は、具体的には、下記実施例に記載の通りである。
本発明の一実施形態に係るペースト(以下「本ペースト」ともいう。)は、メルカプト基を有するポリシロキサン(A)[以下「成分(A)」ともいう。他の成分についても同様。]、1分子中に2個以上のエチレン性不飽和結合を有する基を含む化合物(B)およびラジカル開始剤(C)を含む。
成分(A)は、メルカプト基(-SH)を有するポリシロキサンであれば特に制限されない。
このような成分(A)を用いることで、耐熱性に優れ、加熱増粘後においても固化しないペーストであり、初期粘度が低いにもかかわらず、比較的低い加熱温度による加熱増粘であってもポンプアウトを抑制できるペーストを容易に得ることができる。
本ペーストに用いる成分(A)は、1種でもよく、2種以上でもよい。
直鎖状アルキル基としては、例えば、メチル基、エチル基、プロピル基、ヘキシル基、オクチル基、デシル基等の炭素数1~20、好ましくは炭素数1~6の基が挙げられる。
分岐鎖状アルキル基としては、例えば、イソプロピル基、イソブチル基、t-ブチル基、2-エチルヘキシル基等の炭素数1~20、好ましくは炭素数1~6の基が挙げられる。
環状アルキル基としては、例えば、シクロペンチル基、シクロヘキシル基等の炭素数3~20の基が挙げられる。
アリール基としては、例えば、フェニル基、トリル基等の炭素数6~20の基が挙げられる。
アラルキル基としては、例えば、ベンジル基、2-フェニルエチル基、2-メチル-2-フェニルエチル基等の炭素数7~20の基が挙げられる。
ハロゲン化アルキル基としては、例えば、3,3,3-トリフルオロプロピル基、2-(ノナフルオロブチル)エチル基、2-(ヘプタデカフルオロオクチル)エチル基等の炭素数1~20、好ましくは炭素数1~6の基が挙げられる。
アルコキシ基としては、例えば、メトキシ基、エトキシ基等の炭素数1~20、好ましくは炭素数1~6の基が挙げられる。
つまり、前記オルガノポリシロキサンにおけるメルカプト基を有する部分以外の構造としては、ジメチルポリシロキサン、メチルフェニルポリシロキサンおよびジフェニルポリシロキサンから選ばれる少なくとも1種のポリシロキサン構造を有することが好ましく、ジメチルポリシロキサン構造がより好ましい。
成分(A)の粘度が前記範囲にあると、初期粘度が低く、塗装性に優れるペーストを容易に得ることができる。また、このような初期粘度が低いペーストが放熱ペーストである場合、例えば、発熱体と放熱部の間などの所定の場所に厚みの薄いペースト層を容易に形成することができ、発熱体や放熱部などの相手面と馴染みやすいペースト層を容易に形成することができるため、該ペースト層による熱抵抗を低減することができ、放熱特性に優れる電子部品等を容易に得ることができる。
このようなポリシロキサン(A1)と(A2)とを用いる場合、これらの合計100質量%に対する、ポリシロキサン(A2)の割合は、好ましくは50.0質量%以上、より好ましくは75.0質量%以上であり、好ましくは99.5質量%以下、より好ましくは99.0質量%以下である。
同様の理由から、本ペーストが下記成分(D)を含有する場合、本ペースト中の成分(A)の含有量は、本ペースト100質量%に対し、好ましくは5.0質量%以上、より好ましくは10.0質量%以上であり、好ましくは30.0質量%以下、より好ましくは20.0質量%以下である。
成分(B)は、前記成分(A)以外の、1分子中に2個以上のエチレン性不飽和結合を有する基を含む化合物であれば特に制限されず、従来公知の化合物(共架橋剤)を用いることができる。
成分(B)を用いることで、加熱増粘後のポンプアウトの抑制性に優れるペーストを容易に得ることができる。
本ペーストに用いる成分(B)は、1種でもよく、2種以上でもよい。
前記成分(B)に含まれる2個以上のエチレン性不飽和結合を有する基は、それぞれ同一でも異なっていてもよい。つまり、成分(B)は、2種以上のエチレン性不飽和結合を有する基を含んでいてもよい。
