WO2012029538A1 - ポリシロキサン組成物及びその硬化物 - Google Patents
ポリシロキサン組成物及びその硬化物 Download PDFInfo
- Publication number
- WO2012029538A1 WO2012029538A1 PCT/JP2011/068570 JP2011068570W WO2012029538A1 WO 2012029538 A1 WO2012029538 A1 WO 2012029538A1 JP 2011068570 W JP2011068570 W JP 2011068570W WO 2012029538 A1 WO2012029538 A1 WO 2012029538A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- polysiloxane composition
- group
- composition according
- polysiloxane
- organopolysiloxane
- Prior art date
Links
- -1 Polysiloxane Polymers 0.000 title claims abstract description 147
- 229920001296 polysiloxane Polymers 0.000 title claims abstract description 116
- 239000000203 mixture Substances 0.000 title claims abstract description 88
- 239000002245 particle Substances 0.000 claims abstract description 38
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 32
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 30
- 229920006136 organohydrogenpolysiloxane Polymers 0.000 claims abstract description 23
- 239000010954 inorganic particle Substances 0.000 claims abstract description 20
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims abstract description 17
- 229910052710 silicon Inorganic materials 0.000 claims abstract description 17
- 239000007809 chemical reaction catalyst Substances 0.000 claims abstract description 7
- 238000006459 hydrosilylation reaction Methods 0.000 claims abstract description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 20
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical group [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 18
- 239000002904 solvent Substances 0.000 claims description 16
- 238000002156 mixing Methods 0.000 claims description 14
- 239000010703 silicon Substances 0.000 claims description 13
- 239000003054 catalyst Substances 0.000 claims description 12
- 229910044991 metal oxide Inorganic materials 0.000 claims description 10
- 150000004706 metal oxides Chemical class 0.000 claims description 10
- 239000000377 silicon dioxide Substances 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 239000000047 product Substances 0.000 description 32
- 229920001577 copolymer Polymers 0.000 description 13
- 238000000034 method Methods 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 11
- 239000000463 material Substances 0.000 description 11
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- 125000003342 alkenyl group Chemical group 0.000 description 9
- 125000000962 organic group Chemical group 0.000 description 8
- 229920000642 polymer Polymers 0.000 description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
- 150000002430 hydrocarbons Chemical group 0.000 description 7
- 229910052697 platinum Inorganic materials 0.000 description 7
- 239000000758 substrate Substances 0.000 description 7
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 6
- 125000000524 functional group Chemical group 0.000 description 6
- 239000004065 semiconductor Substances 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 5
- 239000004205 dimethyl polysiloxane Substances 0.000 description 5
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 5
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 5
- 238000007789 sealing Methods 0.000 description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 5
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 4
- 125000003700 epoxy group Chemical group 0.000 description 4
- 239000010419 fine particle Substances 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 229920001843 polymethylhydrosiloxane Polymers 0.000 description 4
- 239000003566 sealing material Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000006482 condensation reaction Methods 0.000 description 3
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 125000006038 hexenyl group Chemical group 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 239000002683 reaction inhibitor Substances 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 229930195734 saturated hydrocarbon Natural products 0.000 description 3
- 125000005372 silanol group Chemical group 0.000 description 3
- 229920002050 silicone resin Polymers 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- 229910004283 SiO 4 Inorganic materials 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- 125000003368 amide group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- 239000012776 electronic material Substances 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- 238000011049 filling Methods 0.000 description 2
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 125000003944 tolyl group Chemical group 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 2
- KWEKXPWNFQBJAY-UHFFFAOYSA-N (dimethyl-$l^{3}-silanyl)oxy-dimethylsilicon Chemical group C[Si](C)O[Si](C)C KWEKXPWNFQBJAY-UHFFFAOYSA-N 0.000 description 1
- HMVBQEAJQVQOTI-SOFGYWHQSA-N (e)-3,5-dimethylhex-3-en-1-yne Chemical compound CC(C)\C=C(/C)C#C HMVBQEAJQVQOTI-SOFGYWHQSA-N 0.000 description 1
- GRGVQLWQXHFRHO-AATRIKPKSA-N (e)-3-methylpent-3-en-1-yne Chemical compound C\C=C(/C)C#C GRGVQLWQXHFRHO-AATRIKPKSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- WZJUBBHODHNQPW-UHFFFAOYSA-N 2,4,6,8-tetramethyl-1,3,5,7,2$l^{3},4$l^{3},6$l^{3},8$l^{3}-tetraoxatetrasilocane Chemical group C[Si]1O[Si](C)O[Si](C)O[Si](C)O1 WZJUBBHODHNQPW-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- CEBKHWWANWSNTI-UHFFFAOYSA-N 2-methylbut-3-yn-2-ol Chemical compound CC(C)(O)C#C CEBKHWWANWSNTI-UHFFFAOYSA-N 0.000 description 1
- KSLSOBUAIFEGLT-UHFFFAOYSA-N 2-phenylbut-3-yn-2-ol Chemical compound C#CC(O)(C)C1=CC=CC=C1 KSLSOBUAIFEGLT-UHFFFAOYSA-N 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
- NECRQCBKTGZNMH-UHFFFAOYSA-N 3,5-dimethylhex-1-yn-3-ol Chemical compound CC(C)CC(C)(O)C#C NECRQCBKTGZNMH-UHFFFAOYSA-N 0.000 description 1
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 1
- KBQVDAIIQCXKPI-UHFFFAOYSA-N 3-trimethoxysilylpropyl prop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C=C KBQVDAIIQCXKPI-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- DWCBWHINVBESJA-UHFFFAOYSA-N [SiH4].CO[Si](OC)(OC)CCCOCC1CO1 Chemical compound [SiH4].CO[Si](OC)(OC)CCCOCC1CO1 DWCBWHINVBESJA-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000002318 adhesion promoter Substances 0.000 description 1
- 239000005456 alcohol based solvent Substances 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000004581 coalescence Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 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
- 238000000354 decomposition reaction Methods 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
- 230000008021 deposition Effects 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 239000003759 ester based solvent Substances 0.000 description 1
- BITPLIXHRASDQB-UHFFFAOYSA-N ethenyl-[ethenyl(dimethyl)silyl]oxy-dimethylsilane Chemical compound C=C[Si](C)(C)O[Si](C)(C)C=C BITPLIXHRASDQB-UHFFFAOYSA-N 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 230000017525 heat dissipation Effects 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
