CN108368268A - 作为硫化催化剂的钛络合物 - Google Patents
作为硫化催化剂的钛络合物 Download PDFInfo
- Publication number
- CN108368268A CN108368268A CN201680070342.8A CN201680070342A CN108368268A CN 108368268 A CN108368268 A CN 108368268A CN 201680070342 A CN201680070342 A CN 201680070342A CN 108368268 A CN108368268 A CN 108368268A
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- China
- Prior art keywords
- independently selected
- formula
- silicon
- alkyl
- methyl
- Prior art date
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- Granted
Links
- 239000010936 titanium Substances 0.000 title claims abstract description 31
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 title claims abstract description 28
- 229910052719 titanium Inorganic materials 0.000 title claims abstract description 26
- 239000003054 catalyst Substances 0.000 title claims description 20
- 239000000203 mixture Substances 0.000 claims abstract description 49
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims abstract description 35
- 229920000642 polymer Polymers 0.000 claims abstract description 34
- 150000001875 compounds Chemical class 0.000 claims abstract description 32
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 31
- 229910052710 silicon Inorganic materials 0.000 claims abstract description 31
- 239000010703 silicon Substances 0.000 claims abstract description 29
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 18
- 239000005864 Sulphur Substances 0.000 claims abstract description 17
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 17
- 239000003446 ligand Substances 0.000 claims abstract description 16
- 125000003118 aryl group Chemical group 0.000 claims abstract description 14
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 11
- 230000005595 deprotonation Effects 0.000 claims abstract description 7
- 238000010537 deprotonation reaction Methods 0.000 claims abstract description 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract description 7
- -1 acetoxyl group Chemical group 0.000 claims description 70
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 36
- 239000003085 diluting agent Substances 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 239000000945 filler Substances 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 239000000565 sealant Substances 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- 150000001412 amines Chemical class 0.000 claims description 8
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 claims description 8
- 239000000853 adhesive Substances 0.000 claims description 7
- 230000001070 adhesive effect Effects 0.000 claims description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 229920005573 silicon-containing polymer Polymers 0.000 claims description 6
- 229920002554 vinyl polymer Polymers 0.000 claims description 6
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 claims description 5
- 239000012963 UV stabilizer Substances 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
- 150000004770 chalcogenides Chemical class 0.000 claims description 4
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 claims description 4
- 150000003903 lactic acid esters Chemical group 0.000 claims description 4
- 238000005259 measurement Methods 0.000 claims description 4
- 229920001568 phenolic resin Polymers 0.000 claims description 4
- 239000005011 phenolic resin Substances 0.000 claims description 4
- HXLAEGYMDGUSBD-UHFFFAOYSA-N 3-[diethoxy(methyl)silyl]propan-1-amine Chemical compound CCO[Si](C)(OCC)CCCN HXLAEGYMDGUSBD-UHFFFAOYSA-N 0.000 claims description 3
- LMVLVUPTDRWATB-UHFFFAOYSA-N 3-[dimethoxy(methyl)silyl]propan-1-ol Chemical compound CO[Si](C)(OC)CCCO LMVLVUPTDRWATB-UHFFFAOYSA-N 0.000 claims description 3
- 239000004425 Makrolon Substances 0.000 claims description 3
- 239000003963 antioxidant agent Substances 0.000 claims description 3
- 230000003078 antioxidant effect Effects 0.000 claims description 3