エチレングリコールジ(メタ)アクリレート、ジエチレングリコールジ(メタ)アクリレート、ポリエチレングリコールジ(メタ)アクリレート、プロピレングリコールジ(メタ)アクリレート、ブチレングリコールジ(メタ)アクリレート、ヘキサンジオールジ(メタ)アクリレート、シクロヘキサンジメタノールジ(メタ)アクリレート、ビスフェノールAアルキレンオキシドジ(メタ)アクリレート、ビスフェノールFアルキレンオキシドジ(メタ)アクリレート、トリメチロールプロパントリ(メタ)アクリレート、ジトリメチロールプロパンテトラ(メタ)アクリレート、グリセリントリ(メタ)アクリレート、ペンタエリスリトールトリ(メタ)アクリレート、ペンタエリスリトールテトラ(メタ)アクリレート、ジペンタエリスリトールペンタ(メタ)アクリレート、ジペンタエリスリトールヘキサ(メタ)アクリレート、トリペンタエリスリトールヘプタ(メタ)アクリレート、トリペンタエリスリトールオクタ(メタ)アクリレート、エチレンオキシド付加トリメチロールプロパントリ(メタ)アクリレート、エチレンオキシド付加ジトリメチロールプロパンテトラ(メタ)アクリレート、エチレンオキシド付加ペンタエリスリトールテトラ(メタ)アクリレート、エチレンオキシド付加ジペンタエリスリトールヘキサ(メタ)アクリレート、プロピレンオキシド付加トリメチロールプロパントリ(メタ)アクリレート、プロピレンオキシド付加ジトリメチロールプロパンテトラ(メタ)アクリレート、プロピレンオキシド付加ペンタエリスリトールテトラ(メタ)アクリレート、プロピレンオキシド付加ジペンタエリスリトールヘキサ(メタ)アクリレート、ε-カプロラクトン付加トリメチロールプロパントリ(メタ)アクリレート、ε-カプロラクトン付加ジトリメチロールプロパンテトラ(メタ)アクリレート、ε-カプロラクトン付加ペンタエリスリトールテトラ(メタ)アクリレート、ε-カプロラクトン付加ジペンタエリスリトールヘキサ(メタ)アクリレート、ジペンタエリスリトールペンタ(メタ)アクリレートコハク酸変性物、ペンタエリスリトールトリ(メタ)アクリレートコハク酸変性物、ジペンタエリスリトールペンタ(メタ)アクリレートフタル酸変性物、ペンタエリスリトールトリ(メタ)アクリレートフタル酸変性物、トリ((メタ)アクリロイルオキシエチル)イソシアヌレート、アルキレンオキシド付加トリ((メタ)アクリロイルオキシエチル)イソシアヌレート等の多官能(メタ)アクリレート化合物;
エチレングリコールジビニルエーテル、ジエチレングリコールジビニルエーテル、ポリエチレングリコールジビニルエーテル、プロピレングリコールジビニルエーテル、ブチレングリコールジビニルエーテル、ヘキサンジオールジビニルエーテル、ビスフェノールAアルキレンオキシドジビニルエーテル、ビスフェノールFアルキレンオキシドジビニルエーテル、トリメチロールプロパントリビニルエーテル、ジトリメチロールプロパンテトラビニルエーテル、グリセリントリビニルエーテル、ペンタエリスリトールテトラビニルエーテル、ジペンタエリスリトールペンタビニルエーテル、ジペンタエリスリトールヘキサビニルエーテル、エチレンオキシド付加トリメチロールプロパントリビニルエーテル、エチレンオキシド付加ジトリメチロールプロパンテトラビニルエーテル、エチレンオキシド付加ペンタエリスリトールテトラビニルエーテル、エチレンオキシド付加ジペンタエリスリトールヘキサビニルエーテル等の多官能ビニルエーテル類;
(メタ)アクリル酸2-ビニロキシエチル、(メタ)アクリル酸3-ビニロキシプロピル、(メタ)アクリル酸1-メチル-2-ビニロキシエチル、(メタ)アクリル酸2-ビニロキシプロピル、(メタ)アクリル酸4-ビニロキシブチル、(メタ)アクリル酸4-ビニロキシシクロヘキシル、(メタ)アクリル酸5-ビニロキシペンチル、(メタ)アクリル酸6-ビニロキシヘキシル、(メタ)アクリル酸4-ビニロキシメチルシクロヘキシルメチル、(メタ)アクリル酸p-ビニロキシメチルフェニルメチル、(メタ)アクリル酸2-(ビニロキシエトキシ)エチル、(メタ)アクリル酸2-(ビニロキシエトキシエトキシエトキシ)エチル等のビニルエーテル基含有(メタ)アクリル酸エステル類;
エチレングリコールジアリルエーテル、ジエチレングリコールジアリルエーテル、ポリエチレングリコールジアリルエーテル、プロピレングリコールジアリルエーテル、ブチレングリコールジアリルエーテル、ヘキサンジオールジアリルエーテル、ビスフェノールAアルキレンオキシドジアリルエーテル、ビスフェノールFアルキレンオキシドジアリルエーテル、トリメチロールプロパントリアリルエーテル、ジトリメチロールプロパンテトラアリルエーテル、ジアリルフタレート、グリセリントリアリルエーテル、ペンタエリスリトールテトラアリルエーテル、ジペンタエリスリトールペンタアリルエーテル、ジペンタエリスリトールヘキサアリルエーテル、エチレンオキシド付加トリメチロールプロパントリアリルエーテル、エチレンオキシド付加ジトリメチロールプロパンテトラアリルエーテル、エチレンオキシド付加ペンタエリスリトールテトラアリルエーテル、エチレンオキシド付加ジペンタエリスリトールヘキサアリルエーテル、トリアリルイソシアヌレート、トリアリルシアヌレート、トリアリルホルマール、トリアリルトリメリテート、テトラアリルテレフタルアミド等の多官能アリル化合物;
(メタ)アクリル酸アリル等のアリル基含有(メタ)アクリル酸エステル類;
N,N-エチレンビス(メタ)アクリルアミド等の多官能(メタ)アクリルアミド化合物;
ジプロパルギルテレフタレート等の多官能プロパルギル化合物;
N,N'-m-フェニレンビスマレイミド等の多官能マレイミド化合物;
トリレンジイソシアネート、イソホロンジイソシアネート、キシリレンジイソシアネート等の多官能イソシアネートと、(メタ)アクリル酸2-ヒドロキシエチル、(メタ)アクリル酸2-ヒドロキシプロピル等の水酸基含有(メタ)アクリル酸エステル類との反応で得られる多官能ウレタン(メタ)アクリレート類;
ジビニルベンゼン等の多官能芳香族ビニル類;
が挙げられる。
R4におけるアルコキシアルキル基としては、例えば、メトキシエチル基、メトキシプロピル基等の炭素数2~10の基が挙げられる。
R3およびR4におけるアルケニル基としては、例えば、前記エチレン性不飽和結合を有する基として例示した基と同様のアルケニル基が挙げられる。
R4におけるアシル基としては、例えば、アセチル基、オクタノイル基等の炭素数2~10の基が挙げられる。
cとdとの和は、好ましくは10~50の整数であり、eは、好ましくは1である。
官能基比=(成分(A)の配合量/成分(A)の官能基当量)/(成分(B)の配合量/成分(B)の官能基当量) ・・・(1)
成分(C)はラジカル開始剤であれば特に制限されず、従来公知のラジカル開始剤を用いることができる。
成分(A)と(B)とを、成分(C)を用いて反応(架橋)させることで、従来のペーストに用いられている白金系触媒を用いることなく、ポンプアウトが抑制されたペーストを得ることができ、例えば、常温下での保管環境であれば、ポットライフがほとんどない(極めて長い)ペーストを容易に得ることができる。
本ペーストに用いる成分(C)は、1種でもよく、2種以上でもよい。
本ペーストを放熱ペーストとして用いる場合、本ペーストは、成分(D)を含有することが好ましい。
本ペーストに成分(D)を用いる場合、用いる成分(D)は、1種でもよく、2種以上でもよい。2種以上の成分(D)を用いる場合、材質の異なる2種以上の成分(D)を用いてもよく、形状や平均粒子径等の異なる2種以上の成分(D)を用いてもよい。
このような成分(D)としては、例えば、金属粉、金属酸化物粉、金属窒化物粉、金属水酸化物粉、金属酸窒化物粉、金属炭化物粉、炭素材料が挙げられ、具体的には、酸化アルミニウム(Al2O3)、酸化ケイ素(SiO2)、酸化マグネシウム(MgO)、酸化ベリリウム(BeO)、酸化亜鉛(ZnO)、窒化ケイ素(Si3N4)、窒化ホウ素(例:六方晶BNや立方晶BN)、窒化アルミニウム(AlN)、炭化ケイ素(SiC)、グラファイト、ダイヤモンド、カーボンナノチューブが挙げられる。
粒状である成分(D)の平均粒子径は、例えば0.1μm以上であり、好ましくは0.5μm以上であり、例えば100μm以下であり、好ましくは50μm以下である。該平均粒子径は、レーザー回折・散乱法(マイクロトラック法)により得られる粒径分布におけるd50の値である。
一方、本ペーストは、初期粘度が低いため、本ペーストによれば、成分(D)の配合量を多くしても、作業性が低下し難い。
従って、本発明の一実施形態によれば、熱特性に特に優れるペーストを得ることを目的として、本ペースト100体積%に対し、成分(D)を、好ましくは40体積%以上、より好ましくは50体積%以上、好ましくは80体積%以下、より好ましくは70体積%以下配合しても、初期粘度が低く、作業性に優れるペーストを得ることができる。
本ペーストは、必要に応じて、本発明の効果を損なわない限り、フッ素系やシリコーン系オイル等の可塑剤;シランカップリング剤;界面活性剤;架橋促進剤;溶剤;分散剤;老化防止剤;酸化防止剤;難燃剤;顔料等の、前記成分(A)~(D)以外のその他の成分を含んでもよい。
該その他の成分はそれぞれ、1種を用いてもよく、2種以上を用いてもよい。
従来のペーストは、白金系触媒を用いていたが、白金系触媒を用いると、ポットライフが短く、ペーストの長期保存ができなかった。
