WO2021002163A1 - Organopolysiloxane compound, composition comprising said compound, and method for preparing same - Google Patents
Organopolysiloxane compound, composition comprising said compound, and method for preparing same Download PDFInfo
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- WO2021002163A1 WO2021002163A1 PCT/JP2020/022790 JP2020022790W WO2021002163A1 WO 2021002163 A1 WO2021002163 A1 WO 2021002163A1 JP 2020022790 W JP2020022790 W JP 2020022790W WO 2021002163 A1 WO2021002163 A1 WO 2021002163A1
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- 229920001296 polysiloxane Polymers 0.000 title claims abstract description 64
- 239000000203 mixture Substances 0.000 title claims abstract description 61
- 150000001875 compounds Chemical class 0.000 title claims abstract description 52
- 238000000034 method Methods 0.000 title description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 35
- 125000003277 amino group Chemical group 0.000 claims abstract description 19
- 229920005645 diorganopolysiloxane polymer Polymers 0.000 claims abstract description 17
- 125000000547 substituted alkyl group Chemical group 0.000 claims abstract description 12
- 125000003107 substituted aryl group Chemical group 0.000 claims abstract description 12
- 125000005372 silanol group Chemical group 0.000 claims abstract description 10
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims abstract description 10
- -1 organosilane compound Chemical class 0.000 claims description 46
- 238000006482 condensation reaction Methods 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 239000003054 catalyst Substances 0.000 claims description 9
- 239000011248 coating agent Substances 0.000 claims description 9
- 239000000853 adhesive Substances 0.000 claims description 8
- 230000001070 adhesive effect Effects 0.000 claims description 8
- 238000007789 sealing Methods 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical group [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 239000000565 sealant Substances 0.000 claims description 5
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims description 2
- 229920001971 elastomer Polymers 0.000 abstract description 9
- 239000004970 Chain extender Substances 0.000 abstract 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 20
- 230000001588 bifunctional effect Effects 0.000 description 16
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 12
- 229910052710 silicon Inorganic materials 0.000 description 12
- 238000001723 curing Methods 0.000 description 8
- 239000011521 glass Substances 0.000 description 8
- 239000000377 silicon dioxide Substances 0.000 description 8
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 7
- 239000004606 Fillers/Extenders Substances 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 230000009257 reactivity Effects 0.000 description 7
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 6
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 229940125904 compound 1 Drugs 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 239000002994 raw material Substances 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 229920005601 base polymer Polymers 0.000 description 5
- 239000003431 cross linking reagent Substances 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 239000010703 silicon Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- HGQSXVKHVMGQRG-UHFFFAOYSA-N dioctyltin Chemical compound CCCCCCCC[Sn]CCCCCCCC HGQSXVKHVMGQRG-UHFFFAOYSA-N 0.000 description 4
- 230000008034 disappearance Effects 0.000 description 4
- 239000000945 filler Substances 0.000 description 4
- 238000004817 gas chromatography Methods 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 150000004756 silanes Chemical class 0.000 description 4
- 230000008719 thickening Effects 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- XQBCVRSTVUHIGH-UHFFFAOYSA-L [dodecanoyloxy(dioctyl)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCCCCCC)(CCCCCCCC)OC(=O)CCCCCCCCCCC XQBCVRSTVUHIGH-UHFFFAOYSA-L 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 229910000019 calcium carbonate Inorganic materials 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 3
- 239000003365 glass fiber Substances 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 125000004430 oxygen atom Chemical group O* 0.000 description 3
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 2
- ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 description 2
- NOGBEXBVDOCGDB-NRFIWDAESA-L (z)-4-ethoxy-4-oxobut-2-en-2-olate;propan-2-olate;titanium(4+) Chemical compound [Ti+4].CC(C)[O-].CC(C)[O-].CCOC(=O)\C=C(\C)[O-].CCOC(=O)\C=C(\C)[O-] NOGBEXBVDOCGDB-NRFIWDAESA-L 0.000 description 2
- ZYAASQNKCWTPKI-UHFFFAOYSA-N 3-[dimethoxy(methyl)silyl]propan-1-amine Chemical compound CO[Si](C)(OC)CCCN ZYAASQNKCWTPKI-UHFFFAOYSA-N 0.000 description 2
- TZZGHGKTHXIOMN-UHFFFAOYSA-N 3-trimethoxysilyl-n-(3-trimethoxysilylpropyl)propan-1-amine Chemical compound CO[Si](OC)(OC)CCCNCCC[Si](OC)(OC)OC TZZGHGKTHXIOMN-UHFFFAOYSA-N 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 2
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- 239000006087 Silane Coupling Agent Substances 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- 229910021536 Zeolite Inorganic materials 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 125000005370 alkoxysilyl group Chemical group 0.000 description 2
- 150000001412 amines Chemical group 0.000 description 2
- XYBQTTAROZGWOZ-UHFFFAOYSA-N bis[[hydroxy(dimethyl)silyl]oxy]-dimethylsilane Chemical compound C[Si](C)(O)O[Si](C)(C)O[Si](C)(C)O XYBQTTAROZGWOZ-UHFFFAOYSA-N 0.000 description 2
- 125000006309 butyl amino group Chemical group 0.000 description 2
- 239000013522 chelant Substances 0.000 description 2
- 229920006026 co-polymeric resin Polymers 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
- 229940126214 compound 3 Drugs 0.000 description 2
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 2
- 239000000806 elastomer Substances 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- CWAFVXWRGIEBPL-UHFFFAOYSA-N ethoxysilane Chemical compound CCO[SiH3] CWAFVXWRGIEBPL-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000011049 filling Methods 0.000 description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 description 2
- 239000011256 inorganic filler Substances 0.000 description 2
- 229910003475 inorganic filler Inorganic materials 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- HZGIOLNCNORPKR-UHFFFAOYSA-N n,n'-bis(3-trimethoxysilylpropyl)ethane-1,2-diamine Chemical compound CO[Si](OC)(OC)CCCNCCNCCC[Si](OC)(OC)OC HZGIOLNCNORPKR-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 125000004193 piperazinyl group Chemical group 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 229920000915 polyvinyl chloride Polymers 0.000 description 2
- 239000004800 polyvinyl chloride Substances 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 238000011085 pressure filtration Methods 0.000 description 2
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
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- 239000011342 resin composition Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229910000077 silane Inorganic materials 0.000 description 2
- 150000003377 silicon compounds Chemical class 0.000 description 2
- 229920005573 silicon-containing polymer Polymers 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000001302 tertiary amino group Chemical group 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 2
- 239000010457 zeolite Substances 0.000 description 2
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
- KYVBNYUBXIEUFW-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine Chemical compound CN(C)C(=N)N(C)C KYVBNYUBXIEUFW-UHFFFAOYSA-N 0.000 description 1
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
- NZZYRBJEGRIYIF-UHFFFAOYSA-N 1-propan-2-yloxyoctane-1,8-diol;titanium Chemical compound [Ti].CC(C)OC(O)CCCCCCCO NZZYRBJEGRIYIF-UHFFFAOYSA-N 0.000 description 1
- KTXWGMUMDPYXNN-UHFFFAOYSA-N 2-ethylhexan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCCC(CC)C[O-].CCCCC(CC)C[O-].CCCCC(CC)C[O-].CCCCC(CC)C[O-] KTXWGMUMDPYXNN-UHFFFAOYSA-N 0.000 description 1
- YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 1
- HXLAEGYMDGUSBD-UHFFFAOYSA-N 3-[diethoxy(methyl)silyl]propan-1-amine Chemical compound CCO[Si](C)(OCC)CCCN HXLAEGYMDGUSBD-UHFFFAOYSA-N 0.000 description 1
- RWLDCNACDPTRMY-UHFFFAOYSA-N 3-triethoxysilyl-n-(3-triethoxysilylpropyl)propan-1-amine Chemical compound CCO[Si](OCC)(OCC)CCCNCCC[Si](OCC)(OCC)OCC RWLDCNACDPTRMY-UHFFFAOYSA-N 0.000 description 1
- LLLVZDVNHNWSDS-UHFFFAOYSA-N 4-methylidene-3,5-dioxabicyclo[5.2.2]undeca-1(9),7,10-triene-2,6-dione Chemical compound C1(C2=CC=C(C(=O)OC(=C)O1)C=C2)=O LLLVZDVNHNWSDS-UHFFFAOYSA-N 0.000 description 1
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- 229920000178 Acrylic resin Polymers 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- OQZWTNCZFSIMRF-UHFFFAOYSA-K C1(C(C(CC=C1)C)C)C(=O)[O-].[Al+3].C1(C(C(CC=C1)C)C)C(=O)[O-].C1(C(C(CC=C1)C)C)C(=O)[O-] Chemical compound C1(C(C(CC=C1)C)C)C(=O)[O-].[Al+3].C1(C(C(CC=C1)C)C)C(=O)[O-].C1(C(C(CC=C1)C)C)C(=O)[O-] OQZWTNCZFSIMRF-UHFFFAOYSA-K 0.000 description 1
- 229920000049 Carbon (fiber) Polymers 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-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
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- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 1
- 101100489867 Mus musculus Got2 gene Proteins 0.000 description 1
- PMDCZENCAXMSOU-UHFFFAOYSA-N N-ethylacetamide Chemical group CCNC(C)=O PMDCZENCAXMSOU-UHFFFAOYSA-N 0.000 description 1
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- 229910004298 SiO 2 Inorganic materials 0.000 description 1
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- FMRLDPWIRHBCCC-UHFFFAOYSA-L Zinc carbonate Chemical compound [Zn+2].[O-]C([O-])=O FMRLDPWIRHBCCC-UHFFFAOYSA-L 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
- NOZAQBYNLKNDRT-UHFFFAOYSA-N [diacetyloxy(ethenyl)silyl] acetate Chemical class CC(=O)O[Si](OC(C)=O)(OC(C)=O)C=C NOZAQBYNLKNDRT-UHFFFAOYSA-N 0.000 description 1
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- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- 125000005595 acetylacetonate group Chemical group 0.000 description 1
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- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 125000002344 aminooxy group Chemical group [H]N([H])O[*] 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
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- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
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- 229910052794 bromium Inorganic materials 0.000 description 1
- MAYCNCJAIFGQIH-UHFFFAOYSA-N buta-1,3-diene 5-phenylpenta-2,4-dienenitrile Chemical compound C=CC=C.N#CC=CC=CC1=CC=CC=C1 MAYCNCJAIFGQIH-UHFFFAOYSA-N 0.000 description 1
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- QAEKNCDIHIGLFI-UHFFFAOYSA-L cobalt(2+);2-ethylhexanoate Chemical compound [Co+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O QAEKNCDIHIGLFI-UHFFFAOYSA-L 0.000 description 1
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- 229910052802 copper Inorganic materials 0.000 description 1
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- 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
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 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
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000009615 deamination Effects 0.000 description 1
- 238000006481 deamination reaction Methods 0.000 description 1
- JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 description 1
- 125000004915 dibutylamino group Chemical group C(CCC)N(CCCC)* 0.000 description 1
- AYOHIQLKSOJJQH-UHFFFAOYSA-N dibutyltin Chemical compound CCCC[Sn]CCCC AYOHIQLKSOJJQH-UHFFFAOYSA-N 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- FVCOIAYSJZGECG-UHFFFAOYSA-N diethylhydroxylamine Chemical compound CCN(O)CC FVCOIAYSJZGECG-UHFFFAOYSA-N 0.000 description 1
- JJQZDUKDJDQPMQ-UHFFFAOYSA-N dimethoxy(dimethyl)silane Chemical compound CO[Si](C)(C)OC JJQZDUKDJDQPMQ-UHFFFAOYSA-N 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- LQRUPWUPINJLMU-UHFFFAOYSA-N dioctyl(oxo)tin Chemical compound CCCCCCCC[Sn](=O)CCCCCCCC LQRUPWUPINJLMU-UHFFFAOYSA-N 0.000 description 1
- 125000004914 dipropylamino group Chemical group C(CC)N(CCC)* 0.000 description 1
- VEVVRTWXUIWDAW-UHFFFAOYSA-N dodecan-1-amine;phosphoric acid Chemical compound OP(O)(O)=O.CCCCCCCCCCCCN VEVVRTWXUIWDAW-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003822 epoxy resin Substances 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
- ZLNAFSPCNATQPQ-UHFFFAOYSA-N ethenyl-dimethoxy-methylsilane Chemical compound CO[Si](C)(OC)C=C ZLNAFSPCNATQPQ-UHFFFAOYSA-N 0.000 description 1
- GBFVZTUQONJGSL-UHFFFAOYSA-N ethenyl-tris(prop-1-en-2-yloxy)silane Chemical compound CC(=C)O[Si](OC(C)=C)(OC(C)=C)C=C GBFVZTUQONJGSL-UHFFFAOYSA-N 0.000 description 1
- DSFYFPPKESVKQE-UHFFFAOYSA-N ethyl-tris(prop-1-en-2-yloxy)silane Chemical compound CC(=C)O[Si](CC)(OC(C)=C)OC(C)=C DSFYFPPKESVKQE-UHFFFAOYSA-N 0.000 description 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
- 125000003916 ethylene diamine group Chemical group 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000002316 fumigant Substances 0.000 description 1
- 239000005350 fused silica glass Substances 0.000 description 1
- 239000011491 glass wool Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical group NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 1
- 125000001245 hexylamino group Chemical group [H]N([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000006316 iso-butyl amino group Chemical group [H]N(*)C([H])([H])C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000007788 liquid 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
- 150000002736 metal compounds Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- ZWXYOPPJTRVTST-UHFFFAOYSA-N methyl-tris(prop-1-en-2-yloxy)silane Chemical compound CC(=C)O[Si](C)(OC(C)=C)OC(C)=C ZWXYOPPJTRVTST-UHFFFAOYSA-N 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 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
- YLBPOJLDZXHVRR-UHFFFAOYSA-N n'-[3-[diethoxy(methyl)silyl]propyl]ethane-1,2-diamine Chemical compound CCO[Si](C)(OCC)CCCNCCN YLBPOJLDZXHVRR-UHFFFAOYSA-N 0.000 description 1
- QMIREOCYHAFOPK-UHFFFAOYSA-N n,n'-bis(3-triethoxysilylpropyl)ethane-1,2-diamine Chemical compound CCO[Si](OCC)(OCC)CCCNCCNCCC[Si](OCC)(OCC)OCC QMIREOCYHAFOPK-UHFFFAOYSA-N 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
- YGHWXXSYVWPXHA-UHFFFAOYSA-N n-[[dimethoxy(methyl)silyl]methyl]-n-ethylethanamine Chemical compound CCN(CC)C[Si](C)(OC)OC YGHWXXSYVWPXHA-UHFFFAOYSA-N 0.000 description 1
- GKTNLYAAZKKMTQ-UHFFFAOYSA-N n-[bis(dimethylamino)phosphinimyl]-n-methylmethanamine Chemical compound CN(C)P(=N)(N(C)C)N(C)C GKTNLYAAZKKMTQ-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl 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])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- OHLUUHNLEMFGTQ-AZXPZELESA-N n-methylacetamide Chemical group C[15NH]C(C)=O OHLUUHNLEMFGTQ-AZXPZELESA-N 0.000 description 1
- NCCHARWOCKOHIH-UHFFFAOYSA-N n-methylbenzamide Chemical group CNC(=O)C1=CC=CC=C1 NCCHARWOCKOHIH-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 125000004894 pentylamino group Chemical group C(CCCC)N* 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- XGIZTLFJCDBRDD-UHFFFAOYSA-N phenyl-tris(prop-1-en-2-yloxy)silane Chemical group CC(=C)O[Si](OC(C)=C)(OC(C)=C)C1=CC=CC=C1 XGIZTLFJCDBRDD-UHFFFAOYSA-N 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229920001707 polybutylene terephthalate Polymers 0.000 description 1
- 229920005668 polycarbonate resin Polymers 0.000 description 1
- 239000004431 polycarbonate resin Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920013716 polyethylene resin Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 239000009719 polyimide resin Substances 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920001955 polyphenylene ether Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920005990 polystyrene resin Polymers 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- SCUZVMOVTVSBLE-UHFFFAOYSA-N prop-2-enenitrile;styrene Chemical compound C=CC#N.C=CC1=CC=CC=C1 SCUZVMOVTVSBLE-UHFFFAOYSA-N 0.000 description 1
- 125000006308 propyl amino group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000012508 resin bead Substances 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- UQMGAWUIVYDWBP-UHFFFAOYSA-N silyl acetate Chemical class CC(=O)O[SiH3] UQMGAWUIVYDWBP-UHFFFAOYSA-N 0.000 description 1
- 239000010454 slate Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- WSFQLUVWDKCYSW-UHFFFAOYSA-M sodium;2-hydroxy-3-morpholin-4-ylpropane-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)CC(O)CN1CCOCC1 WSFQLUVWDKCYSW-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000006318 tert-butyl amino group Chemical group [H]N(*)C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- 150000003608 titanium Chemical class 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 150000004992 toluidines Chemical group 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 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
- QLNOVKKVHFRGMA-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical group [CH2]CC[Si](OC)(OC)OC QLNOVKKVHFRGMA-UHFFFAOYSA-N 0.000 description 1
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
- IXSPLXSQNNZJJU-UHFFFAOYSA-N trimethyl(silyloxy)silane Chemical compound C[Si](C)(C)O[SiH3] IXSPLXSQNNZJJU-UHFFFAOYSA-N 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- 239000011667 zinc carbonate Substances 0.000 description 1
- 229910000010 zinc carbonate Inorganic materials 0.000 description 1
- 235000004416 zinc carbonate Nutrition 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
- C08L83/06—Polysiloxanes containing silicon bound to oxygen-containing groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
- C08L83/08—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
- C09D183/04—Polysiloxanes
- C09D183/08—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen, and oxygen
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J183/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Adhesives based on derivatives of such polymers
- C09J183/04—Polysiloxanes
- C09J183/08—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen, and oxygen
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
- C09K3/10—Materials in mouldable or extrudable form for sealing or packing joints or covers
Definitions
- the present invention relates to an organopolysiloxane compound and a method for producing the same, and more specifically, as a silicon-containing group (hereinafter, also referred to as “reactive silicon-containing group”) that can be increased in molecular weight by forming a siloxane bond.
