JP4954785B2 - Room temperature curable polyorganosiloxane composition - Google Patents
Room temperature curable polyorganosiloxane composition Download PDFInfo
- Publication number
- JP4954785B2 JP4954785B2 JP2007122657A JP2007122657A JP4954785B2 JP 4954785 B2 JP4954785 B2 JP 4954785B2 JP 2007122657 A JP2007122657 A JP 2007122657A JP 2007122657 A JP2007122657 A JP 2007122657A JP 4954785 B2 JP4954785 B2 JP 4954785B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- parts
- weight
- room temperature
- polyorganosiloxane composition
- 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.)
- Active
Links
- 239000000203 mixture Substances 0.000 title claims description 66
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 30
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 22
- 229910000077 silane Inorganic materials 0.000 claims description 22
- 239000003054 catalyst Substances 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 8
- 239000011256 inorganic filler Substances 0.000 claims description 8
- 229910003475 inorganic filler Inorganic materials 0.000 claims description 8
- 125000005371 silicon functional group Chemical group 0.000 claims description 8
- 125000003277 amino group Chemical group 0.000 claims description 7
- 239000003431 cross linking reagent Substances 0.000 claims description 6
- 150000003058 platinum compounds Chemical class 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 239000003063 flame retardant Substances 0.000 claims description 3
- UTAWUDHTUIKOEK-UHFFFAOYSA-N P([O-])([O-])[O-].C1(=CC=CC=C1)[Pt+3](C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound P([O-])([O-])[O-].C1(=CC=CC=C1)[Pt+3](C1=CC=CC=C1)C1=CC=CC=C1 UTAWUDHTUIKOEK-UHFFFAOYSA-N 0.000 claims description 2
- 239000000654 additive Substances 0.000 claims description 2
- 230000000996 additive effect Effects 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical group [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims 1
- -1 2-phenylpropyl group Chemical group 0.000 description 39
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 12
- FMRLDPWIRHBCCC-UHFFFAOYSA-L Zinc carbonate Chemical compound [Zn+2].[O-]C([O-])=O FMRLDPWIRHBCCC-UHFFFAOYSA-L 0.000 description 12
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 12
- 229910000010 zinc carbonate Inorganic materials 0.000 description 12
- 239000011667 zinc carbonate Substances 0.000 description 12
- 235000004416 zinc carbonate Nutrition 0.000 description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
- 239000002245 particle Substances 0.000 description 10
- 150000002430 hydrocarbons Chemical group 0.000 description 9
- 239000000843 powder Substances 0.000 description 8
- 230000004580 weight loss Effects 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 238000002156 mixing Methods 0.000 description 7
- 239000010453 quartz Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 238000002411 thermogravimetry Methods 0.000 description 7
- KAQVOKWBCLGYFT-UHFFFAOYSA-N 4-[dimethoxy(methyl)silyl]-2,2-dimethylbutan-1-amine Chemical compound CO[Si](C)(OC)CCC(C)(C)CN KAQVOKWBCLGYFT-UHFFFAOYSA-N 0.000 description 6
- 125000003545 alkoxy group Chemical group 0.000 description 6
- 239000001569 carbon dioxide Substances 0.000 description 6
- 229910002092 carbon dioxide Inorganic materials 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000013585 weight reducing agent Substances 0.000 description 6
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 229920001971 elastomer Polymers 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 230000000704 physical effect Effects 0.000 description 5
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 5
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 4
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000006229 carbon black Substances 0.000 description 4
- 238000013329 compounding Methods 0.000 description 4
- 239000012975 dibutyltin dilaurate Substances 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 229910044991 metal oxide Inorganic materials 0.000 description 4
- 150000004706 metal oxides Chemical class 0.000 description 4
- 150000003377 silicon compounds Chemical class 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- 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 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 3
- 239000013500 performance material Substances 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 3
- 239000011787 zinc oxide Substances 0.000 description 3
- 235000014692 zinc oxide Nutrition 0.000 description 3
- ZYAASQNKCWTPKI-UHFFFAOYSA-N 3-[dimethoxy(methyl)silyl]propan-1-amine Chemical compound CO[Si](C)(OC)CCCN ZYAASQNKCWTPKI-UHFFFAOYSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 229940045985 antineoplastic platinum compound Drugs 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- WHGNXNCOTZPEEK-UHFFFAOYSA-N dimethoxy-methyl-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](C)(OC)CCCOCC1CO1 WHGNXNCOTZPEEK-UHFFFAOYSA-N 0.000 description 2
- 239000004205 dimethyl polysiloxane Substances 0.000 description 2
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 125000003700 epoxy group Chemical group 0.000 description 2
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 238000007654 immersion Methods 0.000 description 2
- 229910052809 inorganic oxide Inorganic materials 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000002075 main ingredient Substances 0.000 description 2
- 229910000000 metal hydroxide Inorganic materials 0.000 description 2
- 150000004692 metal hydroxides Chemical class 0.000 description 2
- MQWFLKHKWJMCEN-UHFFFAOYSA-N n'-[3-[dimethoxy(methyl)silyl]propyl]ethane-1,2-diamine Chemical compound CO[Si](C)(OC)CCCNCCN MQWFLKHKWJMCEN-UHFFFAOYSA-N 0.000 description 2
- MSRJTTSHWYDFIU-UHFFFAOYSA-N octyltriethoxysilane Chemical compound CCCCCCCC[Si](OCC)(OCC)OCC MSRJTTSHWYDFIU-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- UOURRHZRLGCVDA-UHFFFAOYSA-D pentazinc;dicarbonate;hexahydroxide Chemical group [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Zn+2].[Zn+2].[Zn+2].[Zn+2].[Zn+2].[O-]C([O-])=O.[O-]C([O-])=O UOURRHZRLGCVDA-UHFFFAOYSA-D 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 238000000197 pyrolysis Methods 0.000 description 2
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 2
- 239000003566 sealing material Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 150000004756 silanes Chemical class 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 229920002379 silicone rubber Polymers 0.000 description 2
- 239000004945 silicone rubber Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000005979 thermal decomposition reaction Methods 0.000 description 2
- RRKODOZNUZCUBN-CCAGOZQPSA-N (1z,3z)-cycloocta-1,3-diene Chemical compound C1CC\C=C/C=C\C1 RRKODOZNUZCUBN-CCAGOZQPSA-N 0.000 description 1
- OVSGBKZKXUMMHS-VGKOASNMSA-L (z)-4-oxopent-2-en-2-olate;propan-2-olate;titanium(4+) Chemical compound [Ti+4].CC(C)[O-].CC(C)[O-].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O OVSGBKZKXUMMHS-VGKOASNMSA-L 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- MMEDJBFVJUFIDD-UHFFFAOYSA-N 2-[2-(carboxymethyl)phenyl]acetic acid Chemical compound OC(=O)CC1=CC=CC=C1CC(O)=O MMEDJBFVJUFIDD-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- OTCOSAMIXUWQOA-UHFFFAOYSA-N COC(OC)(OC)CO[SiH2]C Chemical compound COC(OC)(OC)CO[SiH2]C OTCOSAMIXUWQOA-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229920001174 Diethylhydroxylamine Polymers 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 1
- PXAJQJMDEXJWFB-UHFFFAOYSA-N acetone oxime Chemical compound CC(C)=NO PXAJQJMDEXJWFB-UHFFFAOYSA-N 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000002318 adhesion promoter Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 125000003342 alkenyl group Chemical group 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
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 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
- 150000001412 amines Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- AYJRCSIUFZENHW-UHFFFAOYSA-L barium carbonate Chemical class [Ba+2].[O-]C([O-])=O AYJRCSIUFZENHW-UHFFFAOYSA-L 0.000 description 1
- 229920005601 base polymer Polymers 0.000 description 1
- YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 description 1
- BSDOQSMQCZQLDV-UHFFFAOYSA-N butan-1-olate;zirconium(4+) Chemical compound [Zr+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] BSDOQSMQCZQLDV-UHFFFAOYSA-N 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 229910000420 cerium oxide Inorganic materials 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004966 cyanoalkyl group Chemical group 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 description 1
- FVCOIAYSJZGECG-UHFFFAOYSA-N diethylhydroxylamine Chemical compound CCN(O)CC FVCOIAYSJZGECG-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- SLQTWNAJXFHMHM-UHFFFAOYSA-N dimethoxy-methyl-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](C)(OC)OC)CCC2OC21 SLQTWNAJXFHMHM-UHFFFAOYSA-N 0.000 description 1
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- SBRXLTRZCJVAPH-UHFFFAOYSA-N ethyl(trimethoxy)silane Chemical compound CC[Si](OC)(OC)OC SBRXLTRZCJVAPH-UHFFFAOYSA-N 0.000 description 1
- 229910021485 fumed silica Inorganic materials 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 1
- 239000011491 glass wool Substances 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 230000033444 hydroxylation Effects 0.000 description 1
- 238000005805 hydroxylation reaction Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- GIWKOZXJDKMGQC-UHFFFAOYSA-L lead(2+);naphthalene-2-carboxylate Chemical compound [Pb+2].C1=CC=CC2=CC(C(=O)[O-])=CC=C21.C1=CC=CC2=CC(C(=O)[O-])=CC=C21 GIWKOZXJDKMGQC-UHFFFAOYSA-L 0.000 description 1
- DSSXKBBEJCDMBT-UHFFFAOYSA-M lead(2+);octanoate Chemical compound [Pb+2].CCCCCCCC([O-])=O DSSXKBBEJCDMBT-UHFFFAOYSA-M 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- GEMHFKXPOCTAIP-UHFFFAOYSA-N n,n-dimethyl-n'-phenylcarbamimidoyl chloride Chemical compound CN(C)C(Cl)=NC1=CC=CC=C1 GEMHFKXPOCTAIP-UHFFFAOYSA-N 0.000 description 1
- VMESOKCXSYNAKD-UHFFFAOYSA-N n,n-dimethylhydroxylamine Chemical compound CN(C)O VMESOKCXSYNAKD-UHFFFAOYSA-N 0.000 description 1
- WHIVNJATOVLWBW-UHFFFAOYSA-N n-butan-2-ylidenehydroxylamine Chemical group CCC(C)=NO WHIVNJATOVLWBW-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000004043 oxo group Chemical group O=* 0.000 description 1
- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001707 polybutylene terephthalate Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 1
- 125000005415 substituted alkoxy group Chemical group 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 1
- ZQZCOBSUOFHDEE-UHFFFAOYSA-N tetrapropyl silicate Chemical compound CCCO[Si](OCCC)(OCCC)OCCC ZQZCOBSUOFHDEE-UHFFFAOYSA-N 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 1
- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
Description
本発明は、室温硬化性ポリオルガノシロキサン組成物に係り、さらに詳しくは、比較的低硬度で弾性に優れ、伸張性が高く難燃性に優れた硬化物を得ることができるポリオルガノシロキサン組成物に関する。 The present invention relates to a room temperature curable polyorganosiloxane composition, and more particularly, a polyorganosiloxane composition capable of obtaining a cured product having relatively low hardness, excellent elasticity, high extensibility and excellent flame retardancy. About.
