DE60004934T2 - Silsesquioxan-Harz mit hoher Festigkeit und Bruchzähigkeit und Verfahren zu dessen Herstellung - Google Patents
Silsesquioxan-Harz mit hoher Festigkeit und Bruchzähigkeit und Verfahren zu dessen Herstellung Download PDFInfo
- Publication number
- DE60004934T2 DE60004934T2 DE60004934T DE60004934T DE60004934T2 DE 60004934 T2 DE60004934 T2 DE 60004934T2 DE 60004934 T DE60004934 T DE 60004934T DE 60004934 T DE60004934 T DE 60004934T DE 60004934 T2 DE60004934 T2 DE 60004934T2
- Authority
- DE
- Germany
- Prior art keywords
- component
- composition
- curable
- groups
- hydrosilylation reaction
- 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.)
- Expired - Lifetime
Links
- 229920005989 resin Polymers 0.000 title claims description 53
- 239000011347 resin Substances 0.000 title claims description 53
- 238000000034 method Methods 0.000 title claims description 25
- 230000008569 process Effects 0.000 title claims description 8
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- 239000000203 mixture Substances 0.000 claims description 86
- 238000006459 hydrosilylation reaction Methods 0.000 claims description 24
- 229920002379 silicone rubber Polymers 0.000 claims description 16
- 150000002430 hydrocarbons Chemical class 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
- 239000004945 silicone rubber Substances 0.000 claims description 13
- 239000002904 solvent Substances 0.000 claims description 13
- 125000000524 functional group Chemical group 0.000 claims description 10
- 229920001577 copolymer Polymers 0.000 claims description 9
- 238000002156 mixing Methods 0.000 claims description 9
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 9
- UHXCHUWSQRLZJS-UHFFFAOYSA-N (4-dimethylsilylidenecyclohexa-2,5-dien-1-ylidene)-dimethylsilane Chemical compound C[Si](C)C1=CC=C([Si](C)C)C=C1 UHXCHUWSQRLZJS-UHFFFAOYSA-N 0.000 claims description 8
- 239000004215 Carbon black (E152) Substances 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 8
- 229930195733 hydrocarbon Natural products 0.000 claims description 8
- 239000007809 chemical reaction catalyst Substances 0.000 claims description 6
- 239000003112 inhibitor Substances 0.000 claims description 6
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 238000007872 degassing Methods 0.000 claims description 3
- 229910052697 platinum Inorganic materials 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 12
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims 1
- 229910052710 silicon Inorganic materials 0.000 claims 1
- 239000010703 silicon Substances 0.000 claims 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 238000012360 testing method Methods 0.000 description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
- 229920001971 elastomer Polymers 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 239000005060 rubber Substances 0.000 description 8
- 229920002050 silicone resin Polymers 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- WQONPSCCEXUXTQ-UHFFFAOYSA-N 1,2-dibromobenzene Chemical compound BrC1=CC=CC=C1Br WQONPSCCEXUXTQ-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 238000005452 bending Methods 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- QABCGOSYZHCPGN-UHFFFAOYSA-N chloro(dimethyl)silicon Chemical compound C[Si](C)Cl QABCGOSYZHCPGN-UHFFFAOYSA-N 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000011777 magnesium Substances 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 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 4
