JPH07503991A - 架橋性カルボシランポリマー調合物 - Google Patents
架橋性カルボシランポリマー調合物Info
- Publication number
- JPH07503991A JPH07503991A JP5515038A JP51503893A JPH07503991A JP H07503991 A JPH07503991 A JP H07503991A JP 5515038 A JP5515038 A JP 5515038A JP 51503893 A JP51503893 A JP 51503893A JP H07503991 A JPH07503991 A JP H07503991A
- Authority
- JP
- Japan
- Prior art keywords
- crosslinkable
- radical
- hydrogen
- carbosilane
- formulation
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 229920000642 polymer Polymers 0.000 title claims description 83
- 239000000203 mixture Substances 0.000 title claims description 76
- 238000009472 formulation Methods 0.000 title claims description 50
- -1 silicon hydride radicals Chemical class 0.000 claims description 93
- 229910052739 hydrogen Inorganic materials 0.000 claims description 28
- 239000001257 hydrogen Substances 0.000 claims description 28
- 150000002431 hydrogen Chemical group 0.000 claims description 25
- 229920001971 elastomer Polymers 0.000 claims description 19
- 150000004291 polyenes Chemical class 0.000 claims description 19
- 239000000806 elastomer Substances 0.000 claims description 17
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical group C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 239000004971 Cross linker Substances 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 13
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims description 12
- 238000006459 hydrosilylation reaction Methods 0.000 claims description 12
- 239000003431 cross linking reagent Substances 0.000 claims description 11
- 239000003054 catalyst Substances 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 10
- 150000003254 radicals Chemical class 0.000 claims description 9
- OJOWICOBYCXEKR-KRXBUXKQSA-N (5e)-5-ethylidenebicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(=C/C)/CC1C=C2 OJOWICOBYCXEKR-KRXBUXKQSA-N 0.000 claims description 8
- INYHZQLKOKTDAI-UHFFFAOYSA-N 5-ethenylbicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(C=C)CC1C=C2 INYHZQLKOKTDAI-UHFFFAOYSA-N 0.000 claims description 8
- UTBCLIMIBBSDLG-UHFFFAOYSA-N C12=CC=CCC2C2CC2C2C1C2 Chemical compound C12=CC=CCC2C2CC2C2C1C2 UTBCLIMIBBSDLG-UHFFFAOYSA-N 0.000 claims description 7
- 150000001993 dienes Chemical class 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 5
- 229910052990 silicon hydride Inorganic materials 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- 238000005698 Diels-Alder reaction Methods 0.000 claims description 4
- 239000004215 Carbon black (E152) Substances 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 229930195733 hydrocarbon Natural products 0.000 claims description 3
- 150000002430 hydrocarbons Chemical class 0.000 claims description 3
- 238000006884 silylation reaction Methods 0.000 claims description 2
- KAJRUHJCBCZULP-UHFFFAOYSA-N 1-cyclohepta-1,3-dien-1-ylcyclohepta-1,3-diene Chemical compound C1CCC=CC=C1C1=CC=CCCC1 KAJRUHJCBCZULP-UHFFFAOYSA-N 0.000 claims 7
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 241000277269 Oncorhynchus masou Species 0.000 claims 2
- 229920001400 block copolymer Polymers 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 150000001721 carbon Chemical group 0.000 claims 2
- 239000007809 chemical reaction catalyst Substances 0.000 claims 2
- 239000007795 chemical reaction product Substances 0.000 claims 2
- 229920005604 random copolymer Polymers 0.000 claims 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- UCQHUEOREKHIBP-UHFFFAOYSA-N heptacyclo[9.6.1.14,7.113,16.02,10.03,8.012,17]icosa-5,14-diene Chemical compound C1C(C23)C4C(C=C5)CC5C4C1C3CC1C2C2C=CC1C2 UCQHUEOREKHIBP-UHFFFAOYSA-N 0.000 claims 1
- 239000011256 inorganic filler Substances 0.000 claims 1
- 229910003475 inorganic filler Inorganic materials 0.000 claims 1
- 150000003058 platinum compounds Chemical group 0.000 claims 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 33
- 238000004132 cross linking Methods 0.000 description 23
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
- 239000000178 monomer Substances 0.000 description 19
- 229910052697 platinum Inorganic materials 0.000 description 16
- 239000011521 glass Substances 0.000 description 12
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical class [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- 229920001577 copolymer Polymers 0.000 description 10
- 230000009477 glass transition Effects 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 8
- 229920006037 cross link polymer Polymers 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 238000006555 catalytic reaction Methods 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 125000004122 cyclic group Chemical group 0.000 description 6
- 239000000945 filler Substances 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 5
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- 125000000129 anionic group Chemical group 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- 239000003381 stabilizer Substances 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 4
- 239000002131 composite material Substances 0.000 description 4
- 238000007334 copolymerization reaction Methods 0.000 description 4
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 4
- 239000012530 fluid Substances 0.000 description 4
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- 229910052749 magnesium Inorganic materials 0.000 description 4
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 229920001187 thermosetting polymer Polymers 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- KTQYJQFGNYHXMB-UHFFFAOYSA-N dichloro(methyl)silicon Chemical compound C[Si](Cl)Cl KTQYJQFGNYHXMB-UHFFFAOYSA-N 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 239000005048 methyldichlorosilane Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 229920001195 polyisoprene Polymers 0.000 description 3
- 238000007142 ring opening reaction Methods 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- HITROERJXNWVOI-SOFGYWHQSA-N (5e)-octa-1,5-diene Chemical compound CC\C=C\CCC=C HITROERJXNWVOI-SOFGYWHQSA-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
- XWJBRBSPAODJER-UHFFFAOYSA-N 1,7-octadiene Chemical compound C=CCCCCC=C XWJBRBSPAODJER-UHFFFAOYSA-N 0.000 description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical class CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- DYFJAPCYUULYEE-UHFFFAOYSA-N 1-methyl-1$l^{3}-siletane Chemical compound C[Si]1CCC1 DYFJAPCYUULYEE-UHFFFAOYSA-N 0.000 description 2
- OOWHTHSSQDMUPE-UHFFFAOYSA-N 1-phenylsiletane Chemical compound C1C[SiH](C1)c1ccccc1 OOWHTHSSQDMUPE-UHFFFAOYSA-N 0.000 description 2
- SGTNSNPWRIOYBX-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile Chemical compound C1=C(OC)C(OC)=CC=C1CCN(C)CCCC(C#N)(C(C)C)C1=CC=C(OC)C(OC)=C1 SGTNSNPWRIOYBX-UHFFFAOYSA-N 0.000 description 2
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 244000043261 Hevea brasiliensis Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- 239000005062 Polybutadiene Substances 0.000 description 2
- 241000159610 Roya <green alga> Species 0.000 description 2
- 239000004809 Teflon Substances 0.000 description 2
- 229920006362 Teflon® Polymers 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 229920006231 aramid fiber Polymers 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 239000000919 ceramic Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 2
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000005350 fused silica glass Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000005649 metathesis reaction Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229920003052 natural elastomer Polymers 0.000 description 2
- 229920001194 natural rubber Polymers 0.000 description 2
- 229920002857 polybutadiene Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 238000010107 reaction injection moulding Methods 0.000 description 2
- 239000012763 reinforcing filler Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 239000005060 rubber Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- PSFAYRFARRVKFR-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;prop-1-en-2-ylbenzene Chemical compound CC(=C)C1=CC=CC=C1.C=CC1=CC=CC=C1C=C PSFAYRFARRVKFR-UHFFFAOYSA-N 0.000 description 1
- DBYRASAQTCQQMB-UHFFFAOYSA-N 1-chloro-1-phenylsiletane Chemical compound C=1C=CC=CC=1[Si]1(Cl)CCC1 DBYRASAQTCQQMB-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- YJLUBHOZZTYQIP-UHFFFAOYSA-N 2-[5-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-1,3,4-oxadiazol-2-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1=NN=C(O1)CC(=O)N1CC2=C(CC1)NN=N2 YJLUBHOZZTYQIP-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229920000049 Carbon (fiber) Polymers 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- 101000975007 Homo sapiens Transcriptional regulator Kaiso Proteins 0.000 description 1
- 101000697347 Homo sapiens Translocon-associated protein subunit gamma Proteins 0.000 description 1
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
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- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 102100023011 Transcriptional regulator Kaiso Human genes 0.000 description 1
- 102100028160 Translocon-associated protein subunit gamma Human genes 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- RMHVCUSUJVRISJ-UHFFFAOYSA-N [CH]1CCC[SiH]1 Chemical class [CH]1CCC[SiH]1 RMHVCUSUJVRISJ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
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- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 230000000712 assembly Effects 0.000 description 1
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- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
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- 150000004074 biphenyls Chemical class 0.000 description 1
- CFJBHMMJIKLCPF-UHFFFAOYSA-N bis[[ethenyl(dimethyl)silyl]oxy]silyloxy-ethenyl-dimethylsilane Chemical compound C=C[Si](C)(C)O[SiH](O[Si](C)(C)C=C)O[Si](C)(C)C=C CFJBHMMJIKLCPF-UHFFFAOYSA-N 0.000 description 1
- IDXJVMVVQWXPSX-UHFFFAOYSA-N butoxy-ethenyl-dimethylsilane Chemical compound CCCCO[Si](C)(C)C=C IDXJVMVVQWXPSX-UHFFFAOYSA-N 0.000 description 1
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- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- QXJJQWWVWRCVQT-UHFFFAOYSA-K calcium;sodium;phosphate Chemical compound [Na+].[Ca+2].[O-]P([O-])([O-])=O QXJJQWWVWRCVQT-UHFFFAOYSA-K 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
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- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
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- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- VIRVTHOOZABTPR-UHFFFAOYSA-N dichloro(phenyl)silane Chemical compound Cl[SiH](Cl)C1=CC=CC=C1 VIRVTHOOZABTPR-UHFFFAOYSA-N 0.000 description 1
- XNAFLNBULDHNJS-UHFFFAOYSA-N dichloro(phenyl)silicon Chemical compound Cl[Si](Cl)C1=CC=CC=C1 XNAFLNBULDHNJS-UHFFFAOYSA-N 0.000 description 1
- UWHAIVBRBAKZDT-UHFFFAOYSA-N dichloro-(3-chloropropyl)-phenylsilane Chemical compound ClCCC[Si](Cl)(Cl)C1=CC=CC=C1 UWHAIVBRBAKZDT-UHFFFAOYSA-N 0.000 description 1
- MROCJMGDEKINLD-UHFFFAOYSA-N dichlorosilane Chemical compound Cl[SiH2]Cl MROCJMGDEKINLD-UHFFFAOYSA-N 0.000 description 1
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- JEGUKCSWCFPDGT-UHFFFAOYSA-N h2o hydrate Chemical compound O.O JEGUKCSWCFPDGT-UHFFFAOYSA-N 0.000 description 1
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- 210000003127 knee Anatomy 0.000 description 1
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- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
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- 238000003760 magnetic stirring Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
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- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- ACXIAEKDVUJRSK-UHFFFAOYSA-N methyl(silyloxy)silane Chemical compound C[SiH2]O[SiH3] ACXIAEKDVUJRSK-UHFFFAOYSA-N 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 1
- 239000002420 orchard Substances 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 150000003057 platinum Chemical class 0.000 description 1
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- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920002589 poly(vinylethylene) polymer Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
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- 229920001296 polysiloxane Polymers 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000011253 protective coating Substances 0.000 description 1
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- 239000012744 reinforcing agent Substances 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000007152 ring opening metathesis polymerisation reaction Methods 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 239000012798 spherical particle Substances 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- YOUIDGQAIILFBW-UHFFFAOYSA-J tetrachlorotungsten Chemical compound Cl[W](Cl)(Cl)Cl YOUIDGQAIILFBW-UHFFFAOYSA-J 0.000 description 1
- CRHIAMBJMSSNNM-UHFFFAOYSA-N tetraphenylstannane Chemical compound C1=CC=CC=C1[Sn](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 CRHIAMBJMSSNNM-UHFFFAOYSA-N 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 238000002411 thermogravimetry Methods 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 229920006163 vinyl copolymer Polymers 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 239000010456 wollastonite Substances 0.000 description 1
- 229910052882 wollastonite Inorganic materials 0.000 description 1