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- LWIGVRDDANOFTD-UHFFFAOYSA-N hydroxy(dimethyl)silane Chemical group C[SiH](C)O LWIGVRDDANOFTD-UHFFFAOYSA-N 0.000 description 1
- NYMPGSQKHIOWIO-UHFFFAOYSA-N hydroxy(diphenyl)silicon Chemical class C=1C=CC=CC=1[Si](O)C1=CC=CC=C1 NYMPGSQKHIOWIO-UHFFFAOYSA-N 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000005453 ketone based solvent Substances 0.000 description 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N methyl cyanide Natural products CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 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
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002825 nitriles Chemical class 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
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- UPIXZLGONUBZLK-UHFFFAOYSA-N platinum Chemical compound [Pt].[Pt] UPIXZLGONUBZLK-UHFFFAOYSA-N 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical group [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000013519 translation Methods 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- 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
- C08L83/06—Polysiloxanes containing silicon bound to oxygen-containing groups
-
- 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
-
- 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
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/56—Organo-metallic compounds, i.e. organic compounds containing a metal-to-carbon bond
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- 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
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- 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/12—Polysiloxanes containing silicon bound to hydrogen
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- 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
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- 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups
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- 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
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/20—Oxides; Hydroxides
- C08K3/22—Oxides; Hydroxides of metals
- C08K2003/2227—Oxides; Hydroxides of metals of aluminium
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- 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
- C08K2201/00—Specific properties of additives
- C08K2201/016—Additives defined by their aspect ratio
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- 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
- C08K7/00—Use of ingredients characterised by shape
- C08K7/16—Solid spheres
- C08K7/18—Solid spheres inorganic
Definitions
- the present invention relates to a polysiloxane composition excellent in heat resistance and molding processability and a cured product thereof.
- 2007-332104, 2008-19426, and 2008-38137 disclose a method in which the surface of inorganic particles is treated with an appropriate material and dispersed in polysiloxane at a high concentration. Has been. However, the materials obtained by these techniques are not hard and are not suitable for use at high temperatures due to large thermal expansion.
- JP-T-2006-503142 discloses a novel curable silicone resin.
- the cured product of this silicone resin has a low thermal expansion compared to a cured product of a normal silicone resin, but the linear expansion coefficient in the temperature range from room temperature to 100 ° C. is a value of about 100 ppm. Is still big.
- JP-T-2006-503142 describes only the linear expansion coefficient up to around 200 ° C.
- Japanese Patent Application Laid-Open No. 5-105814 discloses a composition in which spherical inorganic particles are blended with a curable polysiloxane. However, since the composition is gel after curing, the heat resistance is insufficient and the linear expansion coefficient. Is also big. Further, Republished 2003-29353 discloses a low thermal expansion material comprising an epoxy group-containing polysiloxane and spherical inorganic particles. This material is a composition that uses a solvent to ensure fluidity. Therefore, it is not suitable as a sealing material.
- solid epoxy resins that can be transfer molded are widely known (see, for example, Japanese Patent Application Laid-Open No. 8-31159).
- a fluid with high viscosity is injected into a mold at a high pressure, molding of a dense shape is possible.
- it is unsuitable for sealing electronic parts and has a low glass transition temperature, and the linear expansion coefficient above that temperature cannot be said to be sufficiently small.
- An object of the present invention is to provide a polysiloxane composition having good workability and having a very low coefficient of thermal expansion after curing and giving a hard cured product, and a cured product thereof.
- the purpose of the present invention is to (A) at least one organopolysiloxane containing at least two unsaturated aliphatic hydrocarbon groups in one molecule (B) at least one containing at least two silicon-bonded hydrogen atoms in one molecule An organohydrogenpolysiloxane (C) hydrosilylation reaction catalyst, and (D) A polysiloxane composition containing inorganic particles having a major axis / minor axis ratio of 1 to 1.5 and a ratio of particles having a particle diameter of 50 ⁇ m or more in all particles of 5% by weight or less, (A) The weight fraction of unsaturated aliphatic hydrocarbon groups in the organopolysiloxane is 0.5 to 10% by weight, The blending ratio of (D) inorganic particles to the polysiloxane composition is 55 to 85% by volume, The value of [(A) weight fraction of unsaturated aliphatic hydrocarbon group in organopolysiloxane] ⁇ [(B) weight
- the viscosity of the (A) organopolysiloxane at 25 ° C. is preferably 0.05 to 20 Pa ⁇ s.
- the weight fraction of silicon atom-bonded hydrogen atoms in the (B) organohydrogenpolysiloxane is preferably 0.1% by weight or more.
- the viscosity of the (B) organohydrogenpolysiloxane at 25 ° C. is preferably 0.1 Pa ⁇ s or less.
- the value of [(A) weight fraction of unsaturated aliphatic hydrocarbon groups in organopolysiloxane] ⁇ [(B) weight fraction of silicon atom-bonded hydrogen atoms in organohydrogenpolysiloxane] is 0.5 to More preferably, it is 4.5.
- the value of [(B) moles of silicon-bonded hydrogen atoms in organohydrogenpolysiloxane] / [(A) moles of unsaturated aliphatic hydrocarbon groups in organopolysiloxane] is 0.5 to 1. 5 is preferable.
- the (C) hydrosilylation reaction catalyst is preferably a platinum group metal catalyst.
- the (D) inorganic particles preferably include at least one metal oxide particle.
- the metal oxide particles are preferably silica.
- the polysiloxane composition of the present invention preferably further contains at least one (E) adhesion promoter.
- the polysiloxane composition of the present invention preferably contains no solvent.
- the polysiloxane composition of the present invention can give a cured product having a linear expansion coefficient at 30 ° C. to 300 ° C. of 80 ⁇ 10 ⁇ 6 / K or less, preferably 50 ⁇ 10 ⁇ 6 / K or less.