- 239000002253 acid Substances 0.000 description 4
- 238000007259 addition reaction Methods 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 229920001296 polysiloxane Polymers 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- QYLFHLNFIHBCPR-UHFFFAOYSA-N 1-ethynylcyclohexan-1-ol Chemical compound C#CC1(O)CCCCC1 QYLFHLNFIHBCPR-UHFFFAOYSA-N 0.000 description 3
- 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
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 0 C*(C)c(cc1)ccc1-c1ccc(C)cc1 Chemical compound C*(C)c(cc1)ccc1-c1ccc(C)cc1 0.000 description 3
- 239000004971 Cross linker Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-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
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 229940045985 antineoplastic platinum compound Drugs 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000005375 organosiloxane group Chemical group 0.000 description 3
- 150000003058 platinum compounds Chemical class 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000010998 test method Methods 0.000 description 3
- 238000010792 warming Methods 0.000 description 3
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 2
- -1 B. dibromobenzene Chemical class 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 238000002679 ablation Methods 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000003060 catalysis inhibitor Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 230000001143 conditioned effect Effects 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 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 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000013001 point bending Methods 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 150000004756 silanes Chemical class 0.000 description 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- RWNUSVWFHDHRCJ-UHFFFAOYSA-N 1-butoxypropan-2-ol Chemical compound CCCCOCC(C)O RWNUSVWFHDHRCJ-UHFFFAOYSA-N 0.000 description 1
- FENFUOGYJVOCRY-UHFFFAOYSA-N 1-propoxypropan-2-ol Chemical compound CCCOCC(C)O FENFUOGYJVOCRY-UHFFFAOYSA-N 0.000 description 1
- CUDYYMUUJHLCGZ-UHFFFAOYSA-N 2-(2-methoxypropoxy)propan-1-ol Chemical compound COC(C)COC(C)CO CUDYYMUUJHLCGZ-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-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
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- QDCWJDYWORENAG-UHFFFAOYSA-N Cc(cc1)ccc1S=C Chemical compound Cc(cc1)ccc1S=C QDCWJDYWORENAG-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- IEPRKVQEAMIZSS-UHFFFAOYSA-N Di-Et ester-Fumaric acid Natural products CCOC(=O)C=CC(=O)OCC IEPRKVQEAMIZSS-UHFFFAOYSA-N 0.000 description 1
- IEPRKVQEAMIZSS-WAYWQWQTSA-N Diethyl maleate Chemical compound CCOC(=O)\C=C/C(=O)OCC IEPRKVQEAMIZSS-WAYWQWQTSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
- 238000003747 Grignard reaction Methods 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
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229910004283 SiO 4 Inorganic materials 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- YKSADNUOSVJOAS-UHFFFAOYSA-N [bis[(dimethyl-$l^{3}-silanyl)oxy]-phenylsilyl]oxy-dimethylsilicon Chemical group C[Si](C)O[Si](O[Si](C)C)(O[Si](C)C)C1=CC=CC=C1 YKSADNUOSVJOAS-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000000732 arylene group Chemical group 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GVTGUOINIMHIRT-WAYWQWQTSA-N bis(1-methoxypropan-2-yl) (z)-but-2-enedioate Chemical compound COCC(C)OC(=O)\C=C/C(=O)OC(C)COC GVTGUOINIMHIRT-WAYWQWQTSA-N 0.000 description 1