- 239000008096 xylene 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
- C08L83/16—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 in which all the silicon atoms are connected by linkages other than oxygen atoms
-
- 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
- C08G77/60—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 in which all the silicon atoms are connected by linkages other than oxygen atoms
-
- 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
- C08K5/01—Hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/54—Silicon-containing compounds
- C08K5/541—Silicon-containing compounds containing oxygen
- C08K5/5415—Silicon-containing compounds containing oxygen containing at least one Si—O bond
- C08K5/5419—Silicon-containing compounds containing oxygen containing at least one Si—O bond containing at least one Si—C bond
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/54—Silicon-containing compounds
- C08K5/541—Silicon-containing compounds containing oxygen
- C08K5/5425—Silicon-containing compounds containing oxygen containing at least one C=C bond
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K1/00—Printed circuits
- H05K1/02—Details
- H05K1/03—Use of materials for the substrate
- H05K1/0313—Organic insulating material
- H05K1/032—Organic insulating material consisting of one material
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Silicon Polymers (AREA)
Abstract
Description
Claims (23)
- 1.水素化珪素ラジカルを含む1個以上のカルボシランポリマー、ヒドロシリル 化反応で反応性のある1個以上の二重結合を含む1個以上の多環ポリエン架橋剤 、および必要に応じてヒドロシリル化触媒からなる架橋性カルボシランポリマー 調合物。
- 2.カルボシランポリマーが、不飽和でかつ次式:[Si(R)(H)CH2C (R1)=C(R2)CH2]n(式中、Rは水素、1〜4個の炭素原子を含む アルキルラジカルまたは芳香族ラジカル;R1およびR2は各々水素、メチルラ ジカルまたはハロゲン;並びにnは5以上の整数である)の繰り返し単位からな る請求の範囲第1項の架橋性カルボシランポリマー調合物。
- 3.ポリマーが、式: [Si(R3)(R4)CH2C(R1)=C(R2)CH2]−[Si(R) (H)CH2C(R1)=C(R2)CH2]n(式中、Rは水素、1〜4個の 炭素原子を含むアルキルラジカルまたは芳香族ラジカル;R1およびR2は各々 水素、メチルラジカルまたはハロゲン;R3およびR4は各々1〜4個の炭素原 子を含むアルキルラジカルまたは芳香族ラジカル;並びにmおよびnは5以上の 整数である)のランダムまたはブロックコポリマーである請求の範囲第1項の架 橋性カルボシランポリマー調合物。
- 4.カルボシランポリマーが飽和でかつ式:[Si(R)(H)CH2CH(R 1)CH(R2)CH2]n(式中、Rは水素、1〜4個の炭素原子を含むアル キルラジカルまたは芳香族ラジカル;R1およびR2は各々水素、メチルラジカ ルまたはハロゲン;並びにnは5以上の整数である)の繰り返し単位からなる請 求の範囲第1項の架橋性カルボシランポリマー調合物。
- 5.カルボシランポリマーが1個以上の次の繰り返し単位:[Si(R)(H) CH2CH(R1)CH(R2)]n(式中、Rは水素、1〜4個の炭素原子を 含むアルキルラジカルまたはフェニル、R1およびR2は各々水素、メチルラジ カルまたはハロゲンまたはフェニル、並びにnは5以上の整数である)からなる 請求の範囲第1項の架橋性カルボシランポリマー調合物。
- 6.カルボシランポリマーが、式の繰り返し単位:▲数式、化学式、表等があり ます▼ (式中、Rは水素、1〜4個の炭素原子を含むアルキルラジカルまたは芳香族ラ ジカル;並びにnは約10〜約10,000の整数である)からなる請求の範囲 第1項の架橋性カルボシランポリマー調合物。
- 7.カルボシランポリマーが、式の繰り返し単位:▲数式、化学式、表等があり ます▼ (式中、Rは水素、1〜4個の炭素原子を持つアルキルまたは芳香族ラジカル、 R1は芳香族ラジカル、並びにnは5以上の整数である)からなる請求の範囲第 1項の架橋性カルボシランポリマー調合物。
- 8.多環ポリエンがシクロペンクジエンのディールスーアルダー反応によって生 成する請求の範囲第1項の架橋性調合物。
- 9.多環ポリエン架橋剤が、ジシクロペンタジエン、トリシクロペンタジエン、 ジメタノヘキサ−ヒドロナフタレン、ビシクロヘプタジエン、テトラシクロペン タジェン、ビニルノルボルネンおよびエチリデンノルボルネンから成る部類中か ら選ばれる請求の範囲第1項の架橋性調合物。
- 10.多環ポリエン架橋剤が、ジシクロペンタジエン、トリシクロペンタジエン 、ジメタノヘキサ−ヒドロナフタレン、ビシクロヘプタジエン、テトラシクロペ ンタジエン、ビニルノルボルネンおよびエチリデンノルボルネンから成る部類中 から選ばれる請求の範囲第2項の架橋性調合物。
- 11.多環ポリエン架橋剤が、ジシクロペンタジエン、トリシクロペンタジエン 、ジメタノヘキサ−ヒドロナフタレン、ビシクロヘプタジエン、テトラシクロペ ンタジエン、ビニルノルボルネンおよびエチリデンノルボルネンから成る部類中 から選ばれる請求の範囲第3項の架橋性調合物。
- 12.多環ポリエン架橋剤が、ジシクロペンタジエン、トリシクロペンタジエン 、ジメタノヘキサ−ヒドロナフタレン、ビシクロヘプタジエン、テトラシクロペ ンタジエン、ビニルノルボルネンおよびエチリデンノルボルネンから成る部類中 から選ばれる請求の範囲第4項の架橋性調合物。
- 13.多環ポリエン架橋剤が、ジシクロペンタジエン、トリシクロペンタジエン 、ジメタノヘキサ−ヒドロナフタレン、ビシクロヘプタジエン、テトラシクロペ ンタジエン、ビニルノルボルネンおよびエチリデンノルボルネンから成る部類中 から選ばれる請求の範囲第5項の架橋性調合物。
