JP2017520659A - 加硫触媒としてのチタン錯体 - Google Patents
加硫触媒としてのチタン錯体 Download PDFInfo
- Publication number
- JP2017520659A JP2017520659A JP2016575057A JP2016575057A JP2017520659A JP 2017520659 A JP2017520659 A JP 2017520659A JP 2016575057 A JP2016575057 A JP 2016575057A JP 2016575057 A JP2016575057 A JP 2016575057A JP 2017520659 A JP2017520659 A JP 2017520659A
- Authority
- JP
- Japan
- Prior art keywords
- group
- amide
- propyl
- alkyl
- formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000003054 catalyst Substances 0.000 title claims description 31
- 150000003608 titanium Chemical class 0.000 title description 2
- 238000004073 vulcanization Methods 0.000 title description 2
- 238000002360 preparation method Methods 0.000 claims abstract description 50
- 239000000203 mixture Substances 0.000 claims abstract description 48
- 229920000642 polymer Polymers 0.000 claims abstract description 31
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims abstract description 29
- 150000001875 compounds Chemical class 0.000 claims abstract description 28
- 150000003609 titanium compounds Chemical class 0.000 claims abstract description 27
- 229910052710 silicon Inorganic materials 0.000 claims abstract description 24
- 239000010703 silicon Substances 0.000 claims abstract description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 20
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 12
- 125000000962 organic group Chemical group 0.000 claims abstract description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 11
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 9
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 9
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000001301 oxygen Substances 0.000 claims abstract description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract 5
- -1 siloxanes Chemical class 0.000 claims description 38
- 125000000217 alkyl group Chemical group 0.000 claims description 30
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 17
- 150000001408 amides Chemical class 0.000 claims description 16
- 239000003085 diluting agent Substances 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 239000002274 desiccant Substances 0.000 claims description 12
- 239000003446 ligand Substances 0.000 claims description 12
- 239000000945 filler Substances 0.000 claims description 11
- 239000004014 plasticizer Substances 0.000 claims description 11
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 11
- 239000000565 sealant Substances 0.000 claims description 11
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 claims description 10
- 239000002318 adhesion promoter Substances 0.000 claims description 9
- 150000002430 hydrocarbons Chemical class 0.000 claims description 9
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 8
- 239000000853 adhesive Substances 0.000 claims description 7
- 230000001070 adhesive effect Effects 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
- 229920005862 polyol Polymers 0.000 claims description 7
- 150000003077 polyols Chemical class 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 239000012963 UV stabilizer Substances 0.000 claims description 5