- 239000003990 capacitor Substances 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 239000004917 carbon fiber Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000013016 damping Methods 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- XAFJSPPHVXDRIE-UHFFFAOYSA-N dichloroplatinum;triphenylphosphanium Chemical compound Cl[Pt]Cl.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 XAFJSPPHVXDRIE-UHFFFAOYSA-N 0.000 description 1
- 239000003989 dielectric material Substances 0.000 description 1
- RVDJLKVICMLVJQ-UHFFFAOYSA-N diethoxy(phenyl)phosphane Chemical compound CCOP(OCC)C1=CC=CC=C1 RVDJLKVICMLVJQ-UHFFFAOYSA-N 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- UOUILILVWRHZSH-UHFFFAOYSA-N dimethyl-tris[(dimethyl-$l^{3}-silanyl)oxy]silyloxysilicon Chemical group C[Si](C)O[Si](O[Si](C)C)(O[Si](C)C)O[Si](C)C UOUILILVWRHZSH-UHFFFAOYSA-N 0.000 description 1
- KUMNEOGIHFCNQW-UHFFFAOYSA-N diphenyl phosphite Chemical compound C=1C=CC=CC=1OP([O-])OC1=CC=CC=C1 KUMNEOGIHFCNQW-UHFFFAOYSA-N 0.000 description 1
- GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000003733 fiber-reinforced composite Substances 0.000 description 1
- 230000009970 fire resistant effect Effects 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000007656 fracture toughness test Methods 0.000 description 1
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000011229 interlayer Substances 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
- KFZMGEQAYNKOFK-UHFFFAOYSA-N isopropyl alcohol Natural products CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 1
- OAADXJFIBNEPLY-UHFFFAOYSA-N methoxy(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(OC)C1=CC=CC=C1 OAADXJFIBNEPLY-UHFFFAOYSA-N 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 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
- 230000006855 networking Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- CLSUSRZJUQMOHH-UHFFFAOYSA-L platinum dichloride Chemical compound Cl[Pt]Cl CLSUSRZJUQMOHH-UHFFFAOYSA-L 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000007348 radical reaction Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000012763 reinforcing filler Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- RMZAYIKUYWXQPB-UHFFFAOYSA-N trioctylphosphane Chemical compound CCCCCCCCP(CCCCCCCC)CCCCCCCC RMZAYIKUYWXQPB-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C08L83/14—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 at least two but not 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
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D183/00—Coating compositions based on 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; Coating compositions based on derivatives of such polymers
- C09D183/14—Coating compositions based on 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; Coating compositions based on derivatives of such polymers in which at least two but not 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
- C08G77/04—Polysiloxanes
- C08G77/12—Polysiloxanes containing silicon bound to hydrogen
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Silicon Polymers (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/345,638 US6310146B1 (en) | 1999-07-01 | 1999-07-01 | Silsesquioxane resin with high strength and fracture toughness and method for the preparation thereof |