- 14.多環ポリエン架橋剤が、ジシクロペンタジエン、トリシクロペンタジエン 、ジメタノヘキサ−ヒドロナフタレン、ビシクロヘプタジエン、テトラシクロペ ンタジエン、ビニルノルボルネンおよびエチリデンノルボルネンから成る部類中 から選ばれる請求の範囲第6項の架橋性調合物。
- 15.多環ポリエンが、ジシクロペンタジエン、トリシクロペンタジエン、ジメ タノヘキサ−ヒドロナフタレン、ビシクロヘプタジエン、テトラシクロペンタジ エン、ビニルノルボルネンおよびエチリデンノルボルネンから成る部類中から選 ばれる請求の範囲第7項の架橋性調合物。
- 16.ヒドロシリル化反応触媒が白金化合物である請求の範囲第1項の調合物。
- 17.架橋性カルボシランポリマー調合物とまた無機フィラーが95重量%以下 の量で添加される請求の範囲第1項の調合物。
- 18.式: [Si(R)(H)CH2C(R1)=C(R2)CH]n(式中、Rは水素、 1〜4個の炭素原子を含むアルキルラジカルまたは芳香族ラジカル;R1および R2は各々水素、メチルラジカルまたはハロゲン;nは5以上の整数である)の カルボシランポリマー、並びに線状ジエン、不飽和エラストマー、芳香族ジエン 、シロキサン系ジエン、複素環系ポリエンおよびシクロペンタジエンのディール スアルダー反応生成物から選ばれるポリエン架橋剤、並びに必要に応じてヒドロ シリル化触媒からなる架橋性カルボシランポリマー調合物。
- 19.式: [Si(R3)(R4)CH2C(R1)=C(R2)CH2]−[ESi(R )(H)CH2C(R1)=C(R2)CH2]n(式中、Rは水素、1〜4個 の炭素原子を含むアルキルラジカルまたは芳香族ラジカル;R1およびR2は各 々水素、メチルラジカルまたはハロゲン;R3およびR4は、各々1個〜4個の 炭素原子を持つアルキルラジカルまたは芳香族ラジカル;並びにmおよびnは5 以上の整数である)のカルボシランのランダムまたはブロックコポリマー、並び に線状ジエン、不飽和エラストマー、芳香族ジエン、シロキサン系ジエン、複素 環系ポリエンおよびシクロペンタジエンのディールスアルダー反応生成物から選 ばれるポリエン架橋剤、並びに必要に応じてヒドロシリル化反応触媒からなる架 橋性カルボシランポリマー調合物。
- 20.式: ▲数式、化学式、表等があります▼ (式中、Rは水素、1〜4個の炭素原子を含むアルキルラジカルまたは芳香族ラ ジカル、およびnは5以上の整数である)のカルボシランポリマー、並びに線状 ジエン、不飽和エラストマー、芳香族ジエン、シロキサン系ジエン及びポリエン 、複素環系ポリエン,およびシクロペンタジエンのディールスアルダー反応生成 物から選ばれるポリエン架橋剤、並びに必要に応じてヒドロシリル化反応触媒か らなる架橋性カルボシランポリマー調合物。
- 21.部分的に反応してプレポリマーを生成する請求の範囲第1項の調合物。
- 22.多環ポリエンがジシクロペンタジエンである請求の範囲第1項の調合物。
- 23.更にエラストマー状領域を含む請求の範囲第1項の架橋性カルボシランポ リマー調合物。
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US84051392A | 1992-02-24 | 1992-02-24 | |
US840,513 | 1992-02-24 | ||
US07/972,250 US5260377A (en) | 1990-12-31 | 1992-11-05 | Crosslinkable carbosilane polymer formulations |
US972,250 | 1992-11-05 | ||
PCT/US1993/001618 WO1993017063A1 (en) | 1992-02-24 | 1993-02-24 | Crosslinkable carbosilane polymer formulations |
Publications (2)
Publication Number | Publication Date |
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JPH07503991A true JPH07503991A (ja) | 1995-04-27 |
JP3467503B2 JP3467503B2 (ja) | 2003-11-17 |
Family
ID=27126195
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP51503893A Expired - Fee Related JP3467503B2 (ja) | 1992-02-24 | 1993-02-24 | 架橋性カルボシランポリマー調合物 |
Country Status (5)
Country | Link |
---|---|
US (1) | US5260377A (ja) |
JP (1) | JP3467503B2 (ja) |
AU (1) | AU3731193A (ja) |
MX (1) | MX9301019A (ja) |
WO (1) | WO1993017063A1 (ja) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2005133073A (ja) * | 2003-10-10 | 2005-05-26 | Shin Etsu Chem Co Ltd | 硬化性組成物 |
JP2006152063A (ja) * | 2004-11-26 | 2006-06-15 | Jsr Corp | 新規ポリカルボシランおよびその製造方法、膜形成用組成物、ならびに膜およびその形成方法 |
JP2016166298A (ja) * | 2015-03-10 | 2016-09-15 | 信越化学工業株式会社 | 両末端変性されたシラシクロブタン開環重合物及びその製造方法 |
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Publication number | Priority date | Publication date | Assignee | Title |
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US5384382A (en) * | 1992-07-31 | 1995-01-24 | Shin-Etsu Chemical Co., Ltd. | Crosslinkable polysilane compositions and cured products thereof |
JP3324166B2 (ja) * | 1992-12-10 | 2002-09-17 | 信越化学工業株式会社 | 接着性シリコーンゴム組成物 |
US6362279B2 (en) * | 1996-09-27 | 2002-03-26 | The United States Of America As Represented By The Secretary Of The Air Force | Preceramic additives as fire retardants for plastics |
CN1265116A (zh) * | 1997-07-28 | 2000-08-30 | 钟渊化学工业株式会社 | 聚合物和聚合物的制备方法 |
US6720395B2 (en) * | 1997-07-28 | 2004-04-13 | Kaneka Corporation | Method for producing a stellar polymer |