室温で硬化しゴム状弾性体を生成するポリオルガノシロキサン組成物の中で、空気中の水分と接触することにより硬化反応が生起する室温硬化性ポリオルガノシロキサン組成物は、使用直前に本体であるベースポリマーや架橋剤、触媒などを秤量したり、混合したりする煩雑さが無く、配合上のミスを生じることがないうえに、接着性に優れているので、電気・電子工業などにおける弾性接着剤やコーティング材として、また建築用シーリング材などとして広く用いられている。 Among polyorganosiloxane compositions that cure at room temperature to form a rubbery elastic body, a room temperature curable polyorganosiloxane composition in which a curing reaction occurs by contact with moisture in the air is a main body immediately before use. There is no need to weigh or mix base polymers, cross-linking agents, catalysts, etc. It is widely used as an agent and coating material, and as a building sealing material.
そして、このような室温硬化性ポリオルガノシロキサン組成物の中でも、末端のケイ素原子にアルコキシル基の結合したポリオルガノシロキサンを主体とし、自己接着性を持たせるために、アミノ基含有シラン（アミノ官能性シラン）を配合した組成物が、接着剤やコーティング材、シール材として使用されている（例えば、特許文献１、特許文献２、特許文献３、特許文献４、特許文献５参照）。 Among such room temperature curable polyorganosiloxane compositions, an amino group-containing silane (amino functional group) is mainly used to provide self-adhesiveness, mainly composed of polyorganosiloxane having alkoxy groups bonded to terminal silicon atoms. A composition containing silane is used as an adhesive, a coating material, and a sealing material (see, for example, Patent Document 1, Patent Document 2, Patent Document 3, Patent Document 4, and Patent Document 5).
しかし、接着性向上剤として通常のアミノ基含有シランを配合した室温硬化性ポリオルガノシロキサン組成物を使用すると、硬化物の硬度が高くなり、さらに難燃性を得るために金属酸化物のような無機充填剤を多量に配合した場合も、得られる組成物の硬度が高くなりすぎる。したがって、硬度が比較的低く、弾性を有する組成物が得にくいという問題があった。 However, when a room temperature-curable polyorganosiloxane composition containing a normal amino group-containing silane is used as an adhesion improver, the hardness of the cured product is increased, and a metal oxide such as a metal oxide is used to obtain flame retardancy. Even when a large amount of the inorganic filler is blended, the hardness of the resulting composition becomes too high. Therefore, there is a problem that the hardness is relatively low and it is difficult to obtain an elastic composition.
従来から、モジュラスが低く伸張性の高いシーリング材として、脱ヒドロキシルアミン型の硬化反応を生起するポリオルガノシロキサン組成物が使用されているが、この組成物は自己接着性を持たないため、プライマーなどを用いて部材を前処理することが必要であり、施工作業が煩雑になるという問題があった。また、プライマーに含有される有機溶剤の作業者の健康や環境に対する影響も懸念されている。 Conventionally, a polyorganosiloxane composition that causes a dehydroxylamine-type curing reaction has been used as a sealant having a low modulus and high extensibility, but since this composition does not have self-adhesive properties, a primer, etc. It was necessary to pre-process the member using the material, and there was a problem that the construction work became complicated. There is also concern about the effects of the organic solvent contained in the primer on the health and environment of workers.
さらに最近、このような空気中の水分と接触するだけで硬化する室温硬化性ポリオルガノシロキサン組成物は、省エネルギーの観点から需要の拡大が期待されるうえに、電子線、紫外線の照射や加熱が不可能な広範な使用部位、例えば建築構造物や既存の設置物への使用が盛んに行われている。そして、建築構造物や使用箇所の安全性の点から、このような室温硬化性ポリオルガノシロキサン組成物においては、難燃性への要求がますます高まってきている。 More recently, room temperature curable polyorganosiloxane compositions that cure only by contact with moisture in the air are expected to increase in demand from the viewpoint of energy saving, and are also subject to electron beam and ultraviolet light irradiation and heating. It is actively used for a wide range of use sites, such as building structures and existing installations. In view of the safety of the building structure and the place where it is used, there is an increasing demand for flame retardancy in such room temperature curable polyorganosiloxane compositions.
しかしながら、自己接着性を有し、比較的低硬度で弾性に優れ、かつ難燃性が良好で伸張性の高い室温硬化性ポリオルガノシロキサン組成物は得られていないのが現状であった。
本発明は、これらの問題を解決するためになされたもので、適度の硬度を有し弾性に優れ、かつ伸張性が高く難燃性に優れた硬化物を得ることができる室温硬化性ポリオルガノシロキサン組成物を提供することを目的とする。 The present invention has been made to solve these problems, and is a room temperature curable polyorgano capable of obtaining a cured product having appropriate hardness, excellent elasticity, high extensibility and excellent flame retardancy. An object is to provide a siloxane composition.
本発明の室温硬化性ポリオルガノシロキサン組成物は、（Ａ）分子鎖末端が水酸基または加水分解性基で封鎖され、２３℃における粘度が２０〜１,０００,０００ｍＰａ・ｓであるポリオルガノシロキサン１００重量部と、
（Ｂ）分子中にケイ素官能基として平均２個を超える数のケトキシマト基を有するシランまたはその部分加水分解物０．５〜２０重量部と、
（Ｃ）無機充填剤１〜４００重量部と、
（Ｄ）一般式：（Ｒ１Ｏ）３−ｍＲ２ ｍＳｉ−Ｒ３………（１）
（式中、Ｒ１およびＲ２は同一または相異なるアルキル基を示す。ｍは０〜２の整数である。また、Ｒ３は、一般式：−（ＣＨ２）ｐ−ＣＨＲ４−（ＣＨ２）ｑ−ＮＨ２または
一般式：−（ＣＨ２）ｐ−Ｃ（Ｒ４）２−（ＣＨ２）ｑ−ＮＨ２
で表される分岐を有するアミノ基置換アルキル基を示す。ここで、Ｒ４は炭素数１〜４のアルキル基を示し、ｐおよびｑはそれぞれ１〜８の整数である。ただし、ｐ＋ｑは９以下の整数である。）で表されるアミノ基置換アルキル基を有するアルコキシシラン０．０５〜１５重量部と、
（Ｅ）硬化触媒０.００１〜１０重量部、および
難燃性添加剤として、（Ｆ）白金系化合物またはその錯化合物
をそれぞれ含むことを特徴としている。
The room temperature curable polyorganosiloxane composition of the present invention comprises (A) a polyorganosiloxane 100 having molecular chain terminals blocked with hydroxyl groups or hydrolyzable groups and having a viscosity at 23 ° C. of 20 to 1,000,000 mPa · s. Parts by weight,
(B) 0.5 to 20 parts by weight of a silane having a ketoximato group having an average number of more than 2 as a silicon functional group in the molecule or a partial hydrolyzate thereof ,
(C) 1 to 400 parts by weight of an inorganic filler,
(D) the general formula: (R 1 O) 3- m R 2 m Si-R 3 ......... (1)
(In the formula, R 1 and R 2 represent the same or different alkyl groups. M is an integer of 0 to 2. Also, R 3 represents a general formula: — (CH 2 ) p —CHR 4 — (CH 2) q -NH 2 or the formula :-( CH 2) p -C (R 4) 2 - (CH 2) q -NH 2
The amino group substituted alkyl group which has the branch represented by these is shown. Here, R 4 represents an alkyl group having 1 to 4 carbon atoms, and p and q are each an integer of 1 to 8. However, p + q is an integer of 9 or less. 0.05 to 15 parts by weight of an alkoxysilane having an amino group-substituted alkyl group represented by :
(E) curing catalyst 0.001 to 10 parts by weight , and
The flame retardant additive is characterized by containing (F) a platinum compound or a complex compound thereof .
本発明の室温硬化性ポリオルガノシロキサン組成物によれば、硬化性に優れ適度な硬度を有し、かつ伸張性が高く難燃性に優れた硬化物を得ることができる。 According to the room temperature curable polyorganosiloxane composition of the present invention, it is possible to obtain a cured product having excellent curability, moderate hardness, high extensibility and excellent flame retardancy.
以下、本発明の実施の形態について説明する。 Embodiments of the present invention will be described below.
本発明の実施形態の室温硬化性ポリオルガノシロキサン組成物は、（Ａ）分子鎖末端が水酸基（ヒドロキシル基）または加水分解性基で封鎖されたポリオルガノシロキサン１００重量部と、（Ｂ）分子中にケイ素官能基として平均２個を超える数のケトキシマト基を有するケイ素化合物０．５〜２０重量部と、（Ｃ）無機充填剤１〜４００重量部と、（Ｄ）アミノ基置換アルキル基を有するアルコキシシラン０．０５〜１５重量部、および（Ｅ）硬化触媒０.００１〜１０重量部をそれぞれ含有する。 The room temperature curable polyorganosiloxane composition of the embodiment of the present invention comprises (A) 100 parts by weight of a polyorganosiloxane in which the molecular chain terminal is blocked with a hydroxyl group (hydroxyl group) or a hydrolyzable group, and (B) in the molecule. 0.5 to 20 parts by weight of a silicon compound having an average of more than two ketoximato groups as silicon functional groups, (C) 1 to 400 parts by weight of an inorganic filler, and (D) an amino group-substituted alkyl group It contains 0.05 to 15 parts by weight of alkoxysilane and 0.001 to 10 parts by weight of (E) curing catalyst.
(Ａ)成分は、分子鎖末端が水酸基（ヒドロキシル基）または加水分解性基で封鎖されたポリオルガノシロキサンであり、実施形態の室温硬化性組成物の主成分である。（Ａ）成分の粘度は、低すぎると硬化後のゴム弾性が乏しくなり、高すぎると作業性が低下することから、２３℃における粘度が２０〜１,０００,０００ｍＰａ・ｓ、より好ましくは１００〜１００,０００ｍＰａ・ｓの範囲にあることが好ましい。 The component (A) is a polyorganosiloxane whose molecular chain end is blocked with a hydroxyl group (hydroxyl group) or a hydrolyzable group, and is a main component of the room temperature curable composition of the embodiment. If the viscosity of the component (A) is too low, the rubber elasticity after curing will be poor, and if it is too high, the workability will be reduced. Therefore, the viscosity at 23 ° C. is 20 to 1,000,000 mPa · s, more preferably 100. It is preferable to be in the range of ~ 100,000 mPa · s.