| US345638 | 1999-07-01 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60004934D1 DE60004934D1 (de) | 2003-10-09 |
| DE60004934T2 true DE60004934T2 (de) | 2004-07-22 |
Family
ID=23355853
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60004934T Expired - Lifetime DE60004934T2 (de) | 1999-07-01 | 2000-06-28 | Silsesquioxan-Harz mit hoher Festigkeit und Bruchzähigkeit und Verfahren zu dessen Herstellung |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US6310146B1 (https=) |
| EP (1) | EP1065248B1 (https=) |
| JP (2) | JP5248720B2 (https=) |
| DE (1) | DE60004934T2 (https=) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6652975B2 (en) * | 2001-03-02 | 2003-11-25 | Lucent Technologies Inc. | Adherent silicones |
| US6509423B1 (en) * | 2001-08-21 | 2003-01-21 | Dow Corning Corporation | Silicone composition and cured silicone product |
| US6689859B2 (en) * | 2002-03-05 | 2004-02-10 | Dow Corning Corporation | High fracture toughness hydrosilyation cured silicone resin |
| US6646039B2 (en) * | 2002-03-05 | 2003-11-11 | Dow Corning Corporation | Hydrosilyation cured silicone resin containing colloidal silica and a process for producing the same |
| US6596821B1 (en) | 2002-03-05 | 2003-07-22 | Dow Corning Corporation | Hydrosilyation cured silicone resins obtained by fractionation |
| US6660395B2 (en) | 2002-03-12 | 2003-12-09 | Dow Corning Corporation | Silicone resin based composites interleaved for improved toughness |
| US7037592B2 (en) | 2003-02-25 | 2006-05-02 | Dow Coming Corporation | Hybrid composite of silicone and organic resins |
| WO2005013361A1 (ja) * | 2003-07-30 | 2005-02-10 | The Kansai Electric Power Co., Inc. | 高耐熱半導体装置 |
| JP2005089671A (ja) * | 2003-09-19 | 2005-04-07 | Shin Etsu Chem Co Ltd | 硬化性シリコーン樹脂組成物 |
| CN100540275C (zh) * | 2003-11-17 | 2009-09-16 | 陶氏康宁公司 | 固化有机硅树脂基底的压花方法 |
| DE602005009971D1 (de) * | 2004-11-19 | 2008-11-06 | Dow Corning | Zusammensetzung aus organohydrogenpolysiloxanharz und silizium |
| WO2006055231A1 (en) * | 2004-11-19 | 2006-05-26 | Dow Corning Corporation | Silicone composition and cured silicone resin |
| JP4339267B2 (ja) * | 2005-01-27 | 2009-10-07 | 関西電力株式会社 | 高耐熱電力用静止機器 |
| US8092910B2 (en) * | 2005-02-16 | 2012-01-10 | Dow Corning Toray Co., Ltd. | Reinforced silicone resin film and method of preparing same |
| KR101271662B1 (ko) | 2005-02-16 | 2013-06-05 | 다우 코닝 도레이 캄파니 리미티드 | 강화 실리콘 수지 필름 및 이의 제조방법 |
| EP1893671B1 (en) * | 2005-06-14 | 2009-12-23 | Dow Corning Corporation | Reinforced silicone resin film and method of preparing same |
| WO2007018756A1 (en) * | 2005-08-04 | 2007-02-15 | Dow Corning Corporation | Reinforced silicone resin film and method of preparing same |
| JP2007063394A (ja) * | 2005-08-31 | 2007-03-15 | Asahi Kasei Corp | かご状シルセスキオキサン重合体 |
| US8912268B2 (en) | 2005-12-21 | 2014-12-16 | Dow Corning Corporation | Silicone resin film, method of preparing same, and nanomaterial-filled silicone composition |
| US8084532B2 (en) | 2006-01-19 | 2011-12-27 | Dow Corning Corporation | Silicone resin film, method of preparing same, and nanomaterial-filled silicone composition |
| JP5178532B2 (ja) * | 2006-02-02 | 2013-04-10 | ダウ・コーニング・コーポレイション | シリコーン樹脂フィルム、その調製方法、およびナノ材料充填シリコーン組成物 |
| WO2007097835A2 (en) * | 2006-02-20 | 2007-08-30 | Dow Corning Corporation | Silicone resin film, method of preparing same, and nanomaterial-filled silicone composition |
