JP2019532924A - シラン及び該シランを含む硬化性組成物 - Google Patents
シラン及び該シランを含む硬化性組成物 Download PDFInfo
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- JP2019532924A JP2019532924A JP2019513955A JP2019513955A JP2019532924A JP 2019532924 A JP2019532924 A JP 2019532924A JP 2019513955 A JP2019513955 A JP 2019513955A JP 2019513955 A JP2019513955 A JP 2019513955A JP 2019532924 A JP2019532924 A JP 2019532924A
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- 239000000203 mixture Substances 0.000 title claims abstract description 110
- 229910000077 silane Inorganic materials 0.000 title claims abstract description 68
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 title description 46
- -1 silane compound Chemical class 0.000 claims abstract description 99
- 239000003431 cross linking reagent Substances 0.000 claims abstract description 23
- 239000003054 catalyst Substances 0.000 claims abstract description 19
- 239000002318 adhesion promoter Substances 0.000 claims abstract description 9
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 9
- 238000000034 method Methods 0.000 claims abstract description 7
- 230000008569 process Effects 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 49
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 33
- 125000000217 alkyl group Chemical group 0.000 claims description 29
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 24
- 150000001875 compounds Chemical class 0.000 claims description 23
- 125000003342 alkenyl group Chemical group 0.000 claims description 18
- 229910052760 oxygen Inorganic materials 0.000 claims description 18
- 125000003118 aryl group Chemical group 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
- 150000001412 amines Chemical class 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 229920001296 polysiloxane Polymers 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 claims description 11
- 239000000853 adhesive Substances 0.000 claims description 10
- 230000001070 adhesive effect Effects 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
- 239000000565 sealant Substances 0.000 claims description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 7
- 150000002430 hydrocarbons Chemical group 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 claims description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 6
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- 238000000576 coating method Methods 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 229910052710 silicon Inorganic materials 0.000 claims description 5
- RXYPXQSKLGGKOL-UHFFFAOYSA-N 1,4-dimethylpiperazine Chemical compound CN1CCN(C)CC1 RXYPXQSKLGGKOL-UHFFFAOYSA-N 0.000 claims description 4
- HWWYDZCSSYKIAD-UHFFFAOYSA-N 3,5-dimethylpyridine Chemical compound CC1=CN=CC(C)=C1 HWWYDZCSSYKIAD-UHFFFAOYSA-N 0.000 claims description 4
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- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 4
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- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 150000003512 tertiary amines Chemical class 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- 239000011248 coating agent Substances 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 2