- 229920000515 polycarbonate Polymers 0.000 claims description 3
- 229920000728 polyester Polymers 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- MZWXWSVCNSPBLH-UHFFFAOYSA-N 3-(3-aminopropyl-methoxy-methylsilyl)oxypropan-1-amine Chemical compound NCCC[Si](C)(OC)OCCCN MZWXWSVCNSPBLH-UHFFFAOYSA-N 0.000 claims description 2
- NSYVWNZRHYLPDY-UHFFFAOYSA-N 6-[dimethoxy(methyl)silyl]-1-n,1-n-dimethylhexane-1,4-diamine Chemical class CO[Si](C)(OC)CCC(N)CCCN(C)C NSYVWNZRHYLPDY-UHFFFAOYSA-N 0.000 claims description 2
- 239000004952 Polyamide Substances 0.000 claims description 2
- 229920000180 alkyd Polymers 0.000 claims description 2
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 2
- PHQOGHDTIVQXHL-UHFFFAOYSA-N n'-(3-trimethoxysilylpropyl)ethane-1,2-diamine Chemical compound CO[Si](OC)(OC)CCCNCCN PHQOGHDTIVQXHL-UHFFFAOYSA-N 0.000 claims description 2
- YPHQUSNPXDGUHL-UHFFFAOYSA-N n-methylprop-2-enamide Chemical compound CNC(=O)C=C YPHQUSNPXDGUHL-UHFFFAOYSA-N 0.000 claims description 2
- 229920002647 polyamide Polymers 0.000 claims description 2
- 229920000098 polyolefin Polymers 0.000 claims description 2
- 239000004814 polyurethane Substances 0.000 claims description 2
- 229920002635 polyurethane Polymers 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 239000003381 stabilizer Substances 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- 229910021529 ammonia Inorganic materials 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
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 37
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 34
- 239000000047 product Substances 0.000 description 32
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 31
- 229910000077 silane Inorganic materials 0.000 description 29
- 239000002585 base Substances 0.000 description 26
- 150000002148 esters Chemical class 0.000 description 20
- 239000012948 isocyanate Substances 0.000 description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 13
- 239000004014 plasticizer Substances 0.000 description 11
- 239000000463 material Substances 0.000 description 10
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 10
- 150000002513 isocyanates Chemical class 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- 230000009257 reactivity Effects 0.000 description 8
- 229920004482 WACKER® Polymers 0.000 description 7
- 229920005989 resin Polymers 0.000 description 7
- 239000011347 resin Substances 0.000 description 7
- 150000003505 terpenes Chemical class 0.000 description 7
- 235000007586 terpenes Nutrition 0.000 description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 5
- 238000009833 condensation Methods 0.000 description 5
- 230000005494 condensation Effects 0.000 description 5
- 125000005442 diisocyanate group Chemical group 0.000 description 5
- 125000000524 functional group Chemical group 0.000 description 5
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- 230000003197 catalytic effect Effects 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
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 4
- 229920003023 plastic Polymers 0.000 description 4
- 239000004033 plastic Substances 0.000 description 4
- 239000005056 polyisocyanate Substances 0.000 description 4
- 229920001228 polyisocyanate Polymers 0.000 description 4
- 229920001296 polysiloxane Polymers 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 238000007711 solidification Methods 0.000 description 4
- 230000008023 solidification Effects 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 150000003609 titanium compounds Chemical class 0.000 description 4
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- 239000003431 cross linking reagent Substances 0.000 description 3
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 125000004185 ester group Chemical group 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