| EP2117836B1 (en) | 2007-02-22 | 2012-11-07 | Dow Corning Corporation | Reinforced silicone resin films |
| JP2010519381A (ja) * | 2007-02-22 | 2010-06-03 | ダウ コーニング コーポレーション | 強化シリコーン樹脂フィルムおよびその調製方法 |
| WO2008103226A1 (en) | 2007-02-22 | 2008-08-28 | Dow Corning Corporation | Reinforced silicone resin films |
| US20100143686A1 (en) * | 2007-05-01 | 2010-06-10 | Bizhong Zhu | Nanomaterial-Filled Silicone Composition and Reinforced Silicone Resin Film |
| JP2009029881A (ja) * | 2007-07-25 | 2009-02-12 | Toyota Industries Corp | 透明有機ガラスおよびその製造方法 |
| US8242181B2 (en) * | 2007-10-12 | 2012-08-14 | Dow Corning Corporation | Aluminum oxide dispersion and method of preparing same |
| CN102272231B (zh) | 2008-11-19 | 2013-10-30 | 陶氏康宁公司 | 硅氧烷组合物和制备该硅氧烷组合物的方法 |
| KR102471220B1 (ko) | 2018-08-17 | 2022-11-25 | 와커 헤미 아게 | 가교성 오르가노실록산 조성물 |
Family Cites Families (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA691206A (en) | 1964-07-21 | Dow Corning Corporation | Method of damping vibration | |
| NL131800C (https=) | 1965-05-17 | |||
| NL129346C (https=) | 1966-06-23 | |||
| US4198131A (en) * | 1978-03-23 | 1980-04-15 | Dow Corning Corporation | Silicone resin optical devices |
| JPS60108839A (ja) * | 1983-11-18 | 1985-06-14 | Mitsubishi Electric Corp | 感光性耐熱材料 |
| US4803244A (en) * | 1987-11-16 | 1989-02-07 | Union Carbide Corporation | Process for the preparation of thermoplastic elastomers |
| FR2641785B1 (fr) * | 1989-01-19 | 1992-07-31 | Essilor Int | Composition de polymeres transparents pour lentilles de contact de type rigide, permeables a l'oxygene |
| JP2550723B2 (ja) * | 1989-10-30 | 1996-11-06 | 信越化学工業株式会社 | 光ファイバのコア用組成物及び光ファイバ |
| JP2550724B2 (ja) * | 1989-10-30 | 1996-11-06 | 信越化学工業株式会社 | 光ファイバ |
| JP2836256B2 (ja) * | 1990-12-10 | 1998-12-14 | 信越化学工業株式会社 | 光ファイバのコア用組成物及び光ファイバ |
| JP2924383B2 (ja) * | 1991-11-11 | 1999-07-26 | 信越化学工業株式会社 | 光ファイバ |
| JP3024439B2 (ja) * | 1993-06-07 | 2000-03-21 | 信越化学工業株式会社 | オルガノポリシロキサン組成物 |
| EP0661332B1 (en) | 1993-12-28 | 2000-04-12 | Kanegafuchi Chemical Industry Co., Ltd. | Silicon-containing reactive polymer and curable resin composition comprising the same |
| JP3615784B2 (ja) * | 1994-04-21 | 2005-02-02 | ダウ コーニング アジア株式会社 | 光学素子用樹脂組成物及び光学素子 |
| JPH07306301A (ja) * | 1994-05-13 | 1995-11-21 | Dow Corning Kk | 光学素子及びその製造方法 |
| JPH08225647A (ja) * | 1994-12-01 | 1996-09-03 | Kanegafuchi Chem Ind Co Ltd | 硬化性組成物及びそれを用いた成形体の作製方法 |
| US5623030A (en) | 1994-12-01 | 1997-04-22 | Kanegafuchi Kagaku Kogyo Kabushiki Kaisha | Curable composition and process for producing molded articles using the same |
| JP3499393B2 (ja) * | 1996-02-16 | 2004-02-23 | 鐘淵化学工業株式会社 | ケイ素系化合物を主成分とする予備硬化物及びそれを用いた成形体の作製方法 |
| JPH10152617A (ja) * | 1996-11-25 | 1998-06-09 | Kanegafuchi Chem Ind Co Ltd | 電気絶縁材料用熱硬化性樹脂組成物 |
| US5747608A (en) | 1996-12-31 | 1998-05-05 | Dow Corning Corporation | Rubber-modified rigid silicone resins and composites produced therefrom |
| US5830950A (en) | 1996-12-31 | 1998-11-03 | Dow Corning Corporation | Method of making rubber-modified rigid silicone resins and composites produced therefrom |
| JP3635180B2 (ja) * | 1997-02-24 | 2005-04-06 | ダウ コーニング アジア株式会社 | シリル化ポリメチルシルセスキオキサン、その製造方法、それを用いた組成物 |
| JP2000231001A (ja) * | 1999-02-10 | 2000-08-22 | Konica Corp | 光学用レンズ |
| JP2000231002A (ja) * | 1999-02-10 | 2000-08-22 | Konica Corp | 光学用レンズ |