なお、白金系触媒を含まないとは、成分(A)および(B)の合計100質量部に対する白金系触媒の含有量が、例えば0.0001質量部以下であることをいい、下限は好ましくは0質量部である。
本ペーストは、前記成分(A)~(C)および必要により用いられる前記成分(D)や前記その他の成分を混合し、ミキサーやロール等を用いて混練分散させることにより調製することができる。
本ペーストのコーンプレート型粘度計で測定した23℃における初期剪断粘度(この粘度は、初期粘度のことである。)は、低いことが好ましく、具体的には、好ましくは500Pa・s以下、より好ましくは300Pa・s以下、特に好ましくは250Pa・s以下であり、好ましくは1Pa・s以上である。
本ペーストの初期粘度が前記範囲にあると、作業性に優れる(塗装や流し込みなどにより所定の場所にペーストを形成しやすい)ペーストを容易に得ることができる。また、このような初期粘度が低いペーストが放熱ペーストである場合、例えば、発熱体と放熱部の間などの所定の場所に厚みの薄いペースト層を容易に形成することができ、発熱体や放熱部などの相手面と馴染みやすいため、該ペースト層による熱抵抗を低減することができ、放熱特性に優れる電子部品等を容易に得ることができる。
通常、初期粘度の低いペーストは、加熱増粘したとしてもポンプアウトしやすかったが、本ペーストによれば、初期粘度が低くても、加熱増粘後にはポンプアウトを抑制することができる。
初期粘度に対する加熱後粘度の比が前記範囲にあると、低い初期粘度と、ポンプアウトの抑制性とにバランスよく優れるペーストを容易に得ることができる。
加熱後粘度が前記範囲にあると、流動抵抗により、加熱増粘後にはポンプアウトを容易に抑制することができる。
本ペーストは、従来のペーストが用いられてきた用途に制限なく用いることができるが、本発明の効果がより発揮される等の点から、高温(例:200℃以上)下に曝される可能性のある用途、温度がかかっても(加熱下でも)所定の場所にペースト状で留まることが求められている用途、特に、塗装や流し込みなどにより所定の場所にペーストを形成する際には粘度が低く、温度がかかっても(加熱下でも)所定の場所にペースト状で留まることが求められている用途に好適に用いることができる。
この際の加熱温度としては本ペーストの調製に用いる各成分に応じて適宜設定すればよく、特に、用いる成分(C)の種類に応じて適宜設定すればよいが、好ましくは80℃以上、より好ましくは100℃以上であり、好ましくは200℃以下、より好ましくは170℃以下である。
表1または2に示す配合比率(数値の単位は質量部である)で、表1または2の各配合成分を混合することでペーストを調製した。
表1および2中の各成分は、以下の通りである。
・ポリシロキサンA-2:信越化学工業(株)製の「KF-2004」(メルカプト基を有するポリシロキサン、官能基当量:30000g/mol)
・ポリシロキサンA-3:信越化学工業(株)製の「X-22-167C」(メルカプト基を有するポリシロキサン、官能基当量:2300g/mol)
・ポリシロキサンA’:信越化学工業(株)製の「KF-96-100CS」(ジメチルポリシロキサン)
・化合物B-1:Gelest社製の「DMS-V25」(1分子中に2個のエチレン性不飽和結合を有する基を含むポリシロキサン、官能基当量:8600g/mol)
・化合物B-2:Gelest社製の「DMS-V35」(1分子中に2個のエチレン性不飽和結合を有する基を含むポリシロキサン、官能基当量:24750g/mol)
・化合物B-3:信越化学工業(株)製の「KE-1950-10A」(1分子中に2個のエチレン性不飽和結合を有する基を含むポリシロキサン、官能基当量:55350g/mol)
・化合物B-4:精工化学(株)製の「ハイクロスM」(トリメチロールプロパントリメタクリレート、官能基当量:112g/mol)
・化合物B-5:三菱ケミカル(株)製の「TAIC」(トリアリルイソシアヌレート、官能基当量:83g/mol)
・化合物B-6:Sigma-Aldrich社製の「ポリ(エチレングリコールジビニルエーテル)」(官能基当量:125g/mol)
・HEMA:2-ヒドロキシエチルメタクリレート
・開始剤C-1:日油(株)製の「パーキュアO」
・開始剤C-2:2,2’-アゾビス(2-メチルブチロニトリル)
・開始剤C-3:2,2’-アゾビス(イソ酪酸ジメチル)
・開始剤C-4:日油(株)製の「パーヘキサ25B」
・フィラーD-1:住友化学(株)製の「アドバンスドアルミナ AA-1.5(アルミナ粉末)
調製したペーストの23℃における粘度(初期粘度)を、コーンプレート型粘度計(Brookfield社製)を用いて測定した。結果を表1および2に示す。
なお、実施例1~10、比較例1~3および比較例5では、回転数を200rpmとして測定し、比較例4では、回転数を100rpmとして測定し、実施例11~21および比較例6では、回転数を1.5rpmとして測定した。
調製したペーストを、各ペーストに用いたラジカル開始剤(C)の1分間半減期温度で10分間加熱した後、23℃まで降温させた際の粘度(加熱後粘度)を、コーンプレート型粘度計(Brookfield社製)を用いて測定した。結果を表1および2に示す。
なお、実施例1~2および比較例2では、回転数を200rpmとして測定し、実施例8では、回転数を100rpmとして測定し、実施例4~7および実施例9では、回転数を10rpmとして測定し、実施例10、比較例1および比較例3~5では、回転数を1.5rpmとして測定し、実施例3では、回転数を0.5rpmとして測定し、実施例11~21および比較例6では、回転数を0.1rpmとして測定した。
調製したペーストを、各ペーストに用いたラジカル開始剤(C)の1分間半減期の温度で、10分間加熱硬化した。次いで、23℃まで降温させて得られた加熱硬化後のサンプル0.2gを5mm角にした後、以下の方法に基づき、23℃下、1.0MPaの圧力で圧縮した際の該サンプルの厚みを測定した。結果を表1および2に示す。
前もって金属円盤2枚を重ね、ねじを締めこむことによって1MPaを負荷してから3分経過後の、1MPaの荷重を負荷した状態における、2枚の金属円盤両端の長さ(サンプルなしの長さ)を測定した。
次いで、金属円盤上に、サンプル0.2gを5mm角に引き延ばした後、もう一枚の金属円盤によって挟み込み、ねじを締めて、該サンプルに1.0MPaの荷重を負荷した。その後、ねじ部の目詰まりを解消するため、ねじを緩めてサンプルを金属円盤上から取り除いた。前記金属円盤上にサンプル0.2gを5mm角に引き延ばすことから、サンプルを金属円盤上から取り除くまでの工程を1サイクルとした。この1サイクルを5回行った後の、該5サイクル目における1MPaの荷重を負荷してから3分経過後の、1MPaの荷重を負荷した状態における、2枚の金属円盤両端の長さ(サンプルありの長さ)を測定した。
前記サンプルありの長さから、前記サンプルなしの長さを引くことで、サンプルの厚みを算出し、このサンプルの厚みにより、ペースト性状を評価した。
なお、前記のように5サイクル目の厚みを測定したのは、測定治具の特性上、排出されるべき流動性サンプルの一部が、前記ねじ部で滞留(目詰まり)し、適切な厚みを測定できない状態になることを防ぐためである。
一方、比較例2で得られたペーストは、加熱増粘後でもポンプアウトを抑制できず、比較例1および3~6で得られたペーストは、加熱硬化後には、ペーストとはいえなかった(流動性はなかった)。
本ペーストでは、特に、前記成分(A)を用いることで、加熱硬化(加熱増粘)の際に、該成分(A)が反応し、適度な可塑剤として作用しながら、架橋を進める役割も担っており、また、ブリードアウトし難いため、ペースト状態を維持しながら増粘できると考えられる。
一方で、比較例3~6のように、成分(A)を用いず、エチレン性不飽和結合を有する基を含むポリシロキサンや一般的なシリコンオイルを用いた場合は、適切な増粘ができない(増粘が進まない)、または、シリコンオイルがブリードアウトすることにより、加熱硬化後にペースト性状を維持できないと考えられる。
Claims (7)
- メルカプト基を有するポリシロキサン(A)、1分子中に2個以上のエチレン性不飽和結合を有する基を含む化合物(B)およびラジカル開始剤(C)を含むペースト。
- 下記式(1)で表される官能基比が3以下である、請求項1に記載のペースト。
官能基比=(前記ポリシロキサン(A)の配合量/前記ポリシロキサン(A)の官能基当量)/(前記化合物(B)の配合量/前記化合物(B)の官能基当量) ・・・(1) - 下記要件(I)を満たす、請求項1に記載のペースト:
要件(I);前記ラジカル開始剤(C)の1分間半減期の温度で、10分間加熱硬化を行い、該加熱硬化後のペースト0.2gを5mm角にした後、23℃、1.0MPaの圧力で圧縮した際の厚みが200μm以下である。 - 23℃における初期剪断粘度が500Pa・s以下である、請求項1~3のいずれか1項に記載のペースト。