- SBRXLTRZCJVAPH-UHFFFAOYSA-N ethyl(trimethoxy)silane Chemical class CC[Si](OC)(OC)OC SBRXLTRZCJVAPH-UHFFFAOYSA-N 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 238000005227 gel permeation chromatography Methods 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical group OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 3
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 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
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 239000000523 sample Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 150000005846 sugar alcohols Polymers 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 2
- NIOYEYDJTAEDFH-UHFFFAOYSA-N 1-(2-hydroxyethoxy)-2-methylpropan-2-ol Chemical compound CC(C)(O)COCCO NIOYEYDJTAEDFH-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
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-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
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- 239000005058 Isophorone diisocyanate Substances 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 2
- 239000006087 Silane Coupling Agent Substances 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 239000013466 adhesive and sealant Substances 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 125000003302 alkenyloxy group Chemical group 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N alpha-methacrylic acid Natural products CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- 239000004411 aluminium Substances 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
- 150000001408 amides Chemical group 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 239000001273 butane Substances 0.000 description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000007822 coupling agent Substances 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 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
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 2
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 210000002615 epidermis Anatomy 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 239000003365 glass fiber Substances 0.000 description 2
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 230000008595 infiltration Effects 0.000 description 2
- 238000001764 infiltration Methods 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- BUZRAOJSFRKWPD-UHFFFAOYSA-N isocyanatosilane Chemical class [SiH3]N=C=O BUZRAOJSFRKWPD-UHFFFAOYSA-N 0.000 description 2
- 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 2
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 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
- 238000002156 mixing Methods 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N o-dicarboxybenzene Natural products OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 239000004800 polyvinyl chloride Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- HCOKJWUULRTBRS-UHFFFAOYSA-N propan-2-yloxysilane Chemical compound CC(C)O[SiH3] HCOKJWUULRTBRS-UHFFFAOYSA-N 0.000 description 2
- 239000005060 rubber Substances 0.000 description 2
- 238000007789 sealing Methods 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 150000003606 tin compounds Chemical class 0.000 description 2
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 2
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 2
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 2
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- UKRDPEFKFJNXQM-UHFFFAOYSA-N vinylsilane Chemical class [SiH3]C=C UKRDPEFKFJNXQM-UHFFFAOYSA-N 0.000 description 2
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- 230000000149 penetrating effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
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- 238000006116 polymerization reaction Methods 0.000 description 1
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- ZMYXZXUHYAGGKG-UHFFFAOYSA-N propoxysilane Chemical compound CCCO[SiH3] ZMYXZXUHYAGGKG-UHFFFAOYSA-N 0.000 description 1
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- 230000004044 response Effects 0.000 description 1
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- 229920002379 silicone rubber Polymers 0.000 description 1
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- 239000010935 stainless steel Substances 0.000 description 1
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- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
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- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
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- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 1
- ZWYDDDAMNQQZHD-UHFFFAOYSA-L titanium(ii) chloride Chemical compound [Cl-].[Cl-].[Ti+2] ZWYDDDAMNQQZHD-UHFFFAOYSA-L 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- BOTMPGMIDPRZGP-UHFFFAOYSA-N triethoxy(isocyanatomethyl)silane Chemical compound CCO[Si](OCC)(OCC)CN=C=O BOTMPGMIDPRZGP-UHFFFAOYSA-N 0.000 description 1
- JCVQKRGIASEUKR-UHFFFAOYSA-N triethoxy(phenyl)silane Chemical compound CCO[Si](OCC)(OCC)C1=CC=CC=C1 JCVQKRGIASEUKR-UHFFFAOYSA-N 0.000 description 1
- NBXZNTLFQLUFES-UHFFFAOYSA-N triethoxy(propyl)silane Chemical compound CCC[Si](OCC)(OCC)OCC NBXZNTLFQLUFES-UHFFFAOYSA-N 0.000 description 1
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 1
- XSIGLRIVXRKQRA-UHFFFAOYSA-N triethoxysilylmethanethiol Chemical compound CCO[Si](CS)(OCC)OCC XSIGLRIVXRKQRA-UHFFFAOYSA-N 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
- 125000005591 trimellitate group Chemical group 0.000 description 1
- ARKBFSWVHXKMSD-UHFFFAOYSA-N trimethoxysilylmethanamine Chemical compound CO[Si](CN)(OC)OC ARKBFSWVHXKMSD-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
- JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical compound OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 description 1
- 238000004073 vulcanization Methods 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- WTARULDDTDQWMU-UHFFFAOYSA-N β-pinene Chemical compound C1C2C(C)(C)C1CCC2=C WTARULDDTDQWMU-UHFFFAOYSA-N 0.000 description 1
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Abstract
本发明涉及可固化组合物，其包含：a)至少一种具有至少一个如本文所定义的式‑Si(R1)k(Y)3–k的含硅基团的聚合物；b)至少一种式TiL(OR3)2的钛络合物，其中每个R3都独立地选自可任选地含有一个或多个杂原子的C1‑20烷基或芳基，所述杂原子优选地选自硅、硫、氮或氧原子，其中优选地R3选自正丁基或异丙基，且L是去质子化的三齿配体，和c)任选存在的至少一种具有可水解的含硅基团且重均分子量在100‑1000g/mol范围内的化合物，含有这些组合物的制备物及其用途。
Description
本发明涉及钛化合物，其可用作含硅聚合物和聚合物混合物的硫化的催化剂并可以替代已知的有毒的锡化合物。所述钛化合物的特征在于即使在基于硅烷的粘合促进剂的存在下也具有良好的催化活性和稳定性。另外，还描述了这些化合物和含有这些催化剂的组合物和制备物(preparations)的适当用途。
有机硅聚合物，特别是聚硅氧烷如聚二甲基硅氧烷(PDMS)，在粘合剂、密封剂和绝缘材料中非常重要。在这些材料中，那些在低温和环境条件下硫化的材料占据相当大的市场份额。典型的配制物含有反应性PDMS聚合物、交联剂和缩合催化剂。虽然有机锡化合物多年来成功地被用作催化剂，并在储存稳定性、固化时间和选择性方面具有优异的结果，但由于毒理学问题和环境保护的原因，它们近来受到批评。
尽管已经提出多种基于金属的催化剂来替代众所周知的锡化合物，但是已知的替代物在稳定性、催化活性或相容性方面通常具有缺点。已知作为替代物的钛化合物具有共同的缺点，即它们与经常用作粘合促进剂的氨基硅烷不相容。
US 4,530,882A，US 5,948,854A和US 5,286,766A中公开了含有具有可水解端基的硅氧烷聚合物、基于钛的水解催化剂和任选存在的氨基硅烷的可固化有机硅组合物。所述基于钛的水解催化剂是钛烷氧化物(titanium alkoxides)，优选四烷氧基钛酸酯，特别优选四异丙氧基钛酸酯。这些催化剂的性能在催化活性方面也不完全令人满意。另外，相应的可固化组合物的储存稳定性不是最佳的，且由其获得的固化产物具有相对低的硬度。
因此，本发明的一个目的是提供已知为缩合催化剂的钛化合物的替代物，其克服了已知的缺点。
本发明实现了其目的，即提供了改进的基于钛的缩合催化剂，所述催化剂将被用于固化含有反应性硅基团的聚合物，其满足上述要求，即其具有足够的催化活性和稳定性并且与通常用作粘合促进剂的氨基硅烷相容。
在第一方面，本发明因此涉及一种可固化组合物，其包含
a)至少一种具有至少一个式(1)的含硅基团的聚合物
-Si(R1)k(Y)3-k (1)，
其中
R1选自含有1-20个C原子的烃基或式-O-Si(R2)3的三有机基硅氧烷基团，其中每个R2都独立地选自含有1-20个C原子的烃基；
每个Y都独立地选自羟基或可水解基团，优选肟基、烷氧基、乙酰氧基或乳酸酯基；且
k是0、1或2；
b)至少一种式(2)的钛络合物
TiL(OR3)2 (2)，
其中
每个R3都独立地选自可任选地含有一个或多个杂原子的C1-20烷基或芳基，所述杂原子优选地选自硅、硫、氮或氧原子，其中优选地R3选自正丁基或异丙基；且
L是去质子化的三齿配体；和
c)任选存在的至少一种具有可水解的含硅基团的化合物，根据DIN 55672-1:2007-08用GPC测量，所述化合物的重均分子量为100-1000g/mol，优选地所述化合物为氨基硅烷。
在另一方面，本发明涉及含有如上所述的可固化组合物的制备物。
本发明还涉及如上定义的组合物或制备物作为粘合剂或密封剂的用途。
而另一方面涉及式(2)的钛络合物
TiL(OR3)2 (2)，
每个R3都独立地选自可任选地含有一个或多个杂原子的C1-20烷基或芳基，所述杂原子优选地选自硅、硫、氮或氧原子，其中优选地R3选自正丁基或异丙基；且L是去质子化的三齿配体。
最后，本发明还涉及上述钛络合物作为催化剂的用途，特别是用于通过形成硅氧烷键来固化含硅聚合物。