- DPMZXMBOYHBELT-UHFFFAOYSA-N 1,3,5-trimethyl-1,3,5-triazinane Chemical compound CN1CN(C)CN(C)C1 DPMZXMBOYHBELT-UHFFFAOYSA-N 0.000 claims description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 claims description 2
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- 238000006136 alcoholysis reaction Methods 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- VGIVLIHKENZQHQ-UHFFFAOYSA-N n,n,n',n'-tetramethylmethanediamine Chemical compound CN(C)CN(C)C VGIVLIHKENZQHQ-UHFFFAOYSA-N 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- SBYHFKPVCBCYGV-UHFFFAOYSA-N quinuclidine Chemical compound C1CC2CCN1CC2 SBYHFKPVCBCYGV-UHFFFAOYSA-N 0.000 claims description 2
- 239000011493 spray foam Substances 0.000 claims description 2
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 claims description 2
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 claims description 2
- 229920002554 vinyl polymer Chemical group 0.000 claims description 2
- VKNUORWMCINMRB-UHFFFAOYSA-N diethyl malate Chemical compound CCOC(=O)CC(O)C(=O)OCC VKNUORWMCINMRB-UHFFFAOYSA-N 0.000 description 21
- 150000004756 silanes Chemical class 0.000 description 16
- XKMYFKVKDCZKPH-UHFFFAOYSA-N butyl(octyl)tin Chemical compound CCCCCCCC[Sn]CCCC XKMYFKVKDCZKPH-UHFFFAOYSA-N 0.000 description 15
- BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 15
- 239000004971 Cross linker Substances 0.000 description 14
- 238000004132 cross linking Methods 0.000 description 14
- 150000002148 esters Chemical class 0.000 description 13
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 11
- 125000000304 alkynyl group Chemical group 0.000 description 11
- 150000003606 tin compounds Chemical class 0.000 description 11
- 239000002274 desiccant Substances 0.000 description 10
- 239000004205 dimethyl polysiloxane Substances 0.000 description 10
- 239000000945 filler Substances 0.000 description 10
- 239000000463 material Substances 0.000 description 10
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- YSEKNCXYRGKTBJ-UHFFFAOYSA-N dimethyl 2-hydroxybutanedioate Chemical compound COC(=O)CC(O)C(=O)OC YSEKNCXYRGKTBJ-UHFFFAOYSA-N 0.000 description 8
- 238000009472 formulation Methods 0.000 description 8
- 239000001630 malic acid Substances 0.000 description 8
- 235000011090 malic acid Nutrition 0.000 description 8
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- 239000004945 silicone rubber Substances 0.000 description 8
- PDSCSYLDRHAHOX-UHFFFAOYSA-N Dibutyl malate Chemical compound CCCCOC(=O)CC(O)C(=O)OCCCC PDSCSYLDRHAHOX-UHFFFAOYSA-N 0.000 description 7
- XQBCVRSTVUHIGH-UHFFFAOYSA-L [dodecanoyloxy(dioctyl)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCCCCCC)(CCCCCCCC)OC(=O)CCCCCCCCCCC XQBCVRSTVUHIGH-UHFFFAOYSA-L 0.000 description 7
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- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 6
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
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- 125000000524 functional group Chemical group 0.000 description 5
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- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
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- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 4