- 前記ペーストの、23℃における初期剪断粘度に対する、前記ペーストをラジカル開始剤(C)の1分間半減期温度で10分間加熱した後、23℃まで降温させた後の加熱後剪断粘度の比が3倍以上である、請求項1~3のいずれか1項に記載のペースト。
- 熱伝導性フィラー(D)を含む、請求項1~3のいずれか1項に記載のペースト。
- 熱伝導性フィラー(D)の含有量が、ペースト100体積%に対し、30~80体積%である、請求項6に記載のペースト。
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Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2013227374A (ja) | 2012-04-24 | 2013-11-07 | Shin-Etsu Chemical Co Ltd | 加熱硬化型熱伝導性シリコーングリース組成物 |
JP2017502102A (ja) * | 2013-11-11 | 2017-01-19 | ダウ コーニング コーポレーションDow Corning Corporation | Uv硬化性シリコーン組成物、その硬化生成物、及びその使用方法 |
JP2017165791A (ja) | 2016-03-14 | 2017-09-21 | 信越化学工業株式会社 | 付加一液加熱硬化型熱伝導性シリコーングリース組成物及びその硬化物の製造方法 |
JP2018510946A (ja) * | 2015-03-27 | 2018-04-19 | モメンティブ パフォーマンス マテリアルズ インコーポレイテッド | シリコーン系親水性コポリマーおよびそれを含むヒドロゲル組成物 |
WO2020170114A1 (en) * | 2019-02-18 | 2020-08-27 | 3M Innovative Properties Company | Radiation-curable composition containing mercapto-functional polyorganosiloxanes for additive-manufacturing technology |
-
2023
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Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2013227374A (ja) | 2012-04-24 | 2013-11-07 | Shin-Etsu Chemical Co Ltd | 加熱硬化型熱伝導性シリコーングリース組成物 |
JP2017502102A (ja) * | 2013-11-11 | 2017-01-19 | ダウ コーニング コーポレーションDow Corning Corporation | Uv硬化性シリコーン組成物、その硬化生成物、及びその使用方法 |
JP2018510946A (ja) * | 2015-03-27 | 2018-04-19 | モメンティブ パフォーマンス マテリアルズ インコーポレイテッド | シリコーン系親水性コポリマーおよびそれを含むヒドロゲル組成物 |
JP2017165791A (ja) | 2016-03-14 | 2017-09-21 | 信越化学工業株式会社 | 付加一液加熱硬化型熱伝導性シリコーングリース組成物及びその硬化物の製造方法 |
WO2020170114A1 (en) * | 2019-02-18 | 2020-08-27 | 3M Innovative Properties Company | Radiation-curable composition containing mercapto-functional polyorganosiloxanes for additive-manufacturing technology |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2024190331A1 (ja) * | 2023-03-16 | 2024-09-19 | 株式会社バルカー | ペースト |
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