- KBJFYLLAMSZSOG-UHFFFAOYSA-N n-(3-trimethoxysilylpropyl)aniline Chemical compound CO[Si](OC)(OC)CCCNC1=CC=CC=C1 KBJFYLLAMSZSOG-UHFFFAOYSA-N 0.000 claims description 5
- 125000003544 oxime group Chemical group 0.000 claims description 5
- 229920001568 phenolic resin Polymers 0.000 claims description 5
- 239000005011 phenolic resin Substances 0.000 claims description 5
- 229920005573 silicon-containing polymer Polymers 0.000 claims description 5
- 229910003849 O-Si Inorganic materials 0.000 claims description 4
- 229910003872 O—Si Inorganic materials 0.000 claims description 4
- VNBLTKHUCJLFSB-UHFFFAOYSA-N n-(trimethoxysilylmethyl)aniline Chemical compound CO[Si](OC)(OC)CNC1=CC=CC=C1 VNBLTKHUCJLFSB-UHFFFAOYSA-N 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 229920002554 vinyl polymer Polymers 0.000 claims description 4
- BIGOJJYDFLNSGB-UHFFFAOYSA-N 3-isocyanopropyl(trimethoxy)silane Chemical group CO[Si](OC)(OC)CCC[N+]#[C-] BIGOJJYDFLNSGB-UHFFFAOYSA-N 0.000 claims description 3
- AZFDSCZMOIHBDJ-UHFFFAOYSA-N CO[Si](CCCNCCNCC(=O)N)(OC)OC Chemical compound CO[Si](CCCNCCNCC(=O)N)(OC)OC AZFDSCZMOIHBDJ-UHFFFAOYSA-N 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 239000003963 antioxidant agent Substances 0.000 claims description 3
- XGIUDIMNNMKGDE-UHFFFAOYSA-N bis(trimethylsilyl)azanide Chemical compound C[Si](C)(C)[N-][Si](C)(C)C XGIUDIMNNMKGDE-UHFFFAOYSA-N 0.000 claims description 3
- 229920001577 copolymer Polymers 0.000 claims description 3
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 claims description 3
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims description 3
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 claims description 3
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 3
- 229920000515 polycarbonate Polymers 0.000 claims description 3
- 239000004417 polycarbonate Substances 0.000 claims description 3
- 229920000728 polyester Polymers 0.000 claims description 3
- 229920000570 polyether Polymers 0.000 claims description 3
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 claims description 2
- HXLAEGYMDGUSBD-UHFFFAOYSA-N 3-[diethoxy(methyl)silyl]propan-1-amine Chemical compound CCO[Si](C)(OCC)CCCN HXLAEGYMDGUSBD-UHFFFAOYSA-N 0.000 claims description 2
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 claims description 2
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- 239000004952 Polyamide Substances 0.000 claims description 2
- 229920000180 alkyd Polymers 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 229920001281 polyalkylene Polymers 0.000 claims description 2
- 229920002647 polyamide Polymers 0.000 claims description 2
- 239000004814 polyurethane Substances 0.000 claims description 2
- 229920002635 polyurethane Polymers 0.000 claims description 2
- 238000000518 rheometry Methods 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 239000003381 stabilizer Substances 0.000 claims description 2
- MZWXWSVCNSPBLH-UHFFFAOYSA-N 3-(3-aminopropyl-methoxy-methylsilyl)oxypropan-1-amine Chemical compound NCCC[Si](C)(OC)OCCCN MZWXWSVCNSPBLH-UHFFFAOYSA-N 0.000 claims 1