US6054549A (en) * | 1998-11-25 | 2000-04-25 | Dow Corning Asia, Ltd. | Alkenyl ether functional polyisobutylenes and methods for the preparation thereof |
JP5089005B2 (ja) * | 2000-06-20 | 2012-12-05 | 三井化学株式会社 | 架橋可能なゴム組成物およびその用途 |
US6794044B2 (en) | 2001-03-02 | 2004-09-21 | Selerity Technologies, Inc. | Chromatographic packing materials and methods of making and using such packing materials |
US7135535B2 (en) * | 2004-07-29 | 2006-11-14 | National Starch And Chemical Investment Holding Corporation | Siloxane resins with oxetane functionality |
US20110315046A1 (en) * | 2010-06-28 | 2011-12-29 | Paul Sheedy | Method for fabricating composite powders |
FR2996228B1 (fr) * | 2012-10-02 | 2015-09-25 | Michelin & Cie | Procede de preparation d'un copolymere statistique a base de monomeres dieniques et de monomeres carbosilanes cycliques |
FR2996229B1 (fr) * | 2012-10-02 | 2015-09-25 | Michelin & Cie | Procede de preparation d'un copolymere de carbosilane a blocs comprenant des insaturations dans la chaine lineaire |
US11499014B2 (en) | 2019-12-31 | 2022-11-15 | L'Air Liquide, Société Anonyme pour l'Etude et l'Exploitation des Procédés Georges Claude | Cureable formulations for forming low-k dielectric silicon-containing films using polycarbosilazane |
CN115667373B (zh) * | 2020-05-28 | 2024-10-18 | 3M创新有限公司 | 可固化组合物、由其形成的反应产物及包含该反应产物的电子制品 |
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BE553159A (ja) * | 1955-12-05 | |||
FR2575085B1 (fr) * | 1984-12-20 | 1987-02-20 | Rhone Poulenc Spec Chim | Complexe platine-triene comme catalyseur de reaction d'hydrosilylation et son procede de preparation |
US4719273A (en) * | 1985-09-04 | 1988-01-12 | Massachusetts Institute Of Technology | Method for forming new preceramic polymers containing silicon |
US4900779A (en) * | 1986-08-27 | 1990-02-13 | Hercules Incorporated | Organosilicon polymers |
US4877820A (en) * | 1987-03-20 | 1989-10-31 | Hercules Incorporated | Cross-linked organosiloxane polymers |
US5169916A (en) * | 1990-12-31 | 1992-12-08 | University Of South California | Crosslinkable poly(unsaturated carbosilane) polymers and methods of making same |
US5171810A (en) * | 1990-12-31 | 1992-12-15 | University Of Southern California | Crosslinkable poly(unsaturated carbosilane) copolymers and methods of making same |
-
1992
- 1992-11-05 US US07/972,250 patent/US5260377A/en not_active Expired - Lifetime
-
1993
- 1993-02-24 MX MX9301019A patent/MX9301019A/es unknown
- 1993-02-24 WO PCT/US1993/001618 patent/WO1993017063A1/en active Application Filing
- 1993-02-24 JP JP51503893A patent/JP3467503B2/ja not_active Expired - Fee Related
- 1993-02-24 AU AU37311/93A patent/AU3731193A/en not_active Abandoned
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2005133073A (ja) * | 2003-10-10 | 2005-05-26 | Shin Etsu Chem Co Ltd | 硬化性組成物 |
JP4520251B2 (ja) * | 2003-10-10 | 2010-08-04 | 信越化学工業株式会社 | 硬化性組成物 |
JP2006152063A (ja) * | 2004-11-26 | 2006-06-15 | Jsr Corp | 新規ポリカルボシランおよびその製造方法、膜形成用組成物、ならびに膜およびその形成方法 |
JP2016166298A (ja) * | 2015-03-10 | 2016-09-15 | 信越化学工業株式会社 | 両末端変性されたシラシクロブタン開環重合物及びその製造方法 |
Also Published As
Publication number | Publication date |
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JP3467503B2 (ja) | 2003-11-17 |
AU3731193A (en) | 1993-09-13 |
MX9301019A (es) | 1994-03-31 |
US5260377A (en) | 1993-11-09 |
WO1993017063A1 (en) | 1993-09-02 |
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