また、このポリオルガノシロキサンの分子構造は、下記一般式（２）で示される直鎖状であることが好ましいが、一部分岐鎖を有する構造でもよい。
式（２）中、Ｒ５は互いに同一でも異なっていてもよい置換または非置換の１価の炭化水素基を表し、Ｒ６は−ＺＳｉＲ７ ３−ｒＸｒで表される１価の有機基を表す。ここで、Ｚは酸素（オキソ基）または２価の炭化水素基を表し、Ｒ７は互いに同一でも異なっていてもよい置換または非置換の１価の炭化水素基を表す。Ｘは水酸基（ヒドロキシル基）または加水分解性基を表し、ｒは１〜３の整数である。また、ｎは当該（Ａ）成分の粘度（２３℃）を２０〜１，０００，０００ｍＰａ・ｓにする数である。 Wherein (2), R 5 represents a monovalent hydrocarbon group which may substituted or unsubstituted be the same or different, monovalent organic R 6 is represented by -ZSiR 7 3-r X r Represents a group. Here, Z represents oxygen (oxo group) or a divalent hydrocarbon group, and R 7 represents a substituted or unsubstituted monovalent hydrocarbon group which may be the same as or different from each other. X represents a hydroxyl group (hydroxyl group) or a hydrolyzable group, and r is an integer of 1 to 3. Moreover, n is a number which makes the viscosity (23 degreeC) of the said (A) component 20-1,000,000 mPa * s.
Ｒ５としては、メチル基、エチル基、プロピル基、ブチル基、ペンチル基、ヘキシル基、オクチル基、デシル基、ドデシル基のようなアルキル基；ビニル基、アリル基のようなアルケニル基；フェニル基、トリル基、キシリル基のようなアリール基；２−フェニルエチル基、２−フェニルプロピル基のようなアラルキル基が例示され、さらにこれらの炭化水素基の水素原子の一部が他の原子または基で置換されたもの、すなわちクロロメチル基、３−クロロプロピル基、３，３，３−トリフルオロプロピル基のようなハロゲン化アルキル基；３−シアノプロピル基のようなシアノアルキル基などの置換炭化水素基が例示される。合成が容易であり、かつ（Ａ）成分が分子量の割に低い粘度を有し、硬化前の組成物に良好な押し出し性を与えること、および硬化後の組成物に良好な物理的性質を与えることから、Ｒ５全体の８５％以上がメチル基であることが好ましく、実質的にすべてのＲ５がメチル基であることがより好ましい。 R 5 includes methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, octyl group, decyl group, alkyl group such as dodecyl group; alkenyl group such as vinyl group and allyl group; phenyl group And aryl groups such as tolyl group and xylyl group; aralkyl groups such as 2-phenylethyl group and 2-phenylpropyl group are exemplified, and some of the hydrogen atoms of these hydrocarbon groups are other atoms or groups. Substituted with, i.e., halogenated alkyl groups such as chloromethyl, 3-chloropropyl, 3,3,3-trifluoropropyl; substituted carbons such as cyanoalkyl such as 3-cyanopropyl A hydrogen group is illustrated. It is easy to synthesize, and the component (A) has a low viscosity with respect to the molecular weight, gives good extrudability to the composition before curing, and gives good physical properties to the composition after curing. it from is preferably 85% or more of the total R 5 is a methyl group, and more preferably substantially all R 5 is a methyl group.
一方、特に耐熱性、耐放射線性、耐寒性または透明性を組成物に付与する場合には、Ｒ５の一部として必要量のフェニル基を、耐油性、耐溶剤性を付与する場合には、Ｒ５の一部として３，３，３−トリフルオロプロピル基や３−シアノプロピル基を、また塗装適性を有する表面を付与する場合には、Ｒ５の一部として長鎖アルキル基やアラルキル基を、それぞれメチル基と併用するなど目的に応じて任意に選択することができる。なお、組成物の粘度を低く抑えて伸張性を良くするには、Ｒ５としてフェニル基を含まない方がよい。 On the other hand, particularly when imparting heat resistance, radiation resistance, cold resistance or transparency to the composition, a necessary amount of phenyl groups as part of R 5 , when imparting oil resistance and solvent resistance, When a 3,3,3-trifluoropropyl group or 3-cyanopropyl group is provided as a part of R 5 , or a surface having paintability is provided, a long chain alkyl group or aralkyl is provided as a part of R 5. The group can be arbitrarily selected depending on the purpose, for example, in combination with a methyl group. In order to improve the extensibility by keeping the viscosity of the composition low, it is better not to include a phenyl group as R 5 .
（Ａ）成分の末端基Ｒ６は、−ＺＳｉＲ７ ３−ｒＸｒで表され、ケイ素官能基である水酸基（ヒドロキシル基）または加水分解性基Ｘを少なくとも１個有するケイ素官能性シロキシ単位である。したがって、実施形態の（Ａ）成分は、分子の両末端にそれぞれ水酸基（ヒドロキシル基）または加水分解性基Ｘを少なくとも１個有する。 (A) end groups of component R 6 is represented by -ZSiR 7 3-r X r, hydroxyl is a silicon functional group (hydroxyl group) or a hydrolyzable group X in the silicon-functional siloxy units having at least one is there. Therefore, the component (A) of the embodiment has at least one hydroxyl group (hydroxyl group) or hydrolyzable group X at both ends of the molecule.
末端基Ｒ６において、ケイ素原子に結合するＲ７は、互いに同一でも異なっていてもよく、またＲ５と同一でも異なっていてもよい置換または非置換の１価の炭化水素基であり、前記したＲ５と同様なものが例示される。合成が容易で、加水分解性基Ｘの反応性に優れていることから、メチル基またはビニル基が好ましい。Ｚは、互いに同一でも異なっていてもよい２価の酸素（オキシ基）または２価の炭化水素基であり、２価の炭化水素基としては、メチレン基、エチレン基、トリメチレン基のようなアルキレン基；フェニレン基などが例示される。合成が容易なことから、オキシ基またはエチレン基が好ましく、オキシ基が特に好ましい。 In the terminal group R 6 , R 7 bonded to the silicon atom is a substituted or unsubstituted monovalent hydrocarbon group which may be the same as or different from each other and may be the same as or different from R 5. Materials similar to those in the R 5 can be exemplified. A methyl group or a vinyl group is preferable because synthesis is easy and the reactivity of the hydrolyzable group X is excellent. Z is a divalent oxygen (oxy group) or a divalent hydrocarbon group which may be the same or different from each other. Examples of the divalent hydrocarbon group include alkylene such as a methylene group, an ethylene group and a trimethylene group. Group; a phenylene group and the like are exemplified. From the viewpoint of easy synthesis, an oxy group or an ethylene group is preferable, and an oxy group is particularly preferable.
Ｘは、末端基であるＲ６に少なくとも１個存在するケイ素官能基である水酸基（ヒドロキシル基）または加水分解性基である。加水分解性基としては、メトキシ基、エトキシ基、プロポキシ基、ブトキシ基のようなアルコキシル基；２−メトキシエトキシ基、２−エトキシエトキシ基のような置換アルコキシル基；イソプロペノキシ基のようなエノキシ基、メチルエチルケトオキシム基のようなケトキシマト基、アセトキシ基などが例示され、互いに同一でも異なっていてもよい。合成の容易さ、硬化前の組成物の物性、保存中の安定性、硬化性、経済性、および広範囲の用途に用いられることから、アルコシキル基またはケトキシマト基が好ましい。 X is a hydroxyl group (hydroxyl group) or a hydrolyzable group that is a silicon functional group present in at least one of R 6 that is a terminal group. Examples of the hydrolyzable group include an alkoxyl group such as a methoxy group, an ethoxy group, a propoxy group, and a butoxy group; a substituted alkoxyl group such as a 2-methoxyethoxy group and a 2-ethoxyethoxy group; an enoxy group such as an isopropenoxy group, Examples include a ketoximato group such as a methyl ethyl ketoxime group, an acetoxy group, and the like, which may be the same or different. An alkoxyl group or a ketoximato group is preferred because of its ease of synthesis, physical properties of the composition before curing, stability during storage, curability, economy, and use in a wide range of applications.
末端基Ｒ６において、ケイ素官能基である水酸基（ヒドロキシル基）または加水分解性基Ｘの数ｒは、１〜３個であることが好ましい。このようなケイ素官能性ポリジオルガノシロキサンは、例えば、オクタメチルシクロシロキサンのような環状ジオルガノシロキサン低量体を、水の存在下に酸性触媒またはアルカリ性触媒によって開環重合または開環共重合させ、得られる直鎖状ポリジオルガノシロキサンの末端にケイ素原子に結合する水酸基を導入することにより得ることができる。 In the terminal group R 6 , the number r of hydroxyl groups (hydroxyl groups) or hydrolyzable groups X which are silicon functional groups is preferably 1 to 3. Such a silicon-functional polydiorganosiloxane is obtained by ring-opening polymerization or ring-opening copolymerization of a cyclic diorganosiloxane low monomer such as octamethylcyclosiloxane in the presence of water with an acidic catalyst or an alkaline catalyst, It can be obtained by introducing a hydroxyl group bonded to a silicon atom into the terminal of the obtained linear polydiorganosiloxane.
Ｘが加水分解性基であるケイ素官能性ポリジオルガノシロキサンは、例えば、末端に水酸基を有するポリオルガノシロキサンに、２個以上の任意の加水分解性基を有するシランを縮合させることによって合成することができる。この場合、シランの有する加水分解性基は、縮合反応によって１個が消費されるので、反応によって得られるポリオルガノシロサンの末端基Ｒ６におけるＸの数は、用いられる加水分解性基含有シランが有する加水分解性基の数よりも１個少なくなる。 The silicon-functional polydiorganosiloxane in which X is a hydrolyzable group can be synthesized, for example, by condensing a silane having two or more arbitrary hydrolyzable groups to a polyorganosiloxane having a hydroxyl group at the terminal. it can. In this case, since one hydrolyzable group possessed by the silane is consumed by the condensation reaction, the number of X in the terminal group R 6 of the polyorganosilosan obtained by the reaction is the hydrolyzable group-containing silane used. One less than the number of hydrolyzable groups possessed by.