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- JLUFWMXJHAVVNN-UHFFFAOYSA-N methyltrichlorosilane Chemical compound C[Si](Cl)(Cl)Cl JLUFWMXJHAVVNN-UHFFFAOYSA-N 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- INJVFBCDVXYHGQ-UHFFFAOYSA-N n'-(3-triethoxysilylpropyl)ethane-1,2-diamine Chemical compound CCO[Si](OCC)(OCC)CCCNCCN INJVFBCDVXYHGQ-UHFFFAOYSA-N 0.000 description 1
- NHBRUUFBSBSTHM-UHFFFAOYSA-N n'-[2-(3-trimethoxysilylpropylamino)ethyl]ethane-1,2-diamine Chemical compound CO[Si](OC)(OC)CCCNCCNCCN NHBRUUFBSBSTHM-UHFFFAOYSA-N 0.000 description 1
- MQWFLKHKWJMCEN-UHFFFAOYSA-N n'-[3-[dimethoxy(methyl)silyl]propyl]ethane-1,2-diamine Chemical compound CO[Si](C)(OC)CCCNCCN MQWFLKHKWJMCEN-UHFFFAOYSA-N 0.000 description 1
- QIOYHIUHPGORLS-UHFFFAOYSA-N n,n-dimethyl-3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN(C)C QIOYHIUHPGORLS-UHFFFAOYSA-N 0.000 description 1
- KFOZMMAXUUCIKU-UHFFFAOYSA-N n-(3-triethoxysilylpropyl)butan-1-amine Chemical compound CCCCNCCC[Si](OCC)(OCC)OCC KFOZMMAXUUCIKU-UHFFFAOYSA-N 0.000 description 1
- YFBFAHMPVMWKIM-UHFFFAOYSA-N n-(3-triethoxysilylpropyl)cyclohexanamine Chemical compound CCO[Si](OCC)(OCC)CCCNC1CCCCC1 YFBFAHMPVMWKIM-UHFFFAOYSA-N 0.000 description 1
- KBJFYLLAMSZSOG-UHFFFAOYSA-N n-(3-trimethoxysilylpropyl)aniline Chemical compound CO[Si](OC)(OC)CCCNC1=CC=CC=C1 KBJFYLLAMSZSOG-UHFFFAOYSA-N 0.000 description 1
- XCOASYLMDUQBHW-UHFFFAOYSA-N n-(3-trimethoxysilylpropyl)butan-1-amine Chemical compound CCCCNCCC[Si](OC)(OC)OC XCOASYLMDUQBHW-UHFFFAOYSA-N 0.000 description 1
- KGNDVXPHQJMHLX-UHFFFAOYSA-N n-(3-trimethoxysilylpropyl)cyclohexanamine Chemical compound CO[Si](OC)(OC)CCCNC1CCCCC1 KGNDVXPHQJMHLX-UHFFFAOYSA-N 0.000 description 1
- VNBLTKHUCJLFSB-UHFFFAOYSA-N n-(trimethoxysilylmethyl)aniline Chemical compound CO[Si](OC)(OC)CNC1=CC=CC=C1 VNBLTKHUCJLFSB-UHFFFAOYSA-N 0.000 description 1
- DRRZZMBHJXLZRS-UHFFFAOYSA-N n-[3-[dimethoxy(methyl)silyl]propyl]cyclohexanamine Chemical compound CO[Si](C)(OC)CCCNC1CCCCC1 DRRZZMBHJXLZRS-UHFFFAOYSA-N 0.000 description 1
- WHIVNJATOVLWBW-UHFFFAOYSA-N n-butan-2-ylidenehydroxylamine Chemical compound CCC(C)=NO WHIVNJATOVLWBW-UHFFFAOYSA-N 0.000 description 1
- WIBFFTLQMKKBLZ-SEYXRHQNSA-N n-butyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCCCC WIBFFTLQMKKBLZ-SEYXRHQNSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- IRUHTDGKUWERCQ-UHFFFAOYSA-N n-propyl-3-triethoxysilylpropan-1-amine Chemical compound CCCNCCC[Si](OCC)(OCC)OCC IRUHTDGKUWERCQ-UHFFFAOYSA-N 0.000 description 1
- ONBPFUKUSJUPES-UHFFFAOYSA-N n-propyl-3-trimethoxysilylpropan-1-amine Chemical compound CCCNCCC[Si](OC)(OC)OC ONBPFUKUSJUPES-UHFFFAOYSA-N 0.000 description 1
- SZVGMOIRUYZMMW-UHFFFAOYSA-N n-silylbenzamide Chemical class [SiH3]NC(=O)C1=CC=CC=C1 SZVGMOIRUYZMMW-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 230000008693 nausea Effects 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 230000009972 noncorrosive effect Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 239000012766 organic filler Substances 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002900 organolithium compounds Chemical class 0.000 description 1
- 150000001282 organosilanes Chemical class 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 239000005054 phenyltrichlorosilane Substances 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 125000005498 phthalate group Chemical class 0.000 description 1
- 150000003021 phthalic acid derivatives Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000000053 physical method Methods 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920001921 poly-methyl-phenyl-siloxane Polymers 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920006294 polydialkylsiloxane Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 150000003151 propanoic acid esters Chemical class 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000006233 propoxy propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])OC([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- GRWFGVWFFZKLTI-UHFFFAOYSA-N rac-alpha-Pinene Natural products CC1=CCC2C(C)(C)C1C2 GRWFGVWFFZKLTI-UHFFFAOYSA-N 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 229920002631 room-temperature vulcanizate silicone Polymers 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 239000003566 sealing material Substances 0.000 description 1
- 150000003329 sebacic acid derivatives Chemical class 0.000 description 1
- 229920005573 silicon-containing polymer Polymers 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000010902 straw Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 229960005137 succinic acid Drugs 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- OLQUZZCKICNADS-PMDAXIHYSA-N tetrakis[(z)-octadec-9-enyl] silicate Chemical compound CCCCCCCC\C=C/CCCCCCCCO[Si](OCCCCCCCC\C=C/CCCCCCCC)(OCCCCCCCC\C=C/CCCCCCCC)OCCCCCCCC\C=C/CCCCCCCC OLQUZZCKICNADS-PMDAXIHYSA-N 0.000 description 1
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- VCDLLOVEJODESP-UHFFFAOYSA-L tin(2+);diphenoxide Chemical compound [Sn+2].[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1 VCDLLOVEJODESP-UHFFFAOYSA-L 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- QHGNHLZPVBIIPX-UHFFFAOYSA-N tin(ii) oxide Chemical class [Sn]=O QHGNHLZPVBIIPX-UHFFFAOYSA-N 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 150000003609 titanium compounds Chemical class 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- GQIUQDDJKHLHTB-UHFFFAOYSA-N trichloro(ethenyl)silane Chemical compound Cl[Si](Cl)(Cl)C=C GQIUQDDJKHLHTB-UHFFFAOYSA-N 0.000 description 1
- ORVMIVQULIKXCP-UHFFFAOYSA-N trichloro(phenyl)silane Chemical compound Cl[Si](Cl)(Cl)C1=CC=CC=C1 ORVMIVQULIKXCP-UHFFFAOYSA-N 0.000 description 1
- OCANZHUXNZTABW-UHFFFAOYSA-N triethoxy(pent-4-enyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCC=C OCANZHUXNZTABW-UHFFFAOYSA-N 0.000 description 1
- ROWWCTUMLAVVQB-UHFFFAOYSA-N triethoxysilylmethanamine Chemical compound CCO[Si](CN)(OCC)OCC ROWWCTUMLAVVQB-UHFFFAOYSA-N 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
- 125000005590 trimellitic acid group Chemical class 0.000 description 1
- HQYALQRYBUJWDH-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical compound CCC[Si](OC)(OC)OC HQYALQRYBUJWDH-UHFFFAOYSA-N 0.000 description 1
- 239000005050 vinyl trichlorosilane Substances 0.000 description 1
- UKRDPEFKFJNXQM-UHFFFAOYSA-N vinylsilane Chemical class [SiH3]C=C UKRDPEFKFJNXQM-UHFFFAOYSA-N 0.000 description 1
- 230000004393 visual impairment Effects 0.000 description 1
- 238000004073 vulcanization Methods 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000002025 wood fiber Substances 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 239000011787 zinc oxide Substances 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
- C07F7/1804—Compounds having Si-O-C linkages
- C07F7/1872—Preparation; Treatments not provided for in C07F7/20
- C07F7/188—Preparation; Treatments not provided for in C07F7/20 by reactions involving the formation of Si-O linkages
-
- 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
- C07F7/1804—Compounds having Si-O-C linkages
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/54—Silicon-containing compounds
- C08K5/541—Silicon-containing compounds containing oxygen
- C08K5/5415—Silicon-containing compounds containing oxygen containing at least one Si—O bond
- C08K5/5419—Silicon-containing compounds containing oxygen containing at least one Si—O bond containing at least one Si—C bond
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
- C08G77/16—Polysiloxanes containing silicon bound to oxygen-containing groups to hydroxyl groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
- C08G77/18—Polysiloxanes containing silicon bound to oxygen-containing groups to alkoxy or aryloxy groups
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Sealing Material Composition (AREA)
- Paints Or Removers (AREA)
Abstract
Description
R1はそれぞれ同一又は異なり、互いに独立に、一般式(II):
R3はそれぞれ同一又は異なり、互いに独立に、置換又は非置換の、1〜22個の炭素原子を有する直鎖状又は分枝状のアルキル基、6〜16個の炭素原子を有するアリール基、及び5〜27個の炭素原子を有するシクロアルキル基からなる群から選択され、ここで、R3はO、N、S及び/又はSiから選択される少なくとも1個のヘテロ原子を含有してもよい〕
を有する基から選択され、
R2はそれぞれ同一又は異なり、互いに独立に、水素原子、ヒドロキシル基、置換又は非置換の一価の炭化水素基からなる群から選択され、好ましくは、1〜18個の炭素原子、好ましくは1〜8個の炭素原子を有する、アルケニル、アルキル又はアリール基、及び、1〜8個の炭素原子、好ましくは1〜3個の炭素原子を有するアルコキシ基から選択され、かつ
nは2、3又は4、好ましくは3又は4である]
を有するシラン化合物を提供する。
一般式(II)中のXはO又はN、好ましくはOである。一般式(II)中のR3はそれぞれ同一又は異なり、互いに独立に、置換又は非置換の、1〜22個の炭素原子、好ましくは1〜8個の炭素原子を有する直鎖状又は分枝状のアルキル基、6〜16個の炭素原子、好ましくは6〜10個の炭素原子を有するアリール基、及び、5〜27個の炭素原子、好ましくは5〜16個の炭素原子を有するシクロアルキル基からなる群から選択される。R3は、O、N、S及び/又はSiから選択される少なくとも1個のヘテロ原子を含有してよい。好ましい態様において、R3は、1〜22個の炭素原子を有する直鎖状又は分枝状アルキル基及び5〜27個の炭素原子を有するシクロアルキル基から選択され、より好ましくは、メチル、エチル、プロピル、又はn−ブチル基から選択される。
a)ケイ素原子に結合する、少なくとも1個のヒドロキシル基、ビニル基又は水素原子を有する、少なくとも1つのポリオルガノシロキサン;及び
b)本発明による一般式(I)を有する少なくとも1つのシラン化合物;及び
c)少なくとも1つの触媒
の少なくとも1つの反応生成物を含む、硬化性組成物にも向けられる。
を有するα,ω−ジヒドロキシル−末端化ポリオルガノシロキサンから選択される。
R7は、
水素、又は
置換又は非置換のアルキル、アルケニル又はアルキニル基
から選択され、
R8は、
水素、
置換又は非置換のアルキル、アルケニル又はアルキニル基、
置換又は非置換の脂環式基又はアリール基、
一般式:−R9−SiR10 o(OR11)3−o〔式中、R9、R10、R11及びoは、以下に定義するとおりである〕を有する基、
一般式:−(CH2)p−COOR12〔式中、pは2〜10の整数、特に2であり、R12は、置換又は非置換のアルキル、アルケニル又はアルキニル基、又は、置換又は非置換の脂環式基、又は、アリール基から選択される〕を有する基
から選択され、
R9は互いに独立に、場合によりヘテロ原子により遮られた、アルキレン基から選択され、
R10は互いに独立に、置換又は非置換のアルキル、アルケニル又はアルキニル基から選択され、かつ
R11は互いに独立に、
置換又は非置換のアルキル、アルケニル又はアルキニル基、
アシル基、又は
一般式:−CR13 2COOR14〔式中、R13は互いに独立に、水素又は置換又は非置換のアルキル、アルケニル又はアルキニル基、又は、式:−CH2COOR3(式中、R3は一般式(II)において定義した意味を有し、R14は置換又は非置換のアルキル、アルケニル又はアルキニル基から選択される)を有する基から選択される〕を有する基
から選択され、かつ
oは0、1又は2である]
を有するアミノシランから選択される。
ビニル−トリ(リンゴ酸ジエチル)シラン(式1)の合成
メチル−トリ(リンゴ酸ジエチル)シラン(式3)の合成
フェニル−トリ(リンゴ酸ジエチル)シラン(式5)の合成
次の処方に従い、硬化性組成物を調製した:20000mPa・sの粘度を有する5gのα,ω−ジヒドロキシル−末端化ポリジメチルシロキサン、0.01gのn−ブチルリチウム(1.5Mヘキサン溶液)及び0.02gのジオクチルスズジラウレート。それぞれの場合において、0.5gのフェニル−トリ(リンゴ酸ジエチル)シラン、メチル−トリ(リンゴ酸ジエチル)シラン及びビニル−トリ(リンゴ酸ジエチル)シランを、それぞれ、実施例4、5及び6について、架橋剤として添加した。
20000mPa・sの粘度を有する5gのα,ω−ジヒドロキシル−末端化ポリジメチルシロキサン、0.5gのビニルトリエチルラクテートシラン、0.1gのn−ブチルリチウム(1.5Mヘキサン溶液)及び0.02gのジオクチルスズジラウレートを用いて硬化性組成物を調製した。
SOT:上記の組成物を均質化し、フレーム(50×130×2mm)中に適用した。フレームが完全に充填されるように、各混合物をむらなく分布させた。それによって、薄いポリマーフィルムが得られた。先端に円形スパチュラを備える道具(150×5mm)を用いて、これらの組成物について、スキンを形成するまでの時間(スキンオーバータイム/SOT)を測定した。1〜5分毎に、スパチュラの先端をポリマーフィルムの表面に静かに接触させ、注意して取り除いた。SOTは、ポリマーフィルムの表面からスパチュラを取り除く際に、スパチュラに製剤の残留物がもはや残らない際に測定される。次いで、得られるひも状物(string)は、残留物なしにスパチュラから取り除かれなければならない。該ポリマーフィルムは、元の形状に戻る。SOTの測定において、毎回、ポリマーフィルムの表面の異なる部分を使用せねばならない。該試験は室温で行った。
次の処方に従い、硬化性組成物を調製した:20000mPa・sの粘度を有する5gのα,ω−ジヒドロキシル−末端化ポリジメチルシロキサン、0.04gの(3−アミノプロピル)−トリメトキシシラン、及び、0.02gのジオクチルスズジラウレート。
比較例2(アルコキシシリコーン):次の処方に従い、硬化性組成物を調製した:20000mPa・sの粘度を有する5gのα,ω−ジヒドロキシル−末端化ポリジメチルシロキサン、0.5gのビニルトリメトキシシラン、0.01gのブチルリチウム(ヘキサン中1.6M)、及び、0.02gのジオクチルスズカルボキシレート。
Claims (15)
- 一般式(I):
R3はそれぞれ同一又は異なり、互いに独立に、置換又は非置換の、1〜22個の炭素原子を有する直鎖状又は分枝状のアルキル基、6〜16個の炭素原子を有するアリール基、及び5〜27個の炭素原子を有するシクロアルキル基からなる群から選択され、ここで、R3は、O、N、S及び/又はSiから選択される少なくとも1つのヘテロ原子を含有してよい〕
を有する基から選択され、
R2はそれぞれ同一又は異なり、互いに独立に、水素原子、ヒドロキシル基、置換又は非置換の、1〜18個の炭素原子を有する一価の炭化水素基及び1〜8個の炭素原子を有するアルコキシ基からなる群から選択され、
nは2、3又は4である]
を有するシラン化合物。 - R3は、1〜22個の炭素原子を有する直鎖状又は分枝状のアルキル基、及び、5〜27個の炭素原子を有するシクロアルキル基からなる群から選択される、請求項1に記載のシラン化合物。
- R3は、メチル、エチル、プロピル、及びn−ブチル基からなる群から選択される、請求項1又は2に記載のシラン化合物。
- nは3又は4である、請求項1〜3の少なくとも1つに記載のシラン化合物。
- 溶媒は、ジエチルエーテル、テトラヒドロフラン、ベンゼン、トルエン、ジクロロメタン、クロロホルム、アセトン、アセトニトリル、1,2−ジクロロエタン、1,2−ジメトキシ−エタン、N,N−ジメチルホルムアミド、1,4−ジオキサン、及びジメチルスルホキシドからなる群から選択される、請求項5に記載の方法。
- 第3級アミンは、トリエチルアミン、トリ(n−プロピル)アミン、トリ(i−プロピル)アミン、トリ(n−ブチル)アミン、トリ(tert−ブチル)アミン、1−メチルイミダゾール、ピリジン、キヌクリジン、4−ジメチルアミノピリジン、2,6−ルチジン、3,5−ルチジン、N,N−ジメチルアニリン、1,4−ジメチルピペラジン、1,3,5−トリメチルヘキサヒドロ−1,3,5−トリアジン、及びN,N,N’,N’−テトラメチルジアミノメタンからなる群から選択される、請求項5又は6に記載の方法。
- 請求項1〜4の少なくとも1つに記載の一般式(I)を有する少なくとも1つのシラン化合物を含む、硬化性シリコーン組成物用の架橋剤。
- 請求項1〜4の少なくとも1つに記載のシラン化合物の、硬化性シリコーン組成物用の架橋剤としての、又は、接着剤又はシーラント用の接着促進剤としての、使用。
- (A)以下:
a)ケイ素原子に結合する、少なくとも1個のヒドロキシル基、ビニル基又は水素原子を有する、少なくとも1つのポリオルガノシロキサン;
b)請求項1〜4の少なくとも1つに記載の一般式(I)を有する少なくとも1つのシラン化合物;及び
c)少なくとも1つの触媒
の少なくとも1つの反応生成物を含む、硬化性組成物。 - 該反応生成物は少なくとも1つのアミノシランをさらに含む、請求項10に記載の硬化性組成物。
- ポリオルガノシロキサンは、少なくとも1つの、好ましくは少なくとも2つの末端ヒドロキシル基を有するポリジオルガノシロキサンである、請求項10又は11に記載の硬化性組成物。
- (B)少なくとも1つの硬化触媒をさらに含む、請求項10〜13の少なくとも1つに記載の硬化性組成物。
- 請求項10〜14の少なくとも1つに記載の組成物の、接着剤、シーラント、スプレーフォーム及び/又はコーティングとしての使用。
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EP16188603.1 | 2016-09-13 | ||
EP16188603.1A EP3293188B1 (en) | 2016-09-13 | 2016-09-13 | Silanes and curable compositions comprising said silanes |
PCT/EP2017/072298 WO2018050503A1 (en) | 2016-09-13 | 2017-09-06 | Silanes and curable compositions comprising said silanes |
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GB201613397D0 (en) | 2016-08-03 | 2016-09-14 | Dow Corning | Cosmetic composition comprising silicone materials |
GB201613399D0 (en) | 2016-08-03 | 2016-09-14 | Dow Corning | Cosmetic composition comprising silicone materials |
GB201613412D0 (en) | 2016-08-03 | 2016-09-14 | Dow Corning | Elastomeric compositions and their applications |
GB201613414D0 (en) | 2016-08-03 | 2016-09-14 | Dow Corning | Elastomeric compositions and their applications |
GB201707437D0 (en) | 2017-05-09 | 2017-06-21 | Dow Corning | Lamination adhesive compositions and their applications |
GB201707439D0 (en) | 2017-05-09 | 2017-06-21 | Dow Corning | Lamination Process |
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CN111073589A (zh) * | 2019-12-12 | 2020-04-28 | 广东顺德裕固精细化工有限公司 | 一种耐高温食品硅酮胶及其制备方法 |
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US10590151B2 (en) | 2020-03-17 |
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