WO2021002163A1 - Composition d'organopolysiloxane, composition comprenant ledit composé, et procédé de préparation associé - Google Patents
Composition d'organopolysiloxane, composition comprenant ledit composé, et procédé de préparation associé 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
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- 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
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- 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
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- 150000003839 salts Chemical class 0.000 description 2
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- 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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- 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
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- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-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
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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
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- 125000003368 amide group Chemical group 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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- 125000004093 cyano group Chemical group *C#N 0.000 description 1
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- 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
L'invention concerne un composé d'organopolysiloxane qui devient un allongeur de chaîne pour une composition vulcanisable à température ambiante (RTV) désalcoolisée qui est rapidement caoutchouté et présente l'élasticité du caoutchouc. Ce composé d'organopolysiloxane est représenté par la formule générale (1), et une composition selon la présente invention contient : ledit composé ; et un diorganopolysiloxane linéaire ayant les deux extrémités d'une chaîne moléculaire scellée avec un groupe silanol ou un groupe silyle hydrolysable. (Dans la formule, R1, R2, et R3 sont chacun indépendamment un groupe alkyle non substitué ou substitué ayant 1 à 10 atomes de carbone, ou un groupe aryle non substitué ou substitué ayant 6 à 10 atomes de carbone ; n est un nombre entier de 0 à 10 ; et X est un groupe amino non substitué ou substitué.)
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WO2023272417A1 (fr) * | 2021-06-28 | 2023-01-05 | Dow Silicones Corporation | Compositions de silicone et leur préparation |
Citations (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4005028A (en) * | 1975-04-22 | 1977-01-25 | The Procter & Gamble Company | Organosilane-containing detergent composition |
US4005030A (en) * | 1975-04-22 | 1977-01-25 | The Procter & Gamble Company | Organosilane-containing anionic detergent composition |
JP2004197097A (ja) * | 2002-12-19 | 2004-07-15 | Wacker Chemie Gmbh | オルガノポリシロキサン組成物、その製造方法、前記組成物から製造された架橋可能な材料、及び前記材料から製造された成形品 |
JP2012511607A (ja) * | 2008-12-11 | 2012-05-24 | ワッカー ケミー アクチエンゲゼルシャフト | アルコキシシラン末端ポリマー含有ポリマー混合物 |
JP2012528823A (ja) * | 2009-06-04 | 2012-11-15 | ワッカー ケミー アクチエンゲゼルシャフト | アミノオルガノシランの製造方法 |
WO2015011259A1 (fr) * | 2013-07-26 | 2015-01-29 | L'oreal | Procédé de traitement capillaire avec au moins un silicone fonctionnalisé avec au moins une unité alcoxysilane, un solvant particulier et moins de 5 % d'eau |
WO2015011258A1 (fr) * | 2013-07-26 | 2015-01-29 | L'oreal | Procédé de traitement capillaire avec au moins un polymère de silicone fonctionnalisé par au mois une unité alcoxysilane et au moins un alcoxysilane spécifique |
FR3008887A1 (fr) * | 2013-07-26 | 2015-01-30 | Oreal | Procede de traitement des cheveux avec au moins un polymere fonctionnalise par au moins un motif alcoxysilane et au moins un polymere cationique |
CN105131899A (zh) * | 2015-10-15 | 2015-12-09 | 成都硅宝科技股份有限公司 | 高稳定性混凝土硅酮接缝胶及其制备方法 |
WO2017063419A1 (fr) * | 2015-10-15 | 2017-04-20 | 成都硅宝科技股份有限公司 | Agent d'extension de chaîne d'organosilicone et application |
JP2017537186A (ja) * | 2014-11-07 | 2017-12-14 | ワッカー ケミー アクチエンゲゼルシャフトWacker Chemie AG | 架橋性オルガノポリシロキサン組成物 |
FR3067603A1 (fr) * | 2017-06-15 | 2018-12-21 | L'oreal | Composition cosmetique comprenant des polymeres silicones a groupements alcoxy-(aminomethyl)-silyle, des tensioactifs et des acides gras, et procede de traitement cosmetique |
CN110256959A (zh) * | 2019-05-21 | 2019-09-20 | 郝建强 | 可uv固化有机硅离型剂 |
CN110922600A (zh) * | 2019-10-22 | 2020-03-27 | 武汉大学 | 一类羟烃基有机硅化合物及其制备方法和应用 |
-
2020
- 2020-06-10 JP JP2021529937A patent/JP7279790B2/ja active Active
- 2020-06-10 WO PCT/JP2020/022790 patent/WO2021002163A1/fr active Application Filing
Patent Citations (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4005028A (en) * | 1975-04-22 | 1977-01-25 | The Procter & Gamble Company | Organosilane-containing detergent composition |
US4005030A (en) * | 1975-04-22 | 1977-01-25 | The Procter & Gamble Company | Organosilane-containing anionic detergent composition |
JP2004197097A (ja) * | 2002-12-19 | 2004-07-15 | Wacker Chemie Gmbh | オルガノポリシロキサン組成物、その製造方法、前記組成物から製造された架橋可能な材料、及び前記材料から製造された成形品 |
JP2012511607A (ja) * | 2008-12-11 | 2012-05-24 | ワッカー ケミー アクチエンゲゼルシャフト | アルコキシシラン末端ポリマー含有ポリマー混合物 |
JP2012528823A (ja) * | 2009-06-04 | 2012-11-15 | ワッカー ケミー アクチエンゲゼルシャフト | アミノオルガノシランの製造方法 |
WO2015011258A1 (fr) * | 2013-07-26 | 2015-01-29 | L'oreal | Procédé de traitement capillaire avec au moins un polymère de silicone fonctionnalisé par au mois une unité alcoxysilane et au moins un alcoxysilane spécifique |
WO2015011259A1 (fr) * | 2013-07-26 | 2015-01-29 | L'oreal | Procédé de traitement capillaire avec au moins un silicone fonctionnalisé avec au moins une unité alcoxysilane, un solvant particulier et moins de 5 % d'eau |
FR3008887A1 (fr) * | 2013-07-26 | 2015-01-30 | Oreal | Procede de traitement des cheveux avec au moins un polymere fonctionnalise par au moins un motif alcoxysilane et au moins un polymere cationique |
JP2017537186A (ja) * | 2014-11-07 | 2017-12-14 | ワッカー ケミー アクチエンゲゼルシャフトWacker Chemie AG | 架橋性オルガノポリシロキサン組成物 |
CN105131899A (zh) * | 2015-10-15 | 2015-12-09 | 成都硅宝科技股份有限公司 | 高稳定性混凝土硅酮接缝胶及其制备方法 |
WO2017063419A1 (fr) * | 2015-10-15 | 2017-04-20 | 成都硅宝科技股份有限公司 | Agent d'extension de chaîne d'organosilicone et application |
FR3067603A1 (fr) * | 2017-06-15 | 2018-12-21 | L'oreal | Composition cosmetique comprenant des polymeres silicones a groupements alcoxy-(aminomethyl)-silyle, des tensioactifs et des acides gras, et procede de traitement cosmetique |
CN110256959A (zh) * | 2019-05-21 | 2019-09-20 | 郝建强 | 可uv固化有机硅离型剂 |
CN110922600A (zh) * | 2019-10-22 | 2020-03-27 | 武汉大学 | 一类羟烃基有机硅化合物及其制备方法和应用 |
Non-Patent Citations (3)
Title |
---|
ANDRIANOV,K.A. ET AL.: "Methods of synthesis of 1-p- diethoxymethylchloromethylsiloxanes and the reaction of substitution of chlorine in the a-chloromethyl group", ZHURNAL OBSHCHEI KHIMII, vol. 30, 1960, pages 2393 - 2397, ISSN: 0044-460X * |
BARYSHOK,V.P. ET AL.: "Interaction of 1,3-dimethyl-1,3-bis(chloromethyl)-1,3- diethoxy-1,3- disiloxane with primary and secondary amines", METALLOORGANICHESKAYA KHIMIYA, vol. 4, no. 5, 1991, pages 1079 - 1082, ISSN: 0235-0114 * |
DATABASE REGISTRY 5 August 2020 (2020-08-05), XP055784118, retrieved from CAS Database accession no. 744999-44-8 * |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2023272417A1 (fr) * | 2021-06-28 | 2023-01-05 | Dow Silicones Corporation | Compositions de silicone et leur préparation |
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