- ZYAASQNKCWTPKI-UHFFFAOYSA-N 3-[dimethoxy(methyl)silyl]propan-1-amine Chemical compound CO[Si](C)(OC)CCCN ZYAASQNKCWTPKI-UHFFFAOYSA-N 0.000 claims 1
- 150000003926 acrylamides Chemical class 0.000 claims 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims 1
- UZBQIPPOMKBLAS-UHFFFAOYSA-N diethylazanide Chemical compound CC[N-]CC UZBQIPPOMKBLAS-UHFFFAOYSA-N 0.000 claims 1
- CTLDFURRFMJGON-UHFFFAOYSA-N dimethoxy-methyl-(3-piperazin-1-ylpropyl)silane Chemical compound CO[Si](C)(OC)CCCN1CCNCC1 CTLDFURRFMJGON-UHFFFAOYSA-N 0.000 claims 1
- INJVFBCDVXYHGQ-UHFFFAOYSA-N n'-(3-triethoxysilylpropyl)ethane-1,2-diamine Chemical compound CCO[Si](OCC)(OCC)CCCNCCN INJVFBCDVXYHGQ-UHFFFAOYSA-N 0.000 claims 1
- PHQOGHDTIVQXHL-UHFFFAOYSA-N n'-(3-trimethoxysilylpropyl)ethane-1,2-diamine Chemical compound CO[Si](OC)(OC)CCCNCCN PHQOGHDTIVQXHL-UHFFFAOYSA-N 0.000 claims 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 claims 1
- PZJJKWKADRNWSW-UHFFFAOYSA-N trimethoxysilicon Chemical group CO[Si](OC)OC PZJJKWKADRNWSW-UHFFFAOYSA-N 0.000 claims 1
- 239000010936 titanium Substances 0.000 abstract description 21
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 19
- 229910052719 titanium Inorganic materials 0.000 description 19
- 238000005259 measurement Methods 0.000 description 10
- 239000012948 isocyanate Substances 0.000 description 9
- 150000002513 isocyanates Chemical class 0.000 description 9
- 239000000460 chlorine Substances 0.000 description 8
- 125000005442 diisocyanate group Chemical group 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 7
- 229920004482 WACKER® Polymers 0.000 description 7
- 229920005989 resin Polymers 0.000 description 7
- 239000011347 resin Substances 0.000 description 7
- 229910000077 silane Inorganic materials 0.000 description 7
- 150000003505 terpenes Chemical class 0.000 description 7
- 235000007586 terpenes Nutrition 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 150000002148 esters Chemical group 0.000 description 6
- 125000000524 functional group Chemical group 0.000 description 6
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000009833 condensation Methods 0.000 description 5
- 230000005494 condensation Effects 0.000 description 5
- 235000014113 dietary fatty acids Nutrition 0.000 description 5
- 239000000194 fatty acid Substances 0.000 description 5
- 229930195729 fatty acid Natural products 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
- 239000005056 polyisocyanate Substances 0.000 description 5
- 229920001228 polyisocyanate Polymers 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 230000009257 reactivity Effects 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 230000003197 catalytic effect Effects 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 4
- 150000002170 ethers Chemical class 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 4
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 229920003023 plastic Polymers 0.000 description 4
- 239000004033 plastic Substances 0.000 description 4
- 229920001223 polyethylene glycol Polymers 0.000 description 4
- 239000002243 precursor Substances 0.000 description 4
- 150000004756 silanes Chemical class 0.000 description 4
- 235000012239 silicon dioxide Nutrition 0.000 description 4