- the present invention relates to a bifunctional organopolysiloxane compound having one monoorganooxy group such as a monoalkoxy group bonded to a silicon atom at the end of each molecular chain (that is, two in the molecule) and a method for producing the same.
- the reactive silicon-containing group particularly the hydrolyzable silyl group
- the polymer having this reactive silicon-containing group is in the presence of water or moisture. It can be used for a curable composition that is cross-linked and cured.
- silicone polymers those having a silicon-containing structure (particularly preferably a linear, organopolysiloxane structure) in the main chain are generally known as silicone polymers.
- a room temperature curable (RTV) organopolysiloxane composition using these as a main agent (base polymer) is liquid at room temperature (23 ° C ⁇ 10 ° C) and becomes a rubber elastic body (elastomer) by curing (crosslinking reaction). It has characteristics and is widely used in coating agents, adhesives, building sealants, etc. by utilizing these characteristics.
- a silane coupling agent In these room temperature curable (RTV) resin compositions, a silane coupling agent, a partially hydrolyzed condensate thereof, or the like is used as a cross-linking agent and a stabilizer.
- a bifunctional silane coupling agent having two hydrolyzable groups in the molecule is called a chain length extender among cross-linking agents, and by extending the chain length of a silicone polymer, it can be used as a sealant or an RTV rubber cured product. Gives moderate elongation.
- RTV room temperature curable organopolysiloxane compositions
- the de-alcohol type which releases alcohol and cures by condensation reaction during cross-linking, has no unpleasant odor and does not corrode metals, so it is suitable for sealing, bonding, and coating of electrical and electronic equipment.
- the de-alcohol type has lower reactivity with water (moisture) in the air than other conventionally known hardening types such as deacetone type, deoxime type, and deamination type. Due to the slow curing rate, no organopolysiloxane compound was an industrially viable dealcohol-type room temperature curable (RTV) composition chain length extender.
- RTV room temperature curable
- the present invention provides an organopolysiloxane compound that serves as a chain length extender for an industrially practical dealcohol-type room temperature curable (RTV) composition that rapidly rubberizes and exhibits rubber elasticity. With the goal.
- RTV room temperature curable
- organooxy groups such as an alkoxy group bonded to a silicon atom at the end of the molecular chain represented by the following general formula (1) in each molecular chain.
- a methylene group having one terminal that is, two mono (organooxy) silyl groups in the molecule
- the present invention has been completed by finding that a bifunctional organopolysiloxane compound having a specific molecular structure having (that is, an ⁇ -amino group and / or an ⁇ -amine residue) is useful for solving the above-mentioned problems. did.
- the present invention relates to the following organopolysiloxane compound, a composition containing the compound, a coating agent composed of the composition, an adhesive and a sealing agent, an article having a cured product of the composition, a method for producing the compound, and the like.
- I will provide a.
- R 1 , R 2 and R 3 are unsubstituted or substituted alkyl groups having 1 to 10 carbon atoms or unsubstituted or substituted aryl groups having 6 to 10 carbon atoms independently of each other.
- n is an integer from 0 to 10
- X is an unsubstituted or substituted amino group.
- a method for producing an organopolysiloxane compound represented by the following general formula (1)' which comprises a step of subjecting an organosilane compound represented by the following general formula (2) to a condensation reaction in the presence of a catalyst to dimerize the compound.
- R 2 and R 3 are unsubstituted or substituted alkyl groups having 1 to 10 carbon atoms, or unsubstituted or substituted aryl groups having 6 to 10 carbon atoms, and X is non-substituted or substituted. Substituted or substituted amino group.)
- R 1 , R 2 and R 3 are independently unsubstituted or substituted alkyl groups having 1 to 10 carbon atoms, or unsubstituted or substituted aryl groups having 6 to 10 carbon atoms.
- X is an unsubstituted or substituted amino group.
- Silanol group-blocking diorganopolysiloxane at both ends of the molecular chain represented by the following general formula (3) and an organosilane compound represented by the following general formula (2) are subjected to a condensation reaction to block silanol groups at both ends of the molecular chain.
- a method for producing an organopolysiloxane compound represented by the following general formula (1)'' which comprises a step of sealing both ends of the molecular chain of the siloxane with a residue of the organosilane compound represented by the following general formula (2).
- R 1 is an alkyl group having 1 to 10 carbon atoms unsubstituted or substituted independently of each other, or an aryl group having 6 to 10 carbon atoms substituted or substituted, and n is an integer of 1 to 10. .
- R 2 and R 3 are unsubstituted or substituted alkyl groups having 1 to 10 carbon atoms, or unsubstituted or substituted aryl groups having 6 to 10 carbon atoms, and X is non-substituted or substituted.
- R 1 , R 2 and R 3 are independently unsubstituted or substituted alkyl groups having 1 to 10 carbon atoms, or unsubstituted or substituted aryl groups having 6 to 10 carbon atoms.
- n is an integer from 1 to 10
- X is an unsubstituted or substituted amino group.
- the organopolysiloxane compound of the present invention has excellent reactivity even in a dealcohol type condensation reaction. Further, a room temperature curable (RTV) organopolysiloxane composition containing such an organopolysiloxane compound as a chain length extender quickly rubberizes due to humidity in the air even at room temperature and exhibits rubber elasticity. It can be suitably used for applications such as adhesives and sealants.
- RTV room temperature curable
- the organopolysiloxane compound according to the present invention has one organooxy group bonded to a silicon atom at the end of the molecular chain represented by the following general formula (1) (one at the end of each molecular chain (1). That is, a methylene group (that is, ⁇ -amino) having a mono (organooxy) silyl group (two in the molecule) and substituted with an amino group and / or an amine residue on each silicon atom at the end of the molecular chain. It is a bifunctional organopolysiloxane compound having a specific molecular structure and having a group and / or an ⁇ -amine residue).
- R 1 , R 2 and R 3 independently represent an unsubstituted or substituted alkyl group having 1 to 10 carbon atoms, or an unsubstituted or substituted aryl group having 6 to 10 carbon atoms.
- the alkyl group having 1 to 10 carbon atoms may be linear, cyclic or branched, and specific examples thereof include methyl, ethyl and n-propyl.
- Alkyl groups Cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, isobornyl groups and the like can be mentioned.
- aryl group having 6 to 10 carbon atoms include phenyl, tolyl, xsilyl, ⁇ -naphthyl, ⁇ -naphthyl group and the like.
- a part or all of the hydrogen atoms of these groups may be substituted with halogen atoms such as alkyl groups, aryl groups, F, Cl and Br, cyano groups and the like, and among these, R 1 , R As 2 and R 3 , a methyl group, an ethyl group, and a phenyl group are preferable, and a methyl group is more preferable from the viewpoints of reactivity, availability, productivity, and cost.
- X is an unsubstituted or substituted amino group, preferably a secondary or tertiary amino group (for example, a monoorgano-substituted amino group or a diorgano-substituted amino group), and a tertiary amino group (for example,).
- Diorgano-substituted amino group is more preferable, and specific examples thereof include methylamino group, dimethylamino group, ethylamino group, diethylamino group, propylamino group, isopropylamino group, dipropylamino group, diisopropylamino group and butylamino.
- those having a small number of carbon atoms such as a dimethylamino group, a diethylamino group, a pyrrolidine residue, and a piperazine residue and which are easily reacted during synthesis are preferable.
- n represents an integer of 0 to 10.
- n represents an integer of 0 to 3.
- Integers are preferred.
- An amino group is introduced at the position, and a bifunctional ⁇ -amino group-containing hydrolyzable organosilane compound having two organooxy groups such as an alkoxysilyl group in the molecule is subjected to a condensation reaction in the presence of a catalyst such as a hydrochloric acid catalyst. It can be obtained by quantifying it.
- the organosilane compound represented by the above general formula (2) are subjected to a condensation reaction to form both ends of the molecular chain of the silanol group-blocking diorganopolysiloxane represented by the above general formula (2). It can be obtained by sealing with a residue of the silane compound.
- a catalyst is used as necessary. May be good.
- R 1 is an alkyl group having 1 to 10 carbon atoms unsubstituted or substituted independently of each other, or an aryl group having 6 to 10 carbon atoms substituted or substituted, and n is an integer of 1 to 10. .
- the bifunctional organopolysiloxane compound of the present invention is mainly composed of a linear diorganopolysiloxane having both ends of the molecular chain sealed with a silanol group or a hydrolyzable silyl group.
- base polymer particularly a dealcohol type room temperature curable (RTV) organopolysiloxane composition
- RTV room temperature curable
- the room temperature curable (RTV) organopolysiloxane composition containing the bifunctional organopolysiloxane compound rapidly condenses with moisture in the atmosphere even at room temperature to have rubber elasticity and excellent extensibility.
- An elastic body elastomer
- the composition of the present invention can be suitably used for applications such as coating agents, adhesives, and sealing agents.
- Articles using the coating agent, adhesive and sealing agent of the present invention include epoxy resin, phenol resin, polyimide resin, polycarbonate resin such as polycarbonate and polycarbonate blend, acrylic resin such as poly (methyl methacrylate), and poly (poly).
- Ethylene terephthalate poly (butylene terephthalate), polyester resins such as unsaturated polyester resins, polyamide resins, acrylonitrile-styrene copolymer resins, styrene-acrylonitrile-butadiene copolymer resins, polyvinyl chloride resins, polystyrene resins, polystyrene Organic resin base material such as blend of polyphenylene ether, cellulose acetate butyrate, polyethylene resin; metal base material such as iron plate, copper plate, steel plate; paint coated surface; glass; ceramic; concrete; slate plate; textile; wood, stone, tile , (Hollow) Inorganic fillers such as silica, titania, zirconia, alumina; glass cloth including glass fiber, glass fiber products such as glass tape, glass mat, glass paper, etc., and the material and shape of the base material Is not particularly limited.
- polyester resins such as unsaturated polyester resins, polyamide resins, acryl
- the organopolysiloxane used as the main agent (base polymer) here has a hydroxyl group (silanol group) or a hydrolyzable silyl group bonded to one silicon atom (two in the molecule) at each end of the molecular chain. It is a thing.
- the molecular terminal group represented by the following general formula (4) or (5) is a hydroxyl group (diorganohydrosilyl group) or a hydrolyzable group (hydrolyzable group-containing tri).
- a linear diorganopolysiloxane sealed with an organosilyl group) is used.
- R 1 is the same as above, X'is an oxygen atom or a divalent hydrocarbon group having 1 to 8 carbon atoms, Y is a hydrolyzable group, and b is 0 or 1.
- m is an integer in which the viscosity of this diorganopolysiloxane at 25 ° C. is 100 to 1,000,000 mPa ⁇ s, and is usually 30 to 2,000, preferably 50 to 1,200, and more preferably 100 to 800. It is an integer of degree.
- the viscosity can be measured with a rotational viscometer (for example, BL type, BH type, BS type, cone plate type, rheometer).
- the number of repetitions (m) or the degree of polymerization of the bifunctional diorganosiloxane unit ((R 1 ) 2 SiO 2/2 ) constituting the main chain of diorganopolysiloxane is determined by gel using, for example, toluene or the like as a developing solvent. It can be determined as a polystyrene-equivalent number average degree of polymerization (or number average molecular weight) or the like in permeation chromatography (GPC) analysis.
- Y is a hydrolyzable group, for example, an alkoxy group such as a methoxy group, an ethoxy group or a propoxy group; an alkoxyalkoxy group such as a methoxyethoxy group, an ethoxyethoxy group or a methoxypropoxy group; an acetoxy group.
- Octanoyloxy group benzoyloxy group and other acyloxy groups
- vinyloxy group allyloxy group, propenyloxy group, isopropenyloxy group, 1-ethyl-2-methylvinyloxy group and other alkoxy group
- dimethylketooxime group Ketooxime groups such as methylethylketooxime group and diethylketooxime group
- amino groups such as dimethylamino group, diethylamino group, butylamino group and cyclohexylamino group
- aminoxy groups such as dimethylaminoxy group and diethylaminoxy group
- N-methylacetamide group N-ethylacetamide group, N-methylbenzamide group and other amide groups and the like.
- a methoxy group, an ethoxy group and a propoxy group are preferable.
- organopolysiloxane used as the main agent (base polymer) include the following diorganopolysiloxane. (In the formula, R 1 , Y, b, m are the same as above.)
- organopolysiloxanes can be used individually by 1 type, or can be used in combination of 2 or more types having different structures and molecular weights.
- the prepared composition is rubberized in a short time and exhibits rubber elasticity.
- the bifunctional organopolysiloxane compound represented by the above general formula (1) is preferably contained in an amount of 0.1 to 10% by mass, more preferably 0.2 to 6% by mass. It is preferably contained in an amount of 0.4 to 4% by mass, more preferably.
- the bifunctional organopolysiloxane compound may be used alone or in combination of two or more.
- the bifunctional organopolysiloxane compound has 0. 0 parts by mass of a linear diorganopolysiloxane having both ends of the molecular chain sealed with a silanol group or a hydrolyzable silyl group. It is preferably contained in an amount of 05 to 5 parts by mass, more preferably 0.1 to 3 parts by mass, and even more preferably 0.2 to 2 parts by mass.
- a cross-linking agent may be used as an arbitrary additive as long as the effect of the present invention is not impaired.
- Organic silicon compounds other than the bifunctional organopolysiloxane compound of the present invention can also be used as the cross-linking agent, and specifically, methyltrimethoxysilane, dimethyldimethoxysilane, vinyltrimethoxysilane, phenyltrimethoxysilane, and methyltri.
- Ekoxysilanes such as ethoxysilane and ⁇ - (dimethoxymethylsilyl) propionic acid 2-ethylhexyl; isopropenoxy such as methyltriisopropenoxysilane, ethyltriisopropenoxysilane, vinyltriisopropenoxysilane, and phenyltriisopropenoxysilane Group-containing silanes; acetoxysilanes such as methyltriacetoxysilanes, ethyltriacetoxysilanes, vinyltriacetoxysilanes; and partial hydrolysis condensates of these silanes. These can be used alone or in combination of two or more.
- the blending amount of the cross-linking agent is 0 to 30% by mass in the composition, preferably 0.1 to 20% by mass, and more preferably 0.5 to 15% by mass.
- the curing catalyst is not particularly limited as long as it is a curing catalyst used for curing a general moisture condensation curing type composition, and specific examples thereof include alkyl tin compounds such as dibutyltin oxide and dioctyltin oxide.
- Alkyltin ester compounds such as dibutyltin diacetate, dibutyltin dilaurate, dioctyltin dilaurate, dibutyltin dioctate, dioctyltin dioctate, dioctyltin diversateate; tetraisopropoxytitanium, tetran-butoxytitanium, tetrakis (2-ethylhexoxy) titanium.
- Titanium esters such as dipropoxybis (acetylacetonato) titanium, titanium diisopropoxybis (ethylacetoacetate), titanium isopropoxyoctylene glycol, and titanium chelate compounds and their partial hydrolyzates; zinc naphthenate, Zinc stearate, zinc-2-ethyloctate, iron-2-ethylhexoate, cobalt-2-ethylhexoate, manganese-2-ethylhexoate, cobalt naphthenate, aluminum trihydroxylate, aluminum alcoholate , Aluminum acylate, salt of aluminum acylate, organosiloxy compound, aluminum chelate compound and other organic metal compounds; 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-aminopropylmethyldimethoxysilane, 3- Aminopropylmethyldiethoxysilane, N- ⁇ (aminoethyl) ⁇ -
- dioctyltin dilaurate dioctyltin diversate, tetraisopropoxytitanium, tetran-butoxytitanium, titanium diisopropoxybis (ethylacetoacetate), 3-aminopropyltrimethoxysilane, because they are more reactive.
- N- ⁇ (aminoethyl) ⁇ -aminopropyltrimethoxysilane, bis [3- (trimethoxysilyl) propyl] amine, N, N'-bis [3- (trimethoxysilyl) propyl] ethane-1,2- Diamine and tetramethylguanidylpropyltrimethoxysilane are preferable, and dioctyltin dilaurate, dioctyltin diversate, 3-aminopropyltrimethoxysilane, and tetramethylguanidylpropyltrimethoxysilane are more preferable from the viewpoint of curability of the composition.
- 3-Aminopropyltrimethoxysilane and tetramethylguanidylpropyltrimethoxysilane are more preferable from the viewpoint of curability of the composition, because they do not contain organic tin compounds and have lower toxicity. Guanidylpropyltrimethoxysilane is particularly preferred.
- the amount of the curing catalyst added is not particularly limited, but is preferably 0.01 to 15% by mass in the composition, preferably 0, in consideration of adjusting the curing rate to an appropriate range to improve workability. .1 to 5% by mass is more preferable.
- fillers can be used, for example, fine powder silica, fumigant silica, precipitated silica, silica whose surface is hydrophobized with an organic silicon compound, glass beads, glass balloons, and transparent.
- inorganic fillers such as silica, calcium carbonate, and zeolite are preferable, and aerosol silica and calcium carbonate whose surface is hydrophobized are particularly preferable
- the blending amount of the filler is preferably 0 to 1,000% by mass, particularly 1 to 1,000% by mass, and particularly preferably 1 to 400% by mass in the composition.
- thermosetting resin composition of the present invention can be produced by the method shown below.
- an organopolysiloxane compound represented by the above general formula (1) and a linear diorganopolysiloxane having both ends of the molecular chain sealed with a silanol group or a hydrolyzable silyl group are required at the same time or separately.
- the mixture may be obtained by mixing with, stirring, dissolving and / or dispersing. Further, depending on the intended use, additives may be added to the mixture and mixed. Each component may be used alone or in combination of two or more.
- the method for producing the composition is not particularly limited with respect to the apparatus for mixing, stirring and dispersing.
- a mixing stirrer manufactured by Dalton Corporation, a universal mixing stirrer manufactured by Dalton Corporation, or the like can be used, and these devices may be used in combination as appropriate.
- Me represents a methyl group
- the viscosity is a value measured at 25 ° C. by a B-type rotational viscometer.
- the peak of the target product was confirmed by GC (gas chromatography) measurement, distilled off under reduced pressure with an evaporator and a vacuum pump, and the disappearance of the raw material peak was confirmed by GC measurement to obtain an organopolysiloxane compound 1 having the above structural formula.
- the organopolysiloxane compound having the above structural formula I got 2.
- Comparative Reference Example 2 As shown in Table 1, the compositions prepared in Reference Examples 2-1 to 2-3 using the organopolysiloxane compounds 1 to 3 obtained in Examples 1-1 to 1-3 are used in Comparative Reference Example 2. It was found that the thickening rate was much higher than that of the composition prepared in -1, and the reactivity as a chain length extender was good. On the other hand, the composition prepared in Comparative Reference Example 2-1 was hardly thickened, and sufficient reactivity could not be ensured.
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Abstract
Provided is an organopolysiloxane compound which becomes a chain extender for a dealcoholized room temperature-vulcanizable (RTV) composition which is rapidly rubberized and exhibits rubber elasticity. This organopolysiloxane compound is represented by general formula (1), and a composition according to the present invention contains: said compound; and a linear diorganopolysiloxane having both ends of a molecular chain sealed with a silanol group or hydrolysable silyl group. (In the formula, R1, R2, and R3 are each independently an unsubstituted or substituted alkyl group having 1 to 10 carbon atoms, or an unsubstituted or substituted aryl group having 6 to 10 carbon atoms; n is an integer of 0 to 10; and X is an unsubstituted or substituted amino group.)
Description
本発明は、オルガノポリシロキサン化合物およびその製造方法等に関し、さらに詳述すると、シロキサン結合を形成することにより高分子量化し得るケイ素含有基（以下、「反応性ケイ素含有基」とも称す。）として、ケイ素原子に結合したモノアルコキシ基等のモノオルガノオキシ基をそれぞれの分子鎖末端に１個ずつ（即ち、分子中に２個）有する２官能性のオルガノポリシロキサン化合物およびその製造方法に関する。
The present invention relates to an organopolysiloxane compound and a method for producing the same, and more specifically, as a silicon-containing group (hereinafter, also referred to as “reactive silicon-containing group”) that can be increased in molecular weight by forming a siloxane bond. The present invention relates to a bifunctional organopolysiloxane compound having one monoorganooxy group such as a monoalkoxy group bonded to a silicon atom at the end of each molecular chain (that is, two in the molecule) and a method for producing the same.
反応性ケイ素含有基、特に加水分解性シリル基は、水存在下にて加水分解縮合する性質を有していることから、この反応性ケイ素含有基を有するポリマーは、水または湿気の存在下で架橋硬化する硬化性組成物に用いることができる。
Since the reactive silicon-containing group, particularly the hydrolyzable silyl group, has the property of hydrolyzing and condensing in the presence of water, the polymer having this reactive silicon-containing group is in the presence of water or moisture. It can be used for a curable composition that is cross-linked and cured.
これらのポリマーの中でも、その主鎖がケイ素含有構造（特に、好ましくは直鎖状の、オルガノポリシロキサン構造）であるものは、一般的にシリコーンポリマーとして知られている。これらを主剤（ベースポリマー）として用いた室温硬化性（ＲＴＶ）オルガノポリシロキサン組成物は、室温（２３℃±１０℃）では液状であり、硬化（架橋反応）によりゴム弾性体（エラストマー）となる特徴を有しており、その特徴を利用してコーティング剤、接着剤、建築用シーリング剤等に広く用いられている。これらの室温硬化性（ＲＴＶ）樹脂組成物には、架橋剤及び安定化剤として、シランカップリング剤やその部分加水分解縮合物等が使用されている。特に分子内に二つの加水分解性基をもつ２官能性のシランカップリング剤は架橋剤の中でも鎖長延長剤と呼ばれ、シリコーンポリマーの鎖長を伸ばすことでシーリング剤やＲＴＶゴム硬化物に適度な伸びを与える。
Among these polymers, those having a silicon-containing structure (particularly preferably a linear, organopolysiloxane structure) in the main chain are generally known as silicone polymers. A room temperature curable (RTV) organopolysiloxane composition using these as a main agent (base polymer) is liquid at room temperature (23 ° C ± 10 ° C) and becomes a rubber elastic body (elastomer) by curing (crosslinking reaction). It has characteristics and is widely used in coating agents, adhesives, building sealants, etc. by utilizing these characteristics. In these room temperature curable (RTV) resin compositions, a silane coupling agent, a partially hydrolyzed condensate thereof, or the like is used as a cross-linking agent and a stabilizer. In particular, a bifunctional silane coupling agent having two hydrolyzable groups in the molecule is called a chain length extender among cross-linking agents, and by extending the chain length of a silicone polymer, it can be used as a sealant or an RTV rubber cured product. Gives moderate elongation.
室温硬化性（ＲＴＶ）オルガノポリシロキサン組成物は、種々のタイプのものが公知である。とりわけ架橋時の縮合反応によりアルコールを放出して硬化する脱アルコールタイプのものは不快臭がない、金属類を腐食しないという特徴により、電気・電子機器等のシーリング用、接着用、コーティング用に好んで使用されている（特許文献１及び２）。
Various types of room temperature curable (RTV) organopolysiloxane compositions are known. In particular, the de-alcohol type, which releases alcohol and cures by condensation reaction during cross-linking, has no unpleasant odor and does not corrode metals, so it is suitable for sealing, bonding, and coating of electrical and electronic equipment. (Patent Documents 1 and 2).
しかしながら、脱アルコールタイプのものは従来公知の他の硬化タイプである脱アセトンタイプ、脱オキシムタイプ、脱アミノキシタイプ等のものと比較すると、空気中の水（湿気）との反応性が低く、硬化速度が遅いことから、工業的に実用可能な脱アルコールタイプの室温硬化性（ＲＴＶ）組成物用の鎖長延長剤となるオルガノポリシロキサン化合物はなかった。
However, the de-alcohol type has lower reactivity with water (moisture) in the air than other conventionally known hardening types such as deacetone type, deoxime type, and deamination type. Due to the slow curing rate, no organopolysiloxane compound was an industrially viable dealcohol-type room temperature curable (RTV) composition chain length extender.
したがって、本発明は、速やかにゴム化し、ゴム弾性を発現する工業的に実用可能な脱アルコールタイプの室温硬化性（ＲＴＶ）組成物用の鎖長延長剤となるオルガノポリシロキサン化合物を提供することを目的とする。
Therefore, the present invention provides an organopolysiloxane compound that serves as a chain length extender for an industrially practical dealcohol-type room temperature curable (RTV) composition that rapidly rubberizes and exhibits rubber elasticity. With the goal.
本発明者らは、上記目的を達成するために鋭意研究した結果、下記一般式（１）で表される、分子鎖末端のケイ素原子に結合したアルコキシ基等のオルガノオキシ基をそれぞれの分子鎖末端に１個ずつ（即ち、モノ（オルガノオキシ）シリル基を分子中に２個）有すると共に、該分子鎖末端のそれぞれのケイ素原子上にアミノ基及び／又はアミン残基で置換されたメチレン基（即ち、α－アミノ基及び／又はα－アミン残基）を有する、特定分子構造の２官能性のオルガノポリシロキサン化合物が、上述した課題の解決に有用であることを見出し、本発明を完成した。
As a result of diligent research to achieve the above object, the present inventors have obtained organooxy groups such as an alkoxy group bonded to a silicon atom at the end of the molecular chain represented by the following general formula (1) in each molecular chain. A methylene group having one terminal (that is, two mono (organooxy) silyl groups in the molecule) and substituted with an amino group and / or an amine residue on each silicon atom at the end of the molecular chain. The present invention has been completed by finding that a bifunctional organopolysiloxane compound having a specific molecular structure having (that is, an α-amino group and / or an α-amine residue) is useful for solving the above-mentioned problems. did.