（Ａ）成分であるポリオルガノシロキサンの具体例としては、例えば、ジメチルポリシロキサン、メチルエチルポリシロキサン、メチルオクチルポリシロキサン、メチルビニルポリシロキサン、メチルフェニルポリシロキサン、メチル（３,３,３−トリフルオロプロピル）ポリシロキサン、ジメチルシロキサンとメチルフェニルシロキサンの共重合体、ジメチルシロキサンとメチル（３,３,３−トリフルオロプロピル）シロキサンの共重合体などが挙げられる。このポリオルガノシロキサンの分子鎖末端は水酸基や加水分解性基（例えば、アルコキシル基）により封鎖されているのであるが、水酸基により封鎖された分子鎖末端としては、ジメチルヒドロキシシロキシ基、メチルフェニルヒドロキシシロキシ基が例示され、アルコキシル基により封鎖された分子鎖末端としては、ビニルジメトキシシロキシ基、メチルジメトキシシロキシ基、トリメトキシシロキシ基、メチルジエトキシシロキシ基、トリエトキシシロキシ基などが例示される。 Specific examples of the polyorganosiloxane as the component (A) include, for example, dimethylpolysiloxane, methylethylpolysiloxane, methyloctylpolysiloxane, methylvinylpolysiloxane, methylphenylpolysiloxane, methyl (3,3,3-tri Fluoropropyl) polysiloxane, a copolymer of dimethylsiloxane and methylphenylsiloxane, a copolymer of dimethylsiloxane and methyl (3,3,3-trifluoropropyl) siloxane, and the like. The molecular chain terminal of this polyorganosiloxane is blocked with a hydroxyl group or a hydrolyzable group (for example, alkoxyl group). The molecular chain terminal blocked with a hydroxyl group includes a dimethylhydroxysiloxy group, methylphenylhydroxysiloxy group. Examples of the molecular chain end blocked with an alkoxyl group include a vinyldimethoxysiloxy group, a methyldimethoxysiloxy group, a trimethoxysiloxy group, a methyldiethoxysiloxy group, and a triethoxysiloxy group.
本発明の実施形態において、（Ｂ）分子中にケイ素官能基として平均２個を超える数の加水分解性基であるケトキシマト基を有するケイ素化合物は、前記（Ａ）成分中のケイ素官能基である水酸基（ヒドロキシル基）または加水分解性基Ｘと反応し、組成物を硬化させるための架橋剤として作用する。このようなケイ素化合物の部分加水分解縮合物も使用することができる。 In an embodiment of the present invention, (B) the silicon compound having a ketoximato group that is an average of more than two hydrolyzable groups as silicon functional groups in the molecule is the silicon functional group in component (A). It reacts with a hydroxyl group (hydroxyl group) or a hydrolyzable group X to act as a crosslinking agent for curing the composition. Such a partial hydrolysis condensate of a silicon compound can also be used.
架橋剤である（Ｂ）成分としては、例えば、一般式：Ｒ８ ４−ｓＳｉＹｓ
（式中、Ｒ８は互いに同一でも異なっていてもよい置換または非置換の１価の炭化水素基を表し、Ｙは加水分解性基であるケトキシマト基を表す。またｓは、平均２を超え４以下の数である。）で表されるシランが使用される。ｓが２であるシランは、ｓが３または４であるシランと併用される。
As the component (B) that is a crosslinking agent, for example, a general formula: R 8 4-s SiY s
(Wherein R 8 represents a substituted or unsubstituted monovalent hydrocarbon group which may be the same as or different from each other, Y represents a ketoximato group which is a hydrolyzable group, and s exceeds 2 on average. A silane represented by the following formula is used. Silane in which s is 2 is used in combination with silane in which s is 3 or 4.
Ｒ８としては、前記（Ａ）成分のケイ素原子に直接結合した炭化水素基Ｒ５と同様な基を例示することができ、入手のしやすさと優れた架橋反応速度が得られることから、メチル基またはビニル基が好ましい。 Examples of R 8 include the same groups as the hydrocarbon group R 5 directly bonded to the silicon atom of the component (A), and the availability and the excellent crosslinking reaction rate are obtained. Group or vinyl group is preferred.
（Ｂ）成分である架橋剤としては、メチルトリス（メチルエチルケトキシマト）シラン、ビニルトリス（メチルエチルケトキシマト）シラン、フェニルトリス（メチルエチルケトキシマト）シランなどが例示され、これらの部分加水分解物も使用することができる。 Examples of the crosslinking agent as component (B) include methyltris (methylethylketoximato) silane, vinyltris (methylethylketoxymato) silane, phenyltris (methylethylketoxymato) silane, and the like, and these partial hydrolysates should also be used. Can do.
（Ｂ）成分である分子中に平均２個を超える数のケトキシマト基を有するケイ素化合物の配合量は、前記(Ａ)成分１００重量部に対して０．５〜２０重量部とする。(Ｂ)成分の配合量が０．５重量部未満では、十分な架橋がなされず、硬化物の強度が不十分になるばかりでなく、１液型（１成分型）の場合には貯蔵安定性が悪くなる。(Ｂ)成分の配合量が２０重量部を超えると、保存中に分離を生じたり、得られる硬化物がもろくなるなどの問題を生じやすくなるため好ましくない。 (B) The compounding quantity of the silicon compound which has an average of more than two ketoximato groups in the molecule | numerator which is a component shall be 0.5-20 weight part with respect to 100 weight part of said (A) component. If the blending amount of component (B) is less than 0.5 parts by weight, sufficient crosslinking will not be achieved, and the strength of the cured product will not be insufficient. Sexuality gets worse. If the blending amount of component (B) exceeds 20 parts by weight, problems such as separation during storage and brittleness of the resulting cured product tend to occur, such being undesirable.
本発明の実施形態において、（Ｃ）成分である無機充填剤は、組成物に粘稠性を付与するとともに硬化物に機械的強度を付与する働きをし、かつ難燃性を付与するものである。従来から公知のものを使用することができる。例えば、アルカリ土類金属塩、無機酸化物、金属水酸化物、カーボンブラックなどが挙げられる。 In the embodiment of the present invention, the inorganic filler as the component (C) functions to impart consistency to the composition and mechanical strength to the cured product, and to impart flame retardancy. is there. A conventionally well-known thing can be used. Examples thereof include alkaline earth metal salts, inorganic oxides, metal hydroxides, and carbon black.
アルカリ土類金属塩としては、カルシウム、マグネシウムまたはバリウムの炭酸塩、重炭酸塩および硫酸塩などが挙げられる。無機酸化物としては、煙霧質シリカ、焼成シリカ、沈澱シリカ、石英微粉末、酸化チタン、酸化鉄、酸化亜鉛などの金属酸化物、けいそう土、アルミナなどが挙げられる。金属水酸化物としては、水酸化アルミニウムなどが挙げられる。また、これらを、シラン類、シラザン類、低重合度シロキサン類または有機化合物により表面処理したものを用いてもよい。さらに、ガラスウール、微粉末マイカを使用することもでき、これらの充填剤を単独で、あるいは任意の混合物として添加する。 Examples of alkaline earth metal salts include calcium, magnesium or barium carbonates, bicarbonates and sulfates. Examples of inorganic oxides include fumed silica, calcined silica, precipitated silica, quartz fine powder, metal oxides such as titanium oxide, iron oxide, and zinc oxide, diatomaceous earth, and alumina. Examples of the metal hydroxide include aluminum hydroxide. Moreover, you may use what surface-treated these with silanes, silazanes, siloxanes with low polymerization degree, or an organic compound. Furthermore, glass wool and fine powder mica can be used, and these fillers are added alone or as an arbitrary mixture.
硬化物の難燃性および組成物の貯蔵安定性の観点から、炭酸亜鉛、炭酸マグネシウムのような金属炭酸塩、石英微粉末、酸化チタン、酸化亜鉛、酸化鉄のような金属酸化物、水酸化アルミニウムのような水酸化物の使用が好ましい。 From the viewpoint of flame retardancy of cured products and storage stability of the composition, metal carbonates such as zinc carbonate and magnesium carbonate, quartz fine powder, metal oxides such as titanium oxide, zinc oxide and iron oxide, hydroxylation The use of hydroxides such as aluminum is preferred.
特に、以下に示す物性を有する炭酸亜鉛を使用した場合には、難燃性に優れかつ接着性が良好な組成物が得られる。すなわち、加熱（例えば、熱重量測定（ＴＧ）における加熱）による重量減少率が３３〜３６％で、熱分解する際の炭酸ガス発生による重量減少率が３０〜３５％であり、化学式：ＺｎＣＯ３で表される純度の高い炭酸亜鉛の使用が好ましい。なお、ＴＧでは、炭酸亜鉛が１３０℃程度の温度から分解をはじめるため、室温（２５℃）から徐々に昇温して５００℃までの加熱を行い、このときの重量減少率が測定される。熱分解時に発生するガスは、ＧＣ−ＭＳを用いた定量法、および発生ガスをアルカリ性水溶液に溶解後、秤量するなどの重量法により測定される。 In particular, when zinc carbonate having the following physical properties is used, a composition having excellent flame retardancy and good adhesion can be obtained. That is, the weight reduction rate due to heating (for example, heating in thermogravimetry (TG)) is 33 to 36%, the weight reduction rate due to carbon dioxide generation during thermal decomposition is 30 to 35%, and the chemical formula: ZnCO 3 It is preferable to use zinc carbonate having a high purity represented by: In TG, since zinc carbonate begins to decompose from a temperature of about 130 ° C., the temperature is gradually raised from room temperature (25 ° C.) and heated to 500 ° C., and the weight loss rate at this time is measured. The gas generated during pyrolysis is measured by a quantitative method using GC-MS and a weight method such as weighing the dissolved gas in an aqueous alkaline solution.
