CN101443381B - 具有改善的回弹性能的烷氧基硅烷交联的聚合物 - Google Patents
具有改善的回弹性能的烷氧基硅烷交联的聚合物 Download PDFInfo
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- CN101443381B CN101443381B CN2007800176261A CN200780017626A CN101443381B CN 101443381 B CN101443381 B CN 101443381B CN 2007800176261 A CN2007800176261 A CN 2007800176261A CN 200780017626 A CN200780017626 A CN 200780017626A CN 101443381 B CN101443381 B CN 101443381B
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- silane
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- alkoxysilane
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- 238000011084 recovery Methods 0.000 title abstract description 10
- 229920006037 cross link polymer Polymers 0.000 title abstract description 3
- 239000000203 mixture Substances 0.000 claims abstract description 39
- 229920000642 polymer Polymers 0.000 claims abstract description 34
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 11
- 238000000034 method Methods 0.000 claims abstract description 10
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 9
- 125000003118 aryl group Chemical group 0.000 claims abstract description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 4
- 239000001257 hydrogen Substances 0.000 claims abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
- -1 alkyl alkoxy silane Chemical compound 0.000 claims description 33
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 30
- 229910000077 silane Inorganic materials 0.000 claims description 27
- 150000001721 carbon Chemical group 0.000 claims description 14
- 229910052799 carbon Inorganic materials 0.000 claims description 14
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- 239000005062 Polybutadiene Substances 0.000 claims description 3
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- 229920002396 Polyurea Polymers 0.000 claims description 3
- 229920002647 polyamide Polymers 0.000 claims description 3
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- 229920000089 Cyclic olefin copolymer Polymers 0.000 claims description 2
- 239000004425 Makrolon Substances 0.000 claims description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 2
- 125000005466 alkylenyl group Chemical group 0.000 claims description 2
- 239000004202 carbamide Substances 0.000 claims description 2
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- 238000002156 mixing Methods 0.000 claims description 2
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- 229920000193 polymethacrylate Polymers 0.000 claims description 2
- 229920001290 polyvinyl ester Polymers 0.000 claims description 2
- GTACSIONMHMRPD-UHFFFAOYSA-N 2-[4-[2-(benzenesulfonamido)ethylsulfanyl]-2,6-difluorophenoxy]acetamide Chemical compound C1=C(F)C(OCC(=O)N)=C(F)C=C1SCCNS(=O)(=O)C1=CC=CC=C1 GTACSIONMHMRPD-UHFFFAOYSA-N 0.000 claims 1
- 101710130081 Aspergillopepsin-1 Proteins 0.000 claims 1
- 102100031007 Cytosolic non-specific dipeptidase Human genes 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 5
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract description 4
- 125000005647 linker group Chemical group 0.000 abstract description 2
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 abstract 1
- 125000004122 cyclic group Chemical class 0.000 abstract 1
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 8
- 238000010276 construction Methods 0.000 description 8
- 239000000945 filler Substances 0.000 description 7
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- 239000003054 catalyst Substances 0.000 description 6
- 238000000576 coating method Methods 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 229910000019 calcium carbonate Inorganic materials 0.000 description 4
- 239000011248 coating agent Substances 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
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- ZLNAFSPCNATQPQ-UHFFFAOYSA-N ethenyl-dimethoxy-methylsilane Chemical compound CO[Si](C)(OC)C=C ZLNAFSPCNATQPQ-UHFFFAOYSA-N 0.000 description 3
- 229910021485 fumed silica Inorganic materials 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- XNGIFLGASWRNHJ-UHFFFAOYSA-N o-dicarboxybenzene Natural products OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- YCTOZRVAMYUFQI-UHFFFAOYSA-N (ethoxy-methoxy-methylsilyl)methyl prop-2-enoate Chemical compound CCO[Si](OC)(C)COC(C=C)=O YCTOZRVAMYUFQI-UHFFFAOYSA-N 0.000 description 2
- QJATYMSFGSZXPG-UHFFFAOYSA-N 3-[ethoxy(dimethoxy)silyl]propyl prop-2-enoate Chemical compound CCO[Si](OC)(OC)CCCOC(=O)C=C QJATYMSFGSZXPG-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- 239000004971 Cross linker Substances 0.000 description 2
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- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
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- 229910019142 PO4 Inorganic materials 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical class [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- VXNUKPNEBNFLHG-UHFFFAOYSA-N [ethoxy(dimethoxy)silyl]methyl prop-2-enoate Chemical compound CCO[Si](OC)(OC)COC(=O)C=C VXNUKPNEBNFLHG-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 239000002318 adhesion promoter Substances 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
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- 230000005494 condensation Effects 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
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- 239000000806 elastomer Substances 0.000 description 2
- 239000008393 encapsulating agent Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 125000001261 isocyanato group Chemical group *N=C=O 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000004014 plasticizer Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 239000000565 sealant Substances 0.000 description 2
- 238000007493 shaping process Methods 0.000 description 2
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- 229920001169 thermoplastic Polymers 0.000 description 2
- 239000004416 thermosoftening plastic Substances 0.000 description 2
- 239000013008 thixotropic agent Substances 0.000 description 2
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 2
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- SIXWIUJQBBANGK-UHFFFAOYSA-N 4-(4-fluorophenyl)-1h-pyrazol-5-amine Chemical compound N1N=CC(C=2C=CC(F)=CC=2)=C1N SIXWIUJQBBANGK-UHFFFAOYSA-N 0.000 description 1
- HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 1
- 229920002367 Polyisobutene Polymers 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000013466 adhesive and sealant Substances 0.000 description 1
- 229920003232 aliphatic polyester Polymers 0.000 description 1
- 125000005370 alkoxysilyl group Chemical group 0.000 description 1
- RREGISFBPQOLTM-UHFFFAOYSA-N alumane;trihydrate Chemical compound O.O.O.[AlH3] RREGISFBPQOLTM-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 125000004103 aminoalkyl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229920005601 base polymer Polymers 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 1
- ZFMQKOWCDKKBIF-UHFFFAOYSA-N bis(3,5-difluorophenyl)phosphane Chemical compound FC1=CC(F)=CC(PC=2C=C(F)C=C(F)C=2)=C1 ZFMQKOWCDKKBIF-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
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- 238000007334 copolymerization reaction Methods 0.000 description 1
- JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 description 1
- AYOHIQLKSOJJQH-UHFFFAOYSA-N dibutyltin Chemical compound CCCC[Sn]CCCC AYOHIQLKSOJJQH-UHFFFAOYSA-N 0.000 description 1
- NBBQQQJUOYRZCA-UHFFFAOYSA-N diethoxymethylsilane Chemical compound CCOC([SiH3])OCC NBBQQQJUOYRZCA-UHFFFAOYSA-N 0.000 description 1
- ZXPDYFSTVHQQOI-UHFFFAOYSA-N diethoxysilane Chemical compound CCO[SiH2]OCC ZXPDYFSTVHQQOI-UHFFFAOYSA-N 0.000 description 1
- XYYQWMDBQFSCPB-UHFFFAOYSA-N dimethoxymethylsilane Chemical compound COC([SiH3])OC XYYQWMDBQFSCPB-UHFFFAOYSA-N 0.000 description 1
- YQGOWXYZDLJBFL-UHFFFAOYSA-N dimethoxysilane Chemical compound CO[SiH2]OC YQGOWXYZDLJBFL-UHFFFAOYSA-N 0.000 description 1
- HGQSXVKHVMGQRG-UHFFFAOYSA-N dioctyltin Chemical compound CCCCCCCC[Sn]CCCCCCCC HGQSXVKHVMGQRG-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- CWAFVXWRGIEBPL-UHFFFAOYSA-N ethoxysilane Chemical compound CCO[SiH3] CWAFVXWRGIEBPL-UHFFFAOYSA-N 0.000 description 1
- 125000006534 ethyl amino methyl group Chemical group [H]N(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
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- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 125000005375 organosiloxane group Chemical group 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
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- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 125000005498 phthalate group Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
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- 229910052710 silicon Inorganic materials 0.000 description 1
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Chemical class [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 239000004590 silicone sealant Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 230000017105 transposition Effects 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- UKRDPEFKFJNXQM-UHFFFAOYSA-N vinylsilane Chemical class [SiH3]C=C UKRDPEFKFJNXQM-UHFFFAOYSA-N 0.000 description 1
- 238000004073 vulcanization Methods 0.000 description 1
- 230000010148 water-pollination Effects 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
- C08L71/02—Polyalkylene oxides
-
- 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
- C08G77/38—Polysiloxanes modified by chemical after-treatment
-
- 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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/336—Polymers modified by chemical after-treatment with organic compounds containing silicon
-
- 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
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Abstract
本发明涉及用于改善已交联的聚合物混合物(P)的回弹性的方法,其中,将A)具有至少一个通式(1)-A-(CH2)m-SiR1 a(OR2)3-a的端基的烷氧基硅烷封端的聚合物(A),其中,A代表选自-O-、-S-、-(R3)N-、-O-CO-N(R3)-、-N(R3)-CO-O-、-N(R3)-CO-NH-、-NH-CO-N(R3)-、-N(R3)-CO-N(R3)-的二价连接基团,R1代表未经取代或被卤素取代的具有1至10个碳原子的烷基、环烷基、烯基或芳基,R2代表具有1至6个碳原子的烷基或具有共计2至10个碳原子的ω-氧杂烷基-烷基,R3代表氢、未经取代或被卤素取代的环状、直链或分支的C1-C18烷基或烯基或C6-C18芳基,a为0至2的整数,及m为1至6的整数,与B)氨基烷基烷氧基硅烷(B)和C)环氧基烷基烷氧基硅烷(C)混合。
Description
技术领域
本发明涉及用于改善烷氧基硅烷封端的聚合物的已交联的混合物的回弹性能的方法。
背景技术
具有反应性烷氧基甲硅烷基的聚合物系统早已是已知的。在存在空气湿度的情况下,该烷氧基硅烷封端的聚合物即使在室温下也会彼此缩合而消去烷氧基。取决于烷氧基硅烷基的含量及其结构,在此主要形成长链聚合物(热塑性塑料)、相对大孔的三维网络(弹性体)或高度交联的系统(热固性塑料)。
其可以是具有有机主链的烷氧基硅烷封端的聚合物,例如聚氨酯、聚酯、聚醚等,特别是在EP-A-269819、EP-A-931800、WO00/37533、US3,971,751和DE 198 49 817中所述,以及主链完全或至少部分地由有机硅氧烷构成的聚合物,特别是在WO96/34030和US5,254,657中所述。
根据用于构成此类硅烷封端的聚合物系统的无数可能性,几乎可以任意地调节未交联的聚合物或含有聚合物的混合物的特性(粘度、熔点、溶解性等)以及完全交联的组合物的特性(硬度、弹性、抗拉强度、断裂伸长率、耐热性等)。因此,使用此类硅烷封端的聚合物系统的可能性相应地是多种多样的。因此,它们例如可用于制备弹性体、密封材料、粘合剂、弹性粘合系统、硬的和软的泡沫、各种不同的涂料系统,或者用于成型模组合物。这些产品可以任何形式使用,例如涂抹、喷射、浇注、压制、刮涂等,取决于配制品的组成。
除组合物的硬化和硫化橡胶的机械性能以外,特别是在用于粘合剂和密封剂领域中时,要求对各种不同的基材具有良好的粘着性以及良好的弹性。在此,硅烷交联的聚合物的配制品通常显示出非常好的性能。
粘着性分布通常通过添加有机官能的粘着促进剂而改善或优化。使用此类硅烷是现有技术,并且在多种专著或出版物中述及。此外还存在特殊的新开发的粘着促进剂硅烷,例如在EP 997 469 A或EP 12 16 263 A中述及,但是硅烷的结合通常也是可用的,例如在EP 11 79 571 A中述及。
粘合剂,特别是密封剂,除了良好的粘着性以外,还必须具有非常好的弹性。在此,伸长率以及在伸长或压缩后的松弛也是相关的因素。这通常作为压缩变形、蠕变特性或回复特性测量。例如,在ISO11600中对于弹性密封剂要求回复率超过60%或者甚至70%。
通常由配制品以及由硅烷交联的基础聚合物的类型决定弹性特性。在此,由硅烷硬化的聚硅氧烷密封剂大多显示出优异的回复特性。在其他的硅烷交联的聚合物中,特别是在聚合物仅具有双官能的端基时,通常显示出回复性不足。在此,配制品对性能是决定性的。例如US6,576,733描述了通过专用催化剂系统改善回复性的可能性。此外,已知使用分支聚合物提高了网状物的密度,并因此改善了弹性。
发明内容
本发明涉及用于改善已交联的聚合物混合物(P)的回弹性的方法,其中,将
A)具有至少一个通式(1)的端基的烷氧基硅烷封端的聚合物(A)
-A-(CH2)m-SiR1 a(OR2)3-a (1),
其中,
A代表选自-O-、-S-、-(R3)N-、-O-CO-N(R3)-、-N(R3)-CO-O-、-N(R3)-CO-NH-、-NH-CO-N(R3)-、-N(R3)-CO-N(R3)-的二价连接基团,
R1代表未经取代或被卤素取代的具有1至10个碳原子的烷基、环烷基、烯基或芳基,
R2代表具有1至6个碳原子的烷基或具有共计2至10个碳原子的ω-氧杂烷基-烷基,
R3代表氢、未经取代或被卤素取代的环状、直链或分支的C1-C18烷基或烯基或C6-C18芳基,
a为0至2的整数,及
m为1至6的整数,
与
B)氨基烷基烷氧基硅烷(B)和
C)环氧基烷基烷氧基硅烷(C)
混合。
添加剂硅烷(C)与氨基硅烷(B)的组合明显地改善了回复特性,这是通过单独使用硅烷无法实现的。单独通过诸如白垩和二氧化硅的填料对回弹性的影响仅是微不足道的。
该聚合物混合物(P)可配制成单组份或双组份的混合物。在双组份聚合物混合物(P)中,优选将两种硅烷(B)和(C)添加至基础组份。然而,特别优选为单组份硬化的聚合物混合物。在制备单组份硬化的聚合物混合物时,优选首先添加硅烷(C),然后添加硅烷(B),这是因为由此实现聚合物混合物(P)的组份的特别均匀的反应。
可用的烷氧基硅烷封端的聚合物(A)的主链可以是分支或非分支的。平均链长度可以根据未交联的混合物以及已硬化的组合物的各种期望的特性任意调节。它们可由不同的结构单元构成。其通常是聚硅氧烷、聚硅氧烷脲/氨基甲酸酯共聚物、聚氨酯、聚脲、聚醚、聚酯、聚丙烯酸酯、聚甲基丙烯酸酯、聚碳酸酯、聚苯乙烯、聚酰胺、聚乙烯基酯或聚烯烃,例如聚乙烯、聚丁二烯、乙烯-烯烃共聚物或苯乙烯-丁二烯共聚物。当然也可使用由具有不同主链的聚合物组成的任意混合物或结合物。
为了制备具有通式(1)的硅烷端基的聚合物(A),已知许多可能性,尤其是包括:
●具有通式(1)的基团的不饱和单体参与的共聚合作用。此类单体的实例有:乙烯基三甲氧基硅烷、乙烯基甲基二甲氧基硅烷、(甲基)丙烯酰氧基丙基三甲氧基硅烷、(甲基)丙烯酰氧基甲基三甲氧基硅烷、(甲基)丙烯酰氧基甲基甲基二甲氧基硅烷或对应的乙氧基甲硅烷基化合物。
●具有通式(1)的基团的不饱和单体接枝至热塑性塑料,如聚乙烯。此类单体的实例有:乙烯基三甲氧基硅烷、乙烯基甲基二甲氧基硅烷、(甲基)丙烯酰氧基丙基三甲氧基硅烷、(甲基)丙烯酰氧基甲基三甲氧基硅烷、(甲基)丙烯酰氧基甲基甲基二甲氧基硅烷或对应的乙氧基甲硅烷基化合物。
●通常在铂催化作用下H-硅烷,如二甲氧基甲基硅烷、二乙氧基甲基硅烷、三甲氧基甲基硅烷或三乙氧基硅烷对位于末端或链上的不饱和双键的氢化硅烷化作用。
●预聚物(A1)与一种或更多种通式(2)的有机硅烷(A2)的反应
C-B-(CH2)m-SiR1 a(OR2)3-a (2),
其中,
R1、R2、R3、m和a具有上述含义,
B代表氧、氮或硫原子,及
C-B-代表对预聚物(A1)的适合的官能团具有反应性的官能团。
在此,若预聚物(A1)本身由多个结构单元(A11、A12…)组成,则并非绝对必需首先由这些结构单元(A11、A12…)制备预聚物(A1)并随后与硅烷(A2)反应生成最终聚合物(A)。在此还可将反应步骤逆转,其中首先使一个或更多个结构单元(A11、A12…)与硅烷(A2)反应,随后在此获得的化合物才与剩余的结构单元(A11、A12…)反应生成最终聚合物(A)。由结构单元A11、A12构成的预聚物(A1)的实例是可由聚异氰酸酯(结构单元A11)和多元醇(结构单元A12)制成的由OH-、NH-或NCO-封端的聚氨酯和聚脲。
具有通式(1)的硅烷端基的聚合物(A)优选为硅烷封端的聚醚和聚氨酯,更优选为聚醚,其由通式(4)的有机硅烷(A2)和预聚物(A1)制得。
在聚合物(A)的一个优选的制备方法中,优选使用选自通式(3)的硅烷的硅烷(A2)
OCN-(CH2)m-SiR1 a(OR2)3-a (3),
其中,
R1、R2、R3和a具有上述的含义,
m等于1或3。
在制备聚合物(A)时,优选地选择参与所有反应步骤的所有异氰酸酯基和所有异氰酸酯反应性基团的浓度以及反应条件,从而在聚合物合成过程中所有的异氰酸酯基均被反应掉。因此,最终聚合物(A)优选不含异氰酸酯。
如文献中多次述及的芳族和脂族聚酯多元醇和聚醚多元醇特别适合作为用于制备聚合物(A)的多元醇。但原则上可以使用具有一个或更多个OH官能团的所有高聚、低聚或单体醇。
R1优选为苯基或具有1至6个碳原子的烷基或烯基,尤其是甲基、乙基或乙烯基。
R2优选为具有1至3个碳原子的烷基,尤其是甲基或乙基。
R3优选为氢、苯基或具有1至6个碳原子的烷基或烯基,尤其是甲基、乙基或正丙基。
m优选为1或3。
氨基烷基烷氧基硅烷(B)优选具有通式(4)
R7 uR8 vSi(OR9)4-u-v (4),
其中,
R7代表未经取代或被卤素取代的具有1至10个碳原子的烷基、环烷基、烯基或芳基,
R8代表具有SiC键结的氨基的、未经取代或被卤素取代的单价C1-C30烃基,
R9代表具有1至6个碳原子的烷基或具有共计2至10个碳原子的ω-氧杂烷基-烷基,
u为0、1或2,及
v为1、2或3,
其条件是:u和v之和小于或等于3。
基团R7的实例和优选的实例是基团R1的上述实例。
基团R8的实例和优选的实例是基团R2的上述实例。
基团R8优选为通式(5)的基团
R10 2NR11- (5),
其中,
R10代表氢原子或未经取代或经取代的单价C1-C10烃基或C1-C10氨基烃基,及
R11代表二价C1-C15烃基。
基团R10的实例是基团R1的以下实例:烃基以及被氨基取代的烃基,如氨基烷基,特别优选为氨基乙基。
基团R11的实例是亚甲基、亚乙基、亚丙基、亚丁基、亚环己基、亚十八烷基、亚苯基和亚丁烯基。基团R11优选为具有1至10个碳原子,特别优选1至4个碳原子的二价烃基,尤其是亚正丙基。
基团R8的实例是氨基丙基、氨基乙基氨基丙基、乙基氨基丙基、丁基氨基丙基、环己基氨基丙基、苯基氨基丙基、氨基甲基、氨基乙基、氨基甲基、乙基氨基甲基、丁基氨基甲基、环己基氨基甲基、苯基氨基甲基。
硅烷(C)优选具有通式(6)
R6(CH2)nSiR5 s(OR4)3-s (6),
其中,
R4代表甲基、乙基或异丙基,
R5代表未经取代或被卤素取代的C1-C10烃基,
R6代表具有环氧基的、可被醚氧原子间隔的、未经取代或被卤素取代的C2-C20烃基,
R9代表具有1至6个碳原子的烷基,
n为1至6的整数,及
s为0、1或2。
n优选代表1或3的数值。s优选代表1或0的数值。R5优选代表甲基或苯基。在具有环氧基的C2-C20烃基R6的情况下,环氧基的碳原子也包括在内。R6优选代表通式(7)的基团
其中,
e为0、1或2,
f为1、2或3,及
g为0、1、2或3。
基团R6的优选的实例是缩水甘油基氧基和(3,4-环氧环己基)乙基。
在该聚合物混合物(P)中,烷氧基硅烷封端的聚合物(A)的含量优选为10至70重量%,更优选为15至50重量%,特别优选为20至40重量%。氨基烷基烷氧基硅烷(B)的含量优选为0.1至10重量%,更优选为0.1至5重量%,特别优选为0.2至3重量%。硅烷(C)的含量优选为0.1至10重量%,更优选为0.5至5重量%,特别优选为1至3重量%。
该聚合物混合物(P)可以包含缩合催化剂,例如钛酸酯,如钛酸四丁基酯、钛酸四丙基酯、钛酸四异丙基酯、钛酸四乙酰丙酮基酯;
锡化合物,如二月桂酸二丁基锡、马来酸二丁基锡、二乙酸二丁基锡、二辛酸二丁基锡、乙酰丙酮酸二丁基锡、氧化二丁基锡,或二辛基锡的对应化合物;
可以等同于氨基烷基烷氧基硅烷(B)的碱性催化剂,如氨基丙基三甲氧基硅烷、氨基丙基三乙氧基硅烷、N-(2-氨基乙基)-氨基丙基三甲氧基硅烷,及其他有机胺,如三乙胺、三丁胺、1,4-二氮杂双环[2.2.2]辛烷、N,N-双(N,N-二甲基-2-氨基乙基)甲基胺、N,N-二甲基环己基胺、N,N-二甲基苯基胺、N-乙基吗啉等;
酸性催化剂,如磷酸或磷酸酯、甲苯磺酸、无机酸。
优选单独使用氨基硅烷或者与二丁基锡化合物结合。
缩合催化剂优选以聚合物混合物(P)的0.01至10重量%,更优选以0.1至2重量%的浓度使用。
可以纯净形式以及作为混合物使用不同的催化剂。
该聚合物混合物(P)可以包含填料,例如天然重质白垩形式的碳酸钙、重质和涂布的白垩形式的碳酸钙、沉积白垩形式的碳酸钙、沉积和涂布的白垩形式的碳酸钙、粘土矿物、膨润土、高岭土、滑石、二氧化钛、氧化铝、三水合铝、氧化镁、氢氧化镁、炭黑、沉积或火成二氧化硅。填料优选以聚合物混合物(P)的10至70重量%,特别优选30至60重量%的浓度使用。
该聚合物混合物(P)可以包含水捕捉剂和硅烷交联剂,例如乙烯基硅烷,如乙烯基三甲氧基硅烷、乙烯基三乙氧基硅烷、乙烯基甲基二甲氧基硅烷、O-甲基氨基甲酸酯基甲基-甲基二甲氧基硅烷、O-甲基氨基甲酸酯基甲基-三甲氧基硅烷、O-乙基氨基甲酸酯基甲基-甲基二乙氧基硅烷、O-乙基氨基甲酸酯基甲基三乙氧基硅烷、通常的烷基烷氧基硅烷或其他有机官能的硅烷。
水捕捉剂和硅烷交联剂优选以聚合物混合物(P)的0.1至10重量%,更优选以0.5至2重量%的浓度使用。
该聚合物混合物(P)可以包含增塑剂,例如邻苯二甲酸酯,如邻苯二甲酸二辛酯、邻苯二甲酸二异辛酯、邻苯二甲酸双十一烷基酯,己二酸酯如己二酸二辛酯,苯甲酸酯、二醇酯、磷酸酯、聚酯、聚醚、聚苯乙烯、聚丁二烯、聚异丁烯、石蜡烃、高级支链烃等。
增塑剂优选以聚合物混合物(P)的最多40重量%的浓度使用。
该聚合物混合物(P)可以包含触变剂,例如亲水性火成二氧化硅、经涂布的火成二氧化硅、沉积二氧化硅、聚酰胺蜡、氢化蓖麻油、硬脂酸盐或沉积白垩。上述填料还可用于调节流变性能。
触变剂优选以聚合物混合物(P)的1至5重量%的浓度使用。
该聚合物混合物(P)还可包含光稳定剂如所谓的HALS稳定剂、杀真菌剂、阻燃剂、颜料等,已知它们用于传统的烷氧基交联的单组份组合物。
优选使用上述添加剂,以在未交联的聚合物混合物(P)中和在已硬化的组合物中产生各种期望的特性分布。
在制备聚合物混合物(P)时,优选首先制备聚合物(A)与填料的混合物,随后混入硅烷(C),然后混入氨基烷基烷氧基硅烷(B)。
对于聚合物混合物(P),在粘合剂、密封材料,包括接缝密封剂、表面涂料领域中以及在制备成型模组合物和模制品时存在许多不同的应用。
在此,聚合物混合物(P)适合于许多不同的基材,如矿物基材、金属、塑料、玻璃、陶瓷等。
上述式中的所有符号均具有彼此独立的含义。在所有式中,硅原子均为四价。
具体实施方式
在以下实施例中,除非另有说明,所有含量和百分比数据均是基于重量。
实施例1
用具有亚甲基甲基二甲氧基甲硅烷基端基(α-二甲氧基)的硅烷封端的聚醚进行配制
将以GENIOSIL STP-E10的商品名购自Wacker Chemie AG的125克硅烷封端的聚醚与75克邻苯二甲酸二异癸酯(Merck公司)和10克商品名为GENIOSIL XL10(Wacker Chemie AG)的乙烯基三甲氧基硅烷以200rpm在约25℃下在PC-Laborsystem公司的装配有两个交叉臂混合器的实验室用行星式混合器中混合2分钟。然后搅入10克亲水性二氧化硅HDK V15(Wacker Chemie AG),直至均匀分散。随后引入252克白垩BLR3(Omya公司),并在搅拌的情况下以600rpm将填料破碎1分钟。在引入白垩之后,将5克缩水甘油基氧基丙基三甲氧基硅烷(GENIOSIL GF80-Wacker Chemie AG)以200rpm分散1分钟。最后,将5克氨基丙基三甲氧基硅烷(GENIOSIL GF96-Wacker ChemieAG)以200rpm分散1分钟,以600rpm均匀化2分钟,并以200rpm在部分真空下(约为100mbar)均匀化1分钟,并搅拌以除去气泡。
将该配制品分装在310ml的PE筒中,并在25℃下储存1天。
类似地实施比较例1b和1c。在表1中给出结果。
表1
根据DIN53504和DIN53505硫化
模量S1以N/mm2计 | 2.15 | 0.89 | 0.56 |
肖氏A | 62 | 48 | 32 |
断裂伸长率S1以%计 | 107 | 289 | 268 |
断裂强度S1以N/mm2计 | 2.2 | 1.1 | 0.8 |
回复性(ISO7389;在室温下4周后) | 50% | 20% | 26% |
*非本发明
测定机械性能
根据DIN53504(拉伸试验)和DIN53505(肖氏A硬度)测定机械性能。在将H试样在23℃和50的相对湿度下预先储存4周后根据ISO7389测定回复性。用伸长25%的试样测定回复性。
比较例1b和1c表明填料没有明显的影响。
实施例2
用具有亚丙基三甲氧基甲硅烷基端基(γ-三甲氧基)的硅烷封端的聚醚进行配制
制备配制品,并测试根据本发明的实施例2a-c以及与实施例1类似地实施的非本发明的实施例2d-e的机械性能。
表2给出了数值:
表2
根据DIN53504和DIN53505硫化
S1模量以N/mm2计 | 0.58 | 0.70 | 0.43 | 0.29 | 0.33 |
肖氏A硬度 | 27 | 33 | 23 | 20 | 20 |
S1断裂伸长率以%计 | 296 | 254 | 192 | 759 | 382 |
S1极限拉伸强度以N/mm2计 | 1.4 | 1.4 | 0.8 | 1.6 | 1.2 |
回弹性(ISO7389;室温下4周后) | 95% | 96% | 94% | 53% | 77% |
*非本发明
Claims (6)
1.用于改善已交联的聚合物混合物(P)的回弹性的方法,其中,使用
A)具有至少一个通式(1)的端基的烷氧基硅烷封端的聚合物(A)
-A-(CH2)m-SiR1 a(OR2)3-a (1),
其中,
A代表选自-O-、-S-、-(R3)N-、-O-CO-N(R3)-、-N(R3)-CO-O-、-N(R3)-CO-NH-、-NH-CO-N(R3)-、-N(R3)-CO-N(R3)-的二价连接基团,
R1代表未经取代或被卤素取代的具有1至10个碳原子的烷基、环烷基、烯基或芳基,
R2代表具有1至6个碳原子的烷基,
R3代表氢、未经取代或被卤素取代的环状、直链或分支的C1-C18烷基或烯基或C6-C18芳基,
a为0至2的整数,及
m为1至6的整数,
并与
B)氨基烷基烷氧基硅烷(B)和
C)环氧基烷基烷氧基硅烷(C)
混合,
其中所述聚合物(A)是通过通式(3)的硅烷与聚酯多元醇或聚醚多元醇的反应获得的
OCN-(CH2)m-SiR1 a(OR2)3-a (3),
其中,
R1、R2、R3和a具有上述的含义,及
m等于1或3。
2.根据权利要求1的方法,其中所述烷氧基硅烷封端的聚合物(A)的主链是由选自以下组中的聚合物构成的:聚硅氧烷、聚硅氧烷脲/氨基甲酸酯共聚物、聚氨酯、聚脲、聚醚、聚酯、聚丙烯酸酯、聚甲基丙烯酸酯、聚碳酸酯、聚苯乙烯、聚酰胺、聚乙烯基酯、聚丁二烯、乙烯-烯烃共聚物或苯乙烯-丁二烯共聚物。
3.根据权利要求1或2的方法,其中R2代表具有1至3个碳原子的烷基。
4.根据权利要求1或2的方法,其中m等于1。
5.根据权利要求1或2的方法,其中制备单组份硬化的聚合物混合物(P)。
6.根据权利要求5的方法,其中首先添加硅烷(C),然后添加硅烷(B)。
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DE102006022834A1 (de) | 2007-11-22 |
KR101032379B1 (ko) | 2011-05-03 |
WO2007131986A3 (de) | 2008-04-17 |
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JP2009537646A (ja) | 2009-10-29 |
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