| JP2001089662A (ja) * | 1999-09-22 | 2001-04-03 | Kanegafuchi Chem Ind Co Ltd | 硬化性組成物及びそれを用いた成形体の作製方法 |
| US6509423B1 (en) * | 2001-08-21 | 2003-01-21 | Dow Corning Corporation | Silicone composition and cured silicone product |
| US6689859B2 (en) * | 2002-03-05 | 2004-02-10 | Dow Corning Corporation | High fracture toughness hydrosilyation cured silicone resin |
| US6646039B2 (en) * | 2002-03-05 | 2003-11-11 | Dow Corning Corporation | Hydrosilyation cured silicone resin containing colloidal silica and a process for producing the same |
| WO2003104329A1 (ja) * | 2002-06-05 | 2003-12-18 | ダウコーニングアジア株式会社 | ポリシロキサンフィルム及びその製造方法 |
-
1999
- 1999-07-01 US US09/345,638 patent/US6310146B1/en not_active Expired - Lifetime
-
2000
- 2000-06-28 DE DE60004934T patent/DE60004934T2/de not_active Expired - Lifetime
- 2000-06-28 EP EP00113618A patent/EP1065248B1/en not_active Expired - Lifetime
- 2000-07-03 JP JP2000201004A patent/JP5248720B2/ja not_active Expired - Fee Related
-
2012
- 2012-05-09 JP JP2012107532A patent/JP2012144748A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JP2012144748A (ja) | 2012-08-02 |
| EP1065248B1 (en) | 2003-09-03 |
| JP5248720B2 (ja) | 2013-07-31 |
| US6310146B1 (en) | 2001-10-30 |
| JP2001026717A (ja) | 2001-01-30 |
| DE60004934D1 (de) | 2003-10-09 |
| EP1065248A1 (en) | 2001-01-03 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE60004934T2 (de) | Silsesquioxan-Harz mit hoher Festigkeit und Bruchzähigkeit und Verfahren zu dessen Herstellung | |
| DE69223366T2 (de) | Silizium-enthaltende Polymere | |
| DE60015872T2 (de) | Durch Kondensationsreaktion vernetzbare Silsesquioxanharzzusammensetzung und Verfahren zu ihrer Herstellung und Vernetzung | |
| EP3467006B1 (de) | Mischungen zyklischer-verzweigter siloxane vom d/t-typ und deren folgeprodukte | |
| DE60223048T2 (de) | Silikonzusammensetzung und gehärtetes produkt daraus | |
| DE3789475T2 (de) | Organosilikon-Polymere. | |
| DE2661091C2 (https=) | ||
| DE69215950T2 (de) | Siloxanelastomere enthaltende Organosiliciummassen | |
| DE2609159C3 (de) | Hitzehärtbare Organopolysiloxanformmasse | |
| DE69214603T2 (de) | Silikonkautschukzusammensetzung und damit behandeltes Gewebe | |
| DE3035866A1 (de) | Warmvernetzbare organopolysiloxanmasse | |
| DE69020842T2 (de) | Organosilikonzusammensetzungen. | |
| DE60310206T2 (de) | Hydrosilylationsaushärtung von kollodiale kieselsäure enthaltendem silikonharz und herstellungsverfahren dafür | |
| DE1445362A1 (de) | Verfahren zur Herstellung von Organopolysiloxanen | |
| EP1580224B1 (de) | Vernetzbare Massen auf der Basis von Organosiliciumverbindungen | |
| DE3927362A1 (de) | Verfahren zur herstellung einer polyorganosiloxanmasse | |
| DE69214726T2 (de) | Hitzestabile Acrylamidpolysiloxanzusammensetzung | |
| DD203064A5 (de) | Verfahren zur herstellung von silikonkautschuk | |
| DE69725482T2 (de) | Härtbare Siliconzusammensetzungen | |
| DE3855943T2 (de) | Vernetzte Organosiloxanpolymer | |
| DE2244644A1 (de) | Bei raumtemperatur vulkanisierbare selbstklebende zweikomponenten-silikongummizusammensetzungen | |
| WO1992021724A2 (de) | Unter abspaltung von alkoholen zu elastomeren vernetzbare organo(poly)siloxanmassen | |
| DE3213053A1 (de) | Fluorsilicon-kautschukmasse, verfahren zu ihrer haertung und polymer | |
| DE4436675B4 (de) | Polyphenylenoxid-Zusammensetzungen | |
| DE69510840T2 (de) | Härtbare Organopolysiloxanzusammensetzungen |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition |