JPH03223362A - Self-adhering silicone rubber composition and silicone rubber-coated fabric - Google Patents
Self-adhering silicone rubber composition and silicone rubber-coated fabricInfo
- Publication number
- JPH03223362A JPH03223362A JP2334569A JP33456990A JPH03223362A JP H03223362 A JPH03223362 A JP H03223362A JP 2334569 A JP2334569 A JP 2334569A JP 33456990 A JP33456990 A JP 33456990A JP H03223362 A JPH03223362 A JP H03223362A
- Authority
- JP
- Japan
- Prior art keywords
- silicone rubber
- group
- parts
- rubber composition
- adhesive
- 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
- 229920002379 silicone rubber Polymers 0.000 title claims abstract description 49
- 239000004945 silicone rubber Substances 0.000 title claims abstract description 49
- 239000004744 fabric Substances 0.000 title claims abstract description 24
- 239000000203 mixture Substances 0.000 title claims description 47
- 229920001296 polysiloxane Polymers 0.000 claims abstract description 23
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 11
- 150000001282 organosilanes Chemical class 0.000 claims abstract description 10
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract 2
- 239000000853 adhesive Substances 0.000 claims description 31
- 239000002759 woven fabric Substances 0.000 claims description 12
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 10
- 239000011248 coating agent Substances 0.000 claims description 7
- 238000000576 coating method Methods 0.000 claims description 7
- 229920001778 nylon Polymers 0.000 abstract description 12
- 239000000835 fiber Substances 0.000 abstract description 11
- 239000004677 Nylon Substances 0.000 abstract description 9
- 239000000919 ceramic Substances 0.000 abstract description 5
- 239000011521 glass Substances 0.000 abstract description 5
- 229910052751 metal Inorganic materials 0.000 abstract description 5
- 239000002184 metal Substances 0.000 abstract description 5
- 239000000758 substrate Substances 0.000 abstract description 5
- 125000003545 alkoxy group Chemical group 0.000 abstract description 4
- 229920003023 plastic Polymers 0.000 abstract description 4
- 239000004033 plastic Substances 0.000 abstract description 4
- 239000004342 Benzoyl peroxide Substances 0.000 abstract description 3
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 abstract description 3
- 235000019400 benzoyl peroxide Nutrition 0.000 abstract description 3
- 229920001971 elastomer Polymers 0.000 abstract description 3
- 239000005060 rubber Substances 0.000 abstract description 3
- 238000013329 compounding Methods 0.000 abstract 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- -1 diaphragms Substances 0.000 description 23
- 230000001070 adhesive effect Effects 0.000 description 22
- 239000000463 material Substances 0.000 description 13
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 239000002585 base Substances 0.000 description 9
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 8
- 229910000077 silane Inorganic materials 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 150000001451 organic peroxides Chemical class 0.000 description 7
- 238000004073 vulcanization Methods 0.000 description 7
- 150000002430 hydrocarbons Chemical group 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- 229920000271 Kevlar® Polymers 0.000 description 4
- 239000004761 kevlar Substances 0.000 description 4
- 238000004898 kneading Methods 0.000 description 4
- 229910052697 platinum Inorganic materials 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 229940126062 Compound A Drugs 0.000 description 3
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 3
- 239000006087 Silane Coupling Agent Substances 0.000 description 3
- 238000007259 addition reaction Methods 0.000 description 3
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- 239000003054 catalyst Substances 0.000 description 3
- 239000004205 dimethyl polysiloxane Substances 0.000 description 3
- 229910021485 fumed silica Inorganic materials 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 230000002209 hydrophobic effect Effects 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 229920002994 synthetic fiber Polymers 0.000 description 3
- 239000012209 synthetic fiber Substances 0.000 description 3
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([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
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- 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 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- IDCBOTIENDVCBQ-UHFFFAOYSA-N TEPP Chemical compound CCOP(=O)(OCC)OP(=O)(OCC)OCC IDCBOTIENDVCBQ-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 230000001680 brushing effect Effects 0.000 description 2
- 238000003490 calendering Methods 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000010073 coating (rubber) Methods 0.000 description 2
- 239000011247 coating layer Substances 0.000 description 2
- 238000000748 compression moulding Methods 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- 238000003618 dip coating Methods 0.000 description 2
- WOXXJEVNDJOOLV-UHFFFAOYSA-N ethenyl-tris(2-methoxyethoxy)silane Chemical compound COCCO[Si](OCCOC)(OCCOC)C=C WOXXJEVNDJOOLV-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000003365 glass fiber Substances 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000012567 medical material Substances 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 229920006306 polyurethane fiber Polymers 0.000 description 2
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 2
- 239000010453 quartz Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000003566 sealing material Substances 0.000 description 2
- 125000005372 silanol group Chemical group 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 238000010345 tape casting Methods 0.000 description 2
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 1
- PAOHAQSLJSMLAT-UHFFFAOYSA-N 1-butylperoxybutane Chemical compound CCCCOOCCCC PAOHAQSLJSMLAT-UHFFFAOYSA-N 0.000 description 1
- NOSXUFXBUISMPR-UHFFFAOYSA-N 1-tert-butylperoxyhexane Chemical compound CCCCCCOOC(C)(C)C NOSXUFXBUISMPR-UHFFFAOYSA-N 0.000 description 1
- DMWVYCCGCQPJEA-UHFFFAOYSA-N 2,5-bis(tert-butylperoxy)-2,5-dimethylhexane Chemical compound CC(C)(C)OOC(C)(C)CCC(C)(C)OOC(C)(C)C DMWVYCCGCQPJEA-UHFFFAOYSA-N 0.000 description 1
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 1
- UUEWCQRISZBELL-UHFFFAOYSA-N 3-trimethoxysilylpropane-1-thiol Chemical compound CO[Si](OC)(OC)CCCS UUEWCQRISZBELL-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 229920000049 Carbon (fiber) Polymers 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 244000043261 Hevea brasiliensis Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 229920002334 Spandex Polymers 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical class [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 229920002978 Vinylon Polymers 0.000 description 1
- YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical compound [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000000732 arylene group Chemical group 0.000 description 1
- 239000010425 asbestos Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- KPDAVHCCTQXUSQ-UHFFFAOYSA-N bis(tert-butylperoxy)-prop-1-enylsilane Chemical compound CC=C[SiH](OOC(C)(C)C)OOC(C)(C)C KPDAVHCCTQXUSQ-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000004917 carbon fiber Substances 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
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- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 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
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 1
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- 239000003822 epoxy resin Substances 0.000 description 1
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 description 1
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 1
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000012765 fibrous filler Substances 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000036541 health Effects 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
- 150000003949 imides Chemical class 0.000 description 1
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- 239000003350 kerosene Substances 0.000 description 1
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- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 238000004643 material aging 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
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
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- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
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- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 125000000286 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
- 229920002647 polyamide Polymers 0.000 description 1
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- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000232 polyglycine polymer Polymers 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
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- BJDCYOLBAMFSMI-UHFFFAOYSA-N tert-butylperoxy(triphenyl)silane Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(OOC(C)(C)C)C1=CC=CC=C1 BJDCYOLBAMFSMI-UHFFFAOYSA-N 0.000 description 1
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- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000001721 transfer moulding Methods 0.000 description 1
- 125000000725 trifluoropropyl group Chemical group [H]C([H])(*)C([H])([H])C(F)(F)F 0.000 description 1
- WCAGGTLUGWSHOV-UHFFFAOYSA-N tris(tert-butylperoxy)-ethenylsilane Chemical compound CC(C)(C)OO[Si](OOC(C)(C)C)(OOC(C)(C)C)C=C WCAGGTLUGWSHOV-UHFFFAOYSA-N 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
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- 239000011787 zinc oxide Substances 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Abstract
Description
【発明の詳細な説明】
［ａ業上の利用分野］
本発明は自己接着型シリコーンゴム組成物、特には金属
、ガラス、セラミックス、プラスチックス、繊維、ゴム
などにプライマー処理することなく接着する自己接着型
シリコーンゴム組成物及びこれを織布に被覆、硬化させ
てなるシリコーンゴム被覆布に関するものである。Detailed Description of the Invention [A Field of Application] The present invention provides a self-adhesive silicone rubber composition, particularly a self-adhesive silicone rubber composition that adheres to metals, glass, ceramics, plastics, fibers, rubber, etc. without priming. The present invention relates to an adhesive silicone rubber composition and a silicone rubber-coated fabric obtained by coating and curing a woven fabric with the adhesive silicone rubber composition.
［従来の技術］
シリコーンゴム組成物を通常の加硫条件下で金属、ガラ
ス、セラミックス、プラスチックス、繊維又はその織布
、ゴムなどに接着しようとすると、シリコーンゴム組成
物が離型性を有するものであるために、これらは接着し
ないので、この場合にはこれら被着体の表面を予めブラ
イマーを処理してから加硫するという方法が採られてい
る。[Prior Art] When attempting to adhere a silicone rubber composition to metals, glass, ceramics, plastics, fibers or their woven fabrics, rubber, etc. under normal vulcanization conditions, the silicone rubber composition has mold releasability. Since these materials do not adhere to each other, in this case, a method is adopted in which the surfaces of these adherends are treated with a brimer in advance and then vulcanized.
一方、各種織布の表面にシリコーンゴム組成物を被覆、
硬化させたシリコーンゴム被覆布は、従来から電気絶縁
材料、ダイヤフラム、シール材、エアバッグ材、テント
膜材、ダクトホース類等として使用されており、又医療
用材料、衣料用材料としての提案もなされているが（特
公昭４２−２６８７号公報、特開昭５５−１５２８６３
号公報）、特に被着体である織布がナイロンやケブラー
の様に−ＣＯＮＨ−基のような極性基を有する繊維て編
まれたものである場合、十分な接着力を有するシリコー
ンゴム被覆布を得ることは困難であった。On the other hand, coating the surface of various woven fabrics with silicone rubber compositions,
Cured silicone rubber-coated fabrics have been used as electrical insulation materials, diaphragms, sealing materials, airbag materials, tent membrane materials, duct hoses, etc., and have also been proposed as medical materials and clothing materials. (Japanese Patent Publication No. 42-2687, Japanese Patent Application Laid-Open No. 55-152863)
Silicone rubber coated fabric with sufficient adhesion, especially when the adherend fabric is knitted from fibers having polar groups such as -CONH- groups, such as nylon or Kevlar. It was difficult to obtain.
しかし、このブライマー処理は成型加工工程を複雑なも
のとするし、このブライマーが通常有機溶剤溶液である
ためにこれには有機溶剤排気設備が必要であるし、この
有機溶剤には安全衛生上の問題もあり、インジェクショ
ン成形のように強い剪断力か加わる１加工条件下てはプ
ライマー層が流出したり、剥離するという問題もある。However, this brimer treatment complicates the molding process, and since this brimer is usually an organic solvent solution, it requires organic solvent exhaust equipment, and this organic solvent has health and safety concerns. There are also problems such as the primer layer flowing out or peeling off under processing conditions such as injection molding where strong shearing force is applied.
そのため、このシリコーンゴム組成物についてブライマ
ー処理を必要としない自己接着性のものが提案されてお
り、これについては例えばビニルトリス（ｔ−ブチルパ
ーオキシ）シラン、トリフェニル（ｔ−ブチルパーオキ
シ）シラン、トリメチル（ｔ−ブチルパーオキシ）シラ
ン、メチルビニルジ（ｔ−ブチルパーオキシ）シランな
どのアルキルパーオキシシランを接着性付与成分として
添加したシリコーンゴム組成物、またはビニルトリメト
キシシラン、ビニルトリエトキシシラン、γ−グリシド
キシプロピルトリメトキシシラン、γ−メタクリロキシ
プロピルトリメトキシシランなどのシランカップリング
剤を添加したシリコーンゴム組成物が知られており、さ
らにはｔ−ブチル−パーオキシ−４−ビニルジメチルシ
リルベンゾエートのようなビニルシリル基含有ベンゾエ
ート化合物を接着成分および有機過酸化物とするシリコ
ーンゴム組成物も知られている。Therefore, self-adhesive silicone rubber compositions that do not require brimer treatment have been proposed, such as vinyltris(t-butylperoxy)silane, triphenyl(t-butylperoxy)silane, A silicone rubber composition containing an alkylperoxysilane such as trimethyl(t-butylperoxy)silane or methylvinyldi(t-butylperoxy)silane as an adhesion-imparting component, or vinyltrimethoxysilane, vinyltriethoxysilane, γ Silicone rubber compositions containing silane coupling agents such as -glycidoxypropyltrimethoxysilane and γ-methacryloxypropyltrimethoxysilane are known, and even t-butyl-peroxy-4-vinyldimethylsilylbenzoate. Silicone rubber compositions containing vinylsilyl group-containing benzoate compounds as adhesive components and organic peroxides are also known.
［発明が解決しようとする課題］
しかし、このアルキルパーオキシシランを添加したシリ
コーンゴム組成物は接着性が充分でなく、シランカップ
リング剤を添加したシリコーンゴム組成物も接着性、接
着耐久性が充分でないという不利があり、上記のヘンシ
ェード化合物についてはその合成が困難であるし、これ
を添加したシリコーンゴム組成物には高湿度下での接着
耐久性が不充分であるという欠点がある。[Problems to be Solved by the Invention] However, this silicone rubber composition containing an alkylperoxysilane does not have sufficient adhesive properties, and the silicone rubber composition containing a silane coupling agent also has poor adhesive properties and adhesive durability. The above-mentioned Henshade compound is difficult to synthesize, and silicone rubber compositions containing it have the disadvantage of insufficient adhesive durability under high humidity.
［課題を解決するための手段］
本発明はこのような不利・欠点を解決した自己接着型シ
リコーンゴム組成物及びこれを織布に被覆、硬化させて
なるシリコーンゴム被覆布に関するもので、これはイ）
平均組成式Ｒ’、５ｉＯａ−ａ（ここにＲ１は同一また
は異種の非置換または置換１価炭化水素基、ａは１．９
８〜２．Ｏｌの正数）で示され、２５℃における粘度が
３００ｃＳ以上であるオルガノポリシロキサン１００重
量部、口）分子中にイソシアナート基と加水分解性基を
含有するオルガノシランまたはその部分加水分解物０．
１〜２０重量部、八）硬化剤とからなることを特徴とす
るシリコーンゴム組成物及びこれを織布に被覆、硬化さ
せてなるシリコーンゴム被覆布に関するものであるすな
わち、本発明者らは種々の被着体と強固に接着し、高湿
下での接着耐久性のすぐれている自己接着型シリコーン
ゴム組成物を間発すへく種々検討した結果、シリコーン
ゴム成分となるオルガノポリシロキサンと硬化剤とから
なる組成物にイソシアナート基（−ＮＣＯ基）とアルコ
キシ基等の加水分解性基とを含有するオルガノシランを
添加するとこの組成物が通常の加硫条件下で各種被着体
に強固に接着し、特にナイロン、ケブラー テトロンな
どの合成繊維の織布との接着性にすぐれたものになり、
高湿下での接着耐久性もすぐれたものになるということ
を見出し、このオルガノシランの種類、配合量などにつ
いての研究を進めて本発明を完成させた。[Means for Solving the Problems] The present invention relates to a self-adhesive silicone rubber composition that solves the above-mentioned disadvantages and disadvantages, and a silicone rubber-coated cloth obtained by coating and curing a woven fabric with the same. stomach)
Average compositional formula R', 5iOa-a (where R1 is the same or different unsubstituted or substituted monovalent hydrocarbon group, a is 1.9
8-2. 100 parts by weight of an organopolysiloxane having a viscosity of 300 cS or more at 25°C; ．．
1 to 20 parts by weight, and 8) a curing agent, and a silicone rubber-coated fabric obtained by coating and curing a woven fabric with the silicone rubber composition. As a result of various studies to develop a self-adhesive silicone rubber composition that adheres strongly to adherends and has excellent adhesive durability under high humidity conditions, we have developed an organopolysiloxane and a curing agent that serve as silicone rubber components. When an organosilane containing an isocyanate group (-NCO group) and a hydrolyzable group such as an alkoxy group is added to a composition consisting of It has excellent adhesion, especially with woven synthetic fibers such as nylon, Kevlar, Tetron, etc.
They discovered that the adhesive had excellent durability under high humidity conditions, and conducted research on the type and amount of organosilane to be added, and completed the present invention.
以下にこれをさらに詳述する。This will be explained in further detail below.
［作 用］
本発明の自己接着型シリコーンゴム組成物はオルガノポ
リシロキサンとイソシアナート基とアルコキシ基等の加
水分解性基を有するオルガノシランおよび硬化剤とから
なるものである。[Function] The self-adhesive silicone rubber composition of the present invention comprises an organopolysiloxane, an organosilane having a hydrolyzable group such as an isocyanate group and an alkoxy group, and a curing agent.
本発明の組成物を構成するイ）成分としてのオルガノボ
リシロキサンは平均組成式Ｒ’、５ｉ０４−．で示され
、Ｒ１はメチル基、エチル基、プロピル基、ブチル基、
ヘキシル基などのアルキル基、シクロヘキシル基などの
シクロアルキル基、ビニル基、アリル基などのアルケニ
ル基、フェニル基、トリル基などのアリール基、または
これらの基の炭素原子に結合している水素原子の一部ま
たは全部をハロゲン原子、シアノ基などで置換したクロ
ロメチル基、トリフルオロプロピル基、シアノエチル基
などから選択される同一または異種の非置換または置換
１価炭化水素で、ａは１．９８〜２．０１の正数である
ものとされるが、このＲ１の好ましいものはメチル基、
エチル基、フェニル基、γ−トリフロロプロピル基、シ
アノエチル基、ビニル基、アリル基であり、特にはメチ
ル基か５０モル％未満であるとメチルポリシロキサン本
来の特性が失われたり、原料コストが高価なものとなる
ということから、メチル基が５０モル％以上、好ましく
は８０モル％以上のものとすることがよい。また、この
オルカッポリシロキサンは２５℃における粘度か３００
ｃＳ未満であるとこのシリコーンゴム組成物を織布等に
接着させたものは機械的強度が不充分となって実用に耐
えないものとなるので、３００ｃＳ以上のものとする必
要があるが、これは１×ｌＯ４〜１０８ｃＳとすること
がよい。なお、このオルガノポリシロキサンは実質的に
線状のものとすればよく、その分子鎮末端はシラノール
基、メチル基、ビニル基、特にはトリビニルシリル基で
封鎖されたものとすればよいが、このものはオソゴマー
としてよく知られている環状ポリシロキサンを酸または
アルカリの存在下で開環重合する公知の方法で製造した
ものとすればよい。The organoborisiloxane as component a) constituting the composition of the present invention has an average composition formula R', 5i04-. , R1 is a methyl group, an ethyl group, a propyl group, a butyl group,
Alkyl groups such as hexyl groups, cycloalkyl groups such as cyclohexyl groups, alkenyl groups such as vinyl groups and allyl groups, aryl groups such as phenyl groups and tolyl groups, or hydrogen atoms bonded to carbon atoms of these groups. The same or different unsubstituted or substituted monovalent hydrocarbons selected from chloromethyl groups, trifluoropropyl groups, cyanoethyl groups, etc. partially or wholly substituted with halogen atoms, cyano groups, etc., where a is 1.98 to It is assumed that R1 is a positive number of 2.01, but preferred R1 is a methyl group,
These include ethyl group, phenyl group, γ-trifluoropropyl group, cyanoethyl group, vinyl group, and allyl group, especially methyl group.If it is less than 50 mol%, the original properties of methylpolysiloxane may be lost or the raw material cost may increase. Since it is expensive, it is preferable that the methyl group content is 50 mol% or more, preferably 80 mol% or more. In addition, this orcappolysiloxane has a viscosity of 300 at 25°C.
If it is less than cS, the mechanical strength of the silicone rubber composition bonded to woven fabric etc. will be insufficient and will not be suitable for practical use. is preferably 1×1O4 to 108cS. Note that this organopolysiloxane may be substantially linear, and its molecular terminals may be capped with a silanol group, a methyl group, a vinyl group, particularly a trivinylsilyl group. This product may be produced by a known method of ring-opening polymerization of a cyclic polysiloxane, which is well known as an osogomer, in the presence of an acid or an alkali.
つぎに本発明の組成物を構成する口）成分としてのオル
ガノシランは一般式
％式％）
で示され、Ｒ２，Ｒ３はＲ１と同一の非置換または置換
１価炭化水素基あるいはメトキシメチル基、エトキシメ
チル基、メトキシエチル基等のアルコキシ置換アルキル
基、フェニルエチル基等のアラルキル基である。又Ｒ４
ハメチレン基、エチレン基、プロピレン基などのアルキ
レン基、フェニレン基などのアリーレン基などから選択
される炭素数１〜１０の２価炭化水素または（ＣＨ２）
２５ （Ｃ）１２） ｓなどのような硫黄置換二価炭
化水素基とされるもの、ｂは０≦ｂ＜３で示される整数
であり、これには下記のものが例示されるか、このオル
ガノシランはこの単独加水分解物あるいは（Ｒ’Ｏ）
２ＳｊＲ’２． （Ｒ’０） ３〜５ｉＲ２との共加水
分解物であってもよい。Next, the organosilane as a component constituting the composition of the present invention is represented by the general formula (%), where R2 and R3 are the same unsubstituted or substituted monovalent hydrocarbon group as R1 or a methoxymethyl group, These include alkoxy-substituted alkyl groups such as ethoxymethyl group and methoxyethyl group, and aralkyl groups such as phenylethyl group. Also R4
Divalent hydrocarbon having 1 to 10 carbon atoms selected from alkylene groups such as hamethylene group, ethylene group, propylene group, arylene group such as phenylene group, or (CH2)
25 (C)12) Those considered to be sulfur-substituted divalent hydrocarbon groups such as s, b is an integer expressed as 0≦b<3, and examples include the following, or Organosilane is this single hydrolyzate or (R'O)
2SjR'2. (R'0) may be a cohydrolyzate with 3-5iR2.
（ＣＩ（３０）３−５ｉ−（ＣＨｚ）３−ＮＣＯＨＢＭ
９００７［信越化学工業（株）シ商品名〕、
（Ｃ２）１５０） ３−５ｉ−（ＣＨ２） ３−ＮＧＯ
にＢＥ９００７ ［信越化学工業（株）製画品名コ、
＼
（Ｃ１１３０Ｃ２）１４０トｒ−５ｉ −ｆ−ｃｕ２
）−ｒ Ｎｃｏ。(CI(30)3-5i-(CHz)3-NCOHBM
9007 [Shin-Etsu Chemical Co., Ltd. product name], (C2)150) 3-5i-(CH2) 3-NGO
BE9007 [Shin-Etsu Chemical Co., Ltd. product name, ＼ (C1130C2) 140 r-5i-f-cu2
)-r Nco.
ＣＨ３
（ＣＨ３０）２−５ｉ−（Ｃ）１２）、−ＮＣＯＫＢＭ
９２０７ ［信越化学工業（株）製部品名］、
Ｈ−ＣＨ２
（ＣＨ３０ｈ−５ｉ−（Ｃ）ｌｚｈ−Ｎ（：Ｏ。CH3 (CH30)2-5i-(C)12), -NCOKBM
9207 [Part name manufactured by Shin-Etsu Chemical Co., Ltd.], H-CH2 (CH30h-5i-(C)lzh-N(:O.
工業（株）製部品名］、
（ＣＨ３０） ３−５ｉ−（Ｃ）１２） ２５ （ＣＨ
２） ３−ＮＧＯ。Part name manufactured by Kogyo Co., Ltd.], (CH30) 3-5i-(C)12) 25 (CH
2) 3-NGO.
なお、二〇口）成分の配合量は前記したイ）成分として
のオルガノポリシロキサン１００重量部に対して０．１
重量部未満ではこの組成物に充分な接着力が与えられず
、２０重量部を越えた量とするとこの組成物から得られ
る硬化物の引張り強さ、伸び、耐熱特性などの物性が低
下するので、０．１〜２０重量部の範囲とする必要があ
るが、この好まししＡ範囲は０．５〜１０重量部とされ
る。The amount of component 20) is 0.1 parts by weight per 100 parts by weight of the organopolysiloxane as component 2).
If the amount is less than 20 parts by weight, sufficient adhesive strength will not be imparted to the composition, and if the amount exceeds 20 parts by weight, physical properties such as tensile strength, elongation, and heat resistance properties of the cured product obtained from this composition will decrease. , 0.1 to 20 parts by weight, and the preferred range A is 0.5 to 10 parts by weight.
また、本発明の組成物を構成する八）成分としての硬化
剤は公知のものでよく、これは通常は有機過酸化物とす
ればよいが、前記したイ）成分としてのオルガノポリシ
ロキサンがアルケニル基を含有するものである場合には
１分子中にけい素原子に結合した水素原子（＝ＳｉＨ）
を３ヶ以上含有するオルガノハイドロジエンポリシロキ
サンと白金系触媒とからなるものを添加してこれを付加
反応加硫型のものとしてもよい。Further, the curing agent as component 8) constituting the composition of the present invention may be a known one, and usually an organic peroxide, but the organopolysiloxane as component 8) mentioned above may be an alkenyl compound. If it contains a group, a hydrogen atom bonded to a silicon atom in one molecule (=SiH)
It is also possible to use an addition reaction vulcanization type by adding an organohydrodiene polysiloxane containing three or more of the following and a platinum catalyst.
この有機過酸化物としてはベンゾイルパーオキサイド、
２．４−ジクロロベンゾイルパーオキサイド、オルソク
ロロベンゾイルパーオキサイド、ジー１−ブチルパーオ
キサイド、ジクミルパーオキサイド、ｔ−ブチルパーベ
ンゾエート、ｔ−ブチルパーアセテート、２．５−ジメ
チル−２，５−ジ（ｔ−ブチルパーオキシ）ヘキサン、
（ｔ−ブチルパーオキシ）ミリスチルカーボネートなど
が例示されるか、これらは前記したイ）成分としてのオ
ルガノポリシロキサン１００重量部に対して０．１〜５
重量部添加すればよい。なお、イ）成分のオルガノポリ
シロキサンがビニル基等のアルケニル基を含有する場合
にこの組成物を付加反応硬化型とするために添加される
オルガノハイドロジエンポリシロキサンは一般式Ｒ５（
）Ｉ（ＩＳ１０４−ｃ−ｄで示され、Ｒ５はメチル基な
どのアルケル基、ｃ、ｄは正数でｃ＋ｄ＝１．０〜３．
０であるもので、分子中にけい素原子に結合した水素原
子（＝ＳｉＨ）を少なくとも３個以上含有するものとし
て、こわを、イ）成分としてのオルガノポリシロキサン
中に含有されるアルケニル基量１モルに対して：ＳｉＨ
結合かその０．５〜５．０倍モルとなる量で添加すれば
よく、ここに使用される白金系触媒は塩化白金酸、塩化
白金酸とオレフィンまたはビニルシロキサンとの錯塩、
塩化白金酸のアルコール溶液としてイ）成分としてのオ
ルガノポリシロキサンに対し、白金量で０．５〜５００
ｐｐｍ、好ましくは２〜２００ｐｐｍ添加すればよい。Examples of this organic peroxide include benzoyl peroxide,
2.4-dichlorobenzoyl peroxide, orthochlorobenzoyl peroxide, di-1-butyl peroxide, dicumyl peroxide, t-butyl perbenzoate, t-butyl peracetate, 2.5-dimethyl-2,5-di (t-butylperoxy)hexane,
Examples include (t-butylperoxy) myristyl carbonate.
It may be added in parts by weight. In addition, when the organopolysiloxane of component (a) contains an alkenyl group such as a vinyl group, the organohydrodiene polysiloxane added to make this composition an addition reaction curing type has the general formula R5 (
)I (represented by IS104-c-d, R5 is an alkyl group such as a methyl group, c and d are positive numbers, and c+d=1.0 to 3.
0 and contains at least three hydrogen atoms bonded to silicon atoms (=SiH) in the molecule, stiffness is defined as (i) the amount of alkenyl groups contained in the organopolysiloxane as a component; For 1 mole: SiH
The platinum-based catalyst used here may be chloroplatinic acid, a complex salt of chloroplatinic acid and an olefin or vinyl siloxane,
As an alcoholic solution of chloroplatinic acid, the amount of platinum is 0.5 to 500 relative to the organopolysiloxane as a component.
ppm, preferably 2 to 200 ppm may be added.
本発明の自己接着型シリコーンゴム組成物は上記イ）１
口）１八）成分の所定量を均一に混練することによって
得ることができるが、この組成物の未硬化時の粘度を増
加して作業性を向上させるため、さらにはこれを硬化し
て得られるシリコーンゴム弾性体の硬さ、引張り強さ、
伸びなどの物性向上、接着性向上のために各種の微粒子
状または繊維状の充填剤を配合してもよく、これにはヒ
ユームドシリカ、沈殿シリカ、石英粉末、けいそう土、
中空ガラス球、酸化鉄、酸化亜鉛、酸化チタン、酸化マ
グネシウム、タルク、アルミニウムシリケート、アルミ
ナ、炭酸カルシウム、カーボンブラック、アスベスト、
ガラス繊維、カーボン繊維、ポリエステル繊維、ポリテ
トラフルオロエチレン粉末、ポリ塩化ビニル粉末などが
挙げられるか、これらは粒子径が５０μｍ以下のものと
すればよく、この添加量はイ）成分とてのオルガノポリ
シロキサン１００重量部に対して０〜２００重量部とす
ればよいので、これはＲ３５ｉＯ０５，Ｒ２５ｉＯ，Ｒ
５１Ｏ＋（Ｒは１価炭化水素基）などの共重合体である
レジン状ポリシロキサンとしてもよい。The self-adhesive silicone rubber composition of the present invention has the above-mentioned 1)
(18) It can be obtained by uniformly kneading a predetermined amount of the ingredients, but in order to increase the viscosity of this composition when uncured and improve workability, it can be obtained by further curing it. hardness, tensile strength,
Various fine particulate or fibrous fillers may be added to improve physical properties such as elongation and adhesion, such as fumed silica, precipitated silica, quartz powder, diatomaceous earth,
Hollow glass bulb, iron oxide, zinc oxide, titanium oxide, magnesium oxide, talc, aluminum silicate, alumina, calcium carbonate, carbon black, asbestos,
Examples include glass fiber, carbon fiber, polyester fiber, polytetrafluoroethylene powder, polyvinyl chloride powder, etc. These may have a particle size of 50 μm or less, and the amount added is determined by The amount may be 0 to 200 parts by weight based on 100 parts by weight of polysiloxane, so this is R35iO05, R25iO, R
It may also be a resinous polysiloxane which is a copolymer such as 51O+ (R is a monovalent hydrocarbon group).
また、本発明の組成物にはその使用目的に応じて従来公
知とされている各種の改質剤を添加してもよく、したが
ってγ−グリシドキシプロピルトリメトキシシラン、γ
−メルカプトプロピルトリメトキシシラン、γ−アミノ
プロピルトリメトキシシラン、ビニルトリアルコキシシ
ランなどのシランカップリング剤や有機カルボン酸の金
属塩類、チタン酸エステル、塩化白金酸、耐熱剤、難燃
剤、分散剤などを添加混合してもよい。なお、本発明の
組成物はこれをナイロン等の各種織布と接着させてシリ
コーンゴム被覆布を作るのに有用とされるが、この織布
との接着およびコーティング加工性の点からはこの組成
物を適宜の有機溶剤に溶解したものとすることがよく、
この有機溶剤としては上記した口）成分と反応するよう
な活性水素を有しないものとするということからベンゼ
ン、トルエン、キシレン、ヘキサン、ヘプタン、灯油な
どとし、これをこの組成物１００重量部に対してＯ〜１
，０００重量部、好ましくは５０〜３００重量部添加す
るようにすればよい。Furthermore, various conventionally known modifiers may be added to the composition of the present invention depending on the purpose of use thereof.
- Silane coupling agents such as mercaptopropyltrimethoxysilane, γ-aminopropyltrimethoxysilane, and vinyltrialkoxysilane, metal salts of organic carboxylic acids, titanate esters, chloroplatinic acid, heat resistant agents, flame retardants, dispersants, etc. may be added and mixed. The composition of the present invention is said to be useful for making silicone rubber-covered cloth by adhering it to various woven fabrics such as nylon, but this composition Often, the substance is dissolved in an appropriate organic solvent,
Since this organic solvent does not have active hydrogen that would react with the above-mentioned component, benzene, toluene, xylene, hexane, heptane, kerosene, etc. are used, and this is used per 100 parts by weight of this composition. teO~1
,000 parts by weight, preferably 50 to 300 parts by weight.
このようにして得られた本発明の自己接着型シリコーン
ゴム組成物はこれを異種の基材表面と接触させた後、加
硫条件に保持すると架橋して所望のシリコーンゴム、シ
リコーンレジン、シリコーンゲル等の種々の架橋密度の
硬化物を形成すると共に、口）成分としてのオルガノシ
ランが配合されていることから基材表面に均一にかつ強
固に接着される。The thus obtained self-adhesive silicone rubber composition of the present invention is brought into contact with the surface of a different type of base material and then maintained under vulcanization conditions to crosslink and form the desired silicone rubber, silicone resin, or silicone gel. In addition to forming cured products with various crosslinking densities such as, etc., since organosilane is blended as a component, it can be bonded uniformly and firmly to the surface of the substrate.
この異種基材としては鉄、アルミニウム、ステンレス、
ニッケル、銅、クロムなどの金属類、ガラス、石英、陶
磁器などのセラミックス類、エポキシ樹脂、アクリル樹
脂、ポリエチレンテレフタレート樹脂、不飽和ポリエス
テル樹脂、ポリアミド樹脂、ポリエチレンテレフタレー
ト樹脂などのプラスチックス類、ナイロン、テトロン、
ビニロン、ポリエステル繊維、ポリウレタン繊維などの
各種合成繊維又はその織布、天然繊維、ガラス繊維のよ
うな無機繊維又はその織布、天然ゴム、各種合成ゴムな
どが例示されるが、この組成物は特にナイロン、ポリア
ミド繊維、イミド繊維などのケブラー繊維、ポリウレタ
ン繊維のようなスパンデックスなどの合成繊維からなる
織布、不織布、編布との接着性にすぐれているので、こ
れはシリコーンゴム被覆布の製造に有用とされる。These different base materials include iron, aluminum, stainless steel,
Metals such as nickel, copper, and chromium, ceramics such as glass, quartz, and ceramics, plastics such as epoxy resin, acrylic resin, polyethylene terephthalate resin, unsaturated polyester resin, polyamide resin, and polyethylene terephthalate resin, nylon, and tetron. ,
Examples include various synthetic fibers such as vinylon, polyester fibers, and polyurethane fibers or their woven fabrics, natural fibers, inorganic fibers such as glass fibers or their woven fabrics, natural rubber, and various synthetic rubbers. It has excellent adhesion to woven, nonwoven, and knitted fabrics made of synthetic fibers such as Kevlar fibers such as nylon, polyamide fibers, and imide fibers, and spandex such as polyurethane fibers, so it is suitable for manufacturing silicone rubber-coated fabrics. Considered useful.
この異種基材に対する本発明の自己接着型シリコーンゴ
ム組成物の接触はカレンダリング、ナイフコーティング
、はけ塗り、デイツプコーティング、スプレーなどの方
法で行えばよいが、このシリコーンゴム組成物が固形状
であるとぎにはカレンダリングが適しており、これが液
状であるときにはナイフコーティング、はけ塗り、デイ
ツプコーティングまたはスプレーが適している。The self-adhesive silicone rubber composition of the present invention may be brought into contact with this dissimilar substrate by methods such as calendering, knife coating, brushing, dip coating, and spraying. For this purpose, calendering is suitable; when it is in liquid form, knife coating, brushing, dip coating or spraying are suitable.
また、このシリコーンゴム組成物の硬化はその硬化機構
に応じて適切な条件を選択すればよく、硬化剤として有
機過酸化物を使用するときには１５０〜５５０℃で数秒
〜２０分間熱気加硫するか、１１０〜１８０℃で３分〜
１５分圧縮成形すればよいし、硬化剤としてオルガノハ
イドロジエンポリシロキサンと白金系触媒を使用して付
加反応硬化型とするときには１００〜４００℃で数秒〜
１０数分熱気加硫するか、トランスファー成形あるいは
１００〜２００℃で３０秒〜１０分圧縮成形すればよい
。In addition, for curing of this silicone rubber composition, appropriate conditions may be selected depending on the curing mechanism. When an organic peroxide is used as a curing agent, hot air vulcanization at 150 to 550°C for several seconds to 20 minutes may be used. , 3 minutes at 110-180℃
Compression molding can be carried out for 15 minutes, or if an addition reaction curing type using organohydrodiene polysiloxane and a platinum-based catalyst is used as a curing agent, it can be done for several seconds at 100 to 400°C.
Hot air vulcanization may be performed for 10 minutes, transfer molding, or compression molding at 100 to 200° C. for 30 seconds to 10 minutes.
このように異種の基材と接触させ、加硫条件とした本発
明の自己接着型シリコーンゴム組成物はこの処理によっ
て硬化し、前記したようにこの硬化物が基材表面に均一
にかつ強固に接着するし、高温度；囲気下での接着耐久
性もすぐれているので、このようにして得られたシリコ
ーンゴム被ｉ物はジ−ソング剤、被１材、包装材として
有用とされるほか、これを前記した繊維質材からなる織
布に被Ｉしたシリコーンゴム被覆布は電気絶縁材料、ダ
イヤフラム、シール材、エアーバック材、テント膜材、
ダクトホース類、医療用材料、衣料用材料などとして有
用とされる。The self-adhesive silicone rubber composition of the present invention, brought into contact with a different type of substrate and subjected to vulcanization conditions, is cured by this treatment, and as described above, the cured product is uniformly and firmly spread over the surface of the substrate. The silicone rubber coating obtained in this way is useful as a G-song agent, coating material, and packaging material because it adheres well and has excellent adhesive durability under high temperature and ambient conditions. The silicone rubber coated cloth covered with the woven cloth made of the above-mentioned fibrous material can be used as an electrical insulating material, a diaphragm, a sealing material, an airbag material, a tent membrane material,
It is said to be useful as duct hoses, medical materials, clothing materials, etc.