一般に、シリコーンゴムの充填剤として配合される炭酸亜鉛は、湿式法により得られる塩基性炭酸亜鉛（透明性亜鉛白）であり、化学式：２ＺｎＣＯ３・３Ｚｎ（ＯＨ）２・Ｈ２Ｏで表される。このような炭酸亜鉛（塩基性炭酸亜鉛）では、ＴＧにおける重量減少率が２８％前後であり、熱分解時の炭酸ガス発生による重量減少率は１５〜１６％程度となる。これに対して、本発明の実施形態で使用が好ましい炭酸亜鉛は、ＴＧにおける重量減少率が３３〜３６％、より好ましくは３４〜３６％であり、熱分解時の炭酸ガス発生による重量減少率が３０〜３５％のものであり、単位重量当りの炭酸ガス発生量が多いものである。因みに、結晶水量および吸着水分量の目安となる１０５℃×３時間加熱条件における重量減量率は、０．１〜０．２重量％となる。また、低モジュラス品を得るためには、炭酸亜鉛の平均粒子径は、１．０〜１０μｍの範囲であることが望ましい。このような炭酸亜鉛は、平均粒子径がレーザー法（例えば、LASER MICRON SIZER 7000S使用）による測定で３．０〜８．０μｍ、フィシャー法（例えば、FISHER SUB-SIEVE SIZER使用）による測定で１．０〜５．０μｍのものが好ましい。また、一般的な石英粉や酸化チタン等の無機質充填材と比較し、粒子径が大きいこのような炭酸亜鉛を用いることにより、作業性の改善にもつながる。 In general, zinc carbonate blended as a filler for silicone rubber is basic zinc carbonate (transparent zinc white) obtained by a wet process, and is represented by the chemical formula: 2ZnCO 3 .3Zn (OH) 2 .H 2 O. The In such zinc carbonate (basic zinc carbonate), the weight reduction rate in TG is around 28%, and the weight reduction rate due to the generation of carbon dioxide during thermal decomposition is about 15 to 16%. On the other hand, the zinc carbonate preferably used in the embodiment of the present invention has a weight reduction rate of 33 to 36%, more preferably 34 to 36% in TG, and a weight reduction rate due to carbon dioxide generation during pyrolysis. Is 30 to 35%, and the amount of carbon dioxide generated per unit weight is large. Incidentally, the weight loss rate under heating conditions of 105 ° C. × 3 hours, which is a measure of the amount of water of crystallization and the amount of adsorbed water, is 0.1 to 0.2% by weight. In order to obtain a low modulus product, the average particle size of zinc carbonate is preferably in the range of 1.0 to 10 μm. Such zinc carbonate has an average particle size of 3.0 to 8.0 μm as measured by a laser method (for example, using LASER MICRON SIZER 7000S) and 1. 1 as measured by a Fischer method (for example, using FISHER SUB-SIEVE SIZER). The thing of 0-5.0 micrometers is preferable. In addition, use of such zinc carbonate having a larger particle diameter compared to general inorganic fillers such as quartz powder and titanium oxide also leads to improvement in workability.
(Ｃ)成分である無機充填剤の配合量は、前記(Ａ)成分１００重量部に対して１〜４００重量部とする。(Ｃ)無機充填剤の配合量が１重量部未満では、得られる硬化物の硬さ、引張強度などの機械的強度が著しく劣り、反対に４００重量部を超えると、良好なゴム弾性を有する硬化物を得ることが困難になるばかりでなく、組成物の粘度が増して作業が困難になる場合がある。 The amount of the inorganic filler as component (C) is 1 to 400 parts by weight per 100 parts by weight of component (A). (C) If the blending amount of the inorganic filler is less than 1 part by weight, the resulting cured product has extremely poor mechanical strength such as hardness and tensile strength. Conversely, if it exceeds 400 parts by weight, it has good rubber elasticity. Not only is it difficult to obtain a cured product, but the viscosity of the composition may increase and the operation may be difficult.
本発明の実施形態で使用される（Ｄ）アミノ基置換アルキル基を有するアルコキシシランは、一般式：（Ｒ１Ｏ）３−ｍＲ２ ｍＳｉ−Ｒ３………（１）で表される。式（１）中、Ｒ１は同一または相異なるアルキル基を示す。メチル基、エチル基、プロピル基、ブチル基、ヘキシル基などが例示されるが、メチル基が好ましい。Ｒ２も同一または相異なるアルキル基を示す。メチル基、エチル基、プロピル基、ブチル基、ヘキシル基などが例示されるが、メチル基が好ましい。ｍは０〜２の整数を示す。 Alkoxysilane having an implementation is used in the form (D) an amino group-substituted alkyl group of the present invention have the general formula: represented by (R 1 O) 3-m R 2 m Si-R 3 ......... (1) The In formula (1), R 1 represents the same or different alkyl groups. A methyl group, an ethyl group, a propyl group, a butyl group, a hexyl group and the like are exemplified, and a methyl group is preferable. R 2 also represents the same or different alkyl group. A methyl group, an ethyl group, a propyl group, a butyl group, a hexyl group and the like are exemplified, and a methyl group is preferable. m shows the integer of 0-2.
Ｒ３は、一般式：−（ＣＨ２）ｐ−ＣＨＲ４−（ＣＨ２）ｑ−ＮＨ２、または一般式：−（ＣＨ２）ｐ−Ｃ（Ｒ４）２−（ＣＨ２）ｑ−ＮＨ２で表される分岐を有するアミノ基置換アルキル基を示す。ここで、Ｒ４は炭素数１〜４のアルキル基を示し、メチル基またはエチル基が好ましく、メチル基がより好ましい。ｐおよびｑはそれぞれ１〜８の整数を示し、特にｑは１であることが好ましい。ただし、ｐ＋ｑは９以下の整数である。 R 3 represents a general formula: — (CH 2 ) p —CHR 4 — (CH 2 ) q —NH 2 , or a general formula: — (CH 2 ) p —C (R 4 ) 2 — (CH 2 ) q — An amino group-substituted alkyl group having a branch represented by NH 2 is shown. Here, R 4 represents an alkyl group having 1 to 4 carbon atoms, preferably a methyl group or an ethyl group, and more preferably a methyl group. p and q each represent an integer of 1 to 8, and q is preferably 1. However, p + q is an integer of 9 or less.
このようなＲ３として特に好ましいものは、式：−（ＣＨ２）２Ｃ（ＣＨ３）２ＣＨ２ＮＨ２で表される４−アミノ−３，３−ジメチルブチル基、または式：−（ＣＨ２）２ＣＨ（ＣＨ３）ＣＨ２ＮＨ２で表される４−アミノ−３−メチルブチル基である。 Particularly preferred as such R 3 is a 4-amino-3,3-dimethylbutyl group represented by the formula: — (CH 2 ) 2 C (CH 3 ) 2 CH 2 NH 2 , or the formula: — ( CH 2) a 2 CH (CH 3) 4- amino-3-methylbutyl group represented by CH 2 NH 2.
（Ｄ）成分であるアミノ基含有アルコキシシランは、前記した（Ａ）成分であるポリオルガノシロキサン１００重量部に対して０．０５〜１５重量部配合される。（Ｄ）アミノ基含有アルコキシシランの配合量が０．０５重量部未満では、良好な初期接着性が得られず、とりわけ低温時の接着発現性が低下し、また耐久性が不十分となる。また、１５重量部を超える場合には、保存中に容器内で液分離が生じたり、黄変を引き起こしたり、浸水などにより耐水接着性の低下が生じたりする。（Ｄ）成分であるアミノ基含有アルコキシシランの配合量のより好ましい範囲は、（Ａ）ポリオルガノシロキサン１００重量部に対して０．１〜１０重量部である。さらに、例えば夏期の屋外での作業など、高温多湿下での作業状況の中で十分な作業性を得るためには、０．１〜５重量部の範囲がより好ましい。 The amino group-containing alkoxysilane as the component (D) is blended in an amount of 0.05 to 15 parts by weight with respect to 100 parts by weight of the polyorganosiloxane as the component (A). (D) When the compounding amount of the amino group-containing alkoxysilane is less than 0.05 parts by weight, good initial adhesiveness cannot be obtained, and particularly, adhesion development at low temperatures is lowered and durability is insufficient. On the other hand, if the amount exceeds 15 parts by weight, liquid separation may occur in the container during storage, yellowing may occur, or water-resistant adhesiveness may deteriorate due to water immersion. (D) The more preferable range of the compounding quantity of the amino group containing alkoxysilane which is a component is 0.1-10 weight part with respect to 100 weight part of (A) polyorganosiloxane. Furthermore, in order to obtain sufficient workability in work conditions under high temperature and high humidity such as work outdoors in summer, the range of 0.1 to 5 parts by weight is more preferable.
本発明の実施形態に使用する（Ｅ）成分である硬化触媒は、（Ａ）成分の水酸基（ヒドロキシル基）および／または加水分解性基と、（Ｂ）成分の加水分解性基（ケトキシマト基）ならびに（Ｄ）成分の加水分解性基（アルコキシル基）との縮合反応を促進する触媒である。具体的には、オクタン酸鉄、ナフテン酸鉄、オクタン酸コバルト、ナフテン酸コバルト、オクタン酸スズ、ナフテン酸スズ、オクタン酸鉛、ナフテン酸鉛などの金属有機酸塩、ジブチルスズジアセテート、ジブチルスズジラウレート、ジブチルスズオクトエートなどのアルキルスズエステル化合物、ハロゲン化スズ化合物、スズオルトエステル化合物、テトラブチルチタネート、テトラブチルジルコネートなどの金属アルコレート、ジイソプロポキシビス（アセチルアセトナート）チタン、ジイソプロポキシビス（エチルアセトアセテート）チタンなどのチタンキレート化合物、ジエチルヒドロキシルアミン、ジメチルヒドロキシルアミン、γ−テトラメチルグアニジルプロピルトリメトキシシランなどのアミン類が例示される。これらは１種単独でも２種以上の混合物としても使用することができる。 The curing catalyst which is the component (E) used in the embodiment of the present invention includes a hydroxyl group (hydroxyl group) and / or a hydrolyzable group of the component (A) and a hydrolyzable group (ketoximato group) of the component (B). And a catalyst that promotes the condensation reaction with the hydrolyzable group (alkoxyl group) of component (D). Specifically, metal organic acid salts such as iron octoate, iron naphthenate, cobalt octoate, cobalt naphthenate, tin octoate, tin naphthenate, lead octoate, lead naphthenate, dibutyltin diacetate, dibutyltin dilaurate, Alkyl tin ester compounds such as dibutyltin octoate, tin halide compounds, tin orthoester compounds, metal alcoholates such as tetrabutyl titanate and tetrabutyl zirconate, diisopropoxybis (acetylacetonato) titanium, diisopropoxybis ( Examples include titanium chelate compounds such as ethyl acetoacetate) and amines such as diethylhydroxylamine, dimethylhydroxylamine, and γ-tetramethylguanidylpropyltrimethoxysilane. These can be used alone or as a mixture of two or more.
（Ｅ）成分である硬化触媒の配合量は、（Ａ）成分１００重量部に対して０．００１〜１０重量部とし、より好ましくは０．０２〜２重量部とする。（Ｅ）成分が０．００１重量部未満であると、硬化速度が遅すぎて実用に適さず、実施形態の組成物を空気中に曝露した場合にタックフリーの被膜形成に長時間を要し、かつゴム強度の発現性が悪化することがある。また、（Ｅ）成分の配合量が１０重量部を超えると、被膜形成時間が数秒間と極めて短くなるため、作業性が低下し、また耐熱性の低下などが生じることがある。 (E) The compounding quantity of the curing catalyst which is a component shall be 0.001-10 weight part with respect to 100 weight part of (A) component, More preferably, it shall be 0.02-2 weight part. When the component (E) is less than 0.001 part by weight, the curing rate is too slow to be suitable for practical use, and it takes a long time to form a tack-free film when the composition of the embodiment is exposed to the air. In addition, the developability of rubber strength may deteriorate. On the other hand, when the blending amount of the component (E) exceeds 10 parts by weight, the film formation time is extremely short as a few seconds, so that the workability is lowered and the heat resistance may be lowered.
実施形態の室温硬化性ポリオルガノシロキサン組成物には、硬化性や硬化後のゴム強度を調節するために、前記(Ｄ)成分とは異なるアルコキシシランを架橋剤として添加することができる。このようなアルコキシシランとしては、テトラメトキシシラン、テトラエトキシシラン、メチルセロソルブオルソシリケート、ｎ−プロピルオルソシリケートなどの４官能アルコキシシラン類；メチルトリメトキシシラン、メチルトリエトキシシラン、エチルトリメトキシシラン、ビニルトリメトキシシラン、フェニルトリメトキシシラン、メチルトリメトキシエトキシシランなどの３官能アルコキシシラン類、およびこれらの部分加水分解物などが挙げられる。 In the room temperature curable polyorganosiloxane composition of the embodiment, an alkoxysilane different from the component (D) can be added as a crosslinking agent in order to adjust curability and rubber strength after curing. Examples of such alkoxysilanes include tetrafunctional silanes such as tetramethoxysilane, tetraethoxysilane, methyl cellosolve orthosilicate, and n-propyl orthosilicate; methyltrimethoxysilane, methyltriethoxysilane, ethyltrimethoxysilane, vinyl Examples include trifunctional alkoxysilanes such as trimethoxysilane, phenyltrimethoxysilane, and methyltrimethoxyethoxysilane, and partial hydrolysates thereof.
また、実施形態の室温硬化性ポリオルガノシロキサン組成物には、浸水時の接着信頼性を高めるために、エポキシ基含有アルコキシシランをさらに配合することができる。エポキシ基含有アルコキシシランとしては、γ−グリシドキシプロピルトリメトキシシラン、γ−グリシドキシプロピルメチルジメトキシシラン、β−（３,４−エポキシシクロヘキシル）エチルトリメトキシシラン、β−（３,４−エポキシシクロヘキシル）エチルメチルジメトキシシランなどが例示される。 In addition, the room temperature curable polyorganosiloxane composition of the embodiment may further contain an epoxy group-containing alkoxysilane in order to increase the adhesion reliability during water immersion. Examples of the epoxy group-containing alkoxysilane include γ-glycidoxypropyltrimethoxysilane, γ-glycidoxypropylmethyldimethoxysilane, β- (3,4-epoxycyclohexyl) ethyltrimethoxysilane, β- (3,4- Epoxycyclohexyl) ethylmethyldimethoxysilane and the like are exemplified.
さらに、実施形態の組成物には、難燃性をいっそう向上させるために、白金系化合物またはその錯化合物を配合することができる。白金系化合物またはその錯化合物としては、塩化白金酸およびそれをアルコールまたはその他の溶媒で溶解した溶液、塩化白金酸のような白金化合物をエチレン、シクロオクタジエンまたはビニル基含有シロキサンと反応させたもの、亜リン酸トリフェニル白金錯体のように白金に配位子を配位させたものなどが例示される。このような白金系化合物またはその錯化合物の配合量は、（Ａ）成分１００重量部に対して、白金原子として１〜２０００ｐｐｍとなる量とすることが好ましい。またさらに、有機溶剤、末端トリメチルシロキシ化されたジポリオルガノシロキサンなどの希釈剤、可塑剤、チクソ性付与剤、顔料および染料などの着色剤、通常の接着促進剤、防カビ剤などを、必要に応じて添加することができる。 Furthermore, a platinum-based compound or a complex compound thereof can be added to the composition of the embodiment in order to further improve the flame retardancy. Platinum compounds or their complex compounds include chloroplatinic acid and solutions in which it is dissolved in alcohol or other solvents, and platinum compounds such as chloroplatinic acid reacted with ethylene, cyclooctadiene or vinyl group-containing siloxanes. Examples thereof include those in which a ligand is coordinated to platinum such as a triphenylplatinum phosphite complex. The blending amount of such a platinum compound or its complex compound is preferably set to an amount of 1 to 2000 ppm as platinum atoms with respect to 100 parts by weight of component (A). Furthermore, organic solvents, diluents such as terminal trimethylsiloxylated dipolyorganosiloxane, plasticizers, thixotropic agents, colorants such as pigments and dyes, ordinary adhesion promoters, fungicides, etc. are required It can be added depending on.
本発明の室温硬化性ポリオルガノシロキサン組成物は、（Ａ）〜（Ｅ）の各成分および前記したその他の成分の所定量を乾燥雰囲気中で均一に混合することにより、一液型の室温硬化性組成物として得られる。この組成物は、空気中に暴露すると湿分によって架橋反応を生起し、ゴム弾性体に硬化する。また、（Ａ）および（Ｃ）成分を含有して成る主剤と、（Ｂ）成分および（Ｄ）〜（Ｅ）成分を含有し、さらに必要に応じて（Ｆ）成分およびその他の成分を配合して成る硬化剤との二液型の室温硬化性組成物として調製することもできる。二液型の組成物においては、主剤と硬化剤を空気中で混合することにより、一液型の室温硬化性組成物と同様に硬化する。 The room temperature curable polyorganosiloxane composition of the present invention is a one-component room temperature curing by uniformly mixing the components (A) to (E) and the other components described above in a dry atmosphere. Obtained as a composition. When this composition is exposed to air, it causes a crosslinking reaction due to moisture and cures to a rubber elastic body. In addition, it contains a main ingredient containing the components (A) and (C), the components (B) and the components (D) to (E), and further contains the component (F) and other components as necessary. It can also be prepared as a two-component room temperature curable composition with a curing agent. In the two-pack type composition, the main agent and the curing agent are mixed in the air to be cured in the same manner as the one-pack type room temperature curable composition.
さらに、本発明の実施形態の組成物には、ベンガラおよび酸化セリウムなどの耐熱性向上剤、耐寒性向上剤、脱水剤、防錆剤、トリオルガノシロキサン単位およびＳｉＯ２単位からなる網状ポリシロキサンなどの液状補強剤を、必要に応じて所定量添加することができる。 Furthermore, the composition of the embodiment of the present invention includes a heat resistance improver such as Bengala and cerium oxide, a cold resistance improver, a dehydrating agent, a rust preventive, a reticulated polysiloxane composed of a triorganosiloxane unit and a SiO 2 unit. A predetermined amount of the liquid reinforcing agent can be added as necessary.
以下、実施例を挙げて本発明を具体的に説明するが、本発明は以下の実施例に限定されるものではない。なお、実施例中、「部」とあるのは「重量部」を示し、粘度は２３℃での測定値を示したものである。 EXAMPLES Hereinafter, although an Example is given and this invention is demonstrated concretely, this invention is not limited to a following example. In the examples, “parts” means “parts by weight”, and the viscosity is a value measured at 23 ° C.
実施例１
分子鎖両末端が水酸基で封鎖されたα,ω−ジヒドロキシジメチルポリシロキサン（粘度８０,０００ｍＰａ・s）８０部に、ビニルトリス（メチルエチルケトキシマト）シラン１．５部とメチルトリス（メチルエチルケトキシマト）シラン２．５部を、それぞれ配合して均一に混合した。次いで、フィシャー法により測定された平均粒子径（以下、単に平均粒子径と示す。）が４．０μｍの石英微粉末（商品名：クリスタライトVX-S：株式会社龍森製）１００部とカーボンブラック１０部をそれぞれ配合して均一に混合した後、さらにα,ω−ジヒドロキシジメチルポリシロキサン（粘度８０,０００ｍＰａ・s）２０部を加え、均一に混合した。
Example 1
80 parts of α, ω-dihydroxydimethylpolysiloxane (viscosity 80,000 mPa · s) blocked at both ends of the molecular chain with hydroxyl groups, 1.5 parts of vinyltris (methylethylketoxymato) silane and methyltris (methylethylketoxymato) silane 2 .5 parts were blended and mixed uniformly. Next, 100 parts of quartz fine powder (trade name: Crystallite VX-S: manufactured by Tatsumori Co., Ltd.) having an average particle diameter (hereinafter simply referred to as an average particle diameter) measured by the Fischer method of 4.0 μm and carbon After 10 parts of black were blended and mixed uniformly, 20 parts of α, ω-dihydroxydimethylpolysiloxane (viscosity 80,000 mPa · s) was further added and mixed uniformly.
次いで、この混合物に、硬化触媒であるジブチルスズジラウレート０．０８部、亜燐酸トリフェニル白金錯体溶液（亜燐酸トリフェニル０．１８部、塩化白金酸プロパノール溶液）１部を添加して混合した後、メチルケトオキシム1部、メチルトリス（メチルエチルケトキシマト）シラン３．３部、および４−アミノ−３，３−ジメチルブチルメチルジメトキシシラン１．２部をそれぞれ添加し、均一に混合することにより、ポリオルガノシロキサン組成物を得た。 Next, after adding 0.08 part of dibutyltin dilaurate as a curing catalyst and 1 part of triphenyl phosphite complex solution (0.18 part of triphenyl phosphite, chloroplatinic acid propanol solution) to the mixture, By adding 1 part of methyl ketoxime, 3.3 parts of methyltris (methylethylketoximato) silane, and 1.2 parts of 4-amino-3,3-dimethylbutylmethyldimethoxysilane, and mixing them uniformly, polyorgano A siloxane composition was obtained.