- the present invention also relates to a cured product obtained by curing the polysiloxane composition.
- the polysiloxane composition of the present invention contains a relatively large amount of inorganic particles, the polysiloxane composition has a low viscosity and good workability and gives a hard cured product having a very low coefficient of thermal expansion after curing. Can do.
- the polysiloxane composition of the present invention does not contain a solvent, there is no fear of deterioration of the substrate, electronic material, etc. due to the solvent, and voids resulting from the solvent in the cured product, Cracks do not occur. Therefore, it can be suitably used as a sealing material for semiconductors and the like.
- the cured product of the present invention 30 ° C. ⁇ 300 linear expansion coefficient ° C. is 100 ⁇ 10 -6 / K or less, preferably 70 ⁇ 10 -6 / K or less, more preferably 50 ⁇ 10 -6 / K or less
- the expansion coefficient is very small, and sufficient hardness can be maintained. Therefore, the cured product of the present invention can be used continuously for a long time even in an environment exceeding 200 ° C., and for example, it is not peeled off from the substrate, so that it is particularly suitable for sealing a power semiconductor.
- the at least one organopolysiloxane containing at least two unsaturated aliphatic hydrocarbon groups in one molecule has a structure as long as it has at least two aliphatic unsaturated hydrocarbon groups in one molecule.
- limiting on the top For example, linear, branched, or network-like organopolysiloxane can be used.
- the component (A) can be used alone, or two or more organopolysiloxanes having different structures can be used in combination.
- the unsaturated aliphatic hydrocarbon group in component (A) is preferably one having 2 to 20 carbon atoms.
- Examples of the monovalent unsaturated aliphatic hydrocarbon group having 2 to 20 carbon atoms include vinyl, 1-propenyl, allyl, isopropenyl, 1-butenyl, 2-butenyl, pentenyl, and hexenyl.
- a linear or branched alkenyl group such as a group, a cycloalkenyl group such as a cyclopentenyl group and a cyclohexenyl group, and a cycloalkenylalkyl group such as a cyclopentenylethyl group, a cyclohexenylethyl group and a cyclohexenylpropyl group Is mentioned.
- Alkenyl groups are preferred, with vinyl and hexenyl groups being particularly preferred.
- bonded with silicon atoms other than the unsaturated aliphatic hydrocarbon group of a component is a monovalent organic group which has a substituted or unsubstituted monovalent hydrocarbon group, or a reactive functional group.
- a substituted or unsubstituted monovalent hydrocarbon group is typically a substituted or unsubstituted one having 1 to 20 carbon atoms, preferably 1 to 10 carbon atoms, more preferably 1 to 4 carbon atoms. And a monovalent aromatic hydrocarbon group having 6 to 20 carbon atoms, more preferably 6 to 12 carbon atoms.
- the component (A) may have an alkoxy group having 1 to 12 carbon atoms such as a hydroxyl group, a methoxy group, an ethoxy group, a propoxy group, or a butoxy group as a monovalent organic group.
- Examples of the monovalent saturated hydrocarbon group having 1 to 20 carbon atoms include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, and a tert-butyl group.
- a linear or branched alkyl group such as a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group and a decyl group, and a cycloalkyl group such as a cyclopentyl group, a cyclohexyl group, a cycloheptyl group and a cyclooctyl group.
- a cycloalkyl group such as a cyclopentyl group, a cyclohexyl group, a cycloheptyl group and a cyclooctyl group.
- Examples of the monovalent aromatic hydrocarbon group having 6 to 20 carbon atoms include aryl groups such as phenyl group, tolyl group, xylyl group, and mesityl group.
- a phenyl group is preferred.
- the aromatic hydrocarbon group includes a group in which an aromatic hydrocarbon and an aliphatic saturated hydrocarbon are combined in addition to a group consisting of only an aromatic hydrocarbon.
- Examples of the group in which an aromatic hydrocarbon and a saturated hydrocarbon are combined include an aralkyl group such as a benzyl group or a phenethyl group.
- the hydrogen atom on the monovalent hydrocarbon group may be substituted with one or more substituents, and examples of the substituent include a halogen atom (a fluorine atom, a chlorine atom, a bromine atom and an iodine atom), a hydroxyl group , An amide group, an ester group, a carboxyl group, and an isocyanate group.
- a monovalent saturated or aromatic hydrocarbon group having at least one substituent is preferred.
- Examples of the monovalent organic group having a reactive functional group include a reactive functional group selected from the group consisting of a hydroxyl group, a mercapto group, an epoxy group, an amino group, an amide group, an ester group, a carboxyl group, and an isocyanate group. And monovalent saturated or aromatic hydrocarbon groups. There may be one or more reactive functional groups present in the monovalent organic group.
- Preferred R 1 is a monovalent saturated or aromatic hydrocarbon group having at least one reactive functional group as described above. Specific examples of the reactive functional group include 3-hydroxypropyl group, 3- (2-hydroxyethoxy) propyl group, 3-mercaptopropyl group, 2,3-epoxypropyl group, and 3,4-epoxybutyl group.
- the component (A) is preferably a linear or branched polysiloxane, but may contain a small amount of cyclic methyl vinyl polysiloxane.
- the linear component (A) is preferably a polymer containing a diorganosiloxane unit and a triorganosiloxy unit, such as a dimethylpolysiloxane blocked with a dimethylvinylsiloxy group at both ends of a molecular chain, and a dimethylpolysiloxane with both ends of a molecular chain.
- Examples of the substituted polymer and a mixture of two or more of these polymers are exemplified, and in particular, a linear diorganopoly having an unsaturated aliphatic hydrocarbon group, particularly an alkenyl group, only at both ends of the molecular chain. Siloxane is preferred.
- the branched chain (A) component is particularly preferably a polymer containing a diorganosiloxane unit, an organosilsesquioxane unit, and a triorganosiloxy unit.
- silicon-bonded organic groups in these units include alkyl groups such as methyl, ethyl, and propyl; alkenyl groups such as vinyl, allyl, butenyl, and hexenyl; and aryls such as phenyl and tolyl.
