JP7102521B2 - ヒドロシリル化-硬化性シリコーン組成物 - Google Patents
ヒドロシリル化-硬化性シリコーン組成物 Download PDFInfo
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- JP7102521B2 JP7102521B2 JP2020526276A JP2020526276A JP7102521B2 JP 7102521 B2 JP7102521 B2 JP 7102521B2 JP 2020526276 A JP2020526276 A JP 2020526276A JP 2020526276 A JP2020526276 A JP 2020526276A JP 7102521 B2 JP7102521 B2 JP 7102521B2
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- sio
- group
- component
- curable silicone
- hydrosilylated
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims description 82
- 229920001296 polysiloxane Polymers 0.000 title claims description 60
- -1 Maleic acid ester compound Chemical class 0.000 claims description 52
- 125000003342 alkenyl group Chemical group 0.000 claims description 19
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 19
- 238000006459 hydrosilylation reaction Methods 0.000 claims description 16
- 239000003054 catalyst Substances 0.000 claims description 14
- 229920006136 organohydrogenpolysiloxane Polymers 0.000 claims description 14
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 14
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 13
- 239000011976 maleic acid Substances 0.000 claims description 13
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 13
- GWXLDORMOJMVQZ-UHFFFAOYSA-N cerium Chemical compound [Ce] GWXLDORMOJMVQZ-UHFFFAOYSA-N 0.000 claims description 11
- 229910052684 Cerium Inorganic materials 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 239000003112 inhibitor Substances 0.000 claims description 8
- VMAWODUEPLAHOE-UHFFFAOYSA-N 2,4,6,8-tetrakis(ethenyl)-2,4,6,8-tetramethyl-1,3,5,7,2,4,6,8-tetraoxatetrasilocane Chemical compound C=C[Si]1(C)O[Si](C)(C=C)O[Si](C)(C=C)O[Si](C)(C=C)O1 VMAWODUEPLAHOE-UHFFFAOYSA-N 0.000 claims description 6
- 230000003287 optical effect Effects 0.000 claims description 6
- 239000004065 semiconductor Substances 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 239000004615 ingredient Substances 0.000 claims description 4
- 239000000853 adhesive Substances 0.000 claims description 3
- 230000001070 adhesive effect Effects 0.000 claims description 3
- 239000011248 coating agent Substances 0.000 claims description 2
- 238000000576 coating method Methods 0.000 claims description 2
- 238000007789 sealing Methods 0.000 claims description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical group [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 28
- 239000000047 product Substances 0.000 description 15
- 238000001723 curing Methods 0.000 description 14
- 229920001577 copolymer Polymers 0.000 description 12
- 229910052697 platinum Inorganic materials 0.000 description 11
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 229910052710 silicon Inorganic materials 0.000 description 7