比較例１、２
実施例１の構成成分である４−アミノ−３，３−ジメチルブチルメチルジメトキシシラン１．２部の代わりに、γ−アミノプロピルメチルジメトキシシラン（商品名Silquest A-2100：モメンティブ・パフォーマンス・マテリアル・ジャパン合同会社製)１．２部（比較例１）、およびＮ−(β−アミノエチル)−アミノプロピルメチルジメトキシシラン（商品名Silquest A-2120：モメンティブ・パフォーマンス・マテリアル・ジャパン合同会社製)１．２部（比較例２）をそれぞれ使用した。それ以外は実施例１と同様にして、ポリオルガノシロキサン組成物を得た。
Comparative Examples 1 and 2
In place of 1.2 parts of 4-amino-3,3-dimethylbutylmethyldimethoxysilane which is a constituent of Example 1, γ-aminopropylmethyldimethoxysilane (trade name Silquest A-2100: Momentive Performance Material 1.2 parts (comparative example 1) and N- (β-aminoethyl) -aminopropylmethyldimethoxysilane (trade name Silquest A-2120: made by Momentive Performance Material Japan LLC) 1 .2 parts (comparative example 2) were used respectively. Other than that was carried out similarly to Example 1, and obtained the polyorganosiloxane composition.
実施例２
分子鎖両末端が水酸基で封鎖されたα,ω−ジヒドロキシジメチルポリシロキサン（粘度８０,０００ｍＰａ・s）８０部に、フェニルトリス（メチルエチルケトキシマト）シラン５．０部を配合し、均一に混合した。次いで、平均粒子径が４．０μｍの石英微粉末（商品名：クリスタライトVX-S）１００部とカーボンブラック１０部をそれぞれ配合して均一に混合した後、さらにα,ω−ジヒドロキシジメチルポリシロキサン（粘度８０,０００ｍＰａ・s）２０部を加え、均一に混合した。
Example 2
To 80 parts of α, ω-dihydroxydimethylpolysiloxane (viscosity 80,000 mPa · s) blocked at both ends of the molecular chain with a hydroxyl group, 5.0 parts of phenyltris (methylethylketoximato) silane was blended and mixed uniformly. . Next, 100 parts of quartz fine powder (trade name: Crystallite VX-S) having an average particle size of 4.0 μm and 10 parts of carbon black were blended and mixed uniformly, and then α, ω-dihydroxydimethylpolysiloxane. (Viscosity 80,000 mPa · s) 20 parts were added and mixed uniformly.
次いで、この混合物に、硬化触媒であるジブチルスズジラウレート０．０８部、亜燐酸トリフェニル白金錯体溶液（亜燐酸トリフェニル０．１８部、塩化白金酸プロパノール溶液）１部を添加して混合した後、フェニルトリス（メチルエチルケトキシマト）シラン３．５部、ｎ−オクチルトリエトキシシラン１部、および４−アミノ−３，３−ジメチルブチルメチルジメトキシシラン１．２部をそれぞれ添加し、均一に混合することにより、ポリオルガノシロキサン組成物を得た。 Next, after adding 0.08 part of dibutyltin dilaurate as a curing catalyst and 1 part of triphenyl phosphite complex solution (0.18 part of triphenyl phosphite, chloroplatinic acid propanol solution) to the mixture, Add 3.5 parts of phenyltris (methylethylketoximato) silane, 1 part of n-octyltriethoxysilane, and 1.2 parts of 4-amino-3,3-dimethylbutylmethyldimethoxysilane, and mix uniformly. Thus, a polyorganosiloxane composition was obtained.
比較例３、４
実施例２の構成成分である４−アミノ−３，３−ジメチルブチルメチルジメトキシシラン１．２部の代わりに、γ−アミノプロピルメチルジメトキシシラン（商品名Silquest A-2100)１．２部（比較例３）、およびＮ−(β−アミノエチル)−アミノプロピルメチルジメトキシシラン（商品名Silquest A-2120)１．２部（比較例４）をそれぞれ使用した。それ以外は実施例２と同様にして、ポリオルガノシロキサン組成物を得た。
Comparative Examples 3 and 4
Instead of 1.2 parts of 4-amino-3,3-dimethylbutylmethyldimethoxysilane which is a constituent of Example 2, 1.2 parts of γ-aminopropylmethyldimethoxysilane (trade name Silquest A-2100) (comparison) Example 3) and 1.2 parts of N- (β-aminoethyl) -aminopropylmethyldimethoxysilane (trade name Silquest A-2120) (Comparative Example 4) were used. Other than that was carried out similarly to Example 2, and obtained the polyorganosiloxane composition.
実施例３
分子鎖両末端が水酸基で封鎖されたα,ω−ジヒドロキシジメチルポリシロキサン（粘度８０,０００ｍＰａ・s）８０部に、フェニルトリス（メチルエチルケトキシマト）シラン５．０部を配合し、均一に混合した。次いで、平均粒径が４．０μｍの石英微粉末（商品名：クリスタライトVX-S）８０部と、平均粒子径が１.９１μｍの炭酸亜鉛（１０５℃×３時間加熱における重量減量率が０．０７％でＴＧでの重量減少率が３４．７％。炭酸ガス発生による重量減少率が３４％。）２０部、およびカーボンブラック１０部をそれぞれ配合し、均一に混合した後、さらにα,ω−ジヒドロキシジメチルポリシロキサン（粘度８０,０００ｍＰａ・s）２０部を加え、均一に混合した。
Example 3
To 80 parts of α, ω-dihydroxydimethylpolysiloxane (viscosity 80,000 mPa · s) blocked at both ends of the molecular chain with a hydroxyl group, 5.0 parts of phenyltris (methylethylketoximato) silane was blended and mixed uniformly. . Next, 80 parts of quartz fine powder (trade name: Crystallite VX-S) having an average particle diameter of 4.0 μm and zinc carbonate having an average particle diameter of 1.91 μm (the weight loss rate upon heating at 105 ° C. × 3 hours is 0) 0.07% and the weight loss rate by TG is 34.7% .The weight loss rate due to the generation of carbon dioxide gas is 34%.) 20 parts and 10 parts of carbon black were mixed and mixed uniformly. 20 parts of ω-dihydroxydimethylpolysiloxane (viscosity 80,000 mPa · s) was added and mixed uniformly.
次いで、この混合物に、硬化触媒であるジブチルスズジラウレート０．０８部、亜燐酸トリフェニル白金錯体溶液（亜燐酸トリフェニル０．１８部、塩化白金酸プロパノール溶液）１部を添加して混合した後、フェニルトリス（メチルエチルケトキシマト）シラン３．５部、ｎ−オクチルトリエトキシシラン１部、および４−アミノ−３，３−ジメチルブチルメチルジメトキシシラン１．２部をそれぞれ添加し、均一に混合することにより、ポリオルガノシロキサン組成物を得た。 Next, after adding 0.08 part of dibutyltin dilaurate as a curing catalyst and 1 part of triphenyl phosphite complex solution (0.18 part of triphenyl phosphite, chloroplatinic acid propanol solution) to the mixture, Add 3.5 parts of phenyltris (methylethylketoximato) silane, 1 part of n-octyltriethoxysilane, and 1.2 parts of 4-amino-3,3-dimethylbutylmethyldimethoxysilane, and mix uniformly. Thus, a polyorganosiloxane composition was obtained.
参考例４
分子鎖両末端が水酸基で封鎖されたα,ω−ジヒドロキシジメチルポリシロキサン（粘度２０,０００ｍＰａ・s）５０部と、片末端が水酸基で封鎖されたα−（トリメチルシリルオキシ）−ω−（ヒドロキシ）ジメチルシリルオキシ−ジメチルポリシロキサン（粘度１０,０００ｍＰａ・s）５０部との混合物に、平均粒径が４．０μｍの石英微粉末（商品名：クリスタライトVX-S）８０部と、平均粒子径が１.９１μｍの炭酸亜鉛（１０５℃×３時間加熱における重量減量率が０．０７％でＴＧでの重量減少率が３４．７％。炭酸ガス発生による重量減少率が３４％。）２０部をそれぞれ配合して均一に混合し、これを主剤とした。
Reference example 4
50 parts of α, ω-dihydroxydimethylpolysiloxane (viscosity 20,000 mPa · s) blocked at both ends of the molecular chain with a hydroxyl group, and α- (trimethylsilyloxy) -ω- (hydroxy) blocked at one end with a hydroxyl group A mixture of 50 parts of dimethylsilyloxy-dimethylpolysiloxane (viscosity 10,000 mPa · s), 80 parts of quartz fine powder (trade name: Crystallite VX-S) having an average particle diameter of 4.0 μm, and an average particle diameter 1.19 μm zinc carbonate (weight loss rate when heated at 105 ° C. for 3 hours is 0.07%, weight loss rate at TG is 34.7%, weight loss rate due to generation of carbon dioxide gas is 34%) 20 parts Were mixed and uniformly mixed, and this was used as the main agent.
また、両末端がビニルジメチルシリル基で封鎖されたα,ω−ビニルジメチルシリルジメチルポリシロキサン（粘度３，０００ｍＰａ・ｓ）４．４７５部に、カーボンブラック２．５部、フェニルトリス（メチルエチルケトキシマト）シラン２．０部、４−アミノ−３，３−ジメチルブチルメチルジメトキシシラン０．５部、γ−グリシドキシプロピルメチルジメトキシシラン１．０部、およびジブチルスズオキサイド０．０２５部をそれぞれ添加して混合し、これを硬化剤とした。そして、主剤と硬化剤を１０：１の重量比で混合し、ポリオルガノシロキサン組成物を得た。 In addition, 4.475 parts of α, ω-vinyldimethylsilyldimethylpolysiloxane (viscosity: 3,000 mPa · s) blocked at both ends with vinyldimethylsilyl groups, 2.5 parts of carbon black, phenyltris (methylethylketoximato ) 2.0 parts of silane, 0.5 parts of 4-amino-3,3-dimethylbutylmethyldimethoxysilane, 1.0 part of γ-glycidoxypropylmethyldimethoxysilane and 0.025 part of dibutyltin oxide were added respectively. And mixed to obtain a curing agent. And the main ingredient and the hardening | curing agent were mixed by the weight ratio of 10: 1, and the polyorganosiloxane composition was obtained.
次いで、実施例１〜３、参考例４および比較例１〜４でそれぞれ得られたポリオルガノシロキサン組成物について、指触乾燥時間、物理的特性、難燃性および接着性を、以下に示すようにして測定し評価した。 Next, with respect to the polyorganosiloxane compositions obtained in Examples 1 to 3, Reference Example 4 and Comparative Examples 1 to 4, the touch drying time, physical properties, flame retardancy and adhesiveness are as shown below. Was measured and evaluated.
（ａ）指触乾燥時間：組成物を２３℃、５０％ＲＨの雰囲気中に押し出した後、指で表面に接触して、乾燥状態にあることを確認するに至る時間を測定した。 (A) Drying time of finger touch: After extruding the composition in an atmosphere of 23 ° C. and 50% RH, the time to contact the surface with a finger and confirm that it was in a dry state was measured.
