TWI240726B - Polyurethane prepolymers comprising alkoxysilane terminal groups, a method of producing them and their use for the production of sealing materials - Google Patents
Polyurethane prepolymers comprising alkoxysilane terminal groups, a method of producing them and their use for the production of sealing materials Download PDFInfo
- Publication number
- TWI240726B TWI240726B TW088118634A TW88118634A TWI240726B TW I240726 B TWI240726 B TW I240726B TW 088118634 A TW088118634 A TW 088118634A TW 88118634 A TW88118634 A TW 88118634A TW I240726 B TWI240726 B TW I240726B
- Authority
- TW
- Taiwan
- Prior art keywords
- polyurethane prepolymer
- patent application
- scope
- alkoxysilane
- molecular weight
- Prior art date
Links
- 229920001730 Moisture cure polyurethane Polymers 0.000 title claims abstract description 32
- 239000003566 sealing material Substances 0.000 title claims abstract description 19
- 238000000034 method Methods 0.000 title claims abstract description 9
- 238000004519 manufacturing process Methods 0.000 title claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 230000002079 cooperative effect Effects 0.000 claims description 10
- 229920000768 polyamine Polymers 0.000 claims description 8
- 229920001451 polypropylene glycol Polymers 0.000 claims description 8
- 125000005442 diisocyanate group Chemical group 0.000 claims description 7
- 229920000570 polyether Polymers 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims description 4
- 229920000642 polymer Polymers 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 3
- 125000004429 atom Chemical group 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
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 235000019253 formic acid Nutrition 0.000 claims 1
- 239000011230 binding agent Substances 0.000 abstract description 3
- 239000000203 mixture Substances 0.000 description 16
- 238000011049 filling Methods 0.000 description 12
- -1 amino amino ester Chemical class 0.000 description 10
- 239000003054 catalyst Substances 0.000 description 10
- 239000012948 isocyanate Substances 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 150000002513 isocyanates Chemical class 0.000 description 9
- 229920002635 polyurethane Polymers 0.000 description 9
- 229920005862 polyol Polymers 0.000 description 8
- 150000003077 polyols Chemical class 0.000 description 8
- 239000004814 polyurethane Substances 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 7
- 239000004721 Polyphenylene oxide Substances 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 239000000853 adhesive Substances 0.000 description 5
- 230000001070 adhesive effect Effects 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 239000004615 ingredient Substances 0.000 description 5
- 239000005058 Isophorone diisocyanate Substances 0.000 description 4
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- 238000010276 construction Methods 0.000 description 4
- 150000002009 diols Chemical class 0.000 description 4
- 239000010408 film Substances 0.000 description 4
- 229920002457 flexible plastic Polymers 0.000 description 4
- 150000002334 glycols Chemical class 0.000 description 4
- 238000002329 infrared spectrum Methods 0.000 description 4
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 239000004575 stone Substances 0.000 description 3
- 239000000052 vinegar Substances 0.000 description 3
- 235000021419 vinegar Nutrition 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 235000003704 aspartic acid Nutrition 0.000 description 2
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000007767 bonding agent Substances 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000002274 desiccant Substances 0.000 description 2
- QZUFYZAIYPHVTL-UHFFFAOYSA-L diacetyloxy(butyl)tin Chemical compound CCCC[Sn](OC(C)=O)OC(C)=O QZUFYZAIYPHVTL-UHFFFAOYSA-L 0.000 description 2
- VSNLCLFPPHBFLV-LBPRGKRZSA-N diethyl (2s)-2-(3-trimethoxysilylpropylamino)butanedioate Chemical compound CCOC(=O)C[C@@H](C(=O)OCC)NCCC[Si](OC)(OC)OC VSNLCLFPPHBFLV-LBPRGKRZSA-N 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
- 239000000945 filler Substances 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 239000004014 plasticizer Substances 0.000 description 2
- 238000012643 polycondensation polymerization Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000013008 thixotropic agent Substances 0.000 description 2
- 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 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 1
- VGHSXKTVMPXHNG-UHFFFAOYSA-N 1,3-diisocyanatobenzene Chemical compound O=C=NC1=CC=CC(N=C=O)=C1 VGHSXKTVMPXHNG-UHFFFAOYSA-N 0.000 description 1
- WMNGKXHWVSJWLQ-UHFFFAOYSA-N 1,5-diisocyanato-5,6-dimethylcyclohexa-1,3-diene Chemical group CC1C(N=C=O)=CC=CC1(C)N=C=O WMNGKXHWVSJWLQ-UHFFFAOYSA-N 0.000 description 1
- NFDXQGNDWIPXQL-UHFFFAOYSA-N 1-cyclooctyldiazocane Chemical compound C1CCCCCCC1N1NCCCCCC1 NFDXQGNDWIPXQL-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
- JMHDUGPVXOVUMR-UHFFFAOYSA-N 3-[ethoxy(methyl)silyl]propan-1-amine Chemical compound CCO[SiH](C)CCCN JMHDUGPVXOVUMR-UHFFFAOYSA-N 0.000 description 1
- YBXSYMIDZDBSFD-UHFFFAOYSA-L 3-acetyl-2,4-dioxopentanoate;dibutyltin(2+) Chemical compound CCCC[Sn+2]CCCC.CC(=O)C(C(C)=O)C(=O)C([O-])=O.CC(=O)C(C(C)=O)C(=O)C([O-])=O YBXSYMIDZDBSFD-UHFFFAOYSA-L 0.000 description 1
- 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 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- OWIKHYCFFJSOEH-UHFFFAOYSA-N Isocyanic acid Chemical compound N=C=O OWIKHYCFFJSOEH-UHFFFAOYSA-N 0.000 description 1
- FDFQNMNHTZLBMA-UHFFFAOYSA-N NCCNCCC[Si](OC)(OC)C1=CC=CC=2C3=CC=CC=C3CC12 Chemical compound NCCNCCC[Si](OC)(OC)C1=CC=CC=2C3=CC=CC=C3CC12 FDFQNMNHTZLBMA-UHFFFAOYSA-N 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 229910008326 Si-Y Inorganic materials 0.000 description 1
- 229910006773 Si—Y Inorganic materials 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001278 adipic acid derivatives Chemical class 0.000 description 1
- 125000005370 alkoxysilyl group Chemical group 0.000 description 1
- 125000005103 alkyl silyl group Chemical group 0.000 description 1
- XLJMAIOERFSOGZ-UHFFFAOYSA-N anhydrous cyanic acid Natural products OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 238000001723 curing Methods 0.000 description 1
- 239000012973 diazabicyclooctane Substances 0.000 description 1
- JQTLQMOFVUEIKU-UHFFFAOYSA-M dibutyl(dodecanoyloxy)tin Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)CCCC JQTLQMOFVUEIKU-UHFFFAOYSA-M 0.000 description 1
- AOXQJPCMTUAMCY-JTQLQIEISA-N dimethyl (2s)-2-(3-trimethoxysilylpropylamino)butanedioate Chemical compound COC(=O)C[C@@H](C(=O)OC)NCCC[Si](OC)(OC)OC AOXQJPCMTUAMCY-JTQLQIEISA-N 0.000 description 1
- LRCFXGAMWKDGLA-UHFFFAOYSA-N dioxosilane;hydrate Chemical compound O.O=[Si]=O LRCFXGAMWKDGLA-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000007046 ethoxