WO2011069954A1 - Produits d'étanchéité - Google Patents
Produits d'étanchéité Download PDFInfo
- Publication number
- WO2011069954A1 WO2011069954A1 PCT/EP2010/068952 EP2010068952W WO2011069954A1 WO 2011069954 A1 WO2011069954 A1 WO 2011069954A1 EP 2010068952 W EP2010068952 W EP 2010068952W WO 2011069954 A1 WO2011069954 A1 WO 2011069954A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- alkoxysilane
- mixture
- modified polyurethanes
- mol
- several
- Prior art date
Links
- 239000000565 sealant Substances 0.000 title claims abstract description 17
- 239000000203 mixture Substances 0.000 claims description 24
- 229920002635 polyurethane Polymers 0.000 claims description 21
- 239000004814 polyurethane Substances 0.000 claims description 21
- 239000004014 plasticizer Substances 0.000 claims description 19
- 239000003054 catalyst Substances 0.000 claims description 15
- 229920000570 polyether Polymers 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 229920005862 polyol Polymers 0.000 claims description 10
- 150000003077 polyols Chemical class 0.000 claims description 10
- 239000000945 filler Substances 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 8
- 229920000642 polymer Polymers 0.000 claims description 5
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 3
- 229910008326 Si-Y Inorganic materials 0.000 claims description 2
- 229910006773 Si—Y Inorganic materials 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 238000004132 cross linking Methods 0.000 claims description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 2
- 239000012963 UV stabilizer Substances 0.000 claims 2
- 239000003381 stabilizer Substances 0.000 claims 2
- 239000011230 binding agent Substances 0.000 abstract description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 150000001412 amines Chemical class 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 6
- 239000012975 dibutyltin dilaurate Substances 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- FMGBDYLOANULLW-UHFFFAOYSA-N 3-isocyanatopropyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CCCN=C=O FMGBDYLOANULLW-UHFFFAOYSA-N 0.000 description 5
- -1 DMC compounds Chemical class 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical class [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 4
- FZQMJOOSLXFQSU-UHFFFAOYSA-N 3-[3,5-bis[3-(dimethylamino)propyl]-1,3,5-triazinan-1-yl]-n,n-dimethylpropan-1-amine Chemical compound CN(C)CCCN1CN(CCCN(C)C)CN(CCCN(C)C)C1 FZQMJOOSLXFQSU-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 229920001730 Moisture cure polyurethane Polymers 0.000 description 3
- 239000004721 Polyphenylene oxide Substances 0.000 description 3
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 3
- 239000002318 adhesion promoter Substances 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- 238000010276 construction Methods 0.000 description 3
- 239000002274 desiccant Substances 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 238000006068 polycondensation reaction Methods 0.000 description 3
- 229920001451 polypropylene glycol Polymers 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 229910000077 silane Inorganic materials 0.000 description 3
- 150000004756 silanes Chemical class 0.000 description 3
- 235000012239 silicon dioxide Nutrition 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 2
- 238000004566 IR spectroscopy Methods 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 238000004497 NIR spectroscopy Methods 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- AIXMJTYHQHQJLU-UHFFFAOYSA-N chembl210858 Chemical compound O1C(CC(=O)OC)CC(C=2C=CC(O)=CC=2)=N1 AIXMJTYHQHQJLU-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 150000002902 organometallic compounds Chemical class 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 230000001698 pyrogenic effect Effects 0.000 description 2
- 230000003014 reinforcing effect Effects 0.000 description 2
- 239000012763 reinforcing filler Substances 0.000 description 2
- 125000005624 silicic acid group Chemical class 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 239000013008 thixotropic agent Substances 0.000 description 2
- 239000012974 tin catalyst Substances 0.000 description 2
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
- SGUVLZREKBPKCE-UHFFFAOYSA-N 1,5-diazabicyclo[4.3.0]-non-5-ene Chemical compound C1CCN=C2CCCN21 SGUVLZREKBPKCE-UHFFFAOYSA-N 0.000 description 1
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 1
- RWLALWYNXFYRGW-UHFFFAOYSA-N 2-Ethyl-1,3-hexanediol Chemical compound CCCC(O)C(CC)CO RWLALWYNXFYRGW-UHFFFAOYSA-N 0.000 description 1
- NNTRMVRTACZZIO-UHFFFAOYSA-N 3-isocyanatopropyl-dimethoxy-methylsilane Chemical compound CO[Si](C)(OC)CCCN=C=O NNTRMVRTACZZIO-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- DOCTVZHOVSYBHN-UHFFFAOYSA-N C(C)(=O)OC.C(CCCCCCC)[Sn]CCCCCCCC Chemical compound C(C)(=O)OC.C(CCCCCCC)[Sn]CCCCCCCC DOCTVZHOVSYBHN-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- 102100035474 DNA polymerase kappa Human genes 0.000 description 1
- 101710108091 DNA polymerase kappa Proteins 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 150000001278 adipic acid derivatives Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000005370 alkoxysilyl group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 150000001409 amidines Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 238000005815 base catalysis Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000013256 coordination polymer Substances 0.000 description 1
- 238000001723 curing Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- AYOHIQLKSOJJQH-UHFFFAOYSA-N dibutyltin Chemical compound CCCC[Sn]CCCC AYOHIQLKSOJJQH-UHFFFAOYSA-N 0.000 description 1
- PJIFJEUHCQYNHO-UHFFFAOYSA-N diethoxy-(3-isocyanatopropyl)-methylsilane Chemical compound CCO[Si](C)(OCC)CCCN=C=O PJIFJEUHCQYNHO-UHFFFAOYSA-N 0.000 description 1
- OCNXBDSYTXVOIV-UHFFFAOYSA-N diethoxy-(isocyanatomethyl)-methylsilane Chemical compound CCO[Si](C)(OCC)CN=C=O OCNXBDSYTXVOIV-UHFFFAOYSA-N 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- HBGGXOJOCNVPFY-UHFFFAOYSA-N diisononyl phthalate Chemical compound CC(C)CCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCC(C)C HBGGXOJOCNVPFY-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- RSKGMYDENCAJEN-UHFFFAOYSA-N hexadecyl(trimethoxy)silane Chemical compound CCCCCCCCCCCCCCCC[Si](OC)(OC)OC RSKGMYDENCAJEN-UHFFFAOYSA-N 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- QRFPECUQGPJPMV-UHFFFAOYSA-N isocyanatomethyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CN=C=O QRFPECUQGPJPMV-UHFFFAOYSA-N 0.000 description 1
- HENJUOQEQGBPSV-UHFFFAOYSA-N isocyanatomethyl-dimethoxy-methylsilane Chemical compound CO[Si](C)(OC)CN=C=O HENJUOQEQGBPSV-UHFFFAOYSA-N 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013008 moisture curing Methods 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 150000003021 phthalic acid derivatives Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- TXDNPSYEJHXKMK-UHFFFAOYSA-N sulfanylsilane Chemical class S[SiH3] TXDNPSYEJHXKMK-UHFFFAOYSA-N 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 150000003609 titanium compounds Chemical class 0.000 description 1
- FRGPKMWIYVTFIQ-UHFFFAOYSA-N triethoxy(3-isocyanatopropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCN=C=O FRGPKMWIYVTFIQ-UHFFFAOYSA-N 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
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4825—Polyethers containing two hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/2805—Compounds having only one group containing active hydrogen
- C08G18/2815—Monohydroxy compounds
- C08G18/282—Alkanols, cycloalkanols or arylalkanols including terpenealcohols
-
- 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
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/71—Monoisocyanates or monoisothiocyanates
- C08G18/718—Monoisocyanates or monoisothiocyanates 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
- C08G2190/00—Compositions for sealing or packing joints
Definitions
- the present invention relates to polyoxysilane-modified polyurethanes and their use as binders for sealants.
- Alkoxysilane-functional polyurethanes which crosslink via a silane polycondensation have long been known. A review on this topic can be found eg in "Adhesives Age” 4/1995, page 30 ff. (Authors: Ta-Min Feng, BA Waldmann). Such alkoxysilane-terminated, moisture-curing, one-component polyurethanes are increasingly being used as soft-elastic coating, sealing and adhesive compounds in construction and in the automotive industry. Preparation processes for such alkoxysilane-functional polyurethanes are described in various publications, inter alia in US Pat. No. 3,627,722 or US Pat. No. 3,632,557.
- a disadvantage of these methods is the high resulting viscosity, which requires the use of solvents or, at low viscosity, the poor suitability for use in low-modulus sealants.
- various approaches are described, for example, in US Pat. No. 3,627,722 and EP-A 0 596 360, all of which have the disadvantage that in the preparation of the alkoxysilane-functional polyurethanes, intermediates are passed through which are very unstable and thus pose a high safety risk and severely limit the reproducibility of the reactions.
- prepolymers having the required properties can be prepared by reacting polyethers having a number-average molecular weight of> 20,000 g / mol with OH-reactive silane building blocks.
- the invention therefore relates to polyurethanes modified with alkoxysilane groups, which are obtainable by reacting the components A and B in the sense of a urethanization:
- X, Y, Z are independently linear, cyclic or branched Ci-Cg-alkyl or Ci-C 8 alkoxy, wherein at least one of Radicals is a C 1 -C 8 -alkoxy group and X, Y or Z can also be bridged independently of one another,
- R is any at least difunctional organic radical, preferably a straight-chain, branched or cyclic Alkylenradical having 1 to 8 carbon atoms.
- X, Y, and Z in formula (I) are independently methoxy or ethoxy.
- radical R a methylene or propylene radical is particularly preferred.
- component A) has a number average molecular weight of 21,000 g / mol to 25,000 g / mol.
- the invention further provides sealants based on the alkoxysilane-modified polyurethanes according to the invention which have a modulus at 100% elongation of not more than 0.4 N / mm 2 (according to ISO 11600) and a maximum of 30% by weight of plasticizer, preferably at most Contain 25 wt .-% plasticizer, more preferably at most 20 wt .-% plasticizer.
- Polyol component A) which can be used according to the invention are the polyether polyols customary in polyurethane chemistry. These are accessible in a manner known per se by alkoxylation of suitable starter molecules with base catalysis or use of double metal cyanide compounds (DMC compounds).
- suitable starter molecules for the preparation of polyether polyols are molecules having at least 2 element-hydrogen bonds which are reactive toward epoxides or any mixtures of such starter molecules.
- Suitable starter molecules for the preparation of polyether polyols are, for example, simple, low molecular weight polyols, water, ethylene glycol, propanediol 1, 2, 2,2-bis (4-hydroxyphenyl) propane, Propylene glycol-1,3- and 1,4-butanediol, 1,6-hexanediol, neopentyl glycol, 2-ethylhexanediol-1, 3, trimethylolpropane, glycerol, pentaerythritol, sorbitol, organic polyamines having at least two NH bonds such as triethanolamine, ammonia , Methylamine or ethylenediamine or any mixtures of such starter molecules.
- Alkylene oxide suitable for the alkoxylation is in particular propylene oxide.
- propylene oxide polyethers having from 1.5 to 3.5 hydroxyl groups, more preferably from 1.8 to 2.5.
- Polyethers prepared by double metal cyanide catalysis generally have a particularly low content of unsaturated end groups of less than or equal to 0.02 meq / gram of polyol (meq / g), preferably less than or equal to 0.015 meq / g, more preferably less than or equal to 0, 01 meq / g (method of determination ASTM D2849-69), contain significantly fewer monols and usually have a low polydispersity of less than 1.5.
- polyethers prepared by double metal cyanide catalysis.
- Particularly preferred are polyethers which have a polydispersity of 1.0-1.5; most preferably a polydispersity of 1.0 to 1.3.
- Such polyethers are e.g. in US Pat. No. 5,158,922 and EP-A 0 654 302.
- polyoxyalkylene polyols can be used in pure form or as a mixture of different polyethers.
- isocyanate- and alkoxysilane-containing compounds B all alkoxysilane-containing monoisocyanates are suitable in principle.
- Examples of such compounds are isocyanatomethyltrimethoxysilane, isocyanatomethyltriethoxysilane, (isocyanatomethyl) methyldimethoxysilane, (isocyanatomethyl) methyldiethoxysilane, 3-isocyanatopropyltrimethoxysilane, 3-isocyanatopropylmethyldimethoxysilane, 3-isocyanato propyltriethoxysilane and 3-isocyanatopropylmethyldiethoxysilane.
- Preferred here is the use of 3-isocyanatopropyltrimethoxysilane.
- isocyanate-functional silanes prepared by reacting a diisocyanate with an amino or thiosilane, as described in US Pat. No. 4,146,585 or EP-A 1 136 495.
- the urethanization of components A) and B) may optionally be carried out using a catalyst.
- Suitable catalytically active compounds which are known to the person skilled in the art are known urethanization catalysts such as organotin compounds or amine catalysts.
- organotin compounds are: dibutyltin diacetate, dibutyltin dilaurate, dibutyltin bis-acetoacetonate and tin carboxylates such as, for example, tin octoate.
- the said tin catalysts may optionally be used in combination with amine catalysts such as aminosilanes or 1,4-diazabicyclo [2.2.2] octane.
- Dibutyltin dilaurate is particularly preferably used as the urethanization catalyst.
- the course of the urethanization reaction can be monitored by suitable measuring devices installed in the reaction vessel and / or by analyzes on samples taken. Suitable methods are known to the person skilled in the art. These are, for example, viscosity measurements, measurements of the NCO content, the refractive index, the OH content, gas chromatography (GC), nuclear magnetic resonance spectroscopy (NMR), infrared spectroscopy (IR) and near near-infrared spectroscopy (NIR).
- the NCO content of the mixture is determined titrimetrically.
- the urethanization of components A) and B) is continued until a complete conversion of the OH groups of the compounds of component A) is reached.
- the first possibility involves the addition of a further NCO-reactive component, which in a subsequent Reaction step is reacted with the remaining NCO groups.
- a further NCO-reactive component which in a subsequent Reaction step is reacted with the remaining NCO groups.
- These may be, for example, low molecular weight alcohols.
- the second possibility for the further reduction of the NCO content of the reaction product of components A) and B) is an allophanatization reaction.
- the remaining NCO groups are reacted with the previously formed urethane groups, preferably by adding a catalyst which promotes allophanatization.
- the alkoxysilane-group-modified polyurethanes of the invention generally have a viscosity of less than 200,000 mPas, preferably less than 100,000 mPas, in each case measured at 23 ° C.
- the compounds according to the invention are very suitable as binders for the preparation of low-modulus elastic sealants, preferably for vehicle construction and construction. These adhesives crosslink under the action of atmospheric moisture via a silanol polycondensation.
- the polymers obtained by this crosslinking are also an object of the present invention, their chemical and physical properties are responsible for the outstanding quality of the seals produced.
- the polyurethanes of the invention modified with alkoxysilane groups may be used together with the customary fillers, pigments, plasticizers, drying agents, additives, light stabilizers, antioxidants, thixotropic agents, catalysts, adhesion promoters and optionally other auxiliaries and additives are formulated by known methods of sealant production.
- Suitable basic fillers used are precipitated or ground chalks, metal oxides, sulfates, silicates, hydroxides, carbonates and bicarbonates. Further fillers are e.g. reinforcing and non-reinforcing fillers such as carbon black, precipitated silicas, fumed silicas, quartz powder or various fibers. Both the basic fillers and the further reinforcing or non-reinforcing fillers may optionally be surface-modified. Particular preference is given to using as basic fillers precipitated or ground chalks and pyrogenic silicic acids. Mixtures of fillers can also be used.
- plasticizers examples include phthalic acid esters, adipic acid esters, alkylsulfonic acid esters of phenol or phosphoric acid esters. Long-chain hydrocarbons, polyethers and vegetable oils can also be used as plasticizers. Due to the special properties of the polymer according to the invention, the proportion of plasticizer in the sealant formulation can be limited to ⁇ 30% by weight, preferably to ⁇ 25% by weight, particularly preferably to ⁇ 20% by weight.
- thixotropic agents which may be mentioned are pyrogenic silicic acids, polyamides, hydrogenated castor oil derived products or else polyvinyl chloride.
- suitable catalysts for curing it is possible to use all organometallic compounds and amine catalysts which, as is known, promote silane polycondensation.
- Particularly suitable organometallic compounds are especially compounds of tin and titanium.
- Preferred tin compounds are, for example: dibutyltin diacetate, dibutyltin dilaurate, dioctyltin methyl acetate and tin carboxylates such as stannous octoate or dibutyltin-bis-acetoacetonate.
- the said tin catalysts may optionally be used in combination with amine catalysts such as aminosilanes or 1,4-diazabicyclo [2.2.2] octane.
- amine catalysts such as aminosilanes or 1,4-diazabicyclo [2.2.2] octane.
- Preferred titanium compounds are, for example, alkyl titanates, such as diisobutyl-bisacetoacetic acid ethyl ester titanate.
- amine catalysts are particularly suitable those having a particularly high base strength, such as amines with amidine structure.
- Preferred amine catalysts are therefore, for example, l, 8-diazabicyclo [5.4.0] undec-7-ene or 1, 5-diazabicyclo [4.3.0] non-5-ene.
- drying agents include alkoxysilyl compounds such as vinyl trimethoxysilane, methyltrimethoxysilane, z '-Butyltrimethoxysilan, Hexadecyltrimeth- oxysilane.
- Adhesion promoters used are the known functional silanes, such as, for example, amino silanes, epoxysilanes and / or mercaptosilanes or mixtures of functional silanes.
- the viscosity measurements were carried out according to ISO / DIS 3219: 1990 at a constant temperature of 23 ° C. and a constant shear rate of 250 / sec using a Physica MCR disk-viscous rotational viscometer (Anton Paar Germany GmbH, Ostfildern, DE) of the measuring cone CP 25-1 (25mm diameter, 1 ° cone angle).
- RT The ambient temperature of 23 ° C prevailing at the time of the experiment.
- Example 1 (according to the invention):
- a film is applied to a previously cleaned with ethyl acetate glass plate and immediately loaded into the Drying Recorder.
- the needle is loaded with 10 g and moves over a period of 24 hours over a distance of 35 cm.
- the Drying Recorder is located in a climate room at 23 ° C and 50% rel. Humidity.
- the skin-forming time is the time at which the permanent trace of the needle disappears from the film.
- the binder with filler Socal ® UiS 2
- plasticizer DINP Jayfiex TM
- desiccant Desiccant
- the adhesion promoter (Dynasylan ® 1146) is added and stirred in within 5 min at 1000 U / min.
- the catalyst (Lupragen ® N700) is stirred at 1000 U / min and, finally, the finished mixture in vacuo tet deaerated.
- the level of plasticizer was classified below 20% by weight:
- the sealant obtained with this low-softening formulation exhibits the following mechanical properties:
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Sealing Material Composition (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polyethers (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP10790748A EP2510029A1 (fr) | 2009-12-09 | 2010-12-06 | Produits d'étanchéité |
CN2010800562013A CN102741308A (zh) | 2009-12-09 | 2010-12-06 | 密封剂 |
US13/514,742 US8981030B2 (en) | 2009-12-09 | 2010-12-06 | Sealants |
JP2012542488A JP2013513674A (ja) | 2009-12-09 | 2010-12-06 | シーラント |
Applications Claiming Priority (2)
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DE102009057599.5 | 2009-12-09 | ||
DE200910057599 DE102009057599A1 (de) | 2009-12-09 | 2009-12-09 | Dichtstoffe |
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WO2011069954A1 true WO2011069954A1 (fr) | 2011-06-16 |
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PCT/EP2010/068952 WO2011069954A1 (fr) | 2009-12-09 | 2010-12-06 | Produits d'étanchéité |
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US (1) | US8981030B2 (fr) |
EP (1) | EP2510029A1 (fr) |
JP (1) | JP2013513674A (fr) |
CN (1) | CN102741308A (fr) |
DE (1) | DE102009057599A1 (fr) |
WO (1) | WO2011069954A1 (fr) |
Families Citing this family (4)
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DE102014101949A1 (de) * | 2014-02-17 | 2015-08-20 | Franken Systems Gmbh | Verfahren zur druckwasserfesten Abdichtung von Bauwerken |
US20160244549A1 (en) * | 2015-02-25 | 2016-08-25 | Bayer Materialscience Llc | Alkoxysilane-group modified polyurethanes and low modulus sealants formed therefrom |
KR101901020B1 (ko) * | 2016-10-25 | 2018-11-08 | 한국타이어 주식회사 | 공명음 저감 타이어 |
DE102020117919A1 (de) * | 2020-07-07 | 2022-01-13 | Franken Systems Gmbh | 2-Komponenten-Beschichtungszusammensetzung zur Bauwerksabdichtung |
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US3632557A (en) | 1967-03-16 | 1972-01-04 | Union Carbide Corp | Vulcanizable silicon terminated polyurethane polymers |
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EP0596360A1 (fr) | 1992-11-06 | 1994-05-11 | Bayer Ag | Composés d'alcoxysilanes contenant des groupes amino |
EP0654302A1 (fr) | 1993-11-23 | 1995-05-24 | ARCO Chemical Technology, L.P. | Catalyseur amélioré à base de complexe de cyanure métallique double |
EP1136495A2 (fr) | 2000-03-18 | 2001-09-26 | Degussa AG | 1:1 Monoadducts d'aminoalkylalkoxysilanes et diisocyanates, leur préparation et utilisation |
EP1591464A1 (fr) | 2004-04-28 | 2005-11-02 | Bayer MaterialScience LLC | Polyéther-uréthanes réticulables sous humidité et leur utilisation comme agent d'étanchéité, adhésif et revêtement |
WO2007025668A1 (fr) * | 2005-09-03 | 2007-03-08 | Bayer Materialscience Ag | Prepolymeres contenant des groupes alcoxysilane de faible viscosite, procede de production et utilisation associes |
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US6833423B2 (en) * | 2002-06-18 | 2004-12-21 | Bayer Polymers Llc | Moisture-curable, polyether urethanes with reactive silane groups and their use as sealants, adhesives and coatings |
JP4885540B2 (ja) * | 2003-04-11 | 2012-02-29 | 株式会社カネカ | 硬化性組成物 |
WO2009011329A1 (fr) * | 2007-07-19 | 2009-01-22 | Kaneka Corporation | Composition durcissable |
DE102007039648A1 (de) * | 2007-08-22 | 2009-02-26 | Sustech Gmbh & Co. Kg | Mischungen, multifunktioneller sternförmiger Präpolymere, deren Herstellung und Verwendung sowie Beschichtungen daraus |
EP2238826A4 (fr) | 2007-12-07 | 2010-12-15 | Suntory Holdings Ltd | Plante transgénique capable de fleurir dans des conditions de faible intensité lumineuse |
-
2009
- 2009-12-09 DE DE200910057599 patent/DE102009057599A1/de not_active Withdrawn
-
2010
- 2010-12-06 WO PCT/EP2010/068952 patent/WO2011069954A1/fr active Application Filing
- 2010-12-06 JP JP2012542488A patent/JP2013513674A/ja active Pending
- 2010-12-06 EP EP10790748A patent/EP2510029A1/fr not_active Withdrawn
- 2010-12-06 US US13/514,742 patent/US8981030B2/en active Active
- 2010-12-06 CN CN2010800562013A patent/CN102741308A/zh active Pending
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EP0596360A1 (fr) | 1992-11-06 | 1994-05-11 | Bayer Ag | Composés d'alcoxysilanes contenant des groupes amino |
EP0654302A1 (fr) | 1993-11-23 | 1995-05-24 | ARCO Chemical Technology, L.P. | Catalyseur amélioré à base de complexe de cyanure métallique double |
EP1136495A2 (fr) | 2000-03-18 | 2001-09-26 | Degussa AG | 1:1 Monoadducts d'aminoalkylalkoxysilanes et diisocyanates, leur préparation et utilisation |
EP1591464A1 (fr) | 2004-04-28 | 2005-11-02 | Bayer MaterialScience LLC | Polyéther-uréthanes réticulables sous humidité et leur utilisation comme agent d'étanchéité, adhésif et revêtement |
WO2007025668A1 (fr) * | 2005-09-03 | 2007-03-08 | Bayer Materialscience Ag | Prepolymeres contenant des groupes alcoxysilane de faible viscosite, procede de production et utilisation associes |
EP1924621A1 (fr) | 2005-09-03 | 2008-05-28 | Bayer MaterialScience AG | Prepolymeres contenant des groupes alcoxysilane de faible viscosite, procede de production et utilisation associes |
WO2008036364A1 (fr) * | 2006-09-21 | 2008-03-27 | Momentive Performance Materials Inc. | Procédé de préparation d'une résine polyuréthanne silylé durcissable |
WO2009071542A1 (fr) * | 2007-12-04 | 2009-06-11 | Henkel Ag & Co. Kgaa | Compositions durcissables contenant des polyuréthannes silylés |
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ADHESIVES AGE, April 1995 (1995-04-01), pages 30 |
See also references of EP2510029A1 * |
Also Published As
Publication number | Publication date |
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DE102009057599A1 (de) | 2011-06-16 |
JP2013513674A (ja) | 2013-04-22 |
US8981030B2 (en) | 2015-03-17 |
CN102741308A (zh) | 2012-10-17 |
US20120245279A1 (en) | 2012-09-27 |
EP2510029A1 (fr) | 2012-10-17 |
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