（ｂ）物理的特性：組成物を厚さ２ｍｍのシート状に押し出して得られたシートを、２３℃、５０％ＲＨで１６８時間放置し、空気中の湿気により硬化させた。そして、硬化物の物理的特性をＪＩＳ Ｋ ６３０１に拠り測定した。 (B) Physical properties: A sheet obtained by extruding the composition into a sheet having a thickness of 2 mm was allowed to stand at 23 ° C. and 50% RH for 168 hours, and cured by moisture in the air. And the physical characteristic of hardened | cured material was measured based on JISK6301.
（ｃ）難燃性：ＵＬ９４に準拠した方法により難燃性試験を行い、燃焼時間を測定した。 (C) Flame retardancy: A flame retardancy test was performed by a method based on UL94, and the burning time was measured.
（ｄ）接着性：表１に示す各被着体上に組成物を塗布し、２３℃、５０％ＲＨで１６８時間放置して空気中の湿気により硬化させた後、硬化物と被着体とを１８０°の方向に引張って剥離させ、その凝集破壊率を測定した。なお、被着体であるポリブチレンテレフタレート樹脂としては、ジュラネックス2012（ウィンテックポリマー株式会社製）を使用した。また、難燃性シリコーンゴムとしては、TSE2183U（モメンティブ・パフォーマンス・マテリアル・ジャパン合同会社製)を使用した。 (D) Adhesiveness: The composition was applied on each adherend shown in Table 1, and allowed to stand at 23 ° C. and 50% RH for 168 hours to be cured by moisture in the air, and then the cured product and the adherend. Were pulled and peeled in the direction of 180 °, and the cohesive failure rate was measured. In addition, as a polybutylene terephthalate resin which is an adherend, Duranex 2012 (manufactured by Wintech Polymer Co., Ltd.) was used. Moreover, TSE2183U (made by Momentive Performance Material Japan GK) was used as the flame retardant silicone rubber.
これらの結果を表１に示す。表中の略号は、Ｔmaxが最大引張応力、Ｅmaxが最大荷重時の伸びをそれぞれ表す。 These results are shown in Table 1. In the abbreviations in the table, Tmax represents maximum tensile stress, and Emax represents elongation at maximum load.
表１からわかるように、実施例１〜３で得られた硬化性ポリオルガノシロキサン組成物は、硬化性および接着性に優れている。また、硬化物が高伸張性を有するうえに、難燃性に優れている。 As can be seen from Table 1, the curable polyorganosiloxane compositions obtained in Examples 1 to 3 are excellent in curability and adhesiveness. In addition, the cured product has high extensibility and excellent flame retardancy.
本発明の室温硬化性ポリオルガノシロキサン組成物は、被着体に対して優れた接着性を有し、かつ硬化物が高伸張性で難燃性に優れているので、シーリング材や接着材料として有用である。 The room temperature curable polyorganosiloxane composition of the present invention has excellent adhesion to the adherend, and the cured product is highly extensible and excellent in flame retardancy. Useful.
Claims (4)
（Ｂ）分子中にケイ素官能基として平均２個を超える数のケトキシマト基を有するシランまたはその部分加水分解物０．５〜２０重量部と、
（Ｃ）無機充填剤１〜４００重量部と、
（Ｄ）一般式：（Ｒ１Ｏ）３−ｍＲ２ ｍＳｉ−Ｒ３………（１）
（式中、Ｒ１およびＲ２は同一または相異なるアルキル基を示す。ｍは０〜２の整数である。また、Ｒ３は、一般式：−（ＣＨ２）ｐ−ＣＨＲ４−（ＣＨ２）ｑ−ＮＨ２または
一般式：−（ＣＨ２）ｐ−Ｃ（Ｒ４）２−（ＣＨ２）ｑ−ＮＨ２
で表される分岐を有するアミノ基置換アルキル基を示す。ここで、Ｒ４は炭素数１〜４のアルキル基を示し、ｐおよびｑはそれぞれ１〜８の整数である。ただし、ｐ＋ｑは９以下の整数である。）で表されるアミノ基置換アルキル基を有するアルコキシシラン０．０５〜１５重量部と、
（Ｅ）硬化触媒０.００１〜１０重量部、および
難燃性添加剤として、（Ｆ）白金系化合物またはその錯化合物
をそれぞれ含むことを特徴とする室温硬化性ポリオルガノシロキサン組成物。 (A) 100 parts by weight of a polyorganosiloxane having a molecular chain terminal blocked with a hydroxyl group or a hydrolyzable group and having a viscosity at 23 ° C. of 20 to 1,000,000 mPa · s;
(B) 0.5 to 20 parts by weight of a silane having a ketoximato group having an average number of more than 2 as a silicon functional group in the molecule or a partial hydrolyzate thereof ,
(C) 1 to 400 parts by weight of an inorganic filler,
(D) the general formula: (R 1 O) 3- m R 2 m Si-R 3 ......... (1)
(In the formula, R 1 and R 2 represent the same or different alkyl groups. M is an integer of 0 to 2. Also, R 3 represents a general formula: — (CH 2 ) p —CHR 4 — (CH 2) q -NH 2 or the formula :-( CH 2) p -C (R 4) 2 - (CH 2) q -NH 2
The amino group substituted alkyl group which has the branch represented by these is shown. Here, R 4 represents an alkyl group having 1 to 4 carbon atoms, and p and q are each an integer of 1 to 8. However, p + q is an integer of 9 or less. 0.05 to 15 parts by weight of an alkoxysilane having an amino group-substituted alkyl group represented by :
(E) curing catalyst 0.001 to 10 parts by weight , and
A room temperature curable polyorganosiloxane composition comprising (F) a platinum compound or a complex compound thereof as a flame retardant additive .
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2007122657A JP4954785B2 (en) | 2007-05-07 | 2007-05-07 | Room temperature curable polyorganosiloxane composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2007122657A JP4954785B2 (en) | 2007-05-07 | 2007-05-07 | Room temperature curable polyorganosiloxane composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2008274189A JP2008274189A (en) | 2008-11-13 |
| JP4954785B2 true JP4954785B2 (en) | 2012-06-20 |
Family
ID=40052578
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007122657A Active JP4954785B2 (en) | 2007-05-07 | 2007-05-07 | Room temperature curable polyorganosiloxane composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP4954785B2 (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101357530B1 (en) * | 2007-12-19 | 2014-01-29 | 모멘티브 파포만스 마테리아루즈 쟈판 고도가이샤 | Room-temperature-curable polyorganosiloxane composition |
| JP5155024B2 (en) * | 2008-06-04 | 2013-02-27 | モメンティブ・パフォーマンス・マテリアルズ・ジャパン合同会社 | Room temperature curable silicone rubber composition |
| JP7006058B2 (en) * | 2017-09-12 | 2022-01-24 | 信越化学工業株式会社 | Sealing material and sealing method |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8419106D0 (en) * | 1984-07-26 | 1984-08-30 | Dow Corning Sa | Adhesion promoter |
| JP4149030B2 (en) * | 1998-05-15 | 2008-09-10 | モメンティブ・パフォーマンス・マテリアルズ・ジャパン合同会社 | Room temperature curable polyorganosiloxane composition |
| JP4137235B2 (en) * | 1998-07-01 | 2008-08-20 | モメンティブ・パフォーマンス・マテリアルズ・ジャパン合同会社 | Low specific gravity polyorganosiloxane composition |
| SE520169C2 (en) * | 1999-08-23 | 2003-06-03 | Sandvik Ab | Method for the manufacture of steel products of precipitated hardened martensitic steel, and the use of these steel products |
| US20050192387A1 (en) * | 2004-03-01 | 2005-09-01 | Williams David A. | RTV silicone composition offering rapid bond strength |
| JP2005255863A (en) * | 2004-03-12 | 2005-09-22 | Shin Etsu Chem Co Ltd | Flame-retardant silicone rubber composition |
| US8481668B2 (en) * | 2005-09-16 | 2013-07-09 | Momentive Performance Materials Inc. | Silane-containing adhesion promoter composition and sealants, adhesives and coatings containing same |
-
2007
- 2007-05-07 JP JP2007122657A patent/JP4954785B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| JP2008274189A (en) | 2008-11-13 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR101527231B1 (en) | Room temperature curable organopolysiloxane composition | |
| JP6092491B1 (en) | Room temperature curable polyorganosiloxane composition and preparation method thereof | |
| JP5068451B2 (en) | Room temperature curable polyorganosiloxane composition | |
| JP2010084062A (en) | Room temperature-curable organopolysiloxane composition | |
| JPS6262863A (en) | Room temperature curing polyorganosiloxane composition | |
| JP4864318B2 (en) | Room temperature curable polyorganosiloxane composition | |
| JP5008913B2 (en) | Room temperature curable polyorganosiloxane composition | |
| JP5009042B2 (en) | Room temperature curable polyorganosiloxane composition | |
| JP4954785B2 (en) | Room temperature curable polyorganosiloxane composition | |
| JP2010084063A (en) | Room temperature-curable organopolysiloxane composition | |
| JP2003119385A (en) | Room temperature-curing polyorganosiloxane composition | |
| JP5545924B2 (en) | Room temperature curable polyorganosiloxane composition | |
| JP2014218558A (en) | Room temperature curable polyorganosiloxane composition | |
| JP2008144042A (en) | Room temperature-curable organopolysiloxane composition | |
| JP2003128917A (en) | Room temperature curing polyorganosiloxane composition | |
| JP4085177B2 (en) | Room temperature curable polyorganosiloxane composition | |
| JP4183940B2 (en) | Room temperature curable polyorganosiloxane composition | |
| JP5548112B2 (en) | Room temperature curable organopolysiloxane composition | |
| JP3178998B2 (en) | Room temperature curable polyorganosiloxane composition | |
| JP2005213487A (en) | Room temperature-curing polyorganosiloxane composition | |
| JP5547037B2 (en) | Room temperature curable polyorganosiloxane composition | |
| JP6490367B2 (en) | Room temperature curable polyorganosiloxane composition | |
| JP2008144073A (en) | Room temperature-curable organopolysiloxane composition | |
| JP2002348476A (en) | Room temperature curable polyorganosiloxane composition | |
| JP5734567B2 (en) | Room temperature curable polyorganosiloxane composition |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20100326 |
|
| A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20111222 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20111227 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20120227 |
|
| TRDD | Decision of grant or rejection written | ||
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20120313 |
|
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20120314 |
|
| R150 | Certificate of patent or registration of utility model |
Free format text: JAPANESE INTERMEDIATE CODE: R150 Ref document number: 4954785 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20150323 Year of fee payment: 3 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |