CN103068872B - 不含锡的甲硅烷基-封端的聚合物 - Google Patents
不含锡的甲硅烷基-封端的聚合物 Download PDFInfo
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- CN103068872B CN103068872B CN201180041331.4A CN201180041331A CN103068872B CN 103068872 B CN103068872 B CN 103068872B CN 201180041331 A CN201180041331 A CN 201180041331A CN 103068872 B CN103068872 B CN 103068872B
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- Prior art keywords
- polymkeric substance
- hydrosilylation
- per molecule
- silane
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- 229920000642 polymer Polymers 0.000 title claims abstract description 27
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 title description 3
- 238000006459 hydrosilylation reaction Methods 0.000 claims abstract description 60
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 38
- 239000012948 isocyanate Substances 0.000 claims abstract description 28
- 150000001875 compounds Chemical class 0.000 claims abstract description 26
- 239000000203 mixture Substances 0.000 claims abstract description 25
- 150000002513 isocyanates Chemical class 0.000 claims abstract description 24
- 238000000034 method Methods 0.000 claims abstract description 22
- 239000003054 catalyst Substances 0.000 claims abstract description 21
- 229910052710 silicon Inorganic materials 0.000 claims abstract description 11
- 239000010703 silicon Substances 0.000 claims abstract description 11
- 229920005862 polyol Polymers 0.000 claims abstract description 8
- 150000003077 polyols Chemical class 0.000 claims abstract description 8
- 239000000126 substance Substances 0.000 claims description 79
- -1 boron trifluoride amine Chemical class 0.000 claims description 27
- 238000006243 chemical reaction Methods 0.000 claims description 26
- 239000012675 alcoholic extract Substances 0.000 claims description 21
- 239000002253 acid Substances 0.000 claims description 13
- 239000003795 chemical substances by application Substances 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 9
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Substances FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims description 7
- 239000012974 tin catalyst Substances 0.000 claims description 7
- PKTOVQRKCNPVKY-UHFFFAOYSA-N dimethoxy(methyl)silicon Chemical compound CO[Si](C)OC PKTOVQRKCNPVKY-UHFFFAOYSA-N 0.000 claims description 6
- 238000007711 solidification Methods 0.000 claims description 6
- 230000008023 solidification Effects 0.000 claims description 6
- 229910015900 BF3 Inorganic materials 0.000 claims description 5
- 150000003512 tertiary amines Chemical class 0.000 claims description 4
- CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 0.000 claims description 4
- BQKZEKVKJUIRGH-UHFFFAOYSA-N 2-prop-2-enoxypropan-1-ol Chemical compound OCC(C)OCC=C BQKZEKVKJUIRGH-UHFFFAOYSA-N 0.000 claims description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 3
- GAURFLBIDLSLQU-UHFFFAOYSA-N diethoxy(methyl)silicon Chemical compound CCO[Si](C)OCC GAURFLBIDLSLQU-UHFFFAOYSA-N 0.000 claims description 3
- 239000010936 titanium Substances 0.000 claims description 3
- 229910052719 titanium Inorganic materials 0.000 claims description 3
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 claims description 3
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 claims description 3
- AQVASTXXOZSXRI-UHFFFAOYSA-N [methoxy(methyl)silyl]oxy-trimethylsilane Chemical compound CO[SiH](C)O[Si](C)(C)C AQVASTXXOZSXRI-UHFFFAOYSA-N 0.000 claims description 2
- HGWMRAZZDPSNBU-UHFFFAOYSA-N diethoxysilyloxy(trimethyl)silane Chemical compound CCO[SiH](OCC)O[Si](C)(C)C HGWMRAZZDPSNBU-UHFFFAOYSA-N 0.000 claims description 2
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims 3
- 125000002524 organometallic group Chemical group 0.000 claims 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 abstract description 24
- 230000001476 alcoholic effect Effects 0.000 abstract description 2
- 239000003707 silyl modified polymer Substances 0.000 abstract 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 15
- 229920000570 polyether Polymers 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 125000001261 isocyanato group Chemical group *N=C=O 0.000 description 10
- 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 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 238000007789 sealing Methods 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 230000008878 coupling Effects 0.000 description 6
- 238000010168 coupling process Methods 0.000 description 6
- 238000005859 coupling reaction Methods 0.000 description 6
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 5
- 239000004721 Polyphenylene oxide Substances 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000003999 initiator Substances 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 4
- HUCVOHYBFXVBRW-UHFFFAOYSA-M caesium hydroxide Chemical compound [OH-].[Cs+] HUCVOHYBFXVBRW-UHFFFAOYSA-M 0.000 description 4
- 150000001721 carbon Chemical group 0.000 description 4
- 238000009833 condensation Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- LIKFHECYJZWXFJ-UHFFFAOYSA-N dimethyldichlorosilane Chemical compound C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 229910000077 silane Inorganic materials 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 3
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 3
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 3
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 3
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Natural products CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 3
- 235000013495 cobalt Nutrition 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000001723 curing Methods 0.000 description 3
- 238000005227 gel permeation chromatography Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- UIUXUFNYAYAMOE-UHFFFAOYSA-N methylsilane Chemical compound [SiH3]C UIUXUFNYAYAMOE-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- GLDOVTGHNKAZLK-UHFFFAOYSA-N n-octadecyl alcohol Natural products CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 3
- 239000005056 polyisocyanate Substances 0.000 description 3
- 229920001228 polyisocyanate Polymers 0.000 description 3
- 238000010926 purge Methods 0.000 description 3
- 150000004756 silanes Chemical class 0.000 description 3
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- XWJBRBSPAODJER-UHFFFAOYSA-N 1,7-octadiene Chemical compound C=CCCCCC=C XWJBRBSPAODJER-UHFFFAOYSA-N 0.000 description 2
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 2
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical group CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- 239000004902 Softening Agent Substances 0.000 description 2
- NSOXQYCFHDMMGV-UHFFFAOYSA-N Tetrakis(2-hydroxypropyl)ethylenediamine Chemical compound CC(O)CN(CC(C)O)CCN(CC(C)O)CC(C)O NSOXQYCFHDMMGV-UHFFFAOYSA-N 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 125000004423 acyloxy group Chemical group 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-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 class 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- NLDGJRWPPOSWLC-UHFFFAOYSA-N deca-1,9-diene Chemical compound C=CCCCCCCC=C NLDGJRWPPOSWLC-UHFFFAOYSA-N 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethylcyclohexane Chemical compound CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N perisophthalic acid Natural products OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 230000002028 premature Effects 0.000 description 2
- 238000007348 radical reaction Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000012858 resilient material Substances 0.000 description 2
- 239000010948 rhodium Substances 0.000 description 2
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- VOZKAJLKRJDJLL-UHFFFAOYSA-N tolylenediamine group Chemical group CC1=C(C=C(C=C1)N)N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 2
- ZDHXKXAHOVTTAH-UHFFFAOYSA-N trichlorosilane Chemical compound Cl[SiH](Cl)Cl ZDHXKXAHOVTTAH-UHFFFAOYSA-N 0.000 description 2
- 239000005052 trichlorosilane Substances 0.000 description 2
- 229960004418 trolamine Drugs 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- MEIRRNXMZYDVDW-MQQKCMAXSA-N (2E,4E)-2,4-hexadien-1-ol Chemical compound C\C=C\C=C\CO MEIRRNXMZYDVDW-MQQKCMAXSA-N 0.000 description 1
- WOGVOIWHWZWYOZ-UHFFFAOYSA-N 1,1-diisocyanatoethane Chemical compound O=C=NC(C)N=C=O WOGVOIWHWZWYOZ-UHFFFAOYSA-N 0.000 description 1
- ZWVMLYRJXORSEP-UHFFFAOYSA-N 1,2,6-Hexanetriol Chemical compound OCCCCC(O)CO ZWVMLYRJXORSEP-UHFFFAOYSA-N 0.000 description 1
- PFUKECZPRROVOD-UHFFFAOYSA-N 1,3,5-triisocyanato-2-methylbenzene Chemical compound CC1=C(N=C=O)C=C(N=C=O)C=C1N=C=O PFUKECZPRROVOD-UHFFFAOYSA-N 0.000 description 1
- PRBHEGAFLDMLAL-UHFFFAOYSA-N 1,5-Hexadiene Natural products CC=CCC=C PRBHEGAFLDMLAL-UHFFFAOYSA-N 0.000 description 1
- VYXHVRARDIDEHS-UHFFFAOYSA-N 1,5-cyclooctadiene Chemical compound C1CC=CCCC=C1 VYXHVRARDIDEHS-UHFFFAOYSA-N 0.000 description 1
- 239000004912 1,5-cyclooctadiene Substances 0.000 description 1
- 229940008841 1,6-hexamethylene diisocyanate Drugs 0.000 description 1
- NPDIDUXTRAITDE-UHFFFAOYSA-N 1-methyl-3-phenylbenzene Chemical group CC1=CC=CC(C=2C=CC=CC=2)=C1 NPDIDUXTRAITDE-UHFFFAOYSA-N 0.000 description 1
- BWDHJINUKACSDS-UHFFFAOYSA-N 2,3-bis(prop-2-enoxy)propan-1-ol Chemical compound C=CCOC(CO)COCC=C BWDHJINUKACSDS-UHFFFAOYSA-N 0.000 description 1
- JECYNCQXXKQDJN-UHFFFAOYSA-N 2-(2-methylhexan-2-yloxymethyl)oxirane Chemical compound CCCCC(C)(C)OCC1CO1 JECYNCQXXKQDJN-UHFFFAOYSA-N 0.000 description 1
- LQZDDWKUQKQXGC-UHFFFAOYSA-N 2-(2-methylprop-2-enoxymethyl)oxirane Chemical compound CC(=C)COCC1CO1 LQZDDWKUQKQXGC-UHFFFAOYSA-N 0.000 description 1
- LSWYGACWGAICNM-UHFFFAOYSA-N 2-(prop-2-enoxymethyl)oxirane Chemical compound C=CCOCC1CO1 LSWYGACWGAICNM-UHFFFAOYSA-N 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- MVODTGURFNTEKX-UHFFFAOYSA-N 2-bromo-n-(2-bromoethyl)-n-(thiophen-2-ylmethyl)ethanamine;hydrobromide Chemical compound Br.BrCCN(CCBr)CC1=CC=CS1 MVODTGURFNTEKX-UHFFFAOYSA-N 0.000 description 1
- LRWZZZWJMFNZIK-UHFFFAOYSA-N 2-chloro-3-methyloxirane Chemical compound CC1OC1Cl LRWZZZWJMFNZIK-UHFFFAOYSA-N 0.000 description 1
- LZDXRPVSAKWYDH-UHFFFAOYSA-N 2-ethyl-2-(prop-2-enoxymethyl)propane-1,3-diol Chemical compound CCC(CO)(CO)COCC=C LZDXRPVSAKWYDH-UHFFFAOYSA-N 0.000 description 1
- KLUXGDBEWOUCRD-UHFFFAOYSA-N 2-oxopropanoic acid titanium Chemical compound [Ti].C(C(=O)C)(=O)O KLUXGDBEWOUCRD-UHFFFAOYSA-N 0.000 description 1
- KWSSKCHDFPPOQV-UHFFFAOYSA-N 2-oxopropanoic acid zirconium Chemical compound [Zr].C(C(=O)C)(=O)O KWSSKCHDFPPOQV-UHFFFAOYSA-N 0.000 description 1