- 230000037303 wrinkles Effects 0.000 description 7
- 229910004298 SiO 2 Inorganic materials 0.000 description 6
- 229910052782 aluminium Inorganic materials 0.000 description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 5
- 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 5
- 238000010438 heat treatment Methods 0.000 description 5
- 239000010703 silicon Substances 0.000 description 5
- 229910052693 Europium Inorganic materials 0.000 description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 125000003710 aryl alkyl group Chemical group 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000004205 dimethyl polysiloxane Substances 0.000 description 4
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- 229920005645 diorganopolysiloxane polymer Polymers 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 4
- 125000005372 silanol group Chemical group 0.000 description 4
- 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 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- 230000001771 impaired effect Effects 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- QYLFHLNFIHBCPR-UHFFFAOYSA-N 1-ethynylcyclohexan-1-ol Chemical compound C#CC1(O)CCCCC1 QYLFHLNFIHBCPR-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 150000000703 Cerium Chemical class 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
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- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
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- 239000007983 Tris buffer Substances 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 239000002318 adhesion promoter Substances 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 125000002521 alkyl halide group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- FSIJKGMIQTVTNP-UHFFFAOYSA-N bis(ethenyl)-methyl-trimethylsilyloxysilane Chemical compound C[Si](C)(C)O[Si](C)(C=C)C=C FSIJKGMIQTVTNP-UHFFFAOYSA-N 0.000 description 2
- ZPOLOEWJWXZUSP-WAYWQWQTSA-N bis(prop-2-enyl) (z)-but-2-enedioate Chemical compound C=CCOC(=O)\C=C/C(=O)OCC=C ZPOLOEWJWXZUSP-WAYWQWQTSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 125000004122 cyclic group Chemical group 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
- 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 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 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 2
- 125000006038 hexenyl group Chemical group 0.000 description 2
- 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 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
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- 239000000463 material Substances 0.000 description 2