- a monovalent hydrocarbon group such as a halogenated alkyl group such as a 3,3,3-trifluoropropyl group, and may have a small amount of a hydroxyl group, and further an alkoxy group such as a methoxy group
- the at least two silicon-bonded organic groups in the polymer must be unsaturated aliphatic hydrocarbon groups, especially alkenyl groups.
- the ratio of these units is not limited, but in this polymer, the amount of diorganosiloxane units is in the range of 80.00 to 99.65 mol%, and the organosilsesquioxane units are 0.10 to Preferably the amount is in the range of 10.00 mol% and the remaining mol% is triorganosiloxy units.
- the viscosity of a component (A) points out the viscosity of the mixture.
- the viscosity is measured using a commonly used method, for example, a rheometer, a rotational viscometer, etc., but it is recommended to use the viscosity at a shear rate of 10 s -1 according to the method described in JIS K7117-2. .
- the value is preferably 0.05 Pa ⁇ s or more and 20 Pa ⁇ s or less at 25 ° C. in order to maintain good processability and mechanical strength of the polysiloxane composition.
- a preferable viscosity range is 0.1 Pa ⁇ s or more and 10 Pa ⁇ s or less at 25 ° C.
- the weight fraction of the unsaturated aliphatic hydrocarbon group (A) is the weight fraction of the unsaturated aliphatic hydrocarbon group of the mixture. Refers to the rate.
- the said weight fraction represents content of the unsaturated aliphatic hydrocarbon group of (A) component, and the value is 0.5 weight% or more and 10 weight% or less. When outside this range, it becomes difficult to control the linear expansion coefficient of the cured product of the polysiloxane composition to a desired value, and the cured product may become brittle.
- a preferred range is 0.8 wt% or more and 10 wt% or less, and a more preferred range is 1 wt% or more and 7 wt% or less.
- the blending amount of the component (A) in the composition of the present invention is [(A) weight fraction of unsaturated aliphatic hydrocarbon group in the organopolysiloxane] ⁇ [(B) organo
- the weight fraction of silicon atom-bonded hydrogen atoms in the hydrogen polysiloxane is not particularly limited as long as the value is 0.04 to 8, for example, 1 to 20 mass (weight) of the composition. %, Or 5 to 10 mass (weight)%.
- the at least one organohydrogenpolysiloxane containing at least two silicon atom-bonded hydrogen atoms in one molecule is structural as long as it has at least two silicon atom-bonded hydrogen atoms in one molecule.
- the component (B) can be used alone, or two or more types of organohydrogenpolysiloxanes having different structures can be used in combination.
- the component (B) includes 1,1,3,3-tetramethyldisiloxane, 1,3,5,7-tetramethylcyclotetrasiloxane, trimethylsiloxy group-blocked methylhydrogenpolysiloxane at both molecular chains, Both ends of the chain trimethylsiloxy-blocked dimethylsiloxane / methylhydrogensiloxane copolymer, both ends of the molecular chain dimethylhydrogensiloxy-blocked dimethylpolysiloxane, both ends of the molecular chain dimethylhydrogensiloxy-blocked dimethylsiloxane / methylhydrogensiloxane Polymer, both ends of the molecular chain blocked methylhydrogensiloxane / diphenylsiloxane copolymer, both ends of the molecular chain blocked trimethylsiloxy group blocked methylhydrogensiloxane / diphenylsiloxane / dimethylsiloxane Coal
- the viscosity of a component (B) points out the viscosity of the mixture.
- the viscosity is measured using a commonly used method, for example, a rheometer, a rotational viscometer, etc., but it is recommended to use the viscosity at a shear rate of 10 s -1 according to the method described in JIS K7117-2. .
- the viscosity of the component (B) is preferably 0.1 Pa ⁇ s or less at 25 ° C. in order to keep the processability and mechanical strength of the polysiloxane composition good. If it exceeds 0.1 Pa ⁇ s at 25 ° C., the processability of the polysiloxane composition may be reduced.
- a preferred range is 0.05 Pa ⁇ s or less at 25 ° C.
- the weight fraction of silicon atom-bonded hydrogen atoms as component (B) will be described.
- the weight fraction of silicon-bonded hydrogen atoms in component (B) is the weight fraction of silicon-bonded hydrogen atoms in the mixture.
- the said weight fraction represents content of the silicon atom bond hydrogen atom of (B) component, and the value has preferable 0.1 weight% or more. If it is outside this range, it may be difficult to control the linear expansion coefficient of the cured product of the polysiloxane composition to a desired value.
- a preferable range is 0.15% by weight or more, and a more preferable range is 0.2% by weight or more.
- the blending amount of the component (B) in the composition of the present invention is as follows: [(A) weight fraction of unsaturated aliphatic hydrocarbon group in the organopolysiloxane] ⁇ [(B) organohydrogen with respect to the component (A)
- the value of the weight fraction of silicon-bonded hydrogen atoms in the polysiloxane is 0.04 to 8, it is not particularly limited. For example, 1 to 10% by mass (weight) of the composition, Alternatively, it can occupy 2-5 mass (weight)%.
- Component (C) is a hydrosilylation reaction catalyst, which accelerates the addition reaction between the unsaturated aliphatic hydrocarbon group of component (A) and the silicon-bonded hydrogen atom of component (B) to cure the polysiloxane composition of the present invention. It is a catalyst for making it.
- Examples of the component (C) include chloroplatinic acid, an alcohol solution of chloroplatinic acid, a complex of platinum and olefin, a complex of platinum and 1,3-divinyl-1,1,3,3-tetramethyldisiloxane, platinum Platinum-based catalysts such as powders carrying palladium; palladium-based catalysts such as tetrakis (triphenylphosphine) palladium, palladium black, mixtures with triphenylphosphine; and rhodium-based catalysts such as platinum-based catalysts, palladium A platinum group metal catalyst such as a catalyst is preferable, and a platinum catalyst is more preferable.
- the blending amount of the component (C) is a catalytic amount.
- the platinum metal of the catalyst is 0.01% by weight in the polysiloxane composition of the present invention.
- An amount in the range of ⁇ 1000 ppm is practically preferable, and an amount in the range of 0.1 to 500 ppm is particularly preferable.
- Component (D) is an inorganic particle having a major axis / minor axis ratio of 1 to 1.5.
- the major axis / minor axis ratio is the ratio of [major axis] / [minor axis] of particles measured by a microscope such as a scanning electron microscope. When this ratio exceeds 1.5, the processability of the resulting polysiloxane composition is remarkably lowered, which is not suitable.
- the major axis / minor axis ratio is preferably 1.2 or less, more preferably 1.1 or less, and even more preferably 1.0. Accordingly, spherical inorganic particles are preferred.
- the ratio of particles having a particle diameter of 50 ⁇ m or more in all particles of the component (D) needs to be 5% by weight or less.
- the particle diameter refers to the long diameter of the particle measured by a laser scattering / diffraction particle size distribution measuring device or the like. If this ratio exceeds 5% by weight, the uniformity of the composition tends to be lost, which is not suitable.
- the blending ratio of the component (D) with respect to the total amount of the polysiloxane composition of the present invention is 55 to 85% by volume, more preferably 60 to 85% by volume. If it is less than 55% by volume, both low thermal expansion after curing and good workability before curing cannot be satisfied at the same time.
- the amount of component (D) is preferably 70 to 85% by volume, and more preferably 75 to 82% by volume. In terms of weight percentage, the amount of component (D) is preferably 60 to 95% by weight, more preferably 75 to 90% by weight.
- the component (D) may be a single inorganic particle or a mixture of two or more kinds of inorganic particles.
- the material of the inorganic particles is not particularly limited as long as it is an inorganic substance, but a metal oxide is preferable. Therefore, it is preferable that the inorganic particles of the component (D) include at least one kind of metal oxide particles.
- the metal oxide include silica, alumina, titania, zirconia, talc, glass, zinc oxide, and the like, and silica is preferable from the viewpoint of heat resistance, workability, and economy.
- 90% by weight or more of the component (D) is preferably silica.
- an adhesion imparting agent can be blended.
- Adhesion-imparting agents include silicon-bonded hydrogen atoms, silicon-bonded alkenyl groups (vinyl groups as an example), silicon-bonded alkoxy groups, silicon-bonded epoxy group-containing organic groups, silicon-bonded acrylic group-containing organics in one molecule.
- a linear or cyclic polysiloxane containing at least two reactive groups selected from the group is preferred.
- an adhesion-imparting agent an acryloxy group-containing organoalkoxysilane such as 3-methacryloxypropyltrimethoxysilane or 3-acryloxypropyltrimethoxysilane; an epoxy group such as 3-glycidoxypropyltrimethoxysilane Silane coupling agents such as organoalkoxysilanes; condensation reaction products of ⁇ -glycidoxypropyltrialkoxysilane and molecular chain terminal silanol group-blocked dimethylpolysiloxane, ⁇ -glycidoxypropyltrialkoxysilane and molecular chain terminal silanol group Examples thereof include condensation reaction products of blocked methylvinylpolysiloxane and condensation reaction products of ⁇ -glycidoxypropyltrialkoxysilane and molecular chain terminal silanol-blocked dimethylsiloxane / methylvinylsiloxane copolymer.
- the blending amount of the adhesion imparting agent is not particularly limited, but is preferably in the range of 0.2 to 3% by weight with respect to the total amount of the polysiloxane composition in order to fully exhibit the effect of the adhesion imparting agent. If it is out of this range, the adhesiveness obtained after curing may be insufficient, or the low thermal expansion property may be impaired.
- the polysiloxane composition of the present invention may contain a reaction inhibitor for improving storage stability and handling workability.
- reaction inhibitors include 2-methyl-3-butyn-2-ol, 3,5-dimethyl-1-hexyn-3-ol, 2-phenyl-3-butyn-2-ol, 1-ethynyl- Alkyne alcohols such as 1-cyclohexanol; Enyne compounds such as 3-methyl-3-penten-1-yne, 3,5-dimethyl-3-hexen-1-yne; 1,3,5,7-tetramethyl- Examples include 1,3,5,7-tetravinylcyclotetrasiloxane, 1,3,5,7-tetramethyl-1,3,5,7-tetrahexenylcyclotetrasiloxane, and benzotriazole.
- the blending amount of the reaction inhibitor is not limited, but is preferably in the range of 0.0001 to 5% by weight based on the total amount of the polysiloxane composition of
- the polysiloxane composition of the present invention preferably contains no solvent.
- the solvent include alcohol solvents such as methanol and ethanol, ether solvents such as ethylene glycol monomethyl ether, ketone solvents such as acetone, methyl ethyl ketone, and methyl isobutyl ketone, amide solvents such as N, N-dimethylformamide, Examples include aromatic hydrocarbon solvents such as toluene and xylene, ester solvents such as ethyl acetate, and nitrile solvents such as butyronitrile.
- the polysiloxane composition of the present invention does not contain a solvent, it is not necessary to dry the cured product, so that the processing time can be shortened.
- the polysiloxane composition of the present invention containing no solvent is used as a sealing material such as a semiconductor
- a sealing material such as a semiconductor
- the solvent there is no risk of deterioration of the substrate, electronic material, etc. due to the solvent, and the cured product is caused by the solvent.
- the polysiloxane composition of the present invention can be produced by mixing the components (A), (B), (C) and (D).
- a known mixing method such as a ribbon blender, a rotation / revolution mixer, or a pulverization / mixer can be employed.
- the order of mixing is not limited, and the above components can be mixed together, or two or three components can be mixed in advance, and then the remaining components can be mixed.
- limiting in particular also about the temperature in the case of mixing It selects suitably between room temperature and 200 degreeC.
- the components (A) and (D) or the components (B) and (D) are mixed in advance while heating at about 50 to 150 ° C., and then the remaining components are mixed to achieve better mixing. May be achieved.
- the polysiloxane composition of the present invention has a viscosity at 25 ° C. of 500 Pa ⁇ s or less, preferably 0.05 to 400 Pa ⁇ s, more preferably 0.1 to 300 Pa ⁇ s, and still more preferably 1 to 200 Pa ⁇ s. .