- NRRZGBVXJLJFJM-UHFFFAOYSA-N 3,3-diacetyl-2,4-dioxopentanoic acid Chemical compound CC(=O)C(C(C)=O)(C(C)=O)C(=O)C(O)=O NRRZGBVXJLJFJM-UHFFFAOYSA-N 0.000 description 1
- KTFYQKDYKVOCQV-UHFFFAOYSA-N 3,3-diethyl-2-oxopentanoic acid Chemical compound CCC(CC)(CC)C(=O)C(O)=O KTFYQKDYKVOCQV-UHFFFAOYSA-N 0.000 description 1
- HQNOODJDSFSURF-UHFFFAOYSA-N 3-(1h-imidazol-2-yl)propan-1-amine Chemical class NCCCC1=NC=CN1 HQNOODJDSFSURF-UHFFFAOYSA-N 0.000 description 1
- BTQLWKNIJDKIAB-UHFFFAOYSA-N 6-methylidene-n-phenylcyclohexa-2,4-dien-1-amine Chemical compound C=C1C=CC=CC1NC1=CC=CC=C1 BTQLWKNIJDKIAB-UHFFFAOYSA-N 0.000 description 1
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- HVNOCTHQMBXKRR-UHFFFAOYSA-N C[SiH](Cl)O[Si](C)(C)C Chemical compound C[SiH](Cl)O[Si](C)(C)C HVNOCTHQMBXKRR-UHFFFAOYSA-N 0.000 description 1
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- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
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- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
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- IXSPLXSQNNZJJU-UHFFFAOYSA-N trimethyl(silyloxy)silane Chemical class C[Si](C)(C)O[SiH3] IXSPLXSQNNZJJU-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G18/222—Catalysts containing metal compounds metal compounds not provided for in groups C08G18/225 - C08G18/26
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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
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G18/18—Catalysts containing secondary or tertiary amines or salts thereof
- C08G18/20—Heterocyclic amines; Salts thereof
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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
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- C08G18/288—Compounds containing at least one heteroatom other than oxygen or nitrogen
- C08G18/289—Compounds containing at least one heteroatom other than oxygen or nitrogen containing silicon
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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
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- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
- C08G18/3893—Low-molecular-weight compounds having heteroatoms other than oxygen containing silicon
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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
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- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4825—Polyethers containing two hydroxy 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
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- C08G18/71—Monoisocyanates or monoisothiocyanates
- C08G18/718—Monoisocyanates or monoisothiocyanates containing silicon
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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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
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- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
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- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7614—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring
- C08G18/7621—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring being toluene diisocyanate including isomer mixtures
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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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
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- C08G18/72—Polyisocyanates or polyisothiocyanates
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- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
- C08G18/7664—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups
- C08G18/7671—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups containing only one alkylene bisphenyl group
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/83—Chemically modified polymers
- C08G18/837—Chemically modified polymers by silicon containing compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Polyurethanes Or Polyureas (AREA)
- Polyethers (AREA)
- Paints Or Removers (AREA)
- Structures Or Materials For Encapsulating Or Coating Semiconductor Devices Or Solid State Devices (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
- Sealing Material Composition (AREA)
Abstract
本发明的实施方案提供制备包含每分子具有至少一个可交联的甲硅烷基的可交联的硅烷-封端的聚合物的组合物的方法。该方法包括提供每分子具有至少一个不饱和基团和至少一个醇羟基的聚合物,向该聚合物添加每分子具有氢-硅键和可交联的甲硅烷基的化合物和氢化硅烷化催化剂,从而进行氢化硅烷化反应以形成包含氢化硅烷化的聚氧化烯聚合物的组合物,在第一不含锡的催化剂的存在下将氢化硅烷化的聚氧化烯聚合物与至少一异氰酸酯反应以形成异氰酸酯反应的氢化硅烷化的聚合物,且任选将异氰酸酯反应的氢化硅烷化的聚合物与标称官能度至少为2的多元醇反应以形成多元醇反应的可交联的硅烷-封端的聚合物。
Description
相关申请的交叉引用
本申请要求2010年6月30日提交的美国临时专利申请No.61/360,199的利益,其在此完全引入作为参考。
技术领域
本发明的实施方案涉及甲硅烷基修饰的聚合物和其制备方法。
背景技术
含可交联的甲硅烷基的聚氧化烯聚合物广泛用作建筑或工业用途的密封材料、粘合剂、涂层材料等的原料聚合物。该含可交联的甲硅烷基的聚氧化烯聚合物可根据各种方法制备,如乙烯基封端的聚醚的氢化硅烷化,与异氰酸酯封端的预聚物的氨基硅烷反应,或与羟基-封端的预聚物的异氰酸基硅烷反应。然而,许多这些方法依赖于使用在环境监视下的锡基催化剂。
因此需要在不使用锡催化剂的情况下制备和可固化的含可交联的甲硅烷基的聚合物。
发明内容
本发明的实施方案提供形成含可交联的甲硅烷基的聚合物的方法,该聚合物在不使用锡催化剂的情况下制备和可固化。
在本发明一个实施方案中,提供制备包含每分子具有至少一个可交联的甲硅烷基的可交联的硅烷-封端的聚合物的组合物的方法。该方法包括提供每分子具有至少一个不饱和基团和至少一个醇羟基且数均分子量为约100至约10000的聚合物,向该聚合物添加每分子具有氢-硅键和可交联的甲硅烷基的化合物和氢化硅烷化催化剂,从而进行氢化硅烷化反应以形成包含氢化硅烷化的聚氧化烯聚合物的组合物,其中该氢化硅烷化反应具有的氢化硅烷化效率至少为约70%,其通过1H-NMR测定,以约80至约250的异氰酸酯指数和在第一不含锡的催化剂的存在下将该氢化硅烷化的聚氧化烯聚合物与至少一种异氰酸酯反应以形成异氰酸酯反应的氢化硅烷化的聚合物,且任选将异氰酸酯反应的氢化硅烷化的聚合物与标称官能度至少为2的多元醇反应以形成多元醇反应的可交联的硅烷-封端的聚合物。
该方法可进一步包括在第二不含锡的催化剂的存在下将异氰酸酯反应的氢化硅烷化的聚合物和多元醇反应的可交联的硅烷-封端的聚合物的至少之一固化。
本发明的实施方案的描述
本发明的实施方案提供在不使用锡催化剂的情况下制备和可固化的可交联的甲硅烷基-封端的聚合物(STP)。在本发明一个实施方案中,STP可通过将每分子具有至少一个不饱和基团和至少一个醇羟基的聚合物氢化硅烷化而获得。该氢化硅烷化的聚合物然后可暴露于至少一种异氰酸酯。如果使用低异氰酸酯指数,发生偶联反应,使得所有或大多数NCO基团与每分子具有至少一个不饱和基团和至少一个醇羟基的聚合物的醇羟基偶联。如果使用高异氰酸酯指数,形成NCO封端的预聚物,或NCO封端的聚合物。偶联的聚合物和封端的聚合物都可被湿固化,然而该封端的聚合物可任选与多元醇偶联以用可交联的甲硅烷基终止多元醇。
具有至少一个不饱和基团和至少一个醇羟基的聚合物没有具体限制,且可包括任何聚合物只要它们包括至少一个不饱和基团(如碳-碳双键或碳-碳三键)和至少一个醇羟基。
每分子具有至少一个不饱和基团和至少一个醇羟基的聚合物可具有的数均分子量为约100至约10000。100至10000中所有单独的值和子范围在此包含且在此公开;例如,该数均分子量可从下限100,200,300,400,500,600,700,800,900,1000,1250,1500,1750,2000,2500,3000,4000,5000,6000,或7000独立地至上限1000,1250,1500,1750,2000,2500,3000,3500,4000,4500,或5000,6000,7000,8000,9000,或10000。
在一些实施方案中,其中随后的异氰酸酯指数较低(即为100或低于100),每分子具有至少一个不饱和基团和至少一个醇羟基的聚合物可具有的数均分子量为约4000至约10000。在其它实施方案中,其中随后的异氰酸酯指数较高(即高于100),每分子具有至少一个不饱和基团和至少一个醇羟基的聚合物可具有的数均分子量为约100至约5000。
在一个实施方案中,每分子具有至少一个不饱和基团和至少一个醇羟基的聚合物可为同时待审的美国临时专利申请No.61/348996所述的聚氧化烯聚合物,其于2010年5月27日提交,且名称为“Methods for ProducingCrosslinkable Silyl Group-Containing Polyoxyalkylene Polymers”,其以其整体在此引入作为参考。
在一个实施方案中,每分子具有至少一个不饱和基团和至少一个醇羟基的聚合物可通过使用含不饱和基团和活性氢的化合物作为聚合引发剂在催化剂的存在下将环氧化合物进行开环聚合而制备。用于该聚合的催化可为阴离子型或阳离子型,且催化剂为例如KOH,CsOH,三氟化硼,或双氰化络合物(DMC)催化剂如六氰基钴酸锌或季膦腈鎓化合物。可用作聚合引发剂的含活性氢的化合物没有限制,但可为适于与双金属氰化物络合物联合的任何化合物,例如,包括醇羟基、酚羟基或羧基的化合物。
该含醇羟基的化合物可包括烯丙醇,甲代烯丙醇,三羟甲基丙烷单烯丙基醚,三羟甲基丙烷二烯丙基醚,甘油单烯丙基醚,甘油二烯丙基醚;其环氧乙烷加合物或环氧丙烷加合物和类似的每分子包含至少一个不饱和基团和至少一个醇羟基的化合物;羟基-封端的烃化合物如羟基-封端的聚丁二烯;等。作为聚合引发剂的该含活性氢的化合物可单独使用,或其多个可组合使用。
可用于开环聚合的单环氧化物可尤其包括,不具有不饱和基团的单环氧化物,如环氧乙烷,环氧丙烷,环氧丁烷,异环氧丁烷,环氧氯丙烷和氧化苯乙烯;和含不饱和基团的单环氧化物如烯丙基缩水甘油醚,甲代烯丙基缩水甘油醚,丙烯酸缩水甘油酯,甲基丙烯酸缩水甘油酯,丁二烯一氧化物和环戊二烯一氧化物。这些可单独使用,或其多个可组合使用。
在一个实施方案中,每分子具有至少一个不饱和基团和至少一个醇羟基的聚合物可为丙二醇单烯丙基醚,其具有的数均分子量为约600至约100,且羟值为约50至约90。
每分子具有至少一个不饱和基团和至少一个醇羟基的聚合物可通过在氢化硅烷化催化剂的存在下将该聚合物与具有氢-硅键和可交联的甲硅烷基的化合物反应而氢化硅烷化。
每分子具有氢-硅键和可交联的甲硅烷基的化合物可通过以下所示的通式(I)表示:
H-(Si(R1 2-b)(Xb)OmSi(R2 3-a)Xa (I)
其中R1和R2相同或不同且各自表示含1至20个碳原子的烷基,含6至20个碳原子的芳基或包含7至20个碳原子的芳烷基或R3 3SiO–表示的三有机基甲硅烷氧基,当存在多个R1或R2基团时,它们可相同或不同;R3为包含1至20个碳原子的一价烃基且该三个R3基团可彼此相同或不同;X表示羟基或可水解的基团,且当存在两个或更多个X基团时,它们可彼此相同或不同;a表示0,1,2或3且b表示0,1或2;在–SiR1 2-b)(Xb)O–基团中的b可彼此相同或不同;且m表示0至19的整数条件是应满足a+Σb≥1的关系。
X表示的可水解的基团可为本领域已知的任何可水解的基团,例如卤素原子和烷氧基,酰基氧基,酮肟基,氨基,酰胺基,酰胺,氨基氧基,疏基和链烯基氧基。其中,优选烷氧基如甲氧基,乙氧基,丙氧基和异丙氧基,取决于它们适度的水解性和易处理性。1至3个这种可水解的基团可连接至1个硅原子,且(a+Σb)之和优选为1至5。当存在两个或更多个可水解的基团时,它们可彼此相同或不同。可交联的甲硅烷基中的硅原子数可为约1至30。
在一些实施方案中,以上通式(I)表示的每分子具有氢-硅键和可交联的甲硅烷基的化合物可包括通式(II)表示的化合物:
H-Si(R4 3-c)(Xc)
其中R4表示含1至20个碳原子的烷基,含6至20个碳原子的芳基或包含7至20个碳原子的芳烷基或R3 3SiO–表示的三有机甲硅烷氧基,且当存在多个R4基团时,它们可相同或不同;R3为包含1至20个碳原子的一价烃基且该三个R3基团可彼此相同或不同;X表示羟基或可水解的基团,且当存在两个或更多个X基团时,它们可彼此相同或不同;且c表示1,2或3。
作为每分子具有氢-硅键和可交联的甲硅烷基的化合物的具体实例,可提及卤代硅烷如三氯硅烷,甲基二氯硅烷,二甲基氯硅烷,苯基二氯硅烷,三甲基甲硅烷氧基甲基氯硅烷和1,1,3,3-四甲基-1-溴二硅氧烷;烷氧基硅烷如三甲氧基硅烷,三乙氧基硅烷,甲基二乙氧基硅烷,甲基二甲氧基硅烷,苯基二甲氧基硅烷,三甲基甲硅烷氧基甲基甲氧基硅烷和三甲基甲硅烷氧基二乙氧基硅烷;酰基氧基硅烷如甲基二乙酰氧基硅烷,苯基二乙酰氧基硅烷,三乙酰氧基硅烷,三甲基甲硅烷氧基甲基乙酰氧基硅烷和三甲基甲硅烷氧基二乙酰氧基硅烷;酮肟基硅烷如二(二甲基酮肟基)甲基硅烷,二(环己基酮肟基)甲基硅烷,二(二乙基酮肟基)三甲基甲硅烷氧基硅烷,二(甲基乙基酮肟基)甲基硅烷和三(丙酮肟基)硅烷;链烯基氧基硅烷如甲基异丙烯基氧基硅烷;等。从适度反应性和易于处理的观点来看,优选的为烷氧基硅烷如甲基二甲氧基硅烷,三甲氧基硅烷,甲基二乙氧基硅烷和三乙氧基硅烷;和卤代硅烷如三氯硅烷和甲基二氯硅烷。
在以氢化硅烷化的方式与不饱和基团反应后,卤代硅烷中的卤素原子可转化为一些其它可水解的基团,其通过本领域已知的合适方法与含活性氢的化合物如羧酸,肟,酰胺或羟胺或酮-衍生的碱金属烯醇化物反应而转化。
该氢化硅烷化催化剂可为其中金属选自第VIII族过渡金属如铂,铑,钴,钯和镍的那些金属络合物的任一种。根据氢化硅烷化反应性的观点,优选H2PtCl6.6H2O,铂-二乙烯基硅氧烷络合物,铂-烯烃络合物,Pt金属,RhCl(PPh3)3,RhCl3,Rh/Al2O3,RuCl3,IrCl3,FeCl3,AlCl3,PdCl2.2H2O,NiCl2,TiCl4等。该铂-乙烯基硅氧烷络合物统称为由含分子内乙烯基的硅氧烷、聚硅氧烷或环状硅氧烷(作为配体)与铂原子的配位得到的化合物。作为配体的典型实例,可提及1,1,3,3-四甲基-1,3-二乙烯基硅氧烷等。作为铂-烯烃络合物中烯烃配体的具体实例,可提及1,5-己二烯,1,7-辛二烯,1,9-癸二烯,1,11-十二碳二烯和1,5-环辛二烯。在以上具体所述的配体中,从氢化硅烷化反应性的观点看优选1,1,3,3-四甲基-1,3-二乙烯基硅氧烷和1,9-癸二烯。在本发明的实践中使用的氢化硅烷化催化剂可单独使用,或可使用多种物质的组合。
待使用的氢化硅烷化催化剂的量没有具体限制,但通常为0.00001至1重量份,优选0.00005至0.05重量份,更优选0.0001至0.01重量份,基于催化剂中金属的重量,每100重量份每分子具有至少一个不饱和基团和至少一个醇羟基的聚氧化烯聚合物。当所述量少于0.00001重量份,在一些情况下可能不能获得任何足够的反应活性,而超过1重量份的量在经济上可能是不利的或在一些情况下引起聚合物变色。
在上述反应中,溶剂的使用基本上是不需要的。然而,为均匀溶解催化剂和/或底物,为控制反应体系温度和/或促进底物和/或催化剂组分的添加,可使用溶剂。适合这些目的的溶剂尤其包括,但不限于,烃化合物如己烷,环己烷,乙基环己烷,庚烷,辛烷,十二烷,苯,甲苯,二甲苯和十二烷基苯;卤代烃化合物如氯仿,二氯甲烷,氯苯和邻二氯苯;和醚如乙醚,四氢呋喃和乙二醇二甲基醚。可用作聚氧化烯聚合物的增塑剂的那些增塑剂,如邻苯二甲酸酯和聚醚,也可用作反应溶剂。这些可单独使用,或其多个可组合使用。
该氢化硅烷化反应温度没有具体限制但可例如在0°C至150°C的范围,或20°C至100°C的范围。在低于0°C,在一些情况下反应速率可能低,而在高于150°C,涉及羟基、氢-硅键和/或可交联的甲硅烷基的副反应在一些情况下可能发生。在一个实施方案中,该氢化硅烷化反应温度为约60°C。
在本发明的实施方案中,每分子具有至少一个不饱和基团和至少一个醇羟基的聚合物以至少约70%,如约70%至约100%的氢化硅烷化效率进行氢化硅烷化。约70至约100中所有单独的值和子范围在此包含且在此公开;例如,该氢化硅烷化效率可从下限约70,75,80,90,或92%,独立地至上限约80,85,90,92,94,95,96,98,99,或100%。这包括氢化硅烷化效率为80至95%的氢化硅烷化的聚合物,且进一步包括氢化硅烷化效率为85至95%的封端的氢化硅烷化的聚合物。如本文所述,该“氢化硅烷化效率”=[100x((氢化硅烷化的多元醇上的不饱和基团数)/(最初可用于氢化硅烷化的多元醇上的不饱和基团总数)],且可使用1H-NMR测量。
通过上述方法制备的每分子具有至少一个可交联的甲硅烷基和至少一个羟基的氢化硅烷化的聚合物(下文称为“氢化硅烷化的聚合物”)可与水或大气水分反应以得到交联的固化产物,因此可用作密封,粘合剂,涂层的原料或原料中间体以及建筑或工业用途的类似材料或组合物。然而,该具有至少一个可交联的甲硅烷基和至少一个羟基的聚合物的高百分比的剩余羟基可用聚异氰酸酯化合物偶联或封端。
在本发明的实施方案的实践中可使用的偶联和封端剂中,该聚异氰酸酯化合物,即每分子具有两个或更多个异氰酸基的化合物,包括,但不限于,脂族,环脂族,芳基脂族和芳族异氰酸酯。
合适的芳族异氰酸酯的实例包括二苯基甲烷二异氰酸酯(MDI)的4,4'-,2,4'和2,2'-异构体,其混合物以及聚合的和单体MDI混合物,甲苯-2,4-和2,6-二异氰酸酯(TDI),间和对亚苯基二异氰酸酯,氯亚苯基-2,4-二异氰酸酯,二亚苯基-4,4'-二异氰酸酯,4,4'-二异氰酸酯-3,3'-二甲基二苯基,3-甲基二苯基-甲烷-4,4'-二异氰酸酯和二苯基醚二异氰酸酯和2,4,6-三异氰酸基甲苯和2,4,4'-三异氰酸基二苯基醚。
可使用异氰酸酯混合物,如可商购的甲苯二异氰酸酯的2,4-和2,6-异构体的混合物。在本发明的实施方案的实践中也可使用粗聚异氰酸酯,如通过光气化甲苯二胺的混合物得到的粗甲苯二异氰酸酯或通过光气化粗亚甲基二苯基胺得到的粗二苯基甲烷二异氰酸酯。也可使用TDI/MDI混合物。
脂族聚异氰酸酯的实例包括亚乙基二异氰酸酯,1,6-六亚甲基二异氰酸酯,异佛尔酮二异氰酸酯,环己烷1,4-二异氰酸酯,4,4'-二环己基甲烷二异氰酸酯,1,3-二(异氰酸基甲基)环己烷,1,4-二(异氰酸基甲基)环己烷,上述芳族异氰酸酯的饱和类似物,及其混合物。
该偶联反应可以100或更少,例如约80至约100,或约90至约100的异氰酸酯指数进行。在这些指数,异氰酸酯的两个NCO基团都与氢化硅烷化的聚合物的羟基反应,得到具有两个末端甲硅烷基的聚合物。该封端反应可以大于100至约250的异氰酸酯指数进行。大于100至低于250中所有单独的值和子范围在此包含且在此公开;例如,该异氰酸酯指数可从下限大于100,110,125,140,150,160,170,175,180,190,200,225,独立地至上限150,175,200,225,或250。在一些实施方案中该指数可为约160至约200,约140至约170,或约150至约180。在这些指数,至少一部分氢化硅烷化的聚合物将为NCO封端的预聚物(NCO封端的)。
如本文所述,该异氰酸酯指数为异氰酸酯-基团相对于制剂中存在的异氰酸酯-反应性氢原子的比例,以百分比给出。因此,该异氰酸酯指数表示制剂中实际使用的异氰酸酯相对与制剂中使用的异氰酸酯-反应性氢的量反应理论上需要的的异氰酸酯的量的百分比。
为增加反应速率或改善转化程度,可使用催化剂。该催化剂可为不含锡的催化剂,如辛酸锌,1,8-二氮杂-二环(5,4,0)十一碳烯-7(DBU),酸封闭的DBU,如例如丙烯酸封闭的DBU,钛催化剂如有机金属钛催化剂,或其组合。
该异氰酸酯封端的聚合物可与标称官能度至少为2的多元醇偶联以形成最终的甲硅烷基-封端的聚合物。可使用任何合适的多元醇。在一个实施方案中,使用聚醚多元醇。在某些实施方案中,使用标称官能度为约2至约4的聚醚多元醇。在一个实施方案中,该标称官能度为约2,且在另一实施方案中约3。在某些实施方案中,可使用聚醚多元醇。
聚醚多元醇可通过将环氧烷,如环氧乙烷,环氧丙烷,环氧丁烷或其组合,添加至具有2至8,优选2至4个活性氢原子的引发剂而制备。该聚合反应的催化可为阴离子的或阳离子的,使用催化剂如KOH,CsOH,三氟化硼,或双氰化络合物(DMC)催化剂如六氰基钴酸锌或季膦腈鎓(quaternary phosphazenium)化合物。该引发剂可选自新戊二醇;1,2-丙二醇;三羟甲基丙烷;季戊四醇;山梨醇;蔗糖;甘油;氨基醇如乙醇胺,二乙醇胺,和三乙醇胺;链烷烃二醇如1,6-己二醇,1,4-丁二醇;1,4-环己烷二醇;1,3-环己烷二甲醇,1,4-环己烷二甲醇,2,5-己二醇;乙二醇;二甘醇,三甘醇;双-3-氨基丙基甲基胺;乙二胺;二亚乙基三胺;9(1)-羟基甲基十八醇,1,4-二羟基甲基环己烷;8,8-二(羟基甲基)三环[5,2,1,02,6]癸烯;Dimerol醇(36个碳的二醇,可获自Henkel Corporation);氢化双酚;9,9(10,10)-二羟基甲基十八醇;1,2,6-己烷三醇及其组合。在一个实施方案中,该引发剂为1,3-环己烷二甲醇和1,4-环己烷二甲醇的混合物且可以商品名UNOXOL商购自The Dow Chemical Company,其为(顺,反)1,3-环己烷二甲醇和(顺,反)1,4-环己烷二甲醇的近似1:1混合物。其它引发剂包括其它包含胺的线性和环状化合物。示例性多胺引发剂包括乙二胺,新戊基二胺,1,6-二氨基己烷;二氨基甲基三环癸烷;二氨基环己烷;二亚乙基三胺;双-3-氨基丙基甲基胺;三亚乙基四胺,甲苯二胺的各种异构体;二苯基甲烷二胺;N-甲基-1,2-乙烷二胺,N-甲基-1,3-丙烷二胺,N,N-二甲基-1,3-二氨基丙烷,N,N-二甲基乙醇胺,3,3’-二氨基-N-甲基二丙基胺,N,N-二甲基二丙烯三胺,氨基丙基-咪唑。
异氰酸酯封端的聚合物与标称官能度至少为2的多元醇的偶联反应可通过适合上述封端反应的相同类型的催化剂催化。或者,封端反应中使用的催化剂可被推进并在偶联反应中使用。
所得甲硅烷基-封端的聚合物可具有低于约50Pa.s的粘度,如低于45,40,35,30,25,20,15,10,或8Pa.s。
根据本发明的实施方案,所得甲硅烷基-封端的聚合物(由NCO封端反应或NCO偶联反应测试)可尤其用于彼此反应以进一步增长分子链以用于如密封剂、粘合剂和涂层,及其组合。当甲硅烷基聚合物暴露于水分(例如,大气中的水分)时,连接至硅原子的可水解的基团水解,被硅键键合的羟基代替。该羟基又彼此反应或与其它可水解的基团反应以形成硅氧烷(Si-O-Si)连接。通过该方法,本发明实施方案的组合物的聚合物分子连接在一起以形成难熔的弹性材料。为避免过早固化,本发明实施方案的组合物可储存且保持于无水分环境中直到需要固化。然后,当需要固化时,可将聚合物暴露于大气水分或其它水分。
根据本发明的实施方案,所得甲硅烷基-封端的聚合物可尤其用于彼此反应以进一步增长分子链以用于如密封剂、粘合剂和涂层,及其组合。当甲硅烷基聚合物暴露于水分(例如,大气中的水分)时,连接至硅原子的可水解的基团水解,被硅键键合的羟基代替。该羟基又彼此反应或与其它可水解的基团反应以形成硅氧烷(Si-O-Si)连接。通过该方法,本发明实施方案的组合物的聚合物分子连接在一起以形成难熔的弹性材料。为避免过早固化,本发明实施方案的组合物可储存且保持于无水分环境中直到需要固化。然后,当需要固化时,可将聚合物暴露于大气水分或其它水分。
所得甲硅烷基-封端的聚合物是储存稳定的。即,如果储存在无水分环境,该甲硅烷基-封端的聚合物在储存很多天,如例如40天之后将显示基本上相同粘度特性,如同其在储存之前显示的特性。该甲硅烷基-封端的聚合物即使在固化催化剂(如以下描述的那些)的存在下储存也可显示该储存稳定性。
甲硅烷基-封端的聚合物的固反应化可通过使用不含锡的硅烷醇缩合催化剂或固化加速剂促进。硅烷醇缩合催化剂或加速剂包括以下:钛酸酯,如四丁基钛酸酯,四丙基钛酸酯,等;有机铝化合物,如三乙酰基丙酮酸铝,三乙基丙酮酸铝,等;反应产物,如铋盐和有机羧酸的产物,如三(2-乙基己酸)铋,三(新硅酸)铋,等;螯合物,如四乙酰基丙酮酸锆,四乙酰基丙酮酸钛,等;胺化合物,如丁基胺,辛基胺,二丁基胺,单乙醇胺,二乙醇胺,三乙醇胺,二亚乙基三胺,环己基胺,苄基胺,等,或它们与羧酸的盐,等。其它缩合催化剂或固化加速剂包括十二烷基苯磺酸,酸封闭的叔胺(1,8-二氮杂二环[5.4.0]十一-7-烯)催化剂如获自TosohCorporation的TOYOCAT-DB30和TOYOCAT-DB41,和三氟化硼胺络合物如获自Air Products的ANCHOR-1040。这些硅烷醇缩合催化剂可单独或组合使用。该催化剂可存在的量为至少约0.1重量%的聚合物,至少约0.5重量%的聚合物,至少约1重量%的聚合物,至少约1.5重量%的聚合物,或至少约2重量%的聚合物和至多约8重量%的聚合物,至多约6重量%的聚合物,至多约5重量%的聚合物,至多约4重量%的聚合物,或至多约3.5%,基于聚合物的重量。该催化剂可通过本领域的手段在密封剂、涂层、或粘合剂的配制过程中与聚合物混合。
所得固化的甲硅烷基聚合物也为本发明的实施方案。类似的,本发明的实施方案包括密封剂,粘合剂,和涂层和其它包含这些聚合物或预聚物的最终用途。甲硅烷基聚合物的优选性质对于各最终用途可有些不同,适合各最终用途的组合物中任选存在的其它组分也有不同。
实施例
提供以下实施例以阐述本发明的实施方案,但不用来限制其范围。所有分数和百分比基于重量,除非另有所述。
使用以下材料:
烯丙基一元醇1 丙烯单烯丙基醚,数均分子量为约6238。
烯丙基一元醇2 丙二醇单烯丙基醚,其具有的烯丙基含量为3.5wt%(0.998mol不饱和/mol一元醇),数均分子量为约800,且羟值为70或2.1wt%OH。
ACCLAIM多元醇8200 基于环氧丙烷的长链双官能聚醚多元醇,其分子量为约8000且羟基数为14mg KOH/g,可获自Bayer MaterialScience。
Karstedt催化剂 铂-二乙烯基四甲基二硅氧烷和二甲苯作为载体溶剂,催化剂中的Pt含量为2wt%,可获自Gelest,Inc。
甲基二甲氧基硅烷 可获自Gelest,Inc。
ISONATE*50OP 50%4,4'-亚甲基二苯基异氰酸酯,50%2,4'-亚甲基二苯基异氰酸酯混合物,其具有的官能度为为2.0且当量为125g/当量,可获自The Dow Chemical Company。
VORANATE*T-80 甲苯二异氰酸酯(80%2,4-甲苯二异氰酸酯和20%2,6-甲苯二异氰酸酯,基于重量)组合物,可获自The Dow Chemical Company。
DABCO T-12 锡催化剂,可获自Air Products。
DBTA 二(乙酰基丙酮酸)二丁基锡,可获自Σ-Aldrich Co.
DBTDL 二月桂酸二丁基锡,可获自Aldrich。
SnAcAc 乙酰基丙酮酸锡(II),可获自Aldrich。
DBU 1,8-二氮杂二环[5.4.0]十一-7-烯,可获自Aldrich。
辛酸锌(Zn Octoate) 可获自Shepherd Chemical Corporation。
SNAPCURE3030 钛基催化剂,可获自Johnson Matthey plc。
TOYOCAT-DB30 丙烯酸封闭的叔胺(1,8-二氮杂二环[5.4.0]十一-7-烯)催化剂,其在30°C解封闭,可获自Tosoh Corporation。
TOYOCAT-DB41 酸封闭的叔胺(1,8-二氮杂二环[5.4.0]十一-7-烯)催化剂,其在60°C解封闭,可获自TosohCorporation。
DDBSA 十二烷基苯磺酸。可获自Aldrich。
ANCHOR-1040 三氟化硼胺络合物。可获自Air Products。
*ISONATE和VORANATE为The Dow Chemical Company的商标。
测试方法
抗拉强度根据ASTM标准测试D1708测量。断裂伸长根据ASTM标准测试D1708测量。100%正割模数根据ASTM标准测试D1708测量。数均分子量通过凝胶渗透色谱法使用PEG标准,根据ASTM标准测试D5296测定。粘度使用流变计AR2000通过TA仪器测量。约1mL样品分配至60mm直径60-度锥板式几何结构中。去除任何过量材料后,粘度测试通过将样品以3oC/min从20oC加热至100oC而进行。测试的剪切速率保持恒定在0.1s-1。
实施例E1-E3和对比例CE1-CE3:
氢化硅烷化反应通过将烯丙基一元醇1(300g)装进4-颈250mL预干燥的装配机械搅拌器的玻璃反应器而进行。然后将Karstedt催化剂(约0.03g)添加至反应器且在连续氮气清洗下混合2分钟。最后添加甲基二甲氧基硅烷(5.37g)且混合5分钟,然后将整个反应器加热至60°C保持2小时。该氢化硅烷化产物(下文称为氢化硅烷化的聚醚1)使用1H分析-显示氢化硅烷化效率为>82%。
NCO-偶联反应通过将氢化硅烷化的聚醚1和催化剂装进250mL4-颈预干燥的装配机械搅拌器的玻璃反应器且填补氮气而进行。连续氮气清洗随着将ISONATE50OP添加至反应器而开始。使NCO-封端反应在70°C以300rpm混合速度进行超过4小时。
所得氢化硅烷化的聚醚聚氨酯(下文称为HPPU)然后用于形成固化的膜,其以25Mil从聚丙烯板上拉下来。该膜然后在25°C和50%相对湿度固化两周。使用的组分的量和使用的催化剂的类型示于表1,以及HPPU(主要GPC分子量峰和25°C的粘度)和相应固化膜的物理性质(抗拉强度,断裂伸长,和正割模数)。该膜(实施例E1-E3和对比例CE2)然后浸在水中7天且抗拉强度、断裂伸长和正割模数在暴露于水的膜上测量。
表1
实施例E4-E10和对比例CE4和CE5:
氢化硅烷化反应通过将烯丙基一元醇2(343.20g)装进4-颈250mL预干燥的装配机械搅拌器的玻璃反应器而进行。然后将Karstedt催化剂(约0.03g)添加至反应器且在连续氮气清洗下混合2分钟。最后添加甲基二甲氧基硅烷(50.02g)且混合5分钟,然后将整个反应器加热至60°C保持2小时。该氢化硅烷化产物(下文称为氢化硅烷化的聚醚2)使用1H分析-显示氢化硅烷化效率>95%。
氢化硅烷化的聚醚2然后与过量的ISONATE50OP或VORANATET-80在辛酸锌催化剂的存在下在70°C且以300rpm混合速度反应5小时以分别制备MDI或TDI封端的氢化硅烷化的聚醚。该封端的氢化硅烷化的聚醚然后与ACCLAIM8200多元醇在70°C反应2小时。
所得氢化硅烷化的聚醚聚氨酯然后在25°C和50%相对湿度固化两周。使用的组分的量和使用的催化剂的类型示于表2中,以及HPPU(主要GPC分子量峰和25°C的粘度)和相应固化膜的物理性质(抗拉强度,断裂伸长,和正割模数)。
尽管以上描述涉及本发明的实施方案,但可设计出本发明的其它和进一步实施方案而不偏离其基本范围,其范围通过所附权利要求确定。
Claims (7)
1.制备包含每分子具有至少一个可交联的甲硅烷基的可交联的硅烷-末端的聚合物的组合物的方法,该方法包括:
提供每分子具有至少一个不饱和基团和至少一个醇羟基且数均分子量为100至10000的聚合物;
向该聚合物添加每分子具有氢-硅键和可交联的甲硅烷基的化合物和氢化硅烷化催化剂,从而进行氢化硅烷化反应以形成包含氢化硅烷化的聚氧化烯聚合物的组合物,其中该氢化硅烷化反应具有的氢化硅烷化效率至少为70%,其通过1H-NMR测定;
以80至250的异氰酸酯指数且在第一无锡化剂的存在下将氢化硅烷化的聚氧化烯聚合物与至少一异氰酸酯反应以形成异氰酸酯反应的氢化硅烷化的聚合物,该第一无锡催化剂包括辛酸锌,1,8-二氮杂-二环(5,4,0)十一碳烯-7,酸阻断的1,8-二氮杂-二环(5,4,0)十一碳烯-7,有机金属钛催化剂的至少一个,或其组合;和
任选将异氰酸酯反应的氢化硅烷化的聚合物与标称官能度至少为2的多元醇反应以形成多元醇反应的可交联的硅烷-末端的聚合物。
2.权利要求1所述的方法,进一步包括在第二无锡催化剂的存在下将异氰酸酯反应的氢化硅烷化的聚合物和多元醇反应的可交联的硅烷-末端的聚合物的至少之一固化。
3.权利要求1或2所述的方法,其中每分子具有至少一个不饱和基团和至少一个醇羟基的聚合物具有的数均分子量为4000至10000,且其中所述指数为80至100。
4.权利要求1或2所述的方法,其中每分子具有至少一个不饱和基团和至少一个醇羟基的聚合物具有的数均分子量为100至1000,且其中所述指数为160至200。
5.权利要求2所述的方法,其中该第二无锡催化剂包括十二烷基苯磺酸、酸阻断的叔胺(1,8-二氮杂二环[5.4.0]十一-7-烯)催化剂和三氟化硼胺络合物的至少一个,或其组合。
6.权利要求1或2所述的方法,其中具有氢-硅键和可交联的甲硅烷基的化合物包括三甲氧基硅烷,三乙氧基硅烷,甲基二乙氧基硅烷,甲基二甲氧基硅烷,苯基二甲氧基硅烷,三甲基甲硅烷氧基甲基甲氧基硅烷和三甲基甲硅烷氧基二乙氧基硅烷的至少一个。
7.权利要求1或2所述的方法,其中每分子具有至少一个不饱和基团和至少一个醇羟基的聚合物包括丙二醇单烯丙基醚,其具有的数均分子量为600至1000,且OH数为50至90。
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EP2952533A1 (de) * | 2014-06-04 | 2015-12-09 | Sika Technology AG | Zinn- und Phthalat-freier Dichtstoff auf Basis von silanterminierten Polymeren |
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CN106833481B (zh) * | 2017-02-06 | 2020-12-15 | 山东一诺威新材料有限公司 | 环保型有机硅改性聚醚密封胶及其制备方法 |
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CN109679556A (zh) * | 2018-12-20 | 2019-04-26 | 烟台德邦科技有限公司 | 一种环保型硅烷改性密封胶的制备方法 |
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PL2588510T3 (pl) | 2015-10-30 |
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EP2588510A1 (en) | 2013-05-08 |
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US20130096252A1 (en) | 2013-04-18 |
ES2538086T3 (es) | 2015-06-17 |
BR112012033615A2 (pt) | 2017-03-01 |
CN103068872A (zh) | 2013-04-24 |
BR112012033615B1 (pt) | 2020-11-03 |
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