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- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 150000004767 nitrides Chemical class 0.000 description 2
- 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 2
- 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 2
- 239000003960 organic solvent Substances 0.000 description 2
- 125000004344 phenylpropyl group Chemical group 0.000 description 2
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- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 2
- 125000005023 xylyl group Chemical group 0.000 description 2
- KWEKXPWNFQBJAY-UHFFFAOYSA-N (dimethyl-$l^{3}-silanyl)oxy-dimethylsilicon Chemical compound C[Si](C)O[Si](C)C KWEKXPWNFQBJAY-UHFFFAOYSA-N 0.000 description 1
- DZSAIHPGHBMBKJ-UTCJRWHESA-N (z)-2-(1-methoxypropan-2-yl)but-2-enedioic acid Chemical compound COCC(C)C(\C(O)=O)=C\C(O)=O DZSAIHPGHBMBKJ-UTCJRWHESA-N 0.000 description 1
- IQBLWPLYPNOTJC-FPLPWBNLSA-N (z)-4-(2-ethylhexoxy)-4-oxobut-2-enoic acid Chemical compound CCCCC(CC)COC(=O)\C=C/C(O)=O IQBLWPLYPNOTJC-FPLPWBNLSA-N 0.000 description 1
- FDNBQVCBHKEDOJ-FPLPWBNLSA-N (z)-4-(6-methylheptoxy)-4-oxobut-2-enoic acid Chemical compound CC(C)CCCCCOC(=O)\C=C/C(O)=O FDNBQVCBHKEDOJ-FPLPWBNLSA-N 0.000 description 1
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- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$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
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- 238000013035 low temperature curing Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- NKHAVTQWNUWKEO-IHWYPQMZSA-N methyl hydrogen fumarate Chemical compound COC(=O)\C=C/C(O)=O NKHAVTQWNUWKEO-IHWYPQMZSA-N 0.000 description 1
- UIUXUFNYAYAMOE-UHFFFAOYSA-N methylsilane Chemical compound [SiH3]C UIUXUFNYAYAMOE-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 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
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000005187 nonenyl group Chemical group C(=CCCCCCCC)* 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 150000003961 organosilicon compounds Chemical class 0.000 description 1
- 125000005375 organosiloxane group Chemical group 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229910052763 palladium Inorganic materials 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
- 239000003208 petroleum Substances 0.000 description 1
- PARWUHTVGZSQPD-UHFFFAOYSA-N phenylsilane Chemical compound [SiH3]C1=CC=CC=C1 PARWUHTVGZSQPD-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 239000002683 reaction inhibitor Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical group [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 235000015096 spirit Nutrition 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- XTQHKBHJIVJGKJ-UHFFFAOYSA-N sulfur monoxide Chemical class S=O XTQHKBHJIVJGKJ-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
- PTUUTGJMRQWABQ-UHFFFAOYSA-N triphenyl(phenylsilyloxy)silane Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)O[SiH2]C1=CC=CC=C1 PTUUTGJMRQWABQ-UHFFFAOYSA-N 0.000 description 1
- 125000005065 undecenyl group Chemical group C(=CCCCCCCCCC)* 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
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Description
(A)1分子当たり少なくとも2個のアルケニル基を有するオルガノポリシロキサン;
(B)1分子当たり少なくとも2個のケイ素-結合水素原子を有するオルガノハイドロジェンポリシロキサン(成分(A)中のアルケニル基1モルに対してケイ素原子-結合水素原子0.1~10.0モルが与えられるような量での);
(C)ヒドロシリル化触媒(組成物の硬化を促進するのに十分な量での);
(D)マレイン酸エステル化合物(質量単位によって組成物に対して50~6,000ppmの量での);及び
(E)マレイン酸エステル以外のヒドロシリル化阻害剤(質量単位によって組成物に対して200~20,000ppmの量での)を含む。
(A)1分子当たり少なくとも2個のアルケニル基を有するオルガノポリシロキサン;
(B)1分子当たり少なくとも2個のケイ素-結合水素原子を有するオルガノハイドロジェンポリシロキサン(成分(A)中のアルケニル基1モルに対してケイ素-結合水素原子0.1~10.0モルが与えられるような量での);
(C)ヒドロシリル化触媒(組成物の硬化を促進するのに十分な量での);
(D)マレイン酸エステル化合物(質量単位によって組成物に対して50~6,000ppmの量での);及び
(E)マレイン酸エステル化合物以外のヒドロシリル化反応阻害剤(質量単位によって組成物に対して200~20,000ppmの量での)
を含む。
ViMe2SiO(Me2SiO)xSiMe2Vi
ViPhMeSiO(Me2SiO)xSiMePhVi
ViPh2SiO(Me2SiO)xSiPh2Vi
ViMe2SiO(Me2SiO)x(Ph2SiO)x’SiMe2Vi
ViPhMeSiO(Me2SiO)x(Ph2SiO)x’SiPhMeVi
ViPh2SiO(Me2SiO)x(Ph2SiO)x’SiPh2Vi
ViMe2SiO(MePhSiO)xSiMe2Vi
MePhViSiO(MePhSiO)xSiMePhVi
Ph2ViSiO(MePhSiO)xSiPh2Vi
ViMe2SiO(Ph2SiO)x(PhMeSiO)x’SiMe2Vi
ViPhMeSiO(Ph2SiO)x(PhMeSiO)x’SiPhMeVi
ViPh2SiO(Ph2SiO)x(PhMeSiO)x’SiPh2Vi
HMe2SiO(Ph2SiO)ySiMe2H
HMePhSiO(Ph2SiO)ySiMePhH
HMeNaphSiO(Ph2SiO)ySiMeNaphH
HMePhSiO(Ph2SiO)y(MePhSiO)y’SiMePhH
HMePhSiO(Ph2SiO)y(Me2SiO)y’SiMePhH
(HMe2SiO1/2)c(PhSiO3/2)d
(HMePhSiO1/2)c(PhSiO3/2)d
(HMePhSiO1/2)c(NaphSiO3/2)d
(HMe2SiO1/2)c(NaphSiO3/2)d
(HMePhSiO1/2)c(HMe2SiO1/2)d(PhSiO3/2)e
(HMe2SiO1/2)c(Ph2SiO2/2)d(PhSiO3/2)e
(HMePhSiO1/2)c(Ph2SiO2/2)d(PhSiO3/2)e
(HMe2SiO1/2)c(Ph2SiO2/2)d(NaphSiO3/2)e
(HMePhSiO1/2)c(Ph2SiO2/2)d(NaphSiO3/2)e
(HMePhSiO1/2)c(HMe2SiO1/2)d(NaphSiO3/2)e
(HMePhSiO1/2)c(HMe2SiO1/2)d(Ph2SiO2/2)e(NaphSiO3/2)f
(HMePhSiO1/2)c(HMe2SiO1/2)d(Ph2SiO2/2)e(PhSiO3/2)f
ヒドロシリル化-硬化性シリコーン組成物の貯蔵安定性は、示差走査熱量測定計(DSC7000;SII Nanotechnologyにより製造された)を使用して、10℃/分の加熱速度で測定された熱発生ピーク温度(℃)に基づいて評価した。
ヒドロシリル化-硬化性シリコーン組成物の硬化性は、レオメータMDR 2000(Alpha Technologies,Ltd.により製造された)を使用して評価した。硬化温度は、150℃であった。測定のために、1%トルク値を得るのに要した時間(分)を、Ts1で示し、90%トルク値を得るのに要した時間(分)を、T90で示した。
5gのヒドロシリル化-硬化性シリコーン組成物を直径60mmのアルミニウムペトリ皿に注ぎ入れ、150℃で1時間加熱することによって硬化性生成物を形成させた。硬化生成物の外観を以下のとおり視覚的に観察した。
N:しわが観察されなかった。
Y:しわが観察された。
以下の成分を、表1~表5に示される組成(質量部)に従って一様に混合して、実施例1~実施例14及び比較例1~比較例16のヒドロシリル化-硬化性シリコーン組成物を調製した。式において、「Me」、「Vi」、「Ph」、及び「Ep」は、それぞれ、メチル基、ビニル基、フェニル基、及び3-グリシドキシプロピル基を表す。さらに、表1~表5において、「SiH/Vi」は、ヒドロシリル化-硬化性シリコーン組成物中の成分(A)中のビニル基1モル当たりの成分(B)中のケイ素-結合水素原子のモルを表す。
成分(a-1):1分子当たり2個以上のビニル基を有し、以下の平均単位式によって表されるオルガノポリシロキサン:
(Me2ViSiO1/2)0.25(PhSiO3/2)0.75
成分(a-2):以下の平均式によって表されるオルガノポリシロキサン:
Me2ViSiO(Me2SiO)200(Ph2SiO)50SiMe2Vi
成分(a-3):1分子当たり2個以上のビニル基を有し、以下の平均単位式によって表されるオルガノポリシロキサン:
(Me2ViSiO1/2)0.13(Me3SiO1/2)0.14(MeSiO3/2)0.53(PhSiO3/2)0.22
成分(a-4):1分子当たり2個以上のビニル基を有し、以下の平均単位式によって表される30質量%のオルガノポリシロキサン:
(Me3SiO1/2)0.47(Me2ViSiO1/2)0.05(SiO4/2)0.48
と、両分子末端にてジメチルビニルシロキシ基で末端化された70質量%のジメチルポリシロキサン(ビニル基の含有量=0.23質量%)との混合物。
成分(a-5):1分子当たり2個以上のビニル基を有し、以下の平均単位式によって表されるオルガノポリシロキサン:
(Me2ViSiO1/2)0.20(PhSiO3/2)0.80
成分(a-6):以下の平均式によって表されるオルガノポリシロキサン:
Me2ViSiO(MePhSiO)25SiMe2Vi
成分(a-7):以下の式によって表されるオルガノポリシロキサン:
(Me2ViSiO)4Si
成分(b-1):以下の式によって表されるオルガノハイドロジェンポリシロキサン:
HMe2SiO(Ph2SiO)SiMe2H
成分(b-2):以下の式によって表されるオルガノハイドロジェンポリシロキサン:
(Me2HSiO1/2)0.60(PhSiO3/2)0.40
成分(b-3):以下の式によって表されるオルガノハイドロジェンポリシロキサン:
Me3SiO(MeHSiO)40SiMe3
成分(c-1):白金の1,3-ジビニルテトラメチルジシロキサン錯体の1,3-ジビニルテトラメチルジシロキサン溶液(白金金属含有量=おおよそ4,000ppm)
成分(d-1):ジアリルマレエート
成分(d-2):ビス(エチルヘキシル)マレエート
成分(e-1):1-エチニルシクロヘキサン-1-オール
成分(e-2):1,3,5,7-テトラメチル-1,3,5,7-テトラビニル-シクロテトラシロキサン
成分(f-1):以下の平均単位式によって表されるオルガノポリシロキサン:
(Me2ViSiO1/2)0.18(MeEpSiO2/2)0.28(PhSiO3/2)0.54
成分(g-1):1.4質量%のセリウム含有量を有するセリウム含有ジメチルポリシロキサン
成分(h-1):100m2/gのBET表面積を有するシリカ充填剤
Claims (6)
- (A)1分子当たり少なくとも2個のアルケニル基を有するオルガノポリシロキサン;
(B)1分子当たり少なくとも2個のケイ素-結合水素を有するオルガノハイドロジェンポリシロキサン(成分(A)中のアルケニル基1モルに対してケイ素-結合水素原子0.1~10.0モルが与えられるような量での)であって、下記式(1)及び(2):
HMe 2 SiO(Ph 2 SiO)SiMe 2 H (1)
(Me 2 HSiO 1/2 ) 0.60 (PhSiO 3/2 ) 0.40 (2)
の平均組成式で表される2つのオルガノハイドロジェンポリシロキサンを含む、オルガノハイドロジェンポリシロキサン;
(C)ヒドロシリル化触媒(組成物の硬化を促進するために十分な量での);
(D)マレイン酸エステル化合物(質量単位によって組成物に対して50~6,000ppmの量での);及び
(E)マレイン酸エステル化合物以外のヒドロシリル化阻害剤(質量単位によって組成物に対して200~20,000ppmの量での)を含む、ヒドロシリル化-硬化性シリコーン組成物。 - 成分(E)が1,3,5,7-テトラメチル-1,3,5,7-テトラビニル-シクロテトラシロキサンである、請求項1に記載のヒドロシリル化-硬化性シリコーン組成物。
- 成分(A)が、
(A-1)以下のもの:
ViPhMeSiO(Me 2 SiO) x SiMePhVi、
ViPh 2 SiO(Me 2 SiO) x SiPh 2 Vi、
ViMe 2 SiO(Me 2 SiO) x (Ph 2 SiO) x’ SiMe 2 Vi、
ViPhMeSiO(Me 2 SiO) x (Ph 2 SiO) x’ SiPhMeVi、
ViPh 2 SiO(Me 2 SiO) x (Ph 2 SiO) x’ SiPh 2 Vi、
ViMe 2 SiO(MePhSiO) x SiMe 2 Vi、
MePhViSiO(MePhSiO) x SiMePhVi、
Ph 2 ViSiO(MePhSiO) x SiPh 2 Vi、
ViMe 2 SiO(Ph 2 SiO) x (PhMeSiO) x’ SiMe 2 Vi、
ViPhMeSiO(Ph 2 SiO) x (PhMeSiO) x’ SiPhMeVi、及び
ViPh 2 SiO(Ph 2 SiO) x (PhMeSiO) x’ SiPh 2 Vi
(式中、Me、Vi、及びPhは、それぞれ、メチル基、ビニル基、及びフェニル基を表し、x及びx’は、それぞれ1~100の整数である)
から選択される直鎖オルガノポリシロキサン、及び、
(A-2)
1分子当たり少なくとも2個のアルケニル基と、アルケニル基以外のケイ素-結合基を有し、かつアルケニル基以外のケイ素-結合基が6~20個の炭素を有するアリール基を含む、部分分岐直鎖及び三次元網状組織構造を有するオルガノポリシロキサン、
を含む、請求項1又は2に記載のヒドロシリル化-硬化性シリコーン組成物。 - (F)接着促進剤(成分(A)~成分(E)の100質量部当たり0.01~50質量部の量での)をさらに含む、請求項1~3のいずれか一項に記載のヒドロシリル化-硬化性シリコーン組成物。
- (G)セリウム含有オルガノポリシロキサン(この成分中のセリウム原子の量が、質量単位によって前記組成物に対して10~2,000ppmであるような量での)をさらに含む、請求項1~4のいずれか一項に記載のヒドロシリル化-硬化性シリコーン組成物。
- 光学半導体素子のためのシーリング、コーティング、又は接着剤である、請求項1~5のいずれか一項に記載のヒドロシリル化-硬化性シリコーン組成物。
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