- the viscosity is measured using a commonly used method, for example, a rheometer, a rotational viscometer, etc., but it is recommended to use the viscosity at a shear rate of 10 s -1 according to the method described in JIS K7117-2. . When the viscosity exceeds 500 Pa ⁇ s, the handleability and workability deteriorate.
- the polysiloxane composition of the present invention is cured at room temperature or by heating, but is preferably heated in order to cure quickly.
- the heating temperature is preferably 300 ° C. or less, and preferably in the range of 50 to 200 ° C.
- the cured product of the polysiloxane composition of the present invention preferably has a linear expansion coefficient at 30 ° C. to 300 ° C. of 100 ⁇ 10 ⁇ 6 / K or less, more preferably 80 ⁇ 10 ⁇ 6 / K or less. 70 ⁇ 10 ⁇ 6 / K or less, more preferably 50 ⁇ 10 ⁇ 6 / K or less.
- the linear expansion coefficient is measured by a method according to JIS K7197. Therefore, the cured product of the present invention has a very low coefficient of thermal expansion.
- the cured product of the polysiloxane composition of the present invention is preferably 20 or more, more preferably 30 or more, and still more preferably 40, when measured by an Asker hardness meter type D based on a method based on ASTM D2240. As described above, the hardness is particularly preferably 50 or more. Therefore, the cured product of the present invention has sufficient hardness.
- the cured product of the polysiloxane composition of the present invention also has good adhesion to various substrates.
- the polysiloxane composition of the present invention has a low viscosity, it has good processability and can give a hard cured product having a very low coefficient of thermal expansion after curing. Therefore, since the cured product of the present invention can be used continuously for a long time even in an environment exceeding 200 ° C., for example, it is not peeled off from the substrate.
- -It is useful as a sealing agent and is suitable for semiconductor sealing, particularly power semiconductor sealing.
- polysiloxane components used in Examples 1 to 9 and Comparative Examples 1 to 5 their vinyl group and hydrogen atom contents, and viscosities are as shown in Tables 1 and 2.
- a polysiloxane solution of chloroplatinic acid vinylsiloxane complex platinum content 0.2 wt% was used as a hydrosilylation reaction catalyst.
- the siloxane composition was blended so that the platinum content was 10 to 15 ppm.
- polysiloxane A1 examples include polydimethylsiloxane blocked with dimethylvinylsiloxy groups at both ends of the molecular chain (Examples 1 to 5, 7 to 9, Comparative Examples 1 and 3 to 5), or dimethylvinylsiloxy group blocked dimethyl with molecular chains.
- a siloxane methylsilsesquioxane copolymer Example 6, Comparative Example 2 was used.
- polysiloxane B a trimethylsilyl group-blocked methylhydrogensilosan / dimethylsiloxane copolymer was used.
- adhesion-imparting agent E a methyl vinyl siloxane / dimethyl siloxane copolymer blocked with glycidoxypropyl dimethoxysilyl group at both molecular chain ends was used.
- Fine particle D1 MSS-7LV (silica) manufactured by Tatsumori Co., Ltd. Average particle size: 9 ⁇ m; Long / Short ratio: 1.05; Does not include particles with a particle size of 50 ⁇ m or more
- Fine particles D2 FEB24D1 (G) (silica) manufactured by Admatechs Co., Ltd. Average particle size: 11 ⁇ m; Long / Short ratio: 1.05; Does not contain particles with a particle size of 50 ⁇ m or more
- Fine particles D3 DAW-07 (alumina) manufactured by Denki Kagaku Kogyo Co., Ltd.
- Fine particles D4 MIN-U-SIL 10 (silica) manufactured by US Silica Average particle size: 10 ⁇ m; Long / Short ratio: 3.0 (non-spherical); Does not include particles with particle size of 50 ⁇ m
- the viscosity of the polysiloxane composition was measured at 25 ° C. at a shear rate of 10 s ⁇ 1 using AR2000EX manufactured by TA Instruments in accordance with JIS K7117-2.
- the linear expansion coefficient of the cured polysiloxane was measured in accordance with JIS K7197, and the value at 30 ° C. to 300 ° C. was measured with TM9200 manufactured by ULVAC-RIKO.
- the hardness of the polysiloxane cured product was measured with an Asker hardness meter type D in accordance with ASTM D2240.
- the adhesiveness of the cured polysiloxane was measured by a bond tester Model SS-100KP manufactured by Seishin Shoji Co., Ltd. for the cured product cured at a circular deposition site with an area of 50 mm 2 to alumina as a heat dissipation substrate.
- Examples 1 to 9 Polysiloxane A and metal oxide particles D were mixed with a rotation / revolution mixer and then heated at 150 ° C. for 30 minutes. The resulting mixture and the remaining components were mixed well to prepare the polysiloxane compositions of Examples 1-9.
- the value of [number of moles of hydrogen atoms in polysiloxane B] / [number of moles of alkenyl groups in polysiloxane A] in this composition was 1.3.
- the viscosities of the compositions of Examples 1 to 9 were all 200 Pa ⁇ s or less, and it was confirmed that the compositions had good fluidity. Further, when the compositions of Examples 1 to 9 were heated at 200 ° C.
- Silicon atom bonded alkenyl in organopolysiloxane having low content (Comparative Example 3), using non-spherical metal oxide particles D (Comparative Example 4), and silicon atom bonded unsaturated aliphatic group
- group content is less than 0.5% by weight (Comparative Example 5)
- the coefficient of linear expansion or viscosity is too high and the heat resistance or workability is poor, or the cured product is brittle and the test piece is Can not be produced.
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Abstract
Description
(A)一分子中に少なくとも2個の不飽和脂肪族炭化水素基を含有する少なくとも1種のオルガノポリシロキサン
(B)一分子中に少なくとも2個のケイ素原子結合水素原子を含有する少なくとも1種のオルガノハイドロジェンポリシロキサン
(C)ヒドロシリル化反応触媒、及び、
(D)長短径比が1~1.5であり、且つ、全粒子中における粒子径50um以上の粒子の割合が5重量%以下である無機粒子
を含むポリシロキサン組成物であり、
(A)オルガノポリシロキサン中の不飽和脂肪族炭化水素基の重量分率が0.5~10重量%であり、
ポリシロキサン組成物に対する(D)無機粒子の配合比率が55~85体積%であり、
[(A)オルガノポリシロキサン中の不飽和脂肪族炭化水素基の重量分率]×[(B)オルガノハイドロジェンポリシロキサン中のケイ素原子結合水素原子の重量分率]の値が0.04~8であり、
25℃における粘度が500Pa・s以下であるポリシロキサン組成物によって達成される。
(A)一分子中に少なくとも2個の不飽和脂肪族炭化水素基を含有する少なくとも1種のオルガノポリシロキサンとしては、一分子中に少なくとも2個の脂肪族不飽和炭化水素基を有する限り構造上の制限はなく、例えば、直鎖状、分岐状又は網状のオルガノポリシロキサンを使用することができる。オルガノポリシロキサン上の脂肪族不飽和炭化水素基の位置についても制限はなく、主鎖上、又は、末端のいずれに位置してもかまわない。(A)成分は単独で使用することもできるし、構造の異なる二種以上のオルガノポリシロキサンを併用することも可能である。
(B)一分子中に少なくとも2個のケイ素原子結合水素原子を含有する少なくとも1種のオルガノハイドロジェンポリシロキサンとしては、一分子中に少なくとも2個のケイ素原子結合水素原子を有する限り構造上の制限はなく、例えば、直鎖状、分岐状又は網状のオルガノハイドロジェンポリシロキサンを使用することができる。オルガノハイドロジェンポリシロキサン上のケイ素原子結合水素原子の位置についても制限はなく、主鎖上、又は、末端のいずれに位置しても問題はない。(B)成分は単独で使用することもできるし、構造の異なる二種以上のオルガノハイドロジェンポリシロキサンを併用することも可能である。
(C)成分はヒドロシリル化反応触媒であり、(A)成分の不飽和脂肪族炭化水素基と(B)成分のケイ素原子結合水素原子の付加反応を促進し本発明のポリシロキサン組成物を硬化させるための触媒である。(C)成分としては、例えば、塩化白金酸、塩化白金酸のアルコール溶液、白金とオレフィンの錯体、白金と1,3-ジビニル-1,1,3,3-テトラメチルジシロキサンの錯体、白金を担持した粉体等の白金系触媒;テトラキス(トリフェニルフォスフィン)パラジウム、パラジウム黒、トリフェニルフォスフィンとの混合物等のパラジウム系触媒;さらに、ロジウム系触媒が挙げられ、白金系触媒、パラジウム系触媒等の白金族金属系触媒が好ましく、白金系触媒がより好ましい。
(D)成分は、長短径比が1以上1.5以下である無機粒子である。ここで、長短径比は、走査型電子顕微鏡等顕微鏡法で測定した粒子の[長径]/[短径]の比率である。この比率が1.5を超える場合、得られるポリシロキサン組成物の加工性が著しく低下するため、不適である。長短径比は1.2以下が好ましく、1.1以下がより好ましく、1.0が更により好ましい。したがって、球状無機粒子が好適である。また、(D)成分の全粒子中における粒子径50um以上の粒子の割合は5重量%以下である必要がある。ここで、粒子径とは、レーザー散乱・回折式粒度分布測定装置等で測定された粒子の長径をさす。この割合が5重量%を超えると、組成物の均一性が失われやすくなるため不適である。
本発明のポリシロキサン組成物には、上述した(A)~(D)成分以外にも、必要に応じて公知の各種添加剤を配合することができる。例えば、接着性を付与するため、(E)接着付与剤を配合することができる。接着付与剤としては、一分子中にケイ素原子結合水素原子、ケイ素原子結合アルケニル基(一例としてビニル基)、ケイ素原子結合アルコキシ基、ケイ素原子結合エポキシ基含有有機基、ケイ素原子結合アクリル基含有有機基から選ばれる反応性基を少なくとも2種含有する直鎖状又は環状のポリシロキサン類であることが好ましい。具体的には、接着付与剤として、3-メタクリロキシプロピルトリメトキシシラン、3-アクリロキシプロピルトリメトキシシラン等のアクリロキシ基含有オルガノアルコキシシラン;3-グリシドキシプロピルトリメトキシシラン等のエポキシ基含有オルガノアルコキシシラン等のシランカップリング剤;γ-グリシドキシプロピルトリアルコキシシランと分子鎖末端シラノール基封鎖ジメチルポリシロキサンの縮合反応生成物、γ-グリシドキシプロピルトリアルコキシシランと分子鎖末端シラノール基封鎖メチルビニルポリシロキサンの縮合反応生成物、γ-グリシドキシプロピルトリアルコキシシランと分子鎖末端シラノール基封鎖ジメチルシロキサン・メチルビニルシロキサン共重合体の縮合反応生成物が挙げられる。接着付与剤の配合量については特に制限は無いが、接着付与剤の効果を十分に発揮させるためにはポリシロキサン組成物の全量に対し0.2~3重量%の範囲が好ましい。この範囲を外れると、硬化後に得られる接着性が不十分であったり、低熱膨張性が損なわれたりする恐れがある。
微粒子D1:株式会社龍森製MSS-7LV(シリカ)
平均粒子径:9μm; 長短比:1.05; 粒子径50um以上の粒子は含まない
微粒子D2:株式会社アドマテックス製FEB24D1(G)(シリカ)
平均粒子径:11μm; 長短比:1.05; 粒子径50um以上の粒子は含まない
微粒子D3:電気化学工業株式会社製DAW-07(アルミナ)
平均粒子径:9μm; 長短比:1.1; 粒子径50um以上の粒子を4重量%含む
微粒子D4:US Silica製MIN-U-SIL 10(シリカ)
平均粒子径:10μm; 長短比:3.0(非球形); 粒子径50um以上の粒子は含まない
ポリシロキサンAと金属酸化物粒子Dを自転・公転ミキサーで混合後、150℃で30分間加熱した。得られた混合物と残りの成分をよく混合し、実施例1~9のポリシロキサン組成物を調製した。この組成物中における[ポリシロキサンB中の水素原子のモル数]/[ポリシロキサンA中のアルケニル基のモル数]の値は1.3とした。表1に示すように、実施例1~9の組成物の粘度はいずれも200Pa・s以下であり、良好な流動性を有することが確認された。また、実施例1~9の組成物を200℃で90分間加熱し、硬化させたところ、白色硬質固体となった。そして、実施例1~9の硬化物の線膨張係数を測定したところ、表1に示すように、線膨張係数はいずれも80×10-6K-1以下であり、低熱膨張性であることが示された。更に、実施例1~9の硬化物の硬度を測定したところ、硬度はいずれも20以上であり、良好な硬度を示した。
実施例1~9と同様にしてポリシロキサン組成物を調製した。[ポリシロキサン中のアルケニル基重量分率]×[水素原子重量分率]の値が0.04未満のもの(比較例1)及び8を超えるもの(比較例2)、金属酸化物粒子Dの含有量が少ないもの(比較例3)、非球形の金属酸化物粒子Dを使用したもの(比較例4)、並びに、ケイ素原子結合不飽和脂肪族基を有するオルガノポリシロキサン中のケイ素原子結合アルケニル基の含有量が0.5重量%未満のもの(比較例5)は、線膨張係数又は粘度が高すぎて耐熱性又は作業性が乏しいものであり、或いは、硬化物が脆弱で試験片が作製できなかった。
Claims (15)
- (A)一分子中に少なくとも2個の不飽和脂肪族炭化水素基を含有する少なくとも1種のオルガノポリシロキサン
(B)一分子中に少なくとも2個のケイ素原子結合水素原子を含有する少なくとも1種のオルガノハイドロジェンポリシロキサン
(C)ヒドロシリル化反応触媒、及び、
(D)長短径比が1~1.5であり、且つ、全粒子中における粒子径50μm以上の粒子の割合が5重量%以下である無機粒子
を含むポリシロキサン組成物であり、
(A)オルガノポリシロキサン中の不飽和脂肪族炭化水素基の重量分率が0.5~10重量%であり、
ポリシロキサン組成物に対する(D)無機粒子の配合比率が55~85体積%であり、
[(A)オルガノポリシロキサン中の不飽和脂肪族炭化水素基の重量分率]×[(B)オルガノハイドロジェンポリシロキサン中のケイ素原子結合水素原子の重量分率]の値が0.04~8であり、
25℃における粘度が500Pa・s以下であるポリシロキサン組成物。 - 前記(A)オルガノポリシロキサンの25℃における粘度が0.05~20Pa・sである、請求項1記載のポリシロキサン組成物。
- 前記(B)オルガノハイドロジェンポリシロキサン中のケイ素原子結合水素原子の重量分率が0.1重量%以上である、請求項1又は2記載のポリシロキサン組成物。
- 前記(B)オルガノハイドロジェンポリシロキサンの25℃における粘度が0.1Pa・s以下である、請求項1乃至3のいずれかに記載のポリシロキサン組成物。
- [(A)オルガノポリシロキサン中の不飽和脂肪族炭化水素基の重量分率]×[(B)オルガノハイドロジェンポリシロキサン中のケイ素原子結合水素原子の重量分率]の値が0.1~7である、請求項1乃至4のいずれかに記載のポリシロキサン組成物。
- [(A)オルガノポリシロキサン中の不飽和脂肪族炭化水素基の重量分率]×[(B)オルガノハイドロジェンポリシロキサン中のケイ素原子結合水素原子の重量分率]の値が0.5~4.5である請求項1乃至5のいずれかに記載のポリシロキサン組成物。
- [(B)オルガノハイドロジェンポリシロキサン中のケイ素原子結合水素原子のモル数]/[(A)オルガノポリシロキサン中の不飽和脂肪族炭化水素基のモル数]の値が0.5~1.5である、請求項1乃至6のいずれかに記載のポリシロキサン組成物。
- 前記(C)ヒドロシリル化反応触媒が白金族金属系触媒である、請求項1乃至7のいずれかに記載のポリシロキサン組成物。
- 前記(D)無機粒子が少なくとも1種の金属酸化物粒子を含む、請求項1乃至8のいずれかに記載のポリシロキサン組成物。
- 前記金属酸化物粒子がシリカである、請求項9記載のポリシロキサン組成物。
- 少なくとも1種の(E)接着付与剤を含む、請求項1乃至10のいずれかに記載のポリシロキサン組成物。
- 溶剤を含まない、請求項1乃至11のいずれかに記載のポリシロキサン組成物。
- 30℃~300℃の線膨張係数が100×10-6/K以下である硬化物を与える、請求項1乃至12のいずれかに記載のポリシロキサン組成物。
- 30℃~300℃の線膨張係数が50×10-6/K以下である硬化物を与える、請求項13記載のポリシロキサン組成物。
- 請求項1乃至14のいずれかに記載のポリシロキサン組成物を硬化させて得られる硬化物。
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US9403982B2 (en) | 2012-09-07 | 2016-08-02 | Dow Corning Corporation | Curable silicone composition and cured product thereof |
KR102142263B1 (ko) * | 2012-09-07 | 2020-08-10 | 듀폰 도레이 스페셜티 머티리얼즈 가부시키가이샤 | 경화성 실리콘 조성물 및 이의 경화물 |
WO2017126199A1 (ja) * | 2016-01-19 | 2017-07-27 | セントラル硝子株式会社 | 硬化性シリコーン樹脂組成物およびその硬化物、並びにこれらを用いた光半導体装置 |
Also Published As
Publication number | Publication date |
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EP2612887A4 (en) | 2016-01-13 |
EP2612887A1 (en) | 2013-07-10 |
CN103180393B (zh) | 2015-04-22 |
US9328242B2 (en) | 2016-05-03 |
EP2612887B1 (en) | 2016-09-21 |
CN103180393A (zh) | 2013-06-26 |
US20130178571A1 (en) | 2013-07-11 |
JPWO2012029538A1 (ja) | 2013-10-28 |
KR101800341B1 (ko) | 2017-11-22 |
KR20130099942A (ko) | 2013-09-06 |
JP5856060B2 (ja) | 2016-02-09 |
TW201211157A (en) | 2012-03-16 |
TWI522423B (zh) | 2016-02-21 |
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