当在本文中提及分子量时，除非另有说明，否则所提及的是数均分子量，即Mn值，而不是重均分子量。所述分子量根据DIN 55672-1：2007-08，优选在35℃下，用四氢呋喃(THF)作为洗脱液通过凝胶渗透色谱法(GPC)测定。
本文中所用的“至少一种”是指1种或多种，即1、2、3、4、5、6、7、8、9或更多。关于成分，所指的是成分的类型，而不是指分子的绝对数量。因此“至少一种聚合物”是指，例如，至少一种类型的聚合物，即可以使用一种类型的聚合物或几种不同聚合物的混合物。该说明与重量说明一起是指包含在组合物/混合物中的所有所述类型的化合物，即所述组合物除了所述量的化合物之外不含有该类型的其他化合物。
这里结合数值使用的术语“约”涉及相应值的±20％，优选±10％的变化。
除非另有明确说明，否则与本文所述组合物一起提供的所有百分比值均指重量％，在每种情况下均基于所讨论的混合物。
对所述至少一种聚合物a)的聚合物骨架没有特别限制，可以使用具有不同类型主链骨架的所有已知聚合物。在各种实施方案中，聚合物a)因此选自醇酸树脂、(甲基)丙烯酸酯和(甲基)丙烯酰胺及其盐、酚醛树脂、聚烯烃、聚酰胺、聚碳酸酯、聚醚、聚酯、聚氨酯、乙烯基聚合物、聚硅氧烷及至少两种上述聚合物的组合。
特别优选使用多元醇/聚醚，特别是聚环氧烷，优选聚环氧乙烷和/或聚环氧丙烷，或聚硅氧烷。
根据本发明组合物的另一个优选实施方案，所述聚合物骨架根据DIN 55672-1：2007-08用GPC在35℃下测量的分子量Mn为500-100,000g/mol。特别优选5000-25,000g/mol的分子量范围，并非常特别优选8000-20,000g/mol。这些分子量是特别有利的，因为具有这些分子量的组合物具有便于加工的粘度。所述聚合物在每种情况下可以是直链或支链的。
所述聚合物中的含硅基团是反应性基团，其中羟基或可水解基团与硅原子键合，且能够通过形成硅氧烷键而交联。所述交联反应可以被硅醇缩合催化剂如本文所述的钛化合物加速。
所述反应性基团具有式-Si(R1)k(Y)3–k，其中R1选自含有1-20个C原子的烃基或式-O-Si(R2)3的三有机基硅氧烷基，其中每个R2独立地选自含有1-20个C原子的烃基，每个Y都独立地选自羟基或可水解基团，优选肟基、烷氧基、乙酰氧基或乳酸酯基，k是0、1或2。在各种实施方案中，R1选自含有1-20个C原子的烷基，含有6-20个C原子的芳基，含有7-20个C原子的芳烷基，或者如上定义的式-O-Si(R2)3的三有机基硅氧烷基团。如果含有多个Y基团，它们可以相同或不同。
可水解基团的实例包括但不限于氢原子、卤素原子、烷氧基、酰氧基、肟基、乙酰氧基、乳酸酯基、氨基、酰胺基、酰胺基(acid amide group)、氨氧基、巯基、烯氧基等。烷氧基，特别是甲氧基和乙氧基，和肟基是特别优选的。本文中所用的术语“肟基”包括酮肟和醛肟，通常是指含有官能团R'2C＝N-O-的基团，其中氧原子与硅原子键接，且R'可以是H或其他基团，优选烷基。
上述通式(1)中的R1的实例包括烷基如甲基和乙基，环烷基如环己基，芳基如苯基，芳烷基如苄基，和三甲基硅氧基。
反应性含硅基团的具体实例包括二甲氧基甲基甲硅烷基、二乙氧基甲基甲硅烷基和二异丙氧基甲基甲硅烷基。
在各种实施方案中，每种情况下一个聚合物分子都含有两个或更多个上述反应性基团。
用于将反应性含硅基团，优选端基插入到聚合物中的方法在现有技术中是公知的。
所述反应性含硅基团可以位于主链的一端或两端，主链内，或者位于一个或多个侧链内或末端。
作为聚合物组分a)，在每种情况下上述聚合物都可以单独使用或以其两种或更多种的组合使用。如果使用两种或更多种聚合物的组合，则所使用的聚合物在单体组成和/或其分子量方面可以不同。
本文所述的可固化组合物含有至少一种式(2)的钛络合物，
TiL(OR3)2 (2)
其中每个R3都独立地选自可任选地含有一个或多个杂原子的C1-20烷基或芳基，所述杂原子优选地选自硅、硫、氮或氧原子，其中优选地R3选自正丁基或异丙基；且L是去质子化的三齿配体。
在优选的实施方案中，L是去质子化的三齿podand配体。在更优选的实施方案中，L选自去质子化形式的式(3)的二酰氨基胺、式(4)的二酰氨基硫属化物和式(5)的二酰氨基吡啶，
其中R4独立地选自式-Si(R7)3的甲硅烷基，其中每个R7都独立地选自含有1-20个C原子的烃基，或可任选地含有一个或多个杂原子的C1-20烷基或芳基，所述杂原子优选地选自硅、硫、氮或氧原子，R5和R6独立地选自可任选地含有一个或多个杂原子的C1-20烷基或芳基，所述杂原子优选地选自硅、硫、氮或氧原子，其中优选地R4独立地选自甲基、苯基、-Si(CH3)3或对甲苯磺酰基，R5和R6独立地选自甲基或苯基，X是硫或氧原子，R6相对于氮的位置位于邻位、间位或对位。最优选式(3)的二酰氨基胺用作配体。
在优选的实施方案中，R4独立地选自甲基、苯基、-Si(CH3)3或对甲苯磺酰基，更优选-Si(CH3)3或对甲苯磺酰基，最优选对甲苯磺酰基，和/或R5和R6独立地选自甲基或苯基。
所述钛络合物可容易地由氯钛酸盐或酰氨基钛酸盐(amidotitanates)和适用的螯合配体制备。优选的配体是podand配体。最优选的配体是三齿酰氨基胺、酰氨基硫属化物、二酰氨基吡啶、或其碱金属盐(alkali salts)。所述配体应首先通过与两当量碱(优选丁基锂)反应而去质子化。
在优选的实施方案中，式(2)的钛络合物通过将式(3)、(4)或(5)的三齿配体在与通式(6)Ti(OR3)2Z2的适用钛酸酯混合时配位而制备，其中R3独立地选自可任选地含有一个或多个杂原子的C1-20烷基或芳基，所述杂原子优选地选自硅、硫、氮或氧原子，且Z独立地为N(R7)2，其中R7独立地选自C1-6烷基，优选甲基或乙基，或卤素(halide)，优选Cl。在优选的实施方案中，R3独立地选自正丁基或异丙基。
所述反应如下进行：
其中Y是碱金属如Na、K、Li或碱土金属如Mg(其中Y是MgX，X是Cl、Br或I)，优选Li。
在优选的实施方案中，所述组合物还含有至少一种化合物c)，其具有可水解的含硅基团，且根据DIN 55672-1:2007-08通过GPC测量的重均分子量为100-1000g/mol。该化合物被用作交联剂，且除了所述可水解的含硅基团之外，还可以含有其他官能团。所述化合物可以是硅烷偶联剂。
这种类型的偶联剂可用作增粘剂，作为影响物理性质的试剂，作为干燥剂，作为分散助剂，或作为填料等。特别地，该硅烷偶联剂可被用作粘合促进剂并增大对各种表面如玻璃、铝、不锈钢、锌、铜、砂浆、PVC、丙烯酸树脂、聚酯、聚乙烯、聚丙烯和聚碳酸酯的粘合性。该硅烷偶联剂可以包括反应性含硅基团，其可以以类似于上面结合聚合物组分a)所描述的基团进行定义。可选地，所述基团也可以是具有式(7)的基团：
-(Si(R1)2–e(Y)e-O)k-Si(R1)3–dYd (7),
其中R1和Y各自独立地为如上文对式(1)所定义的，e是0、1或2，d为0、1、2或3，其中d和e不都是0，k为0或1-19的整数，其中当k为0时，d不为0。
化合物c)可以含有其他官能团，包括但不限于伯氨基、仲氨基、或叔氨基、巯基、环氧基、羧基、乙烯基、异氰酸酯基、异氰脲酸酯基、卤素等。
这些偶联剂的具体实例包括但不限于含有异氰酸酯基团的硅烷，如γ-异氰酸酯丙基三甲氧基硅烷、γ-异氰酸酯丙基三乙氧基硅烷、γ-异氰酸酯丙基甲基二乙氧基硅烷、γ-异氰酸酯丙基甲基二甲氧基硅烷、(异氰酸酯甲基)三甲氧基硅烷、(异氰酸酯甲基)甲基二甲氧基硅烷、(异氰酸酯甲基)三乙氧基硅烷和(异氰酸酯甲基)二乙氧基甲基硅烷；含有氨基的硅烷，如γ-氨基丙基三甲氧基硅烷、γ-氨基丙基三乙氧基硅烷、γ-氨基丙基三异丙氧基硅烷、γ-氨基丙基甲基二甲氧基硅烷、γ-氨基丙基甲基二乙氧基硅烷、γ-(2-氨基乙基)氨基丙基三甲氧基硅烷、γ-(2-氨基乙基)氨基丙基甲基二甲氧基硅烷、γ-(2-氨基乙基)氨基丙基三乙氧基硅烷、γ-(2-氨基乙基)氨基丙基甲基二乙氧基硅烷、γ-(2-氨基乙基)氨基丙基三异丙氧基硅烷、γ-(6-氨基己基)氨基丙基三甲氧基硅烷、3-(N-乙基氨基)-2-甲基丙基三甲氧基硅烷、γ-脲基丙基三甲氧基硅烷、γ-脲基丙基三乙氧基硅烷、N-苯基-γ-氨基丙基三甲氧基硅烷、N-苄基-γ-氨基丙基三甲氧基硅烷、N-乙烯基苄基-γ-氨基丙基三乙氧基硅烷、N-环己基氨基甲基三乙氧基硅烷、N-环己基氨基甲基二乙氧基甲基硅烷、N-苯基氨基甲基三甲氧基硅烷、(2-氨基乙基)氨基甲基三甲氧基硅烷、和N,N’-双[3-(三甲氧基甲硅烷基)丙基]亚乙基二胺；酮亚胺类型的硅烷，如N-(1,3-二甲基亚丁基)-3-(三乙氧基甲硅烷基)-1-丙胺；含有巯基的硅烷，如γ-巯基丙基三甲氧基硅烷、γ-巯基丙基三乙氧基硅烷、γ-巯基丙基甲基二甲氧基硅烷、γ-巯基丙基甲基二乙氧基硅烷、巯基甲基三甲氧基硅烷、和巯基甲基三乙氧基硅烷；含有环氧基的硅烷，如γ-缩水甘油氧基丙基三甲氧基硅烷、γ-缩水甘油氧基丙基三乙氧基硅烷、γ-缩水甘油氧基丙基甲基二甲氧基硅烷、β-(3,4-环氧基环己基)乙基三甲氧基硅烷、和β-(3,4-环氧基环己基)乙基三乙氧基硅烷；羧基硅烷(carboxysilanes)，例如β-羧基乙基三乙氧基硅烷、β-羧基乙基苯基双(2-甲氧基乙氧基)硅烷、和N-β-(羧甲基)氨基乙基-γ-氨基丙基三甲氧基硅烷；含有乙烯基型不饱和基团的硅烷，如乙烯基三甲氧基硅烷、乙烯基三乙氧基硅烷、γ-甲基丙烯酰氧基丙基甲基二甲氧基硅烷、γ-丙烯酰氧基丙基三乙氧基硅烷、和甲基丙烯酰氧基丙基三甲氧基硅烷；含卤素的硅烷，如γ-氯丙基三甲氧基硅烷；和异氰脲酸酯硅烷，如三(3-三甲氧基甲硅烷基丙基)异氰脲酸酯。此外，可以使用上述硅烷的部分缩合产物或反应产物。在本发明的范围内特别优选选自以下的氨基硅烷：双(三甲基甲硅烷基)胺、氨基丙基三乙氧基硅烷、氨基丙基三甲氧基硅烷、双[(3-三乙氧基甲硅烷基)丙基]胺、双[(3-三甲氧基甲硅烷基)丙基]胺、氨基丙基甲基二乙氧基硅烷、氨基乙基氨基丙基三甲氧基硅烷、氨基乙基氨基丙基三乙氧基硅烷、3-[2-(2-氨基乙基氨基)乙基氨基]丙基三甲氧基硅烷、苯基氨基甲基三甲氧基硅烷、氨基乙基氨基丙基甲基二甲氧基硅烷、3-(N-苯基氨基)丙基三甲氧基硅烷、3-哌嗪基丙基甲基二甲氧基硅烷、3-(N,N-二甲基氨基丙基)氨基丙基甲基二甲氧基硅烷，以及两种或更多种上述化合物的组合。
不含另外官能团的化合物c)的实例包括四烷氧基硅烷(四烷基硅酸酯)，如四甲氧基硅烷、四乙氧基硅烷、乙氧基三甲氧基硅烷、二甲氧基二乙氧基硅烷、甲氧基三乙氧基硅烷、四正丙氧基硅烷、四异丙氧基硅烷、四正丁氧基硅烷、四异丁氧基硅烷、四叔丁氧基硅烷；三烷氧基硅烷，如甲基三甲氧基硅烷、甲基三乙氧基硅烷、甲基三异丙氧基硅烷、甲基三苯氧基硅烷、乙基三甲氧基硅烷、丁基三甲氧基硅烷和苯基三甲氧基硅烷；二烷氧基硅烷，如二甲基二甲氧基硅烷、二乙基二甲氧基硅烷、和二苯基二甲氧基硅烷；单烷氧基硅烷，如三甲基甲氧基硅烷和三苯基甲氧基硅烷；烷基异丙烯氧基硅烷(alkylisopropenoxysilanes)，如二甲基二异丙烯氧基硅烷和甲基三异丙烯氧基硅烷；以及这些硅烷的部分水解缩合物。
本发明的另一主题是含有根据本发明的可固化组合物的制备物。根据本发明的制备物的另一个优选实施方案，所述制备物还含有至少一种选自增塑剂、稳定剂、抗氧化剂、填料、反应性稀释剂、干燥剂、粘合促进剂、UV稳定剂、流变助剂和/或溶剂的化合物。上述钛催化剂或各种钛催化剂的混合物，即钛络合物b)，在所述制备物中的用量为0.001-约5重量％，优选0.001-1.5重量％，更优选0.001-1重量％，最优选0.01-0.5重量％，基于所述制备物的总重量。
本文所述制备物中的反应性聚合物a)的量可以为30-90重量％，更优选35-80重量％，最优选40-70重量％，基于制备物的总重量。交联剂c)的量可以是2.5-7重量％，更优选2.7-6.5重量％，最优选3-6重量％，基于制备物的总重量。粘合促进剂的用量可以为0-5重量％，更优选0.2-4重量％，基于制备物的总重量。
本文所述的可固化组合物和制备物可以用作粘合剂和密封剂。这种类型的用途同样是本发明的一部分。
可以设想，对于某些应用，根据本发明的粘合剂或密封剂的粘度可能太高。此时，通常可以通过使用反应性稀释剂容易且适当地降低或调节粘度，而不会在固化的化合物中导致分层效果(例如增塑剂迁移)。
所述反应性稀释剂优选具有至少一个在施用后与例如水分或大气氧反应的官能团。这类基团的实例是甲硅烷基、异氰酸酯基、乙烯基不饱和基团和多不饱和体系。
所有可与所述粘合剂或密封剂混溶并降低粘度且具有至少一个与粘合剂具有反应性的基团的化合物都可用作所述反应性稀释剂。
所述反应性稀释剂的粘度优选小于20,000mPas，特别优选为约0.1-6000mPas，非常特别优选1-1000mPas(Brookfield RVT，23℃，转子7，10rpm)。
可以使用例如下列材料作为反应性稀释剂：与异氰酸酯基硅烷反应的聚亚烷基二醇(如Synalox 100-50B，DOW)、氨基甲酸丙基三甲氧基硅烷、烷基三甲氧基硅烷和烷基三乙氧基硅烷如甲基三甲氧基硅烷、甲基三乙氧基硅烷、和乙烯基三甲氧基硅烷(XL 10，Wacker)、乙烯基三乙氧基硅烷、苯基三甲氧基硅烷、苯基三乙氧基硅烷、辛基三甲氧基硅烷、四乙氧基硅烷、乙烯基二甲氧基甲基硅烷(XL12,Wacker)、乙烯基三乙氧基硅烷(GF56，Wacker)、乙烯基三乙酰氧基硅烷(GF62，Wacker)、异辛基三甲氧基硅烷(IO三甲氧基)、异辛基三乙氧基硅烷(IO三乙氧基，Wacker)、N-三甲氧基甲硅烷基甲基-O-甲基氨基甲酸酯(XL63，Wacker)、N-二甲氧基(甲基)甲硅烷基甲基-O-甲基氨基甲酸酯(XL65，Wacker)、十六烷基三甲氧基硅烷、3-辛酰基硫代-1-丙基三乙氧基硅烷，以及这些化合物的部分水解产物。
来自Kaneka Corp.的下述聚合物同样也可用作反应性稀释剂：MS S203H、MSS303H、MS SAT 010和MS SAX 350。
同样可以使用例如由异氰酸酯基硅烷与Synalox类型反应得到的硅烷改性的聚醚。
也可用作反应性稀释剂的是可通过用乙烯基硅烷接枝或通过使多元醇、多异氰酸酯和烷氧基硅烷反应而由有机主链制备的聚合物。
多元醇是指分子中可含有一个或多个羟基(OH)的化合物。所述OH基可以是伯位的也可能是仲位的。
适用的脂族醇的实例包括乙二醇、丙二醇和高级二醇，以及其他多官能醇。所述多元醇可以另外含有其他官能团如酯、碳酸酯和酰胺。
为了制备根据本发明优选的反应性稀释剂，相应的多元醇组分在每种情况下都与至少二官能的异氰酸酯反应。作为所述至少二官能的异氰酸酯，原则上任何具有至少两个异氰酸酯基团的异氰酸酯都是适用的；然而，在本发明的范围内，通常优选具有2-4个异氰酸酯基团，特别是2个异氰酸酯基团的化合物。
在本发明范围内作为反应性稀释剂存在的化合物优选具有至少一个烷氧基甲硅烷基基团，其中在所述烷氧基甲硅烷基基团中优选二烷氧基甲硅烷基和三烷氧基甲硅烷基。
用于制备反应性稀释剂的适用的多异氰酸酯是例如亚乙基二异氰酸酯、1,4-四亚甲基二异氰酸酯、1,4-四甲氧基丁烷二异氰酸酯、1,6-六亚甲基二异氰酸酯(HDI)、环丁烷-1,3-二异氰酸酯、环己烷-1,3-和-1,4-二异氰酸酯、双(2-异氰酸酯基乙基)富马酸酯、及其两种或更多种的混合物、1-异氰酸酯基-3,3,5-三甲基-5-异氰酸酯基甲基环己烷(异佛尔酮二异氰酸酯，IPDI)、2,4-和2,6-六氢甲苯二异氰酸酯、六氢-1,3-或-1,4-亚苯基二异氰酸酯、联苯胺二异氰酸酯、萘-1,5-二异氰酸酯、1,6-二异氰酸酯基-2,2,4-三甲基己烷、1,6-二异氰酸酯基-2,4,4-三甲基己烷、苯二亚甲基二异氰酸酯(XDI)、四甲基苯二亚甲基二异氰酸酯(TMXDI)、1,3-和1,4-亚苯基二异氰酸酯、2,4-或2,6-甲苯二异氰酸酯(TDI)、2,4'-二苯基甲烷二异氰酸酯、2,2'-二苯基甲烷二异氰酸酯、或4,4'-二苯基甲烷二异氰酸酯(MDI)或其部分或完全氢化的环烷基衍生物，例如完全氢化的MDI(H12-MDI)、烷基取代的二苯基甲烷二异氰酸酯，例如单-、二-、三-或四烷基二苯基甲烷二异氰酸酯和其部分或完全氢化的环烷基衍生物、4,4'-二异氰酸酯基苯基全氟乙烷、邻苯二甲酸二异氰酸酯基乙酯、1-氯甲基苯基-2,4-或-2,6-二异氰酸酯、1-溴甲基苯基-2,4-或-2,6-二异氰酸酯、3,3-二氯甲基醚-4,4’-二苯基二异氰酸酯、可通过使2mol二异氰酸酯与1mol硫二甘醇或二羟基二己基硫化物反应获得的含硫二异氰酸酯、二聚体和三聚体脂肪酸的二异氰酸酯和三异氰酸酯、或两种或更多种所述二异氰酸酯的混合物。
例如可通过二异氰酸酯的低聚，特别是通过上述异氰酸酯的低聚可得到的三价或更高价的异氰酸酯也可以用作多异氰酸酯。这种三价和更高价多异氰酸酯的实例是HDI或IPDI的三异氰酸酯或其混合物或其混合三异氰酸酯，以及聚苯基亚甲基多异氰酸酯，其可通过苯胺-甲醛缩合产物的光气化获得。
除了反应性稀释剂之外可使用溶剂和/或增塑剂或可代替反应性稀释剂使用溶剂和/或增塑剂来降低本发明的制备物的粘度。
脂肪或芳香烃、卤代烃、酮、醚、酯、酯醇、酮醇、酮醚、酮酯和醚酯是适用的溶剂。
根据本发明的制备物还可以含有亲水性增塑剂。它们用于改善吸湿性，因此用于提高低温下的反应性。适用的增塑剂是例如松香酸的酯、己二酸酯、壬二酸酯、苯甲酸酯、丁酸酯、乙酸酯、含约8至约44个碳原子的高级脂肪酸的酯、环氧化的脂肪酸的酯、脂肪酸酯和脂肪、乙醇酸酯、磷酸酯、邻苯二甲酸酯、含有1-12个C原子的直链或支链醇的酯、丙酸酯、癸二酸酯、磺酸酯、硫代丁酸酯、偏苯三酸酯、柠檬酸酯，和基于硝化纤维素和聚乙酸乙烯酯的酯，以及其两种或更多种的混合物。
邻苯二甲酸酯中适用的是例如邻苯二甲酸二辛酯、邻苯二甲酸二丁酯、邻苯二甲酸二异十一烷基酯、或邻苯二甲酸丁基苄基酯，己二酸酯中适用的是己二酸二辛酯、己二酸二异癸酯、琥珀酸二异癸酯、癸二酸二丁酯、或油酸丁酯。
同样适用的增塑剂的是单官能、直链或支链C4-16醇的纯的或混合醚或这类醇的两种或更多种不同醚的混合物，例如二辛醚(可作为Cetiol OE获得，Cognis DeutschlandGmbH，Düsseldorf)。
由端基封闭的聚乙二醇也适用为增塑剂。实例为聚乙二醇或聚丙二醇二C1-4烷基醚，特别是二甘醇或二丙二醇的二甲基醚或二乙基醚，及其两种或更多种的混合物。