［実施例コ
つぎに本発明の実施例、比較例をあげるが、例中の部は
重量部を、粘度は２５℃での測定値を示したものであり
、例中の接着力はＪＩＳに−６３０１に規定されている
方法による測定結果を示したものである。[Example] Next, Examples and Comparative Examples of the present invention will be given. In the examples, parts are parts by weight, viscosity is the value measured at 25°C, and the adhesive strength in the examples is according to JIS. -6301 shows the measurement results according to the method specified in JP-6301.
実施例１
ジメチルシロキサン単位９９．８モル％、ビニルメチル
シロキサン単位０．２モル％からなる粘度が５ 、００
０ 、０００ｃＳのメチルビニルポリシロキサン１００
部に、表面をトリメチルシリル基で処理した比表面積２
００ｍ２７Ｈの疎水性ヒユームドシリカ４０部、粘度２
０ｃＳのα、ω−ジメチルポリシロキサンジオール２部
を加え、ニーダ−ミキサーで均一に混練し、１６０℃で
２時間熱処理したコンパウンドＡを調製した。Example 1 Consisting of 99.8 mol% of dimethylsiloxane units and 0.2 mol% of vinylmethylsiloxane units, the viscosity was 5.00%.
0,000cS methylvinylpolysiloxane 100
In part, the specific surface area 2 whose surface was treated with trimethylsilyl group
00m27H hydrophobic fumed silica 40 parts, viscosity 2
Compound A was prepared by adding 2 parts of α,ω-dimethylpolysiloxane diol of 0 cS, uniformly kneading with a kneader mixer, and heat-treating at 160° C. for 2 hours.
ついでこのコンパウンドＡ １００部に式（ＣＨ３０
） ３ｓｉ （ＣＨ２） ３ＮＧＯで示されるイソシア
ナート基含有シラン１．０部と有機過酸化物２，５−ジ
メチル−２，５−ジ（ｔ−ブチルパーオキシ）ヘキサン
０．５部を添加し、２本ロールで均一に混練し、これを
第１表に示した各種被着体上に載せたのち金型に挟み、
１６５℃で１０分間、２０ｋｇｆ／ｃ＋ｎ２の圧力で加
圧加熱したところ、シリコーンゴムが被着体に強固に接
着した接着サンプルが得られ、このものの接着力は第１
表に示したとおりの結果を示した。Next, 100 parts of this compound A was added with the formula (CH30
) 1.0 part of isocyanate group-containing silane represented by 3si (CH2) 3NGO and 0.5 part of organic peroxide 2,5-dimethyl-2,5-di(t-butylperoxy)hexane were added, The mixture was kneaded uniformly with two rolls, placed on various adherends shown in Table 1, and then sandwiched between molds.
When heated under pressure at 165°C for 10 minutes at a pressure of 20 kgf/c+n2, an adhesive sample was obtained in which the silicone rubber was firmly adhered to the adherend, and the adhesive strength of this was the first.
The results were as shown in the table.
第１表
実施例２〜４．比較例１
実施例１て得られたコンパウンドＡ１００部に、式（Ｃ
２Ｈ５Ｏ） ３ｓｉ （ＣＩ（２） ５ＮｃＯで示され
るインシアナート基含有シラン１部、３部、または５部
あるい番：比較例としてイソシアナート含有シランを配
合しないものと有機過酸化物２．４−ジクロロベンゾイ
ルパーオキサイト１．８部を添加し、トルエン２３３部
に溶解して３０重量％のトルエン溶液４種を作寡した。Table 1 Examples 2-4. Comparative Example 1 100 parts of the compound A obtained in Example 1 was added with the formula (C
2H5O) 3si (CI(2) 5NcO 1 part, 3 parts, or 5 parts of inocyanate group-containing silane or number: As a comparative example, one without isocyanate-containing silane and the organic peroxide 2,4-dichloro 1.8 parts of benzoyl peroxide was added and dissolved in 233 parts of toluene to prepare four types of 30% by weight toluene solutions.
ついでこの溶液を６．６−ナイロン基布表面に肋厚１０
θμｍとなるように塗布し、室温で３０分間風刺後に５
０℃で５分間加熱してトルエンを除去し、さらに１８０
℃で５分間加熱処理して試験片を作り、この６．６−１
イロン基布１を外側にし、シリコーンゴムコンパウンド
被覆層２を内側にして、このシリコーンゴムコンパウン
ド被覆層２にＮ ？に硬化性シリコーンゴム・にＥ４５
ＲＴＶ ［信越化学工業■裂開品名］を塗布し、室温
に７２時間放置して第１図ａ）に示したような接着試験
サンプルを作り、これを８０℃、９５％ＲＨの高湿度下
に７２時間放置してから第１図ｂ）に示したようにカ（
Ｆ）を加えてその接着性の湿潤耐久性をしらべたところ
、第２表に示したとおりの結果が得られた。Next, apply this solution to the surface of the 6.6-nylon base fabric with a rib thickness of 10
Apply the film so that it is θ μm, and leave it at room temperature for 30 minutes.
Heat at 0°C for 5 minutes to remove toluene, and then heat at 180°C for 5 minutes.
A test piece was prepared by heating at ℃ for 5 minutes, and this 6.6-1
With the iron base fabric 1 on the outside and the silicone rubber compound coating layer 2 on the inside, N? Curable silicone rubber/E45
RTV [Shin-Etsu Chemical Co., Ltd. splitting product name] was applied and left at room temperature for 72 hours to make an adhesion test sample as shown in Figure 1 a), which was placed under high humidity at 80°C and 95% RH. After leaving it for 72 hours, as shown in Figure 1 b),
F) was added to examine the wet durability of the adhesive, and the results shown in Table 2 were obtained.
第２表
実施例５〜６．比較例２〜５
分子鎖末端がビニルジメチルシリル基で封鎖された、ジ
メチルシロキサン単位９９．８モル％、ビニルメチルシ
ロキサン単位０．２モル％からなる、粘度がＩ Ｘ １
０’ｃＳであるオルガノポリシロキサン１００部に、ト
リメチルシリル基で表面処理した比表面積が２３０ｍ２
７ｇの疎水性ヒユームドシリカ４０部と分子鎖末端がシ
ラノール基で封鎖されたα、ω−ジメチルポリシロキサ
ンジオール１．０部を添加し、ニーダ−中で１８０℃で
２時間熱処理してコンパウンドＢを作った。Table 2 Examples 5-6. Comparative Examples 2 to 5 Comprised of 99.8 mol% dimethylsiloxane units and 0.2 mol% vinylmethylsiloxane units, with molecular chain ends capped with vinyldimethylsilyl groups, with a viscosity of IX1
100 parts of 0'cS organopolysiloxane was surface-treated with trimethylsilyl groups to have a specific surface area of 230 m2.
Compound B was prepared by adding 7 g of 40 parts of hydrophobic fumed silica and 1.0 part of α,ω-dimethylpolysiloxane diol whose molecular chain terminals were capped with silanol groups, and heat-treated at 180°C for 2 hours in a kneader. Ta.
ついでこのコンパウンドＢ １００部に純分５０％の
有機過酸化物２．４−ジクロロベンゾイルパーオキサイ
ト３．５部を添加し均一に混練したのち、３本ロールミ
ルで薄く分出してからトルエンに溶解してコンパウンド
分約２５重量％のトルエン溶液を作り、このコンパウン
ドＢに式
（ＣＨ３０）３ｓｉ（ＣＩ（ｚ）３ＮＧＯで示されるイ
ソシアナート基含有シラン５部（実施例５）、式
（Ｃ２Ｈ５Ｏ） ３ｓｉ （ＣＨ２） 、ＮｃＯで示さ
れるイソシアナート基含有シラン５部（実施例６）、ビ
ニルトリス（β−メトキシエトキシ）シラン
［ＣＨａ＝ＣＨ５ｉ （ＯＣ２Ｈ４０Ｃ：Ｈ３） ３］
（比較例２）、γ−グリシドキブロビルトリメトキシ
シラン
［ＣＨ２−ＣＨ−ＣＨ２０（ＣＨ２） 、ｓｉ （ＯＣ
Ｈ３） ３］ （比較例３）、γ−アミノプロピルト
リエトキシシラン（Ｈ２ＮＧ３Ｈ６Ｓｉ （［１Ｃ２Ｈ
５）３） （比較例４）、γ−メタアクリロキシプロ
ピルトリメトキシシランぞれ５部添加して試料を作り、
これを織密度が１８×１７本７２５ｍｍの平織のナイロ
ン繊維織物の片面に厚さ７０μｍで被覆し、２５℃で３
０分間風乾したのち、１８０℃に７分間加熱して加硫し
、その表面キュア性と、実施例２と同様な方法でナイロ
ン基布への接着性をしらべると共に、８５℃、９５％Ｒ
ＨＯ高湿度で１週間老化試験をしたのちの接着性をしら
べたところ、第３表に示したとおりの結果が得られた。Next, 3.5 parts of 2.4-dichlorobenzoyl peroxide, an organic peroxide with a purity of 50%, was added to 100 parts of this compound B, and after kneading the mixture uniformly, it was separated into a thin layer using a three-roll mill, and then dissolved in toluene. A toluene solution having a compound content of about 25% by weight was prepared, and 5 parts of an isocyanate group-containing silane represented by the formula (CH30)3si(CI(z)3NGO) (Example 5) and the formula (C2H5O)3si were added to this compound B. (CH2), 5 parts of isocyanate group-containing silane represented by NcO (Example 6), vinyltris(β-methoxyethoxy)silane [CHa=CH5i (OC2H40C:H3) 3]
(Comparative Example 2), γ-glycidquibrobyltrimethoxysilane [CH2-CH-CH20(CH2), si(OC
H3) 3] (Comparative Example 3), γ-aminopropyltriethoxysilane (H2NG3H6Si ([1C2H
5) Prepare a sample by adding 5 parts each of 3) (Comparative Example 4) and γ-methacryloxypropyltrimethoxysilane,
This was coated on one side of a plain weave nylon fiber fabric with a weave density of 18 x 17 pieces and 725 mm to a thickness of 70 μm, and
After air drying for 0 minutes, vulcanization was performed by heating at 180°C for 7 minutes, and its surface curing properties and adhesion to a nylon base fabric were examined in the same manner as in Example 2.
After conducting an aging test for one week under HO high humidity, the adhesive properties were examined and the results shown in Table 3 were obtained.
実施例７．比較例６
上記実施例５．６で使用したコンパウンドＢ１００部に
メチルハイドロジエンシロキサン・にＦｅ２［信越化学
工業■裂開品名］１．５部とエチニルシクロヘキサノー
ル０．０５部および式（ＣＬＯ） ３５＋ （ＣＨ２）
５Ｎｃｏで示されるイソシアナート基含有シラン】、
５部またはビニルトリス（β−メトキシエトキシ）シラ
ン１．５部を加え、均一に混練したのち、トルエン ４
１２部に溶解してコンパウンド分２０％のトルエン溶液
を作り、ついでこれに塩化白金酸の２−エチルヘキサノ
ール溶液０．０５部を添加して試料を作り、これを前記
した実施例５（濃度１％）、６と同根のナイロン繊維織
物に同林の方法で処理し、得られたシリコーン被覆ナイ
ロン基布についての表面キュア性、接着性、高湿度下で
の接着性をしらへたところ、第４表に示したとおりの結
果が得られた。Example 7. Comparative Example 6 100 parts of the compound B used in Example 5.6 above, 1.5 parts of methylhydrodienesiloxane/Fe2 [Shin-Etsu Chemical Co., Ltd. cleavage product name], 0.05 parts of ethynylcyclohexanol, and formula (CLO) 35+ (CH2)
Isocyanate group-containing silane represented by 5Nco],
Add 5 parts or 1.5 parts of vinyltris(β-methoxyethoxy)silane, mix uniformly, and add 4 parts of toluene.
12 parts to make a toluene solution with a compound content of 20%, and then 0.05 part of a 2-ethylhexanol solution of chloroplatinic acid was added to make a sample. %), nylon fiber fabric with the same roots as 6 was treated by Dobayashi's method, and the surface curing properties, adhesion properties, and adhesion properties under high humidity of the silicone-coated nylon base fabric obtained were investigated. The results shown in Table 4 were obtained.
第４表
実施例８
分子鎖両末端がジメチルビニルシロキシ基で封鎖された
、粘度１０，０００ ｃｓのジメチルポリシロキサン１
００部に、表面をトリメチルシリル基で処理した比表面
積２００ｍ’／ｇの疎水性ヒユームシリカ２０部を加え
、品用ミキサーで混合してコンパウンドＣを調製した。Table 4 Example 8 Dimethylpolysiloxane 1 with a viscosity of 10,000 cs, with both molecular chain ends capped with dimethylvinylsiloxy groups
20 parts of hydrophobic hume silica having a specific surface area of 200 m'/g and whose surface was treated with trimethylsilyl groups was added to 00 parts and mixed with a product mixer to prepare Compound C.
ついで、このコンパウンドＣ１００部にメチルハイドロ
ジエンポリシロキサン・にＦ９９（前出）２．０部とエ
チニルシクロヘキサノール０．１部および式ｔ−（Ｃ）
１３０） ３５１ （Ｃ）１２） ３ＮＧＯで示される
イソシアナート基含有シラン３部を加えて均一に混練り
したのち、さらに塩化白金酸の２−エチルヘキサノール
溶液０，１部を添加して混合し、実施例１と間柱にして
第５表に示した被着体上に載せ、１２０℃で１０分間、
５ ｋｇｆ／ｃｍ２の圧力で加圧加熱して接着サンプル
を作成したところ、これらは第５表に併記したとおりの
接着力を示した。Next, to 100 parts of this compound C, 2.0 parts of methylhydrodiene polysiloxane F99 (described above), 0.1 part of ethynylcyclohexanol, and formula t-(C) were added.
130) 351 (C) 12) After adding 3 parts of isocyanate group-containing silane represented by 3NGO and kneading uniformly, further adding 0.1 part of a 2-ethylhexanol solution of chloroplatinic acid and mixing, The studs of Example 1 were placed on the adherends shown in Table 5, and heated at 120°C for 10 minutes.
Adhesive samples were prepared by pressurizing and heating at a pressure of 5 kgf/cm2, and these exhibited adhesive strength as shown in Table 5.
第５表
［発明の効果コ
本発明は自己接着型シリコーンゴム組成物及びこれを織
布に被覆、硬化してなるシリコーンゴム被覆布に関する
ものであり、これは前記したようにオルガノポリシロキ
サンと硬化剤とからなる組成物に分子中にイソシアナー
ト基とアルコキシ基等の加水分解性基を含有するオルガ
ノシランを添加したものであるが、この組成物はイソシ
アナート基含有シランが添加されているのでこれを各種
基材と接触させたものは基材表面を予めブライマーｍ埋
をしていなくても、これを加硫すると基材と強く接触し
、この接着面は高湿度での接着耐久性にすぐれたものに
なるという有利性が与えられる。Table 5 [Effects of the Invention] The present invention relates to a self-adhesive silicone rubber composition and a silicone rubber-coated fabric obtained by coating a woven fabric with the same and curing it. An organosilane containing hydrolyzable groups such as an isocyanate group and an alkoxy group in the molecule is added to a composition consisting of a silane containing an isocyanate group. When this is brought into contact with various base materials, even if the surface of the base material is not filled with brimer m beforehand, when it is vulcanized, it comes into strong contact with the base material, and this adhesive surface has excellent adhesive durability even under high humidity. It gives you the advantage of being superior.
なお、このシリコーンゴム組成物はナイロン繊維、ケブ
ラーｆａ維などの織布との接着性にすぐれているので、
これはシリコーンゴム被覆布の製造に特に有用とされる
。In addition, this silicone rubber composition has excellent adhesion to woven fabrics such as nylon fibers and Kevlar FA fibers, so
It is said to be particularly useful in the production of silicone rubber coated fabrics.
第１図ａ）は実施例における、シリコーンゴム組成物と
繊維買物との接着力をテストするための接着試験サンプ
ルの縦断面図、第１図ｂ）はその接着力テスト方法を示
す縦断面図である。
１・・・６．６ナイロン
２・・・シリコーンゴム被覆層
３・・・被着体
】
第
図Figure 1 a) is a longitudinal cross-sectional view of an adhesion test sample for testing the adhesive force between a silicone rubber composition and a textile product in an example, and Figure 1 b) is a longitudinal cross-sectional view showing the adhesive force test method. It is. 1... 6.6 nylon 2... silicone rubber coating layer 3... adherend] Figure
Claims (1)
＿￥（ここにＲ＾１は同一または異種の非置換または置
換１価炭化水素 基、ａは１．９８〜２．０１の正数）で示され、２５℃
における粘度が３００ｃＳ以上であるオルガノポリシロ
キサン１００重量部、 ロ）分子中にイソシアナート基と加水分解性基を含有す
るオルガノシランまたはその部分加水分解物 ０．１〜２０重量部、 ハ）硬化剤 とからなることを特徴とする自己接着型シリコーンゴム
組成物。 ２、請求項１に記載のシリコーンゴム組成物を織布に被
覆、硬化させてなるシリコーンゴム被覆布。[Claims] 1. A) Average compositional formula R^1_aSiO_\_4_-_a
_￥ (where R^1 is the same or different unsubstituted or substituted monovalent hydrocarbon group, a is a positive number from 1.98 to 2.01), 25°C
100 parts by weight of an organopolysiloxane having a viscosity of 300 cS or more; b) 0.1 to 20 parts by weight of an organosilane containing an isocyanate group and a hydrolyzable group in the molecule or a partial hydrolyzate thereof; c) a curing agent. A self-adhesive silicone rubber composition comprising: 2. A silicone rubber-coated fabric obtained by coating a woven fabric with the silicone rubber composition according to claim 1 and curing it.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP33456990A JPH0798902B2 (en) | 1989-12-05 | 1990-11-30 | Self-adhesive silicone rubber composition and silicone rubber-coated cloth |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1-315585 | 1989-12-05 | ||
| JP31558589 | 1989-12-05 | ||
| JP33456990A JPH0798902B2 (en) | 1989-12-05 | 1990-11-30 | Self-adhesive silicone rubber composition and silicone rubber-coated cloth |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH03223362A true JPH03223362A (en) | 1991-10-02 |
| JPH0798902B2 JPH0798902B2 (en) | 1995-10-25 |
Family
ID=26568368
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP33456990A Expired - Fee Related JPH0798902B2 (en) | 1989-12-05 | 1990-11-30 | Self-adhesive silicone rubber composition and silicone rubber-coated cloth |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0798902B2 (en) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0525435A (en) * | 1991-07-17 | 1993-02-02 | Toray Dow Corning Silicone Co Ltd | Silicone rubber coating composition for air bag |
| JPH05214295A (en) * | 1992-01-31 | 1993-08-24 | Toray Dow Corning Silicone Co Ltd | Liquid silicone rubber coating material composition for air bag |
| US5296298A (en) * | 1991-11-22 | 1994-03-22 | Toshiba Silicone Co., Ltd. | Silicone rubber composition and silicone rubber-processed fabric |
| JP2011099090A (en) * | 2009-10-05 | 2011-05-19 | Shin-Etsu Chemical Co Ltd | Addition curable type self-adhesive silicone rubber composition |
| WO2013035736A1 (en) * | 2011-09-08 | 2013-03-14 | 積水化学工業株式会社 | Curable composition for optical semiconductor device |
| WO2016103836A1 (en) * | 2014-12-24 | 2016-06-30 | 信越化学工業株式会社 | Organosilicon compound containing isocyanate group, process for producing same, adhesive, pressure-sensitive adhesive, and coating material |
| KR20160078265A (en) * | 2014-12-24 | 2016-07-04 | 신에쓰 가가꾸 고교 가부시끼가이샤 | Organopolysiloxane compound containing isocyanate group, method for producing the same, adhesive, tackifier and coating composition |
| WO2017094357A1 (en) * | 2015-11-30 | 2017-06-08 | 信越化学工業株式会社 | Self-adhesive silicone gel composition and silicone gel |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2020203597A1 (en) | 2019-04-01 | 2020-10-08 | 信越化学工業株式会社 | Self-adhesive silicone gel composition and silicone gel comprising cured product thereof |
-
1990
- 1990-11-30 JP JP33456990A patent/JPH0798902B2/en not_active Expired - Fee Related
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0525435A (en) * | 1991-07-17 | 1993-02-02 | Toray Dow Corning Silicone Co Ltd | Silicone rubber coating composition for air bag |
| JP2571986B2 (en) * | 1991-07-17 | 1997-01-16 | 東レ・ダウコーニング・シリコーン株式会社 | Silicone rubber composition for airbag coating |
| US5296298A (en) * | 1991-11-22 | 1994-03-22 | Toshiba Silicone Co., Ltd. | Silicone rubber composition and silicone rubber-processed fabric |
| JPH05214295A (en) * | 1992-01-31 | 1993-08-24 | Toray Dow Corning Silicone Co Ltd | Liquid silicone rubber coating material composition for air bag |
| JP2011099090A (en) * | 2009-10-05 | 2011-05-19 | Shin-Etsu Chemical Co Ltd | Addition curable type self-adhesive silicone rubber composition |
| WO2013035736A1 (en) * | 2011-09-08 | 2013-03-14 | 積水化学工業株式会社 | Curable composition for optical semiconductor device |
| WO2016103836A1 (en) * | 2014-12-24 | 2016-06-30 | 信越化学工業株式会社 | Organosilicon compound containing isocyanate group, process for producing same, adhesive, pressure-sensitive adhesive, and coating material |
| KR20160078265A (en) * | 2014-12-24 | 2016-07-04 | 신에쓰 가가꾸 고교 가부시끼가이샤 | Organopolysiloxane compound containing isocyanate group, method for producing the same, adhesive, tackifier and coating composition |
| JP2016121075A (en) * | 2014-12-24 | 2016-07-07 | 信越化学工業株式会社 | Isocyanate group-containing organosilicon compound, method for producing the same, adhesive, tackiness agent, and coating agent |
| JP2016121215A (en) * | 2014-12-24 | 2016-07-07 | 信越化学工業株式会社 | Isocyanate group-containing organopolysiloxane compound, method for producing the same, adhesive, tackiness agent, and coating agent |
| US10323049B2 (en) | 2014-12-24 | 2019-06-18 | Shin-Etsu Chemical Co., Ltd. | Organosilicon compound containing isocyanate group, process for producing same, adhesive, pressure-sensitive adhesive, and coating material |
| WO2017094357A1 (en) * | 2015-11-30 | 2017-06-08 | 信越化学工業株式会社 | Self-adhesive silicone gel composition and silicone gel |
| JPWO2017094357A1 (en) * | 2015-11-30 | 2018-08-30 | 信越化学工業株式会社 | Self-adhesive silicone gel composition and silicone gel |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0798902B2 (en) | 1995-10-25 |
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