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 4
- 239000002023 wood Substances 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 239000005058 Isophorone diisocyanate Substances 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000006087 Silane Coupling Agent Substances 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 239000004205 dimethyl polysiloxane Substances 0.000 description 3
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 3
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 3
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 3
- 229920001451 polypropylene glycol Polymers 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- RLJWTAURUFQFJP-UHFFFAOYSA-N propan-2-ol;titanium Chemical compound [Ti].CC(C)O.CC(C)O.CC(C)O.CC(C)O RLJWTAURUFQFJP-UHFFFAOYSA-N 0.000 description 3
- 238000007789 sealing Methods 0.000 description 3
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- VXUYXOFXAQZZMF-UHFFFAOYSA-N tetraisopropyl titanate Substances CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 3
- 125000003396 thiol group Chemical group [H]S* 0.000 description 3
- NNOZGCICXAYKLW-UHFFFAOYSA-N 1,2-bis(2-isocyanatopropan-2-yl)benzene Chemical compound O=C=NC(C)(C)C1=CC=CC=C1C(C)(C)N=C=O NNOZGCICXAYKLW-UHFFFAOYSA-N 0.000 description 2
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 2
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
- GRWFGVWFFZKLTI-IUCAKERBSA-N 1S,5S-(-)-alpha-Pinene Natural products CC1=CC[C@@H]2C(C)(C)[C@H]1C2 GRWFGVWFFZKLTI-IUCAKERBSA-N 0.000 description 2
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- IRIAEXORFWYRCZ-UHFFFAOYSA-N Butylbenzyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCC1=CC=CC=C1 IRIAEXORFWYRCZ-UHFFFAOYSA-N 0.000 description 2
- TYJFMLFZOHGQOA-UHFFFAOYSA-N CC(C)O[Ti](C)(OC(C)C)OC(C)C Chemical compound CC(C)O[Ti](C)(OC(C)C)OC(C)C TYJFMLFZOHGQOA-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- 229930194542 Keto Natural products 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- JJLKTTCRRLHVGL-UHFFFAOYSA-L [acetyloxy(dibutyl)stannyl] acetate Chemical compound CC([O-])=O.CC([O-])=O.CCCC[Sn+2]CCCC JJLKTTCRRLHVGL-UHFFFAOYSA-L 0.000 description 2
- 239000013466 adhesive and sealant Substances 0.000 description 2
- 235000011037 adipic acid Nutrition 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 125000005370 alkoxysilyl group Chemical group 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 239000007822 coupling agent Substances 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 239000003431 cross linking reagent Substances 0.000 description 2
- 150000001983 dialkylethers Chemical class 0.000 description 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 125000003700 epoxy group Chemical group 0.000 description 2
- SBRXLTRZCJVAPH-UHFFFAOYSA-N ethyl(trimethoxy)silane Chemical compound CC[Si](OC)(OC)OC SBRXLTRZCJVAPH-UHFFFAOYSA-N 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- BUZRAOJSFRKWPD-UHFFFAOYSA-N isocyanatosilane Chemical class [SiH3]N=C=O BUZRAOJSFRKWPD-UHFFFAOYSA-N 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 238000006384 oligomerization reaction Methods 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 239000004800 polyvinyl chloride Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- 239000005060 rubber Substances 0.000 description 2
- 150000003335 secondary amines Chemical class 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000009864 tensile test Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 150000003606 tin compounds Chemical class 0.000 description 2
- 125000004665 trialkylsilyl group Chemical group 0.000 description 2
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- NMEPHPOFYLLFTK-UHFFFAOYSA-N trimethoxy(octyl)silane Chemical compound CCCCCCCC[Si](OC)(OC)OC NMEPHPOFYLLFTK-UHFFFAOYSA-N 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical group C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical group CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- UOKUUKOEIMCYAI-UHFFFAOYSA-N trimethoxysilylmethyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)COC(=O)C(C)=C UOKUUKOEIMCYAI-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- 239000010457 zeolite Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
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- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
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- 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
- C08G77/06—Preparatory processes
- C08G77/08—Preparatory processes characterised by the catalysts used
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- 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
-
- 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
- C07F7/28—Titanium compounds
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- 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
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- 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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- 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
- C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
- C08G77/26—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen nitrogen-containing groups
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- 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
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/34—Silicon-containing compounds
- C08K3/36—Silica
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- 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
- C08K5/0091—Complexes with metal-heteroatom-bonds
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- 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
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- 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
- C09J183/06—Polysiloxanes containing silicon bound to oxygen-containing groups
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- 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
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- 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
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0025—Crosslinking or vulcanising agents; including accelerators
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- Health & Medical Sciences (AREA)
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- Compositions Of Macromolecular Compounds (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Sealing Material Composition (AREA)
Abstract
Description
R1は、1〜20の炭素原子を含有する炭化水素基又は式−O−Si(R2)3(式中、各R2は独立して、1〜20の炭素原子を含有する炭化水素基である)で表されるトリオルガノシロキサン基であり;
各Yは独立して、ヒドロキシ基又は加水分解性基、特にオキシム基及び/又はアルコキシ基であり;及び
kは0、1、又は2である]
で表される少なくとも1つのケイ素含有基を有する少なくとも1つのポリマー:
下記式(2):
各Xは独立して、水素原子、任意に1以上のヘテロ原子、特に窒素原子を含有し得る1〜20の炭素原子を含有する炭化水素基、又はケイ素含有有機基であり、又は2つのXはそれらに結合する窒素原子とともにヘテロ環を形成し;
各Lは独立して、加水分解性酸素又は窒素含有有機基、特にアルコキシ基であり;
R3は、任意に1以上のヘテロ原子、特にケイ素原子を含有し得る1〜20の炭素原子を含有する炭化水素基であり;及び
mは1、2、3又は4であり、nは0、1、2又は3であるが、m+n=4である]
で表される少なくとも1つのチタン化合物;及び
任意に、
c)加水分解性ケイ素含有基及び100〜1000g/molの範囲の分子量を有する少なくとも1つの化合物、特にアミノシラン
を含んでなる、硬化性組成物に関する。
各R4は独立して、C1−8アルキル、特にエチル、イソプロピル、又はn−ブチルであり;Xは水素、C1−20アルキル、又はアリールであり、ここで、アルキル基は任意に1以上の窒素原子、又は式−(CH2)p−Si(Alk)q(OAlk)r(式中、pは0〜9の整数であり、qは0、1、又は2であり、及びrは1、2又は3であるが、q+r=3であり、及びAlkはC1−4アルキル基、特にメチル基又はエチル基である)で表されるケイ素含有有機基を含有してよく、及び
X’は式−(CH2)p−Si(Alk)q(OAlk)r(式中、pは1〜9の整数であり、特に3であり、qは0、1又は2、特に0であり、rは1、2又は3、特に3であるが、q+r=3であり、AlkはC1−4アルキル基、特にメチル基又はエチル基である)で表されるケイ素含有有機基である]
で表されるチタン化合物に関する。
で表される少なくとも1つのチタン化合物を含有する。
各R4は独立して、C1−8アルキル、特にエチル、イソプロピル、又はn−ブチルであり、各Xは独立して、水素、C1−20アルキル、又はC6−20アリールであり、ここで、アルキル基は任意に1以上の窒素原子、又は式−(CH2)p−Si(Alk)q(OAlk)r(式中、pは0〜9の整数であり、q及びrはいずれの場合においても0、1、2又は3であるが、q+r=3であり、及びAlkはC1−4アルキル基、特にメチル基又はエチル基である)で表されるケイ素含有有機基を含有し得る]
で表されるチタン化合物である。
で表されるチタン化合物である。
で表される基であってもよい。
X’は式−(CH2)p−Si(Alk)q(OAlk)r(式中、pは1〜9の整数であり、特に3であり、qは0、1又は2、特に0であり、rは1、2又は3、特に3であるが、q+r=3であり、AlkはC1−4アルキル基、特にメチル基又はエチル基である)で表されるケイ素含有有機基である]
で表されるチタン化合物にも関する。
以下の方法は、J.Chem.Soc.A、1968年、第1940−1945頁に開示された方法に基づくものであり、本明細書に記載される触媒を合成するのに適する。
メチル−トリス(イソプロポキシ)チタンの製造は、J.Organomet.Chem、1974年、第74巻、第85−90頁に開示された方法に基づくものである。
膜形成時間の測定は、標準的な気候条件(23±2℃、相対湿度50±5%)下で実施される。シーラントの温度は実験室で少なくとも24時間保管されたシーラントで、23±2℃にしなければならない。シーラントを紙のシートに塗布し、パテナイフで広げて表皮(厚み約2mm、幅約7cm)を形成する。ストップウォッチをすぐに開始する。間隔をおいて、表面を指先で軽く触れ、膜形成時間に達したときに表面に跡が残るように表面上に十分な圧力をかけて指を引き離す。シーリング化合物がもはや指先に付着しなくなったときに、膜形成時間に達する。膜形成時間は分で表される。
この手順はISO 868に従って実施される。
硬度深さの測定
高さ10mm(±1mm)及び幅20mm(±2mm)のシーラントストランド(sealant strand)を適当なスパチュラで、プラスチックシートに塗布する。標準的な気候条件(23±2℃、相対湿度50±5%)下で24時間保管後、ストランドから片を切断し、硬化層の厚みをスライドゲージで測定する。硬度深さ(hardness depth)はmm/24hで表される。
破断強度、破断点伸び及び引張応力値(弾性率)は、DIN 53504に従った引張試験によって決定される。
<規範からの逸脱>:以下の寸法を有するダンベル試験試料を試験片として使用する:厚さ:2±0.2mm;ウェブの幅:10±0.5mm;ウェブの長さ:約45mm;全長:9cm。試験は標準的な気候条件(23±2℃、50±5%の相対湿度)下で実施する。この試験は、7日間硬化させた後に行う。
V1=本発明により提供されるチタン触媒に代えて、1.30重量%のテトラ−n−ブチルチタネートを用いた調製物1;
V2=本発明により提供されるチタン触媒に代えて、0.17重量%のテトラ−n−ブチルチタネートを用いた調製物2;
V2’=本発明により提供されるチタン触媒に代えて、0.17重量%のテトラ−イソプロピルチタネートを用いた調製物2
V3=本発明により提供されるチタン触媒に代えて、0.05重量%のジブチルスズアセテートを用いた調製物3。
V4=本発明により提供されるチタン触媒に代えて、0.17重量%のテトラ−n−ブチルチタネートを用いた調製物4;
V5=本発明により提供されるチタン触媒に代えて、0.17重量%のテトラ−n−ブチルチタネートを用いた調製物5;
V6=本発明により提供されるチタン触媒に代えて、0.05重量%のジブチルスズアセテートを用いた調製物6;
V6’=本発明により提供されるチタン触媒に代えて、0.05重量%のテトラ−n−ブチルチタネートを用いた調製物6;
V6''=本発明により提供されるチタン触媒に代えて、0.05重量%のテトラ−イソプロピルチタネートを用いた調製物6。
Claims (11)
- a)下記式(1):
R1は、1〜20の炭素原子を含有する炭化水素基又は式−O−Si(R2)3(式中、各R2は独立して、1〜20の炭素原子を含有する炭化水素基である)で表されるトリオルガノシロキサン基であり;
各Yは独立して、ヒドロキシ基又は加水分解性基、特にオキシム基及び/又はアルコキシ基であり;及び
kは0、1、又は2である]
で表される少なくとも1つのケイ素含有基を有する少なくとも1つのポリマー:
下記式(2):
各Xは独立して、水素原子、任意に1以上のヘテロ原子、特に窒素原子を含有し得る1〜20の炭素原子を含有する炭化水素基、又はケイ素含有有機基であり、又は2つのXはそれらに結合する窒素原子とともにヘテロ環を形成し;
各Lは独立して、加水分解性酸素又は窒素含有有機基、特にアルコキシ基であり;
R3は、任意に1以上のヘテロ原子、特にケイ素原子を含有し得る1〜20の炭素原子を含有する炭化水素基であり;及び
mは1、2、3又は4であり、nは0、1、2又は3であるが、m+n=4である]
で表される少なくとも1つのチタン化合物;及び
任意に、
c)加水分解性ケイ素含有基及び100〜1000g/molの範囲の分子量を有する少なくとも1つの化合物、特にアミノシラン
を含んでなる、硬化性組成物。 - ポリマーa)は、アルキド樹脂、(メタ)アクリレート及び(メタ)アクリルアミド並びにそれらの塩、フェノール樹脂、ポリアルキレン、ポリアミド、ポリカーボネート、ポリオール、ポリエーテル、ポリエステル、ポリウレタン、ビニルポリマー、シロキサン、並びに上記ポリマーの種類の少なくとも2つから構成されるコポリマーから選択されるポリマー骨格を有することを特徴とする、請求項1に記載の硬化性組成物。
- 少なくとも1つのチタン化合物は、下記式(4):
各R4は独立して、C1−8アルキル、特にエチル、イソプロピル、又はn−ブチルであり;各Xは独立して、水素、C1−20アルキル、又はC6−20アリールであり、ここで、アルキル基は任意に1つ以上の窒素原子を含有してよく、又は式−(CH2)p−Si(Alk)q(OAlk)r(式中、pは0〜9の整数であり、q及びrはいずれの場合においても0、1、2又は3であるが、q+r=3であり、及びAlkはC1−4アルキル基、特にメチル基又はエチル基である)で表されるケイ素含有有機基である]
で表されるチタン化合物であることを特徴とする、請求項1又は2に記載の硬化性組成物。 - 式(4)で表されるチタン化合物において、式(NX2)の配位子は、ジエチルアミド、ビス(トリメチルシリル)アミド、3−(トリエトキシシリル)プロピル−1−アミド(4a)、3−(トリメトキシシリル)プロピル−1−アミド(4b)、ビス[(3−トリエトキシシリル)プロピル]アミド(4c)、ビス[(3−トリメトキシシリル]プロピル]アミド(4d)、3−[ジエトキシ(メチル)シリル]プロピル−1−アミド(4e)、2−((3−(トリメトキシシリル)プロピル)アミノ)エチル−1−アミド(4f)、2−((3−(トリエトキシシリル)プロピル)アミノ)エチル−1−アミド(4g)、9−(トリメトキシシリル)−3,6−ジアザノナン−1−アミド(4h)、フェニル((トリメトキシシリル)メチル)アミド(4i)、フェニル(3−(トリメトキシシリル)プロピル)アミド(4j)、及び2−((3−(ジメトキシ(メチル)シリル)プロピル)アミノ)エチル−1−アミド(4k)から選択されることを特徴とする、請求項3に記載の硬化性組成物。
- 組成物は、化合物c)として、アミノシラン、特に、ビス(トリメチルシリル)アミン、アミノプロピルトリエトキシシラン、アミノプロピルトリメトキシシラン、ビス[(3−トリエトキシシリル)プロピル]アミン、ビス[(3−トリメトキシシリル)プロピル]アミン、アミノプロピルメチルジエトキシシラン、アミノエチルアミノプロピルトリメトキシシラン、アミノエチルアミノプロピルトリエトキシシラン、3−[2−(2−アミノエチルアミノ)エチルアミノ]プロピルトリメトキシシラン、フェニルアミノメチルトリメトキシシラン、アミノエチルアミノプロピルメチルジメトキシシラン、3−(N−フェニルアミノ)プロピルトリメトキシシラン、3−ピペラジニルプロピルメチルジメトキシシラン、3−(N,N−ジメチルアミノプロピル)アミノプロピルメチルジメトキシシラン、及び上記化合物の2以上の組み合わせを含む群から選択されるアミノシランを含有することを特徴とする、請求項1〜5のいずれかに記載の硬化性組成物。
- 請求項1〜6のいずれかに記載の硬化性組成物を含有する調製物。
- 調製物は、可塑剤、安定剤、酸化防止剤、フィラー、反応性希釈剤、乾燥剤、接着促進剤、UV安定剤、レオロジー助剤、及び溶剤を含む群から選択される少なくとも1つの化合物をさらに含有することを特徴とする、請求項7に記載の調製物。
- 請求項1〜6のいずれかに記載の組成物、若しくは請求項7又は8に記載の調製物の接着剤又はシーラントとしての使用。
- 下記式(6):
各R4は独立して、C1−8アルキル、特にエチル、イソプロピル、又はn−ブチルであり;Xは水素、C1−20アルキル、又はアリールであり、ここで、アルキル基は任意に、1以上の窒素原子、又は式−(CH2)p−Si(Alk)q(OAlk)r(式中、pは0〜9の整数であり、qは0、1又は2であり、及びrは1、2又は3であるが、q+r=3であり、及びAlkはC1−4アルキル基、特にメチル基又はエチル基である)で表されるケイ素含有有機基を含有してよく;及び
X’は式−(CH2)p−Si(Alk)q(OAlk)r(式中、pは1〜9の整数であり、特に3であり、qは0、1又は2、特に0であり、rは1、2又は3、特に3であるが、q+r=3であり、AlkはC1−4アルキル基、特にメチル基又はエチル基である)で表されるケイ素含有有機基である]
で表されるチタン化合物。 - 触媒としての、特にシロキサン結合を形成することによりケイ素含有ポリマーを硬化するための、請求項10に記載のチタン化合物の使用。
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JP2021505742A (ja) * | 2017-12-12 | 2021-02-18 | ヘンケル・アクチェンゲゼルシャフト・ウント・コムパニー・コマンディットゲゼルシャフト・アウフ・アクチェンHenkel AG & Co. KGaA | 加硫触媒としての常磁性チタン混合物 |
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US20170081479A1 (en) | 2017-03-23 |
ES2708831T3 (es) | 2019-04-11 |
EP3161092B1 (de) | 2018-11-28 |
US10273335B2 (en) | 2019-04-30 |
CA2953435C (en) | 2023-03-07 |
CN106414648A (zh) | 2017-02-15 |
HUE041524T2 (hu) | 2019-05-28 |
CN106414648B (zh) | 2020-02-07 |
CA2953435A1 (en) | 2015-12-30 |
PL3161092T3 (pl) | 2019-05-31 |
DE102014212291A1 (de) | 2015-12-31 |
JP6660312B2 (ja) | 2020-03-11 |
EP3161092A1 (de) | 2017-05-03 |
WO2015197829A1 (de) | 2015-12-30 |
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