然而，特别优选的增塑剂是被端基封闭的聚乙二醇，例如聚乙二醇二烷基醚或聚丙二醇二烷基醚，其中烷基为1-4个碳原子，特别是二甘醇和二丙二醇的二甲基醚和二乙基醚。特别地，即使在相当不利的应用条件(低湿度，低温)下，使用二甲基二甘醇(dimethyldiethylene glycol)也可以实现可接受的固化。有关增塑剂的进一步详情可参阅技术化学相关文献。
同样适用为本发明范围内的增塑剂的是二氨基甲酸酯，其可以通过，例如，使具有OH端基的二醇与单官能异氰酸酯反应，通过选择化学计量以使得基本上所有的游离OH基团都反应来制备。随后可通过例如蒸馏从反应混合物中除去任何过量的异氰酸酯。制备二氨基甲酸酯的另一种方法是使单官能醇与二异氰酸酯反应，优选全部NCO基团都反应。
根据本发明的制备物还可以含有至多约20重量％的常规粘合促进剂(增粘剂)。适用的粘合促进剂是例如树脂、萜烯低聚物、香豆酮/茚树脂、脂族石油化学树脂、和改性酚醛树脂。在本发明范围内适用的是例如通过主要是α-或β-蒎烯的萜烯、二戊烯或柠檬烯的聚合获得的烃树脂。这些单体的聚合通常用Friedel-Crafts催化剂引发以阳离子形式进行。所述萜烯树脂还包括例如萜烯和其他单体的共聚物，例如苯乙烯、α-甲基苯乙烯、异戊二烯等。所述树脂被用作例如接触粘合剂和涂料的粘合促进剂。同样适用的是萜烯酚醛树脂，其通过酸催化将酚加成到萜烯或松香中而制备。萜烯酚醛树脂可溶于大多数有机溶剂和油类中，并可与其他树脂、蜡和橡胶混溶。同样适用于本发明范围内的添加剂的是松香树脂及其衍生物，例如其酯。
此外，根据本发明的制备物可以另外含有至多约7重量％，特别是至多约5重量％的抗氧化剂。
根据本发明的制备物可以含有至多约2重量％，优选约1重量％的UV稳定剂。所谓的受阻胺光稳定剂(HALS)特别适用作UV稳定剂。在本发明的范围内，优选使用带有甲硅烷基并且在交联和固化过程中被引入到最终产物中的UV稳定剂。Lowilite 75和Lowilite 77(美国Great Lakes)产品特别适用于此目的。另外，也可以加入苯并三唑、二苯甲酮、苯甲酸酯、氰基丙烯酸酯、丙烯酸酯、位阻酚、磷和/或硫。
为了进一步延长保质期，通过使用干燥剂进一步加强根据本发明的制备物对渗透水分的稳定性通常是有利的。
这种保质期的改善可例如通过使用干燥剂来实现。所有与水反应以形成对组合物中存在的反应性基团呈惰性并且在该过程中其分子量变化较小的化合物都适用作干燥剂。此外，所述干燥剂对渗透到组合物中的水分的反应性必须高于制备物中存在的本发明的含甲硅烷基的聚合物的基团的反应性。
例如，异氰酸酯适用作干燥剂。
硅烷可有利地用作干燥剂。实例是乙烯基硅烷如3-乙烯基丙基三乙氧基硅烷，肟硅烷如甲基-O,O',O”-丁烷-2-酮-三肟基硅烷或O,O',O”,O”'-丁烷-2-酮四肟基硅烷(CASNo.022984-54-9和034206-40-1)，或苯甲酰氨基硅烷如双(N-甲基苯甲酰氨基)甲基乙氧基硅烷(CAS No.16230-35-6)或氨基甲酸基硅烷如氨基甲酸甲基三甲氧基硅烷。然而，使用甲基三甲氧基硅烷、乙基三甲氧基硅烷或乙烯基三甲氧基硅烷或四甲基乙氧基硅烷或四乙基乙氧基硅烷也是可能的。关于效率和成本，在此特别优选乙烯基三甲氧基硅烷和四乙氧基硅烷。
同样适用为干燥剂的是上述反应性稀释剂，条件是它们的分子量(Mn)小于约5,000g/mol并且对渗透的水分的反应性至少相当于，优选高于，根据本发明的带有甲硅烷基的聚合物的反应性基团的反应性。
最后，烷基原甲酸酯或原乙酸酯，例如原甲酸甲酯或原甲酸乙酯、原乙酸甲酯或原乙酸乙酯，也可用作干燥剂，
根据本发明的粘合剂和密封剂通常含有约0至约6重量％的干燥剂。
根据本发明的制备物可以另外含有填料。适用的实例是白垩、石灰粉、沉淀法和/或热解法硅酸、沸石、膨润土、碳酸镁、硅藻土、氧化铝、粘土、滑石、氧化钛、氧化铁、氧化锌、砂子、石英、燧石、云母、玻璃粉、和其他研磨的矿物质。此外，还可以使用有机填料，特别是炭黑、石墨、木纤维、木粉、锯末、纤维素、棉花、纸浆、木片、碎秸秆和谷壳。此外，可以加入短纤维如玻璃纤维、玻璃丝、聚丙烯腈、碳纤维、Kevlar纤维、或者还有聚乙烯纤维。粉状铝同样适用作填料。
所述热解法和/或沉淀法硅酸可有利地具有10-90m2/g的BET表面积。在使用过程中，它们不会引起根据本发明的制备物的粘度的另外增加，但有助于强化固化的制备物。
同样可以设想，可以使用具有更大的BET表面积，有利地为100-250m2/g，特别是110-170m2/g的热解法和/或沉淀法硅酸作为填料。由于较大的BET表面积，可以以较低的重量分数获得相同的效果，例如强化固化的制备物。其他物质因此可以根据其他要求而用于改善根据本发明的制备物。
此外，具有矿物壳或塑料壳的空心球适用为填料。其可以是例如可以商品名Glass商购的中空玻璃球。基于塑料的空心球，例如或描述于EP0520426B1中。它们由无机或有机物质组成，每种的直径都是1mm或更小，优选500μm或更小。
对于某些应用，优选填料可赋予所述制备物触变性。这种填料也被描述为流变助剂，例如氢化蓖麻油、脂肪酸酰胺、或可膨胀塑料如PVC。为了使它们可容易从适当的配料装置(如管)中压出，这种制备物的粘度为3000-15,000mPas，优选40,000-80,000mPas，或者50,000-60,000mPas。
基于所述制备物的总重量，所述填料的用量优选为1-80重量％。
根据本明的制备物根据已知方法通过将所述组分在适用的分散单元如高速混合器中充分混合来制备。
本发明的另一主题涉及根据本发明的组合物或根据本发明的制备物作为粘合剂、密封剂或填充化合物、以及用于生产模制部件的用途。根据本发明的组合物的另一个应用领域是用作堵漏剂、填孔剂或膏剂化合物(spackling compound)。
因此，根据本发明的组合物和制备物适用于粘合性地结合塑料、金属、玻璃、陶瓷、木材、木基材料、纸张、纸基材料、橡胶和纺织品，用于粘结地板，密封建筑元件、窗户、墙壁和地板覆盖物，以及一般的接合。就这一点而言，所述材料在每种情况下都可以自身粘合或与任何其他所述的材料粘合。
最后，本发明还涉及钛络合物作为催化剂，特别是作为缩合催化剂用于固化含硅聚合物的用途。在该固化过程中，所述反应性含硅基团交联以形成硅氧烷键。
下述实施例用于解释本发明；但是，本发明不限于此。
实施例
实施例1：钛络合物1的制备
向搅拌的冷却至0℃的配体(式(3)，R4＝对甲苯磺酰基；2.01g，3.54mmol)的甲苯(30mL)悬浮液中，通过滴液漏斗缓慢加入Ti(NEt2)2(n-BuO)2的甲苯溶液(1.12mL，3.54mmol)。将反应混合物在0℃下搅拌2小时，然后升温至室温。在室温下再搅拌5小时后，该反应混合物变成橙色并澄清。减压蒸发溶剂。用甲苯/正己烷重结晶，得到钛络合物1，为橙色固体。
产率：1.6g(2.11mmol,65％)。
根据C33H47N3O8S3Ti(757.80g·mol-1)计算：C 52.30,H 6.25,N 5.54,S 12.69。
实验数据：C 52.18,H 6.32,N 5.98,S 12.36。1H NMR(500MHz,d8-甲苯,298K):δ0.43–0.95(m,6H,CH3),0.96–1.53(m,8H,CH2),1.58–1.64(m,9H,Ts–CH3),2.96–3.64(m,8H,N–CH2),3.85–3.98(m,2H,O–CH2),6.30–6.79(m,m-Ar-H),7.05–7.17(m,o-Ar-H),7.26–7.45(m,o-Ar-H),7.00–8.00(m,o-Ar-H).13C NMR(126MHz,d8-甲苯,298K):δ14.5(CH3),14.5(CH3),14.7(CH3),19.9(CH2),20.0(CH2),21.3(CH3),21.5(CH3),21.6(CH3),32.4(CH2),35.8(CH2),48.2(N–CH2),51.7(N–CH2),53.5(N–CH2),54.2(N–CH2),75.6(O–CH2),76.6(O–CH2),79.9(O–CH2),125.8(m-CH),127.9(m-CH),130.0(o-CH),130.1(o-CH),135.7(p-C),135.9(p-C),143.2(i-C),143.4(i-C),143.7(i-C).CI-MS m/z:758[M]+,684[M-nBuO]+.IR(neat,cm-1,297K):ν＝2956(m),2930(m),2868(m).
实施例2：钛络合物2的制备
向搅拌的冷却至-60℃的配体(式(3)，R4＝对甲苯磺酰基；3.44g，6.08mmol)的THF(10mL)悬浮液中，缓慢加入12.12mmol的n-BuLi(4.85mL的2.5M正己烷溶液)和另外的10mL甲苯。在室温下搅拌12小时后，真空除去溶剂，分离出橙色固体。将其悬浮于甲苯(10mL)中并冷却至-60℃。逐滴加入TiCl2(i-PrO)2(1.45g，6.01mmol)在甲苯(10mL)中的溶液。将反应混合物升温至室温并搅拌4小时。过滤除去形成的LiCl并蒸发溶剂，得到钛络合物2，为微紫色固体。
产率：3.89g(5.33mmol,89％)。
根据C31H43N6O8S3Ti(729.75g·mol-1)的计算结果：C 51.02,H 5.94,N 5.76,S13.18。
实验数据：C 51.85,H 6.23,N 5.51,S 12.02.1H NMR(250MHz,d6-苯,298K):δ1.47(d,3JHH 6.0Hz,12H,CH3),1.93(s,9H,CH3),2.89(br s,4H,NH2),3.72(br s,4H,N–CH2),5.30(br s,2H,O–CH),6.78(d,3JHH 8.0Hz,2H,m-Ar-H),6.97(d,3JHH 8.1Hz,4H,m-Ar-H),7.48(d,3JHH 8.2Hz,2H,o-Ar-H),8.35(d,3JHH8.3Hz,4H,o-Ar-H).13C NMR(63MHz,d6-苯,298K):δ21.2(CH3),21.4(CH3),25,7(CH3),47.5(CH2),51.1(CH2),82.7(CH),125.7(m-CH),129.3(m-CH),129.6(o-CH),129.6(o-CH),135.5(p-C),138.9(p-C),142.7(i-C),143.3(i-C).MS m/z(CI):730[M]+,670[M–iPrO+1]+,628[M–2iPrO+1]+,574[M–Ts]+.IR(neat,cm-1,297K):ν＝2928(m),2925(m),2892(m)。
实施例3：钛络合物3的制备
将配体(式(3)，R4＝三甲基甲硅烷基；1.32g，4.11mmol)溶解于甲苯(10mL)中，边搅拌边冷却至-55℃。将8.22mmol的n-BuLi(3.3mL的2.5M正己烷溶液)和另外的7mL的甲苯缓慢加入冷却的溶液中，得到白色沉淀。将该悬浮液搅拌24小时，然后冷却至-40℃。逐滴滴加无色的TiCl2(i-PrO)2(0.97g,4.11mmol)的甲苯(3mL)溶液。在室温下搅拌72小时后，真空除去甲苯。将残余物溶于正庚烷中。过滤除去沉淀的LiCl，并蒸发溶剂，得到深红色液体钛络合物3。
产率：1.20g(2.48mmol,60％)。
根据C19H49N3O2Si3Ti(483.73g·mol-1)的计算结果：C 47.18,H 10.21,N 8.69。
实验数据：C 40.88,H 9.34,N 9.29.1H NMR(300MHz,d6-苯,298K):δ0.10–0.44(m,27H,3·TMS),1.20–1.39(m,12H,CH3),2.43–3.98(m,8H,N–CH2)2.48(t,2H,N–CH2),3.39(t,2H,N–CH2),4.50–4.69(m,1H,O–CH),4.72–4.90(m,1H,O–CH).13C NMR(75MHz,d6-苯,298K):δ0.8(TMS),1.6(2·TMS),27.2(CH3),52.7(CH2),56.1(CH2),76.7(CH).).29Si NMR(59.6MHz,d6-苯,298K):δ0.33,1.93,5.20,15.51.MS m/z(CI):484[M]+,468[M–CH3]+,424[M–iPrO]+,382[M–OiPr+CH3]+,320[2b]+.IR(neat,cm-1,297K):ν＝2955(m),2896(m),2863(m)。
实施例4：固化性能测试
将所合成的钛络合物在由α,ω-二-二烷氧基乙烯基甲硅烷基-聚二甲基硅氧烷(粘度为约80,000cST，根据US 5663269A合成，71％)、聚二甲基硅氧烷(粘度为约100cST，17％)，和热解法二氧化硅(104，Evonik，11％)所组成的有机硅混合物的交联反应中进行测试。35g未固化的有机硅和1.385mmol的所述催化剂。将所述组分在双不对称离心混合器(SpeedMixerTM DAC 150.1FVZ-K)中在3000RPM下混合150秒。制备了有机硅混合物的测试条并使其在标准大气下固化。
按照国际质量标准测量了结皮时间(SOT)和24小时后的固化深度(DOC)。结皮时间(SOT)被定义为材料形成非粘性表面膜所需的时间。在标准气候条件(23+/-2℃，相对湿度50+/-5％)下根据DIN 50014进行结皮时间的测定。密封剂的温度必须为23+/-2℃，密封剂在实验室中预先保存至少24小时。将密封剂施加在一张纸上，用腻刀铺开以形成表皮(厚度约2mm，宽约7cm)。立即秒表启动。每隔一段时间，用指尖轻轻触摸表面，并将手指拉开，并在表面上形成足够的压力，以便在达到表皮形成时间时留下印痕。当密封化合物不再附着在指尖上时，就达到了所述的结皮时间。结皮时间以分钟表示。
根据ISO 4049，在1厘米高的探针中测量作为固化材料的厚度的固化深度(DOC)。
表1：不同络合物在有机硅橡胶中的固化性能
*DOTL：月桂酸二辛基锡。
Claims (10)
1.可固化组合物，其包含
a)至少一种具有至少一个式(1)的含硅基团的聚合物
-Si(R1)k(Y)3-k (1)，
其中
R1选自含有1-20个C原子的烃基或式-O-Si(R2)3的三有机基硅氧烷基团，其中每个R2都独立地选自含有1-20个C原子的烃基；
每个Y都独立地选自羟基或可水解基团，优选肟基、烷氧基、乙酰氧基或乳酸酯基；且
k是0、1或2；
b)至少一种式(2)的钛络合物
TiL(OR3)2 (2)，
其中
每个R3都独立地选自可任选地含有一个或多个杂原子的C1-20烷基或芳基，所述杂原子优选地选自硅、硫、氮或氧原子，其中优选地R3选自正丁基或异丙基；且
L是去质子化的三齿配体；和
c)任选存在的至少一种具有可水解的含硅基团的化合物，根据DIN55672-1:2007-08用GPC测量，所述化合物的重均分子量为100-1000g/mol，优选地所述化合物为氨基硅烷。
2.根据权利要求1所述的可固化组合物，其特征在于聚合物a)的聚合物骨架选自醇酸树脂、(甲基)丙烯酸酯和(甲基)丙烯酰胺及其盐、酚醛树脂、聚烯烃、聚酰胺、聚碳酸酯、聚醚、聚酯、聚氨酯、乙烯基聚合物、硅氧烷、及至少两种上述聚合物的组合。
3.根据权利要求1或2的可固化组合物，其特征在于L选自去质子化形式的式(3)的二酰氨基胺、式(4)的二酰氨基硫属化物和式(5)的二酰氨基吡啶，
其中R4独立地选自式-Si(R7)3的甲硅烷基，其中每个R7都独立地选自含有1-20个C原子的烃基，或可任选地含有一个或多个杂原子的C1-20烷基或芳基，所述杂原子优选地选自硅、硫、氮或氧原子，R5和R6独立地选自可任选地含有一个或多个杂原子的C1-20烷基或芳基，所述杂原子优选地选自硅、硫、氮或氧原子，X是硫或氧原子，R6相对于氮位于邻位、间位或对位。
4.根据权利要求3所述的组合物，其特征在于R4独立地选自甲基、苯基、-Si(CH3)3或对甲苯磺酰基。
5.根据权利要求3或4所述的可固化组合物，其特征在于R5和R6独立地选自甲基或苯基。
6.根据权利要求1-5中至少一项所述的可固化组合物，其特征在于化合物c)的组成含有氨基硅烷，所述氨基硅烷优选地选自双(三甲基甲硅烷基)胺、氨基丙基三乙氧基硅烷、氨基丙基三甲氧基硅烷、双[(3-三乙氧基甲硅烷基)丙基]胺、双[(3-三甲氧基甲硅烷基)丙基]胺、氨基丙基甲基二乙氧基硅烷、氨基乙基氨基丙基三甲氧基硅烷、氨基乙基氨基丙基三乙氧基硅烷、3-[2-(2-氨基乙基氨基)乙基氨基]丙基三甲氧基硅烷、苯基氨基甲基三甲氧基硅烷、氨基乙基氨基丙基甲基二甲氧基硅烷、3-(N-苯基氨基)丙基三甲氧基硅烷、3-哌嗪基丙基甲基二甲氧基硅烷、3-(N,N-二甲基氨基丙基)氨基丙基甲基二甲氧基硅烷、以及两种或更多种上述化合物的组合。
7.含有根据权利要求1-6中至少一项所述的可固化组合物的制备物。
8.根据权利要求7所述的制备物，其特征在于所述制备物另外含有至少一种选自增塑剂、稳定剂、抗氧化剂、填料、反应性稀释剂、干燥剂、粘合促进剂、UV稳定剂、流变剂、溶剂及其混合物的化合物。
9.根据权利要求1-6中至少一项所述的组合物或根据权利要求6或7所述的制备物作为粘合剂或密封剂的用途。
10.式(2)的钛络合物作为用于通过形成硅氧烷键而固化含硅聚合物的催化剂的用途：
TiL(OR3)2 (2)，
其中
每个R3都独立地选自可任选地含有一个或多个杂原子的C1-20烷基或芳基，所述杂原子优选地选自硅、硫、氮或氧原子，其中优选地R3选自正丁基或异丙基；且
L是选自去质子化形式的式(3)的二酰氨基胺、式(4)的二酰氨基硫属化物和式(5)的二酰氨基吡啶的三齿配体，
其中R4独立地选自式-Si(R7)3的甲硅烷基，其中每个R7都独立地选自含有1-20个C原子的烃基，或可任选地含有一个或多个杂原子的C1-20烷基或芳基，所述杂原子优选地选自硅、硫、氮或氧原子，R5和R6独立地选自可任选地含有一个或多个杂原子的C1-20烷基或芳基，所述杂原子优选地选自硅、硫、氮或氧原子，其中优选地R4独立地选自甲基、苯基、-Si(CH3)3或对甲苯磺酰基，R5和R6独立地选自甲基或苯基，X是硫或氧原子，R6相对于氮位于邻位、间位或对位。
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