すなわち、本発明は下記のオルガノポリシロキサン化合物、該化合物を含む組成物、該組成物からなるコーティング剤、接着剤及びシーリング剤、該組成物の硬化物を有する物品、並びに該化合物の製造方法等を提供する。
That is, the present invention relates to the following organopolysiloxane compound, a composition containing the compound, a coating agent composed of the composition, an adhesive and a sealing agent, an article having a cured product of the composition, a method for producing the compound, and the like. I will provide a.
［１］
下記一般式（１）で表されるオルガノポリシロキサン化合物。
（式中、Ｒ1、Ｒ2及びＲ3は互いに独立して非置換もしくは置換の炭素原子数１～１０のアルキル基、または非置換もしくは置換の炭素原子数６～１０のアリール基であり、ｎは０～１０の整数であり、Ｘは非置換又は置換のアミノ基である。）
［２］
［１］に記載のオルガノポリシロキサン化合物と、分子鎖両末端がシラノール基又は加水分解性シリル基で封鎖された直鎖状ジオルガノポリシロキサンとを含有する組成物。
［３］
［２］に記載の組成物を含有するコーティング剤。
［４］
［２］に記載の組成物を含有する接着剤。
［５］
［２］に記載の組成物を含有するシーリング剤。
［６］
［２］に記載の組成物の硬化物。
［７］
［３］に記載のコーティング剤の硬化物を有する物品。
［８］
［４］に記載の接着剤の硬化物を有する物品。
［９］
［５］に記載のシーリング剤の硬化物を有する物品。
［１０］
下記一般式（２）で表されるオルガノシラン化合物を触媒存在下で縮合反応させて二量化する工程を含む下記一般式（１）’で表されるオルガノポリシロキサン化合物の製造方法。
（式中、Ｒ2及びＲ3は互いに独立して非置換もしくは置換の炭素原子数１～１０のアルキル基、または非置換もしくは置換の炭素原子数６～１０のアリール基であり、Ｘは非置換又は置換のアミノ基である。）
（式中、Ｒ1、Ｒ2及びＲ3は互いに独立して非置換もしくは置換の炭素原子数１～１０のアルキル基、または非置換もしくは置換の炭素原子数６～１０のアリール基であり、Ｘは非置換又は置換のアミノ基である。）
［１１］
下記一般式（３）で表される分子鎖両末端シラノール基封鎖ジオルガノポリシロキサンと下記一般式（２）で表されるオルガノシラン化合物を縮合反応させて分子鎖両末端シラノール基封鎖ジオルガノポリシロキサンの分子鎖両末端を下記一般式（２）で表されるオルガノシラン化合物の残基で封鎖する工程を含む下記一般式（１）’’で表されるオルガノポリシロキサン化合物の製造方法。
（Ｒ1は互いに独立して非置換もしくは置換の炭素原子数１～１０のアルキル基、または非置換もしくは置換の炭素原子数６～１０のアリール基であり、ｎは１～１０の整数である。）
（式中、Ｒ2及びＲ3は互いに独立して非置換もしくは置換の炭素原子数１～１０のアルキル基、または非置換もしくは置換の炭素原子数６～１０のアリール基であり、Ｘは非置換又は置換のアミノ基である。）
（式中、Ｒ1、Ｒ2及びＲ3は互いに独立して非置換もしくは置換の炭素原子数１～１０のアルキル基、または非置換もしくは置換の炭素原子数６～１０のアリール基であり、ｎは１～１０の整数であり、Ｘは非置換又は置換のアミノ基である。）
[1]
An organopolysiloxane compound represented by the following general formula (1).
(In the formula, R 1 , R 2 and R 3 are unsubstituted or substituted alkyl groups having 1 to 10 carbon atoms or unsubstituted or substituted aryl groups having 6 to 10 carbon atoms independently of each other. n is an integer from 0 to 10, and X is an unsubstituted or substituted amino group.)
[2]
A composition containing the organopolysiloxane compound according to [1] and a linear diorganopolysiloxane having both ends of the molecular chain sealed with a silanol group or a hydrolyzable silyl group.
[3]
A coating agent containing the composition according to [2].
[4]
An adhesive containing the composition according to [2].
[5]
A sealant containing the composition according to [2].
[6]
A cured product of the composition according to [2].
[7]
An article having a cured product of the coating agent according to [3].
[8]
An article having a cured product of the adhesive according to [4].
[9]
An article having a cured product of the sealant according to [5].
[10]
A method for producing an organopolysiloxane compound represented by the following general formula (1)', which comprises a step of subjecting an organosilane compound represented by the following general formula (2) to a condensation reaction in the presence of a catalyst to dimerize the compound.
(In the formula, R 2 and R 3 are unsubstituted or substituted alkyl groups having 1 to 10 carbon atoms, or unsubstituted or substituted aryl groups having 6 to 10 carbon atoms, and X is non-substituted or substituted. Substituted or substituted amino group.)
(In the formula, R 1 , R 2 and R 3 are independently unsubstituted or substituted alkyl groups having 1 to 10 carbon atoms, or unsubstituted or substituted aryl groups having 6 to 10 carbon atoms. X is an unsubstituted or substituted amino group.)
[11]
Silanol group-blocking diorganopolysiloxane at both ends of the molecular chain represented by the following general formula (3) and an organosilane compound represented by the following general formula (2) are subjected to a condensation reaction to block silanol groups at both ends of the molecular chain. A method for producing an organopolysiloxane compound represented by the following general formula (1)'', which comprises a step of sealing both ends of the molecular chain of the siloxane with a residue of the organosilane compound represented by the following general formula (2).
(R 1 is an alkyl group having 1 to 10 carbon atoms unsubstituted or substituted independently of each other, or an aryl group having 6 to 10 carbon atoms substituted or substituted, and n is an integer of 1 to 10. .)
(In the formula, R 2 and R 3 are unsubstituted or substituted alkyl groups having 1 to 10 carbon atoms, or unsubstituted or substituted aryl groups having 6 to 10 carbon atoms, and X is non-substituted or substituted. Substituted or substituted amino group.)
(In the formula, R 1 , R 2 and R 3 are independently unsubstituted or substituted alkyl groups having 1 to 10 carbon atoms, or unsubstituted or substituted aryl groups having 6 to 10 carbon atoms. n is an integer from 1 to 10, and X is an unsubstituted or substituted amino group.)
下記一般式（１）で表されるオルガノポリシロキサン化合物。
［２］
［１］に記載のオルガノポリシロキサン化合物と、分子鎖両末端がシラノール基又は加水分解性シリル基で封鎖された直鎖状ジオルガノポリシロキサンとを含有する組成物。
［３］
［２］に記載の組成物を含有するコーティング剤。
［４］
［２］に記載の組成物を含有する接着剤。
［５］
［２］に記載の組成物を含有するシーリング剤。
［６］
［２］に記載の組成物の硬化物。
［７］
［３］に記載のコーティング剤の硬化物を有する物品。
［８］
［４］に記載の接着剤の硬化物を有する物品。
［９］
［５］に記載のシーリング剤の硬化物を有する物品。
［１０］
下記一般式（２）で表されるオルガノシラン化合物を触媒存在下で縮合反応させて二量化する工程を含む下記一般式（１）’で表されるオルガノポリシロキサン化合物の製造方法。
［１１］
下記一般式（３）で表される分子鎖両末端シラノール基封鎖ジオルガノポリシロキサンと下記一般式（２）で表されるオルガノシラン化合物を縮合反応させて分子鎖両末端シラノール基封鎖ジオルガノポリシロキサンの分子鎖両末端を下記一般式（２）で表されるオルガノシラン化合物の残基で封鎖する工程を含む下記一般式（１）’’で表されるオルガノポリシロキサン化合物の製造方法。
An organopolysiloxane compound represented by the following general formula (1).
[2]
A composition containing the organopolysiloxane compound according to [1] and a linear diorganopolysiloxane having both ends of the molecular chain sealed with a silanol group or a hydrolyzable silyl group.
[3]
A coating agent containing the composition according to [2].
[4]
An adhesive containing the composition according to [2].
[5]
A sealant containing the composition according to [2].
[6]
A cured product of the composition according to [2].
[7]
An article having a cured product of the coating agent according to [3].
[8]
An article having a cured product of the adhesive according to [4].
[9]
An article having a cured product of the sealant according to [5].
[10]
A method for producing an organopolysiloxane compound represented by the following general formula (1)', which comprises a step of subjecting an organosilane compound represented by the following general formula (2) to a condensation reaction in the presence of a catalyst to dimerize the compound.
[11]
Silanol group-blocking diorganopolysiloxane at both ends of the molecular chain represented by the following general formula (3) and an organosilane compound represented by the following general formula (2) are subjected to a condensation reaction to block silanol groups at both ends of the molecular chain. A method for producing an organopolysiloxane compound represented by the following general formula (1)'', which comprises a step of sealing both ends of the molecular chain of the siloxane with a residue of the organosilane compound represented by the following general formula (2).
本発明のオルガノポリシロキサン化合物は、脱アルコールタイプの縮合反応であっても反応性に優れている。またこのようなオルガノポリシロキサン化合物を鎖長延長剤として含む室温硬化性（ＲＴＶ）オルガノポリシロキサン組成物は室温においても大気中の湿気により速やかにゴム化し、ゴム弾性を発現するため、コーティング剤、接着剤、シーリング剤等の用途に好適に用いることができる。
The organopolysiloxane compound of the present invention has excellent reactivity even in a dealcohol type condensation reaction. Further, a room temperature curable (RTV) organopolysiloxane composition containing such an organopolysiloxane compound as a chain length extender quickly rubberizes due to humidity in the air even at room temperature and exhibits rubber elasticity. It can be suitably used for applications such as adhesives and sealants.
以下、本発明について具体的に説明する。
Hereinafter, the present invention will be specifically described.
２官能性オルガノポリシロキサン化合物
本発明に係るオルガノポリシロキサン化合物は、下記一般式（１）で示される、分子鎖末端のケイ素原子に結合したオルガノオキシ基をそれぞれの分子鎖末端に１個ずつ（即ち、モノ（オルガノオキシ）シリル基を分子中に２個）有すると共に、該分子鎖末端のそれぞれのケイ素原子上にアミノ基及び／又はアミン残基で置換されたメチレン基（即ち、α－アミノ基及び／又はα－アミン残基）を有する、特定分子構造の２官能性オルガノポリシロキサン化合物である。 Bifunctional Organopolysiloxane Compound The organopolysiloxane compound according to the present invention has one organooxy group bonded to a silicon atom at the end of the molecular chain represented by the following general formula (1) (one at the end of each molecular chain (1). That is, a methylene group (that is, α-amino) having a mono (organooxy) silyl group (two in the molecule) and substituted with an amino group and / or an amine residue on each silicon atom at the end of the molecular chain. It is a bifunctional organopolysiloxane compound having a specific molecular structure and having a group and / or an α-amine residue).
本発明に係るオルガノポリシロキサン化合物は、下記一般式（１）で示される、分子鎖末端のケイ素原子に結合したオルガノオキシ基をそれぞれの分子鎖末端に１個ずつ（即ち、モノ（オルガノオキシ）シリル基を分子中に２個）有すると共に、該分子鎖末端のそれぞれのケイ素原子上にアミノ基及び／又はアミン残基で置換されたメチレン基（即ち、α－アミノ基及び／又はα－アミン残基）を有する、特定分子構造の２官能性オルガノポリシロキサン化合物である。 Bifunctional Organopolysiloxane Compound The organopolysiloxane compound according to the present invention has one organooxy group bonded to a silicon atom at the end of the molecular chain represented by the following general formula (1) (one at the end of each molecular chain (1). That is, a methylene group (that is, α-amino) having a mono (organooxy) silyl group (two in the molecule) and substituted with an amino group and / or an amine residue on each silicon atom at the end of the molecular chain. It is a bifunctional organopolysiloxane compound having a specific molecular structure and having a group and / or an α-amine residue).
式中、Ｒ1、Ｒ2及びＲ3は互いに独立して非置換もしくは置換の炭素原子数１～１０のアルキル基、または非置換もしくは置換の炭素原子数６～１０のアリール基を表す。上記Ｒ1、Ｒ2及びＲ3において、炭素原子数１～１０のアルキル基としては、直鎖状、環状、分枝状のいずれでもよく、その具体例としては、メチル、エチル、ｎ－プロピル、ｉ－プロピル、ｎ－ブチル、ｓ－ブチル、ｔ－ブチル、ｎ－ペンチル、ネオペンチル、ｎ－ヘキシル、ｎ－ヘプチル、ｎ－オクチル、ｎ－ノニル、ｎ－デシル基等の直鎖または分岐鎖アルキル基；シクロプロピル、シクロブチル、シクロペンチル、シクロヘキシル、シクロヘプチル、シクロオクチル、イソボルニル基等のシクロアルキル基が挙げられる。また、炭素原子数６～１０のアリール基の具体例としては、フェニル、トリル、キシリル、α－ナフチル、β－ナフチル基等が挙げられる。なお、これらの基の水素原子の一部または全部は、アルキル基、アリール基、Ｆ、Ｃｌ、Ｂｒ等のハロゲン原子やシアノ基等で置換されていてもよく、これらの中でも、Ｒ1、Ｒ2及びＲ3としては、メチル基、エチル基、フェニル基が好ましく、反応性や入手の容易さ、生産性、コストの面からメチル基がより好ましい。
In the formula, R 1 , R 2 and R 3 independently represent an unsubstituted or substituted alkyl group having 1 to 10 carbon atoms, or an unsubstituted or substituted aryl group having 6 to 10 carbon atoms. In the above R 1 , R 2 and R 3 , the alkyl group having 1 to 10 carbon atoms may be linear, cyclic or branched, and specific examples thereof include methyl, ethyl and n-propyl. , I-propyl, n-butyl, s-butyl, t-butyl, n-pentyl, neopentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl group, etc. Alkyl groups: Cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, isobornyl groups and the like can be mentioned. Specific examples of the aryl group having 6 to 10 carbon atoms include phenyl, tolyl, xsilyl, α-naphthyl, β-naphthyl group and the like. In addition, a part or all of the hydrogen atoms of these groups may be substituted with halogen atoms such as alkyl groups, aryl groups, F, Cl and Br, cyano groups and the like, and among these, R 1 , R As 2 and R 3 , a methyl group, an ethyl group, and a phenyl group are preferable, and a methyl group is more preferable from the viewpoints of reactivity, availability, productivity, and cost.
上記一般式（１）において、Ｘは非置換又は置換のアミノ基であり、２級又は３級アミノ基（例えば、モノオルガノ置換アミノ基又はジオルガノ置換アミノ基）が好ましく、３級アミノ基（例えば、ジオルガノ置換アミノ基）がより好ましく、その具体例としては、メチルアミノ基、ジメチルアミノ基、エチルアミノ基、ジエチルアミノ基、プロピルアミノ基、イソプロピルアミノ基、ジプロピルアミノ基、ジイソプロピルアミノ基、ブチルアミノ基、イソブチルアミノ基、ｓｅｃ－ブチルアミノ基、ｔｅｒｔ－ブチルアミノ基、ジブチルアミノ基、ジイソブチルアミノ基、ジｓｅｃ－ブチルアミノ基、ジｔｅｒｔ－ブチルアミノ基、ペンチルアミノ基、ヘキシルアミノ基、ヘプチルアミノ基、オクチルアミノ基、ノニルアミノ基、エチレンジアミン残基、ヘキサメチレンジアミン残基、アニリン残基、フェネチルアミン残基、トルイジン残基、ピロリジン残基、ピペリジン残基、ピペラジン残基、モルホリン残基、ピロール残基、ピラゾール残基、イミダゾール残基等が挙げられる。特にジメチルアミノ基、ジエチルアミノ基や、ピロリジン残基、ピペラジン残基のような炭素数が少なく、合成時に反応しやすいものが好ましい。
In the above general formula (1), X is an unsubstituted or substituted amino group, preferably a secondary or tertiary amino group (for example, a monoorgano-substituted amino group or a diorgano-substituted amino group), and a tertiary amino group (for example,). , Diorgano-substituted amino group) is more preferable, and specific examples thereof include methylamino group, dimethylamino group, ethylamino group, diethylamino group, propylamino group, isopropylamino group, dipropylamino group, diisopropylamino group and butylamino. Group, isobutylamino group, sec-butylamino group, tert-butylamino group, dibutylamino group, diisobutylamino group, disec-butylamino group, ditert-butylamino group, pentylamino group, hexylamino group, heptylamino group Group, octylamino group, nonylamino group, ethylenediamine residue, hexamethylenediamine residue, aniline residue, phenethylamine residue, toluidine residue, pyrrolidine residue, piperidine residue, piperazine residue, morpholin residue, pyrrole residue , Pyrazole residue, imidazole residue and the like. In particular, those having a small number of carbon atoms such as a dimethylamino group, a diethylamino group, a pyrrolidine residue, and a piperazine residue and which are easily reacted during synthesis are preferable.
上記一般式（１）において、ｎは、０～１０の整数を表す。上記一般式（１）において、特にｎが０～３の整数のとき、化合物の分子量が小さくなり、該化合物を組成物に配合する際、添加量が少なくて済むため、ｎは０～３の整数が好ましい。
In the above general formula (1), n represents an integer of 0 to 10. In the above general formula (1), especially when n is an integer of 0 to 3, the molecular weight of the compound becomes small, and when the compound is blended into the composition, the amount added can be small, so n is 0 to 3. Integers are preferred.
２官能性オルガノポリシロキサン化合物の製造方法
上記一般式（１）で表されるオルガノポリシロキサン化合物（ｎ＝０の場合）は、例えば、下記一般式（２）で表される、ケイ素原子のα位にアミノ基を導入し、アルコキシシリル基等のオルガノオキシ基を分子中に２個有する２官能性のα－アミノ基含有加水分解性オルガノシラン化合物を塩酸触媒等の触媒存在下で縮合反応させて二量化することにより得ることができる。 Method for Producing Bifunctional Organopolysiloxane Compound The organopolysiloxane compound represented by the above general formula (1) (when n = 0) is, for example, α of a silicon atom represented by the following general formula (2). An amino group is introduced at the position, and a bifunctional α-amino group-containing hydrolyzable organosilane compound having two organooxy groups such as an alkoxysilyl group in the molecule is subjected to a condensation reaction in the presence of a catalyst such as a hydrochloric acid catalyst. It can be obtained by quantifying it.
上記一般式（１）で表されるオルガノポリシロキサン化合物（ｎ＝０の場合）は、例えば、下記一般式（２）で表される、ケイ素原子のα位にアミノ基を導入し、アルコキシシリル基等のオルガノオキシ基を分子中に２個有する２官能性のα－アミノ基含有加水分解性オルガノシラン化合物を塩酸触媒等の触媒存在下で縮合反応させて二量化することにより得ることができる。 Method for Producing Bifunctional Organopolysiloxane Compound The organopolysiloxane compound represented by the above general formula (1) (when n = 0) is, for example, α of a silicon atom represented by the following general formula (2). An amino group is introduced at the position, and a bifunctional α-amino group-containing hydrolyzable organosilane compound having two organooxy groups such as an alkoxysilyl group in the molecule is subjected to a condensation reaction in the presence of a catalyst such as a hydrochloric acid catalyst. It can be obtained by quantifying it.
また、上記一般式（１）で表されるオルガノポリシロキサン化合物（ｎ＝１～１０の整数の場合）は、下記一般式（３）で表される分子鎖両末端シラノール基封鎖ジオルガノポリシロキサンと、上記一般式（２）で表されるオルガノシラン化合物とを縮合反応させて、分子鎖両末端シラノール基封鎖ジオルガノポリシロキサンの分子鎖両末端を上記一般式（２）で表されるオルガノシラン化合物の残基で封鎖することで得ることができる。下記一般式（３）で表される分子鎖両末端シラノール基封鎖ジオルガノポリシロキサンと、上記一般式（２）で表されるオルガノシラン化合物との縮合反応では、必要に応じて触媒を用いてもよい。
Further, the organopolysiloxane compound represented by the above general formula (1) (in the case of an integer of n = 1 to 10) is a diorganopolysiloxane containing silanol groups at both ends of the molecular chain represented by the following general formula (3). And the organosilane compound represented by the above general formula (2) are subjected to a condensation reaction to form both ends of the molecular chain of the silanol group-blocking diorganopolysiloxane represented by the above general formula (2). It can be obtained by sealing with a residue of the silane compound. In the condensation reaction between the silanol group-blocking diorganopolysiloxane represented by the following general formula (3) and the organosilane compound represented by the above general formula (2), a catalyst is used as necessary. May be good.
２官能性オルガノポリシロキサン化合物を含む組成物
本発明の２官能性オルガノポリシロキサン化合物は、分子鎖両末端がシラノール基又は加水分解性シリル基で封鎖された直鎖状ジオルガノポリシロキサンを主剤（ベースポリマー）として含有する室温硬化性オルガノポリシロキサン組成物、特に、脱アルコールタイプの室温硬化性（ＲＴＶ）オルガノポリシロキサン組成物中に配合すると、ベースポリマーの鎖長延長剤として作用する。該２官能性オルガノポリシロキサン化合物を含有する室温硬化性（ＲＴＶ）オルガノポリシロキサン組成物は室温においても大気中の湿気により速やかに縮合反応してゴム弾性を有すると共に高伸張性に優れたシリコーンゴム弾性体（エラストマー）を与えることができる。該組成物の縮合反応による架橋時には、加熱及び／又は加湿してもかまわない。本発明の組成物は、コーティング剤、接着剤、シーリング剤等の用途に好適に用いることができる。本発明のコーティング剤、接着剤及びシーリング剤を用いる物品としては、エポキシ樹脂、フェノール樹脂、ポリイミド樹脂、ポリカーボネート類およびポリカーボネートブレンド等のポリカーボネート樹脂、ポリ（メタクリル酸メチル）等のアクリル系樹脂、ポリ（エチレンテレフタレート）やポリ（ブチレンテレフタレート）、不飽和ポリエステル樹脂等のポリエステル樹脂、ポリアミド樹脂、アクリロニトリル－スチレン共重合体樹脂、スチレン－アクリロニトリル－ブタジエン共重合体樹脂、ポリ塩化ビニル樹脂、ポリスチレン樹脂、ポリスチレンとポリフェニレンエーテルのブレンド、セルロースアセテートブチレート、ポリエチレン樹脂等の有機樹脂基材；鉄板、銅板、鋼板等の金属基材；塗料塗布面；ガラス；セラミック；コンクリート；スレート板；テキスタイル；木材、石材、瓦、（中空）シリカ、チタニア、ジルコニア、アルミナ等の無機フィラー；ガラス繊維をはじめとしたガラスクロス、ガラステープ、ガラスマット、ガラスペーパー等のガラス繊維製品などが挙げられ、基材の材質および形状については特に限定されるものではない。ここで主剤（ベースポリマー）として用いられるオルガノポリシロキサンは、分子鎖両末端にそれぞれ１個ずつ（分子中に２個の）ケイ素原子に結合した水酸基（シラノール基）又は加水分解性シリル基を有するものである。このようなオルガノポリシロキサンとして、具体的には、下記一般式（４）又は（５）で表される分子末端基が水酸基（ジオルガノヒドロシリル基）又は加水分解性基（加水分解性基含有トリオルガノシリル基）で封鎖された直鎖状のジオルガノポリシロキサンが用いられる。 Composition Containing Bifunctional Organopolysiloxane Compound The bifunctional organopolysiloxane compound of the present invention is mainly composed of a linear diorganopolysiloxane having both ends of the molecular chain sealed with a silanol group or a hydrolyzable silyl group. When blended in a room temperature curable organopolysiloxane composition (base polymer), particularly a dealcohol type room temperature curable (RTV) organopolysiloxane composition, it acts as a chain length extender for the base polymer. The room temperature curable (RTV) organopolysiloxane composition containing the bifunctional organopolysiloxane compound rapidly condenses with moisture in the atmosphere even at room temperature to have rubber elasticity and excellent extensibility. An elastic body (elastomer) can be provided. During cross-linking by the condensation reaction of the composition, heating and / or humidification may be performed. The composition of the present invention can be suitably used for applications such as coating agents, adhesives, and sealing agents. Articles using the coating agent, adhesive and sealing agent of the present invention include epoxy resin, phenol resin, polyimide resin, polycarbonate resin such as polycarbonate and polycarbonate blend, acrylic resin such as poly (methyl methacrylate), and poly (poly). Ethylene terephthalate), poly (butylene terephthalate), polyester resins such as unsaturated polyester resins, polyamide resins, acrylonitrile-styrene copolymer resins, styrene-acrylonitrile-butadiene copolymer resins, polyvinyl chloride resins, polystyrene resins, polystyrene Organic resin base material such as blend of polyphenylene ether, cellulose acetate butyrate, polyethylene resin; metal base material such as iron plate, copper plate, steel plate; paint coated surface; glass; ceramic; concrete; slate plate; textile; wood, stone, tile , (Hollow) Inorganic fillers such as silica, titania, zirconia, alumina; glass cloth including glass fiber, glass fiber products such as glass tape, glass mat, glass paper, etc., and the material and shape of the base material Is not particularly limited. The organopolysiloxane used as the main agent (base polymer) here has a hydroxyl group (silanol group) or a hydrolyzable silyl group bonded to one silicon atom (two in the molecule) at each end of the molecular chain. It is a thing. Specifically, as such an organopolysiloxane, the molecular terminal group represented by the following general formula (4) or (5) is a hydroxyl group (diorganohydrosilyl group) or a hydrolyzable group (hydrolyzable group-containing tri). A linear diorganopolysiloxane sealed with an organosilyl group) is used.
本発明の２官能性オルガノポリシロキサン化合物は、分子鎖両末端がシラノール基又は加水分解性シリル基で封鎖された直鎖状ジオルガノポリシロキサンを主剤（ベースポリマー）として含有する室温硬化性オルガノポリシロキサン組成物、特に、脱アルコールタイプの室温硬化性（ＲＴＶ）オルガノポリシロキサン組成物中に配合すると、ベースポリマーの鎖長延長剤として作用する。該２官能性オルガノポリシロキサン化合物を含有する室温硬化性（ＲＴＶ）オルガノポリシロキサン組成物は室温においても大気中の湿気により速やかに縮合反応してゴム弾性を有すると共に高伸張性に優れたシリコーンゴム弾性体（エラストマー）を与えることができる。該組成物の縮合反応による架橋時には、加熱及び／又は加湿してもかまわない。本発明の組成物は、コーティング剤、接着剤、シーリング剤等の用途に好適に用いることができる。本発明のコーティング剤、接着剤及びシーリング剤を用いる物品としては、エポキシ樹脂、フェノール樹脂、ポリイミド樹脂、ポリカーボネート類およびポリカーボネートブレンド等のポリカーボネート樹脂、ポリ（メタクリル酸メチル）等のアクリル系樹脂、ポリ（エチレンテレフタレート）やポリ（ブチレンテレフタレート）、不飽和ポリエステル樹脂等のポリエステル樹脂、ポリアミド樹脂、アクリロニトリル－スチレン共重合体樹脂、スチレン－アクリロニトリル－ブタジエン共重合体樹脂、ポリ塩化ビニル樹脂、ポリスチレン樹脂、ポリスチレンとポリフェニレンエーテルのブレンド、セルロースアセテートブチレート、ポリエチレン樹脂等の有機樹脂基材；鉄板、銅板、鋼板等の金属基材；塗料塗布面；ガラス；セラミック；コンクリート；スレート板；テキスタイル；木材、石材、瓦、（中空）シリカ、チタニア、ジルコニア、アルミナ等の無機フィラー；ガラス繊維をはじめとしたガラスクロス、ガラステープ、ガラスマット、ガラスペーパー等のガラス繊維製品などが挙げられ、基材の材質および形状については特に限定されるものではない。ここで主剤（ベースポリマー）として用いられるオルガノポリシロキサンは、分子鎖両末端にそれぞれ１個ずつ（分子中に２個の）ケイ素原子に結合した水酸基（シラノール基）又は加水分解性シリル基を有するものである。このようなオルガノポリシロキサンとして、具体的には、下記一般式（４）又は（５）で表される分子末端基が水酸基（ジオルガノヒドロシリル基）又は加水分解性基（加水分解性基含有トリオルガノシリル基）で封鎖された直鎖状のジオルガノポリシロキサンが用いられる。 Composition Containing Bifunctional Organopolysiloxane Compound The bifunctional organopolysiloxane compound of the present invention is mainly composed of a linear diorganopolysiloxane having both ends of the molecular chain sealed with a silanol group or a hydrolyzable silyl group. When blended in a room temperature curable organopolysiloxane composition (base polymer), particularly a dealcohol type room temperature curable (RTV) organopolysiloxane composition, it acts as a chain length extender for the base polymer. The room temperature curable (RTV) organopolysiloxane composition containing the bifunctional organopolysiloxane compound rapidly condenses with moisture in the atmosphere even at room temperature to have rubber elasticity and excellent extensibility. An elastic body (elastomer) can be provided. During cross-linking by the condensation reaction of the composition, heating and / or humidification may be performed. The composition of the present invention can be suitably used for applications such as coating agents, adhesives, and sealing agents. Articles using the coating agent, adhesive and sealing agent of the present invention include epoxy resin, phenol resin, polyimide resin, polycarbonate resin such as polycarbonate and polycarbonate blend, acrylic resin such as poly (methyl methacrylate), and poly (poly). Ethylene terephthalate), poly (butylene terephthalate), polyester resins such as unsaturated polyester resins, polyamide resins, acrylonitrile-styrene copolymer resins, styrene-acrylonitrile-butadiene copolymer resins, polyvinyl chloride resins, polystyrene resins, polystyrene Organic resin base material such as blend of polyphenylene ether, cellulose acetate butyrate, polyethylene resin; metal base material such as iron plate, copper plate, steel plate; paint coated surface; glass; ceramic; concrete; slate plate; textile; wood, stone, tile , (Hollow) Inorganic fillers such as silica, titania, zirconia, alumina; glass cloth including glass fiber, glass fiber products such as glass tape, glass mat, glass paper, etc., and the material and shape of the base material Is not particularly limited. The organopolysiloxane used as the main agent (base polymer) here has a hydroxyl group (silanol group) or a hydrolyzable silyl group bonded to one silicon atom (two in the molecule) at each end of the molecular chain. It is a thing. Specifically, as such an organopolysiloxane, the molecular terminal group represented by the following general formula (4) or (5) is a hydroxyl group (diorganohydrosilyl group) or a hydrolyzable group (hydrolyzable group-containing tri). A linear diorganopolysiloxane sealed with an organosilyl group) is used.
なお、粘度は回転粘度計（例えば、ＢＬ型、ＢＨ型、ＢＳ型、コーンプレート型、レオメータ）により測定することができる。また、ジオルガノポリシロキサンの主鎖を構成する２官能性ジオルガノシロキサン単位（（Ｒ1）2ＳｉＯ2/2）の繰り返し数（ｍ）又は重合度は、例えば、トルエン等を展開溶媒としてゲルパーミエーションクロマトグラフィ（ＧＰＣ）分析におけるポリスチレン換算の数平均重合度（又は数平均分子量）等として求めることができる。
The viscosity can be measured with a rotational viscometer (for example, BL type, BH type, BS type, cone plate type, rheometer). The number of repetitions (m) or the degree of polymerization of the bifunctional diorganosiloxane unit ((R 1 ) 2 SiO 2/2 ) constituting the main chain of diorganopolysiloxane is determined by gel using, for example, toluene or the like as a developing solvent. It can be determined as a polystyrene-equivalent number average degree of polymerization (or number average molecular weight) or the like in permeation chromatography (GPC) analysis.
上記式（４）及び（５）において、Ｘ’は酸素原子又は炭素数１～８の二価炭化水素基であり、－（ＣＨ2ＣＨ2）q－、又は－（ＣＨ＝ＣＨ）q－（ｑは１～４を表す）であることが好ましい。これらの中でも特に酸素原子、－ＣＨ2ＣＨ2－、又は－ＣＨ＝ＣＨ－が好ましい。
In the above formulas (4) and (5), X'is an oxygen atom or a divalent hydrocarbon group having 1 to 8 carbon atoms, and-(CH 2 CH 2 ) q -or-(CH = CH) q-. (Q represents 1 to 4) is preferable. Of these, an oxygen atom, -CH 2 CH 2- , or -CH = CH- is particularly preferable.
上記式（５）において、Ｙは加水分解性基であり、例えば、メトキシ基、エトキシ基、プロポキシ基等のアルコキシ基；メトキシエトキシ基、エトキシエトキシ基、メトキシプロポキシ基等のアルコキシアルコキシ基；アセトキシ基、オクタノイルオキシ基、ベンゾイルオキシ基等のアシロキシ基；ビニロキシ基、アリルオキシ基、プロペニルオキシ基、イソプロぺニルオキシ基、１－エチル－２－メチルビニルオキシ基等のアルケニルオキシ基；ジメチルケトオキシム基、メチルエチルケトオキシム基、ジエチルケトオキシム基等のケトオキシム基；ジメチルアミノ基、ジエチルアミノ基、ブチルアミノ基、シクロヘキシルアミノ基等のアミノ基；ジメチルアミノキシ基、ジエチルアミノキシ基等のアミノキシ基；Ｎ－メチルアセトアミド基、Ｎ－エチルアセトアミド基、Ｎ－メチルベンズアミド基等のアミド基等があげられる。この中でも、メトキシ基、エトキシ基及びプロポキシ基が好ましい。
In the above formula (5), Y is a hydrolyzable group, for example, an alkoxy group such as a methoxy group, an ethoxy group or a propoxy group; an alkoxyalkoxy group such as a methoxyethoxy group, an ethoxyethoxy group or a methoxypropoxy group; an acetoxy group. , Octanoyloxy group, benzoyloxy group and other acyloxy groups; vinyloxy group, allyloxy group, propenyloxy group, isopropenyloxy group, 1-ethyl-2-methylvinyloxy group and other alkoxy group; dimethylketooxime group, Ketooxime groups such as methylethylketooxime group and diethylketooxime group; amino groups such as dimethylamino group, diethylamino group, butylamino group and cyclohexylamino group; aminoxy groups such as dimethylaminoxy group and diethylaminoxy group; N-methylacetamide group , N-ethylacetamide group, N-methylbenzamide group and other amide groups and the like. Of these, a methoxy group, an ethoxy group and a propoxy group are preferable.
主剤（ベースポリマー）として用いられるオルガノポリシロキサンの具体例としては、例えば、下記のジオルガノポリシロキサンが挙げられる。
（式中、Ｒ1、Ｙ、ｂ、ｍは上記と同様である。）
Specific examples of the organopolysiloxane used as the main agent (base polymer) include the following diorganopolysiloxane.
(In the formula, R 1 , Y, b, m are the same as above.)
これらのオルガノポリシロキサンは、１種単独で使用することもできるし、構造や分子量の異なる２種以上を組み合わせて使用することもできる。
These organopolysiloxanes can be used individually by 1 type, or can be used in combination of 2 or more types having different structures and molecular weights.
このようなオルガノポリシロキサンと本発明のオルガノポリシロキサン化合物とを組み合わせることで、調製された組成物は、短時間でゴム化し、ゴム弾性を発現する。
By combining such an organopolysiloxane and the organopolysiloxane compound of the present invention, the prepared composition is rubberized in a short time and exhibits rubber elasticity.
本発明の組成物中、上記一般式（１）で示される２官能性オルガノポリシロキサン化合物は、０．１～１０質量％含有することが好ましく、０．２～６質量％含有することがより好ましく、０．４～４質量％含有することがさらに好ましい。２官能性オルガノポリシロキサン化合物は、一種単独で使用してもよく、２種以上を併用してもよい。
In the composition of the present invention, the bifunctional organopolysiloxane compound represented by the above general formula (1) is preferably contained in an amount of 0.1 to 10% by mass, more preferably 0.2 to 6% by mass. It is preferably contained in an amount of 0.4 to 4% by mass, more preferably. The bifunctional organopolysiloxane compound may be used alone or in combination of two or more.
本発明の組成物中、上記２官能性オルガノポリシロキサン化合物は、分子鎖両末端がシラノール基又は加水分解性シリル基で封鎖された直鎖状ジオルガノポリシロキサン１００質量部に対して、０．０５～５質量部含有することが好ましく、０．１～３質量部含有することがより好ましく、０．２～２質量部含有することがさらに好ましい。
In the composition of the present invention, the bifunctional organopolysiloxane compound has 0. 0 parts by mass of a linear diorganopolysiloxane having both ends of the molecular chain sealed with a silanol group or a hydrolyzable silyl group. It is preferably contained in an amount of 05 to 5 parts by mass, more preferably 0.1 to 3 parts by mass, and even more preferably 0.2 to 2 parts by mass.
また、本発明の効果を損なわない範囲で任意の添加物として架橋剤や硬化触媒、充填剤を使用してもよい。
架橋剤には本発明の２官能性オルガノポリシロキサン化合物以外の有機ケイ素化合物も使用可能であり、具体的にはメチルトリメトキシシラン、ジメチルジメトキシシラン、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、メチルトリエトキシシラン、α-（ジメトキシメチルシリル）プロピオン酸２‐エチルヘキシル等のアルコキシシラン；メチルトリイソプロペノキシシラン、エチルトリイソプロペノキシシラン、ビニルトリイソプロペノキシシラン、フェニルトリイソプロペノキシシラン等のイソプロペノキシ基含有シラン；メチルトリアセトキシシラン、エチルトリアセトキシシラン、ビニルトリアセトキシシラン等のアセトキシシラン；並びにこれらのシランの部分加水分解縮合物が挙げられる。これらは１種単独でも２種以上を組み合わせても使用することができる。
架橋剤の配合量は、組成物中０～３０質量％であるが、０．１～２０質量％であることが好ましく、より好ましくは０．５～１５質量％である。 Further, a cross-linking agent, a curing catalyst, or a filler may be used as an arbitrary additive as long as the effect of the present invention is not impaired.
Organic silicon compounds other than the bifunctional organopolysiloxane compound of the present invention can also be used as the cross-linking agent, and specifically, methyltrimethoxysilane, dimethyldimethoxysilane, vinyltrimethoxysilane, phenyltrimethoxysilane, and methyltri. Ekoxysilanes such as ethoxysilane and α- (dimethoxymethylsilyl) propionic acid 2-ethylhexyl; isopropenoxy such as methyltriisopropenoxysilane, ethyltriisopropenoxysilane, vinyltriisopropenoxysilane, and phenyltriisopropenoxysilane Group-containing silanes; acetoxysilanes such as methyltriacetoxysilanes, ethyltriacetoxysilanes, vinyltriacetoxysilanes; and partial hydrolysis condensates of these silanes. These can be used alone or in combination of two or more.
The blending amount of the cross-linking agent is 0 to 30% by mass in the composition, preferably 0.1 to 20% by mass, and more preferably 0.5 to 15% by mass.
架橋剤には本発明の２官能性オルガノポリシロキサン化合物以外の有機ケイ素化合物も使用可能であり、具体的にはメチルトリメトキシシラン、ジメチルジメトキシシラン、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、メチルトリエトキシシラン、α-（ジメトキシメチルシリル）プロピオン酸２‐エチルヘキシル等のアルコキシシラン；メチルトリイソプロペノキシシラン、エチルトリイソプロペノキシシラン、ビニルトリイソプロペノキシシラン、フェニルトリイソプロペノキシシラン等のイソプロペノキシ基含有シラン；メチルトリアセトキシシラン、エチルトリアセトキシシラン、ビニルトリアセトキシシラン等のアセトキシシラン；並びにこれらのシランの部分加水分解縮合物が挙げられる。これらは１種単独でも２種以上を組み合わせても使用することができる。
架橋剤の配合量は、組成物中０～３０質量％であるが、０．１～２０質量％であることが好ましく、より好ましくは０．５～１５質量％である。 Further, a cross-linking agent, a curing catalyst, or a filler may be used as an arbitrary additive as long as the effect of the present invention is not impaired.
Organic silicon compounds other than the bifunctional organopolysiloxane compound of the present invention can also be used as the cross-linking agent, and specifically, methyltrimethoxysilane, dimethyldimethoxysilane, vinyltrimethoxysilane, phenyltrimethoxysilane, and methyltri. Ekoxysilanes such as ethoxysilane and α- (dimethoxymethylsilyl) propionic acid 2-ethylhexyl; isopropenoxy such as methyltriisopropenoxysilane, ethyltriisopropenoxysilane, vinyltriisopropenoxysilane, and phenyltriisopropenoxysilane Group-containing silanes; acetoxysilanes such as methyltriacetoxysilanes, ethyltriacetoxysilanes, vinyltriacetoxysilanes; and partial hydrolysis condensates of these silanes. These can be used alone or in combination of two or more.
The blending amount of the cross-linking agent is 0 to 30% by mass in the composition, preferably 0.1 to 20% by mass, and more preferably 0.5 to 15% by mass.
硬化触媒としては、一般的な湿気縮合硬化型組成物の硬化に用いられる硬化触媒であれば特に限定されるものではなく、その具体例としては、ジブチル錫オキシド、ジオクチル錫オキシド等のアルキル錫化合物；ジブチル錫ジアセテート、ジブチル錫ジラウレート、ジオクチル錫ジラウレート、ジブチル錫ジオクトエート、ジオクチル錫ジオクトエート、ジオクチル錫ジバーサテート等のアルキル錫エステル化合物；テトライソプロポキシチタン、テトラｎ－ブトキシチタン、テトラキス（２－エチルヘキソキシ）チタン、ジプロポキシビス（アセチルアセトナト）チタン、チタンジイソプロポキシビス（エチルアセトアセテート）、チタニウムイソプロポキシオクチレングリコール等のチタン酸エステル、およびチタンキレート化合物並びにそれらの部分加水分解物；ナフテン酸亜鉛、ステアリン酸亜鉛、亜鉛－２－エチルオクトエート、鉄－２－エチルヘキソエート、コバルト－２－エチルヘキソエート、マンガン－２－エチルヘキソエート、ナフテン酸コバルト、三水酸化アルミニウム、アルミニウムアルコラート、アルミニウムアシレート、アルミニウムアシレートの塩、アルミノシロキシ化合物、アルミニウムキレート化合物等の有機金属化合物；３－アミノプロピルトリメトキシシラン、３－アミノプロピルトリエトキシシラン、３－アミノプロピルメチルジメトキシシラン、３－アミノプロピルメチルジエトキシシラン、Ｎ－β（アミノエチル）γ－アミノプロピルトリメトキシシラン、Ｎ－β（アミノエチル）γ－アミノプロピルトリエトキシシラン、Ｎ－β（アミノエチル）γ－アミノプロピルメチルジメトキシシラン、Ｎ－β（アミノエチル）γ－アミノプロピルメチルジエトキシシラン、ビス［３－（トリメトキシシリル）プロピル］アミン、ビス［３－（トリエトキシシリル）プロピル］アミン、Ｎ，Ｎ′－ビス［３－（トリメトキシシリル）プロピル］エタン－１，２－ジアミン、Ｎ，Ｎ′－ビス［３－（トリエトキシシリル）プロピル］エタン－１，２－ジアミン、Ｎ－フェニル－３－アミノプロピルトリメトキシシラン等のアミノアルキル基置換アルコキシシラン；ヘキシルアミン、リン酸ドデシルアミン、テトラメチルグアニジン等のアミン化合物およびその塩；ベンジルトリエチルアンモニウムアセテート等の第４級アンモニウム塩；酢酸カリウム、酢酸ナトリウム、シュウ酸リチウム等のアルカリ金属の低級脂肪酸塩；ジメチルヒドロキシルアミン、ジエチルヒドロキシルアミン等のジアルキルヒドロキシルアミン；テトラメチルグアニジルプロピルトリメトキシシラン、テトラメチルグアニジルプロピルメチルジメトキシシラン、テトラメチルグアニジルプロピルトリエトキシシラン、テトラメチルグアニジルプロピルメチルジエトキシシラン、テトラメチルグアニジルプロピルトリス（トリメチルシロキシ）シラン等のグアニジル基を含有するシランおよびシロキサン；Ｎ，Ｎ，Ｎ’，Ｎ’，Ｎ''，Ｎ''－ヘキサメチル－Ｎ'''－［３－（トリメトキシシリル）プロピル］－ホスホリミディックトリアミド等のホスファゼン塩基を含有するシランおよびシロキサン等が挙げられ、これらは単独で用いても、２種以上の組み合わせて用いてもよい。
The curing catalyst is not particularly limited as long as it is a curing catalyst used for curing a general moisture condensation curing type composition, and specific examples thereof include alkyl tin compounds such as dibutyltin oxide and dioctyltin oxide. Alkyltin ester compounds such as dibutyltin diacetate, dibutyltin dilaurate, dioctyltin dilaurate, dibutyltin dioctate, dioctyltin dioctate, dioctyltin diversateate; tetraisopropoxytitanium, tetran-butoxytitanium, tetrakis (2-ethylhexoxy) titanium. , Titanium esters such as dipropoxybis (acetylacetonato) titanium, titanium diisopropoxybis (ethylacetoacetate), titanium isopropoxyoctylene glycol, and titanium chelate compounds and their partial hydrolyzates; zinc naphthenate, Zinc stearate, zinc-2-ethyloctate, iron-2-ethylhexoate, cobalt-2-ethylhexoate, manganese-2-ethylhexoate, cobalt naphthenate, aluminum trihydroxylate, aluminum alcoholate , Aluminum acylate, salt of aluminum acylate, organosiloxy compound, aluminum chelate compound and other organic metal compounds; 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-aminopropylmethyldimethoxysilane, 3- Aminopropylmethyldiethoxysilane, N-β (aminoethyl) γ-aminopropyltrimethoxysilane, N-β (aminoethyl) γ-aminopropyltriethoxysilane, N-β (aminoethyl) γ-aminopropylmethyldimethoxy Silane, N-β (aminoethyl) γ-aminopropylmethyldiethoxysilane, bis [3- (trimethoxysilyl) propyl] amine, bis [3- (triethoxysilyl) propyl] amine, N, N'-bis [3- (Trimethoxysilyl) propyl] ethane-1,2-diamine, N, N'-bis [3- (triethoxysilyl) propyl] ethane-1,2-diamine, N-phenyl-3-aminopropyl Aminoalkyl group-substituted alkoxysilanes such as trimethoxysilane; amine compounds such as hexylamine, dodecylamine phosphate, tetramethylguanidine and salts thereof; quaternary ammonium salts such as benzyltriethylammonium acetate; potassium acetate, sodium acetate, shu Richiu acid Lower fatty acid salts of alkali metals such as dimethylylamine; dialkylhydroxylamines such as dimethylhydroxylamine and diethylhydroxylamine; tetramethylguanidylpropyltrimethoxysilane, tetramethylguanidylpropylmethyldimethoxysilane, tetramethylguanidylpropyltri Silanes and siloxanes containing guanidyl groups such as ethoxysilane, tetramethylguanidylpropylmethyldiethoxysilane, tetramethylguanidylpropyltris (trimethylsiloxy) silane; N, N, N', N', N'' , N''-Hexamethyl-N''-[3- (trimethoxysilyl) propyl] -phosphorimidic triamide and other phosphazene-containing silanes and siloxanes, which can be used alone. Two or more kinds may be used in combination.
これらの中でも、より反応性に優れることから、ジオクチル錫ジラウレート、ジオクチル錫ジバーサテート、テトライソプロポキシチタン、テトラｎ－ブトキシチタン、チタンジイソプロポキシビス（エチルアセトアセテート）、３－アミノプロピルトリメトキシシラン、Ｎ－β（アミノエチル）γ－アミノプロピルトリメトキシシラン、ビス［３－（トリメトキシシリル）プロピル］アミン、Ｎ，Ｎ′－ビス［３－（トリメトキシシリル）プロピル］エタン－１，２－ジアミン、テトラメチルグアニジルプロピルトリメトキシシランが好ましく、組成物の硬化性の観点からジオクチル錫ジラウレート、ジオクチル錫ジバーサテート、３－アミノプロピルトリメトキシシラン、テトラメチルグアニジルプロピルトリメトキシシランがより好ましく、有機スズ系化合物を非含有とし、より低毒性とすることから、３－アミノプロピルトリメトキシシラン、テトラメチルグアニジルプロピルトリメトキシシランがより一層好ましく、組成物の硬化性の観点からテトラメチルグアニジルプロピルトリメトキシシランが特に好ましい。
Among these, dioctyltin dilaurate, dioctyltin diversate, tetraisopropoxytitanium, tetran-butoxytitanium, titanium diisopropoxybis (ethylacetoacetate), 3-aminopropyltrimethoxysilane, because they are more reactive. N-β (aminoethyl) γ-aminopropyltrimethoxysilane, bis [3- (trimethoxysilyl) propyl] amine, N, N'-bis [3- (trimethoxysilyl) propyl] ethane-1,2- Diamine and tetramethylguanidylpropyltrimethoxysilane are preferable, and dioctyltin dilaurate, dioctyltin diversate, 3-aminopropyltrimethoxysilane, and tetramethylguanidylpropyltrimethoxysilane are more preferable from the viewpoint of curability of the composition. , 3-Aminopropyltrimethoxysilane and tetramethylguanidylpropyltrimethoxysilane are more preferable from the viewpoint of curability of the composition, because they do not contain organic tin compounds and have lower toxicity. Guanidylpropyltrimethoxysilane is particularly preferred.
硬化触媒の添加量は、特に限定されるものではないが、硬化速度を適切な範囲に調整して作業性を向上させることを考慮すると、組成物中０．０１～１５質量％が好ましく、０．１～５質量％がより好ましい。
The amount of the curing catalyst added is not particularly limited, but is preferably 0.01 to 15% by mass in the composition, preferably 0, in consideration of adjusting the curing rate to an appropriate range to improve workability. .1 to 5% by mass is more preferable.
充填剤としては公知のものを使用することができ、例えば、微粉末シリカ、煙霧質シリカ、沈降性シリカ、これらのシリカ表面を有機ケイ素化合物で疎水化処理したシリカ、ガラスビーズ、ガラスバルーン、透明樹脂ビーズ、シリカエアロゲル、珪藻土、酸化鉄、酸化亜鉛、酸化チタン、煙霧状金属酸化物などの金属酸化物、湿式シリカあるいはこれらの表面をシラン処理したもの、石英粉末、カーボンブラック、タルク、ゼオライト及びベントナイト等の補強剤、アスベスト、ガラス繊維、炭素繊維、炭酸カルシウム、炭酸マグネシウム、炭酸亜鉛などの金属炭酸塩、ガラスウール、微粉マイカ、溶融シリカ粉末、ポリスチレン、ポリ塩化ビニル、ポリプロピレンなどの合成樹脂粉末等が使用される。これらの充填剤のうち、シリカ、炭酸カルシウム、ゼオライトなどの無機質充填剤が好ましく、特に表面を疎水化処理した煙霧質シリカ、炭酸カルシウムが好ましい。
Known fillers can be used, for example, fine powder silica, fumigant silica, precipitated silica, silica whose surface is hydrophobized with an organic silicon compound, glass beads, glass balloons, and transparent. Resin beads, silica aerogel, diatomaceous earth, iron oxide, zinc oxide, titanium oxide, metal oxides such as fuming metal oxides, wet silica or those whose surfaces are silane treated, quartz powder, carbon black, talc, zeolite and Reinforcing agents such as bentonite, asbestos, glass fiber, carbon fiber, calcium carbonate, magnesium carbonate, metal carbonate such as zinc carbonate, glass wool, fine powder mica, fused silica powder, polystyrene, polyvinyl chloride, synthetic resin powder such as polypropylene Etc. are used. Among these fillers, inorganic fillers such as silica, calcium carbonate, and zeolite are preferable, and aerosol silica and calcium carbonate whose surface is hydrophobized are particularly preferable.
充填剤の配合量は、組成物中０～１，０００質量％、特に１～１，０００質量％、とりわけ１～４００質量％とすることが好ましい。
The blending amount of the filler is preferably 0 to 1,000% by mass, particularly 1 to 1,000% by mass, and particularly preferably 1 to 400% by mass in the composition.
２官能性オルガノポリシロキサン化合物を含む組成物の製造方法
本発明の熱硬化性樹脂組成物は、次に示されるような方法で製造することができる。
例えば、上記一般式（１）で表されるオルガノポリシロキサン化合物と、分子鎖両末端がシラノール基又は加水分解性シリル基で封鎖された直鎖状ジオルガノポリシロキサンとを、同時に又は別々に必要により混合し、撹拌、溶解及び／又は分散させることにより、混合物を得てもよい。また、使用用途によって、該混合物に、添加物を添加して混合してもよい。各成分は一種単独で使用してもよく、２種以上を併用してもよい。
組成物の製造方法では、混合、撹拌及び分散を行う装置について、特に限定されない。具体的には、例えば、株式会社ダルトン社製混合撹拌機、株式会社ダルトン社製万能混合撹拌機等を用いることができ、これらの装置を適宜組み合わせて使用してもよい。 Method for Producing Composition Containing Bifunctional Organopolysiloxane Compound The thermosetting resin composition of the present invention can be produced by the method shown below.
For example, an organopolysiloxane compound represented by the above general formula (1) and a linear diorganopolysiloxane having both ends of the molecular chain sealed with a silanol group or a hydrolyzable silyl group are required at the same time or separately. The mixture may be obtained by mixing with, stirring, dissolving and / or dispersing. Further, depending on the intended use, additives may be added to the mixture and mixed. Each component may be used alone or in combination of two or more.
The method for producing the composition is not particularly limited with respect to the apparatus for mixing, stirring and dispersing. Specifically, for example, a mixing stirrer manufactured by Dalton Corporation, a universal mixing stirrer manufactured by Dalton Corporation, or the like can be used, and these devices may be used in combination as appropriate.
本発明の熱硬化性樹脂組成物は、次に示されるような方法で製造することができる。
例えば、上記一般式（１）で表されるオルガノポリシロキサン化合物と、分子鎖両末端がシラノール基又は加水分解性シリル基で封鎖された直鎖状ジオルガノポリシロキサンとを、同時に又は別々に必要により混合し、撹拌、溶解及び／又は分散させることにより、混合物を得てもよい。また、使用用途によって、該混合物に、添加物を添加して混合してもよい。各成分は一種単独で使用してもよく、２種以上を併用してもよい。
組成物の製造方法では、混合、撹拌及び分散を行う装置について、特に限定されない。具体的には、例えば、株式会社ダルトン社製混合撹拌機、株式会社ダルトン社製万能混合撹拌機等を用いることができ、これらの装置を適宜組み合わせて使用してもよい。 Method for Producing Composition Containing Bifunctional Organopolysiloxane Compound The thermosetting resin composition of the present invention can be produced by the method shown below.
For example, an organopolysiloxane compound represented by the above general formula (1) and a linear diorganopolysiloxane having both ends of the molecular chain sealed with a silanol group or a hydrolyzable silyl group are required at the same time or separately. The mixture may be obtained by mixing with, stirring, dissolving and / or dispersing. Further, depending on the intended use, additives may be added to the mixture and mixed. Each component may be used alone or in combination of two or more.
The method for producing the composition is not particularly limited with respect to the apparatus for mixing, stirring and dispersing. Specifically, for example, a mixing stirrer manufactured by Dalton Corporation, a universal mixing stirrer manufactured by Dalton Corporation, or the like can be used, and these devices may be used in combination as appropriate.
以下、実施例および比較例を挙げて本発明をより具体的に説明するが、本発明はこれら実施例に限定されるものではない。
なお下記において、Ｍｅはメチル基を示し、粘度は、Ｂ型回転粘度計による２５℃における測定値である。 Hereinafter, the present invention will be described in more detail with reference to Examples and Comparative Examples, but the present invention is not limited to these Examples.
In the following, Me represents a methyl group, and the viscosity is a value measured at 25 ° C. by a B-type rotational viscometer.
なお下記において、Ｍｅはメチル基を示し、粘度は、Ｂ型回転粘度計による２５℃における測定値である。 Hereinafter, the present invention will be described in more detail with reference to Examples and Comparative Examples, but the present invention is not limited to these Examples.
In the following, Me represents a methyl group, and the viscosity is a value measured at 25 ° C. by a B-type rotational viscometer.
［１］オルガノポリシロキサン化合物の合成
［実施例１－１］オルガノポリシロキサン化合物１の合成
[1] Synthesis of Organopolysiloxane Compound [Example 1-1] Synthesis of Organopolysiloxane Compound 1
［実施例１－１］オルガノポリシロキサン化合物１の合成
撹拌機、還流冷却器、滴下ロートおよび温度計を備えた５００ｍｌ４つ口フラスコに、３５％塩酸０．２ｇ（１．２×１０-3モル）、ジメトキシ（メチル）（ピペリジルメチル）シラン２０３．３６ｇ（１．００モル）を仕込み、５０℃に加熱した。その中に、あらかじめ混合したメタノール２７ｇと水９ｇ（０．５モル）を滴下投入し、３時間撹拌した。エチレンジアミン０．０７２ｇ（１．２×１０-3モル）で中和し、１時間撹拌した。ＧＣ（ガスクロマトグラフィ）測定により目的物のピークを確認し、エバポレータ、真空ポンプにて減圧留去し、ＧＣ測定により原料ピークの消失を確認し、上記構造式のオルガノポリシロキサン化合物１を得た。
0.2 g (1.2 x 10-3 mol) of 35% hydrochloric acid, 203.36 g of dimethoxy (methyl) (piperidylmethyl) silane in a 500 ml four-necked flask equipped with a stirrer, reflux condenser, dropping funnel and thermometer. (1.00 mol) was charged and heated to 50 ° C. 27 g of methanol and 9 g (0.5 mol) of water mixed in advance were added dropwise thereto, and the mixture was stirred for 3 hours. It was neutralized with 0.072 g (1.2 × 10 -3 mol) of ethylenediamine and stirred for 1 hour. The peak of the target product was confirmed by GC (gas chromatography) measurement, distilled off under reduced pressure with an evaporator and a vacuum pump, and the disappearance of the raw material peak was confirmed by GC measurement to obtain an organopolysiloxane compound 1 having the above structural formula.
［実施例１－２］オルガノポリシロキサン化合物２の合成
[Example 1-2] Synthesis of organopolysiloxane compound 2
撹拌機、還流冷却器、滴下ロートおよび温度計を備えた３００ｍｌセパラブルフラスコに、ジメトキシ（メチル）（ピペリジルメチル）シラン２０３．３６ｇ（１．００モル）を仕込み、室温で撹拌した。その中に、両末端に水酸基を有するジオルガノポリシロキサン（１，５－ジヒドロキシ－１，１，３，３，５，５－ヘキサメチルトリシロキサン）４．０７ｇ（０．０２モル）を滴下投入し、室温で２時間撹拌した。その後、９０℃に加熱し、減圧留去、加圧ろ過にて過剰添加した原料およびオリゴマーを除去し、Ｓｉ29ＮＭＲ測定により原料のシラノールピークの消失を確認し、上記構造式のオルガノポリシロキサン化合物２を得た。
203.36 g (1.00 mol) of dimethoxy (methyl) (piperidylmethyl) silane was placed in a 300 ml separable flask equipped with a stirrer, a reflux condenser, a dropping funnel and a thermometer, and the mixture was stirred at room temperature. 4.07 g (0.02 mol) of diorganopolysiloxane (1,5-dihydroxy-1,1,3,3,5,5-hexamethyltrisiloxane) having hydroxyl groups at both ends was added dropwise thereto. Then, the mixture was stirred at room temperature for 2 hours. Then, the mixture was heated to 90 ° C., distilled under reduced pressure, and excessively added raw materials and oligomers were removed by pressure filtration, and the disappearance of the silanol peak of the raw material was confirmed by Si 29 NMR measurement. The organopolysiloxane compound having the above structural formula I got 2.
［実施例１－３］オルガノポリシロキサン化合物３の合成
[Example 1-3] Synthesis of organopolysiloxane compound 3
撹拌機、還流冷却器、滴下ロートおよび温度計を備えた３００ｍｌセパラブルフラスコに、ジメトキシ（メチル）（Ｎ，Ｎ－ジエチルアミノメチル）シラン９７．５９ｇ（０．５１モル）を仕込み、室温で撹拌した。その中に、両末端に水酸基を有するジオルガノポリシロキサン（１，５－ジヒドロキシ－１，１，３，３，５，５－ヘキサメチルトリシロキサン）３．０５ｇ（０．０１５モル）を滴下投入し、室温で２時間撹拌した。その後、９０℃に加熱し、減圧留去、加圧ろ過にて過剰添加した原料およびオリゴマーを除去し、Ｓｉ29ＮＭＲ測定により原料のシラノールピークの消失を確認し、上記構造式のオルガノポリシロキサン化合物３を得た。
97.59 g (0.51 mol) of dimethoxy (methyl) (N, N-diethylaminomethyl) silane was placed in a 300 ml separable flask equipped with a stirrer, a reflux condenser, a dropping funnel and a thermometer, and stirred at room temperature. .. 3.05 g (0.015 mol) of diorganopolysiloxane (1,5-dihydroxy-1,1,3,3,5,5-hexamethyltrisiloxane) having hydroxyl groups at both ends was added dropwise thereto. Then, the mixture was stirred at room temperature for 2 hours. Then, the mixture was heated to 90 ° C., distilled under reduced pressure, and excessively added raw materials and oligomers were removed by pressure filtration. Si 29 NMR measurement was used to confirm the disappearance of the silanol peak of the raw material. The organopolysiloxane compound having the above structural formula I got 3.
［比較例１－１］オルガノポリシロキサン化合物４の合成
[Comparative Example 1-1] Synthesis of Organopolysiloxane Compound 4
撹拌機、還流冷却器、滴下ロートおよび温度計を備えた１Ｌセパラブルフラスコに、３５％塩酸０．３ｇ（１．８×１０-3モル）、ジメトキシ（メチル）（ビニル）シラン３５５．１５ｇ（２．５０モル）を仕込み、５０℃に加熱した。その中に、あらかじめ混合したメタノール６７．５ｇと水２２．５ｇ（１．２５モル）を滴下投入し、５時間撹拌した。エチレンジアミン０．１１ｇ（１．８×１０-3モル）で中和し、減圧精製した。ＧＣ測定により原料ピークの消失を確認し、上記構造式のオルガノポリシロキサン化合物４を得た。
0.3 g (1.8 x 10 -3 mol) of 35% hydrochloric acid, 355.15 g of dimethoxy (methyl) (vinyl) silane in a 1 L separable flask equipped with a stirrer, reflux condenser, dropping funnel and thermometer. 2.50 mol) was charged and heated to 50 ° C. 67.5 g of premixed methanol and 22.5 g (1.25 mol) of water were added dropwise thereto, and the mixture was stirred for 5 hours. It was neutralized with 0.11 g (1.8 × 10 -3 mol) of ethylenediamine and purified under reduced pressure. The disappearance of the raw material peak was confirmed by GC measurement, and the organopolysiloxane compound 4 having the above structural formula was obtained.
［２］アルコキシシリル基の反応性の確認
［参考例２－１］
粘度５，０００ｍＰａ・ｓのα，ω－ジヒドロキシジメチルポリシロキサン１００質量部と、上記実施例１－１で得られたオルガノポリシロキサン化合物１を１．４質量部、湿気遮断下で均一に手もみ混合し、組成物を調製した。 [2] Confirmation of reactivity of alkoxysilyl group [Reference Example 2-1]
100 parts by mass of α, ω-dihydroxydimethylpolysiloxane having a viscosity of 5,000 mPa · s and 1.4 parts by mass of the organopolysiloxane compound 1 obtained in Example 1-1 above were uniformly rubbed under moisture shielding. The mixture was mixed to prepare a composition.
［参考例２－１］
粘度５，０００ｍＰａ・ｓのα，ω－ジヒドロキシジメチルポリシロキサン１００質量部と、上記実施例１－１で得られたオルガノポリシロキサン化合物１を１．４質量部、湿気遮断下で均一に手もみ混合し、組成物を調製した。 [2] Confirmation of reactivity of alkoxysilyl group [Reference Example 2-1]
100 parts by mass of α, ω-dihydroxydimethylpolysiloxane having a viscosity of 5,000 mPa · s and 1.4 parts by mass of the organopolysiloxane compound 1 obtained in Example 1-1 above were uniformly rubbed under moisture shielding. The mixture was mixed to prepare a composition.
［参考例２－２］
上記実施例１－１で得られたオルガノポリシロキサン化合物１の代わりに上記実施例１－２で得られたオルガノポリシロキサン化合物２を１．９質量部、使用した以外は参考例２－１と同様にして組成物を調製した。 [Reference Example 2-2]
1.9 parts by mass of the organopolysiloxane compound 2 obtained in Example 1-2 was used instead of the organopolysiloxane compound 1 obtained in Example 1-1, and Reference Example 2-1 was used except that it was used. The composition was prepared in the same manner.
上記実施例１－１で得られたオルガノポリシロキサン化合物１の代わりに上記実施例１－２で得られたオルガノポリシロキサン化合物２を１．９質量部、使用した以外は参考例２－１と同様にして組成物を調製した。 [Reference Example 2-2]
1.9 parts by mass of the organopolysiloxane compound 2 obtained in Example 1-2 was used instead of the organopolysiloxane compound 1 obtained in Example 1-1, and Reference Example 2-1 was used except that it was used. The composition was prepared in the same manner.
［参考例２－３］
上記実施例１－１で得られたオルガノポリシロキサン化合物１の代わりに上記実施例１－３で得られたオルガノポリシロキサン化合物３を１．８質量部、使用した以外は参考例２－１と同様にして組成物を調製した。 [Reference Example 2-3]
1.8 parts by mass of the organopolysiloxane compound 3 obtained in Example 1-3 was used instead of the organopolysiloxane compound 1 obtained in Example 1-1, and Reference Example 2-1 was used except that it was used. The composition was prepared in the same manner.
上記実施例１－１で得られたオルガノポリシロキサン化合物１の代わりに上記実施例１－３で得られたオルガノポリシロキサン化合物３を１．８質量部、使用した以外は参考例２－１と同様にして組成物を調製した。 [Reference Example 2-3]
1.8 parts by mass of the organopolysiloxane compound 3 obtained in Example 1-3 was used instead of the organopolysiloxane compound 1 obtained in Example 1-1, and Reference Example 2-1 was used except that it was used. The composition was prepared in the same manner.
［比較参考例２－１］
上記実施例１－１で得られたオルガノポリシロキサン化合物１の代わりに上記比較例１－１で得られたオルガノポリシロキサン化合物４を１．３質量部、使用した以外は参考例２－１と同様にして組成物を調製した。 [Comparative Reference Example 2-1]
1.3 parts by mass of the organopolysiloxane compound 4 obtained in Comparative Example 1-1 instead of the organopolysiloxane compound 1 obtained in Example 1-1 was used as Reference Example 2-1 except that it was used. The composition was prepared in the same manner.
上記実施例１－１で得られたオルガノポリシロキサン化合物１の代わりに上記比較例１－１で得られたオルガノポリシロキサン化合物４を１．３質量部、使用した以外は参考例２－１と同様にして組成物を調製した。 [Comparative Reference Example 2-1]
1.3 parts by mass of the organopolysiloxane compound 4 obtained in Comparative Example 1-1 instead of the organopolysiloxane compound 1 obtained in Example 1-1 was used as Reference Example 2-1 except that it was used. The composition was prepared in the same manner.
上記参考例２－１～２－３および比較参考例２－１で調製した組成物について下記の評価を実施した。それらの結果を表１に示す。
〔増粘率〕
上記調製方法にて得た組成物を、窒素ガスを充填したガラス瓶中にて２５℃、５０％ＲＨの空気下で密栓保管した。粘度は、充填直後、及び、充填から６０分及び２４時間保管した後に、それぞれ測定した。測定した粘度から下記式を用いて増粘率を算出した。増粘率の値が大きいほど、鎖長延長剤の反応性が良好であることを示す。
The following evaluations were carried out on the compositions prepared in Reference Examples 2-1 to 2-3 and Comparative Reference Examples 2-1. The results are shown in Table 1.
[Thickening rate]
The composition obtained by the above preparation method was stored in a glass bottle filled with nitrogen gas in a tightly closed container at 25 ° C. and 50% RH. Viscosity was measured immediately after filling and after storage for 60 minutes and 24 hours after filling, respectively. The thickening rate was calculated from the measured viscosity using the following formula. The larger the value of the thickening ratio, the better the reactivity of the chain length extender.
〔増粘率〕
上記調製方法にて得た組成物を、窒素ガスを充填したガラス瓶中にて２５℃、５０％ＲＨの空気下で密栓保管した。粘度は、充填直後、及び、充填から６０分及び２４時間保管した後に、それぞれ測定した。測定した粘度から下記式を用いて増粘率を算出した。増粘率の値が大きいほど、鎖長延長剤の反応性が良好であることを示す。
[Thickening rate]
The composition obtained by the above preparation method was stored in a glass bottle filled with nitrogen gas in a tightly closed container at 25 ° C. and 50% RH. Viscosity was measured immediately after filling and after storage for 60 minutes and 24 hours after filling, respectively. The thickening rate was calculated from the measured viscosity using the following formula. The larger the value of the thickening ratio, the better the reactivity of the chain length extender.
表１に示されるように実施例１－１～１－３で得られたオルガノポリシロキサン化合物１～３を用いた参考例２－１～２－３で調製した組成物は、比較参考例２－１で調製した組成物に比べ増粘率が非常に高く、鎖長延長剤としての反応性が良好であることが分かった。
一方、比較参考例２－１で調製した組成物は、ほとんど増粘しておらず、十分な反応性を確保することができなかった。 As shown in Table 1, the compositions prepared in Reference Examples 2-1 to 2-3 using the organopolysiloxane compounds 1 to 3 obtained in Examples 1-1 to 1-3 are used in Comparative Reference Example 2. It was found that the thickening rate was much higher than that of the composition prepared in -1, and the reactivity as a chain length extender was good.
On the other hand, the composition prepared in Comparative Reference Example 2-1 was hardly thickened, and sufficient reactivity could not be ensured.
一方、比較参考例２－１で調製した組成物は、ほとんど増粘しておらず、十分な反応性を確保することができなかった。 As shown in Table 1, the compositions prepared in Reference Examples 2-1 to 2-3 using the organopolysiloxane compounds 1 to 3 obtained in Examples 1-1 to 1-3 are used in Comparative Reference Example 2. It was found that the thickening rate was much higher than that of the composition prepared in -1, and the reactivity as a chain length extender was good.
On the other hand, the composition prepared in Comparative Reference Example 2-1 was hardly thickened, and sufficient reactivity could not be ensured.
Claims (11)
- 下記一般式（１）で表されるオルガノポリシロキサン化合物。
- 請求項１に記載のオルガノポリシロキサン化合物と、分子鎖両末端がシラノール基又は加水分解性シリル基で封鎖された直鎖状ジオルガノポリシロキサンとを含有する組成物。 A composition containing the organopolysiloxane compound according to claim 1 and a linear diorganopolysiloxane having both ends of the molecular chain sealed with a silanol group or a hydrolyzable silyl group.
- 請求項２に記載の組成物を含有するコーティング剤。 A coating agent containing the composition according to claim 2.
- 請求項２に記載の組成物を含有する接着剤。 An adhesive containing the composition according to claim 2.
- 請求項２に記載の組成物を含有するシーリング剤。 A sealing agent containing the composition according to claim 2.
- 請求項２に記載の組成物の硬化物。 A cured product of the composition according to claim 2.
- 請求項３に記載のコーティング剤の硬化物を有する物品。 An article having a cured product of the coating agent according to claim 3.
- 請求項４に記載の接着剤の硬化物を有する物品。 An article having a cured product of the adhesive according to claim 4.
- 請求項５に記載のシーリング剤の硬化物を有する物品。 An article having a cured product of the sealant according to claim 5.
- 下記一般式（２）で表されるオルガノシラン化合物を触媒存在下で縮合反応させて二量化する工程を含む下記一般式（１）’で表されるオルガノポリシロキサン化合物の製造方法。
- 下記一般式（３）で表される分子鎖両末端シラノール基封鎖ジオルガノポリシロキサンと下記一般式（２）で表されるオルガノシラン化合物を縮合反応させて分子鎖両末端シラノール基封鎖ジオルガノポリシロキサンの分子鎖両末端を下記一般式（２）で表されるオルガノシラン化合物の残基で封鎖する工程を含む下記一般式（１）’’で表されるオルガノポリシロキサン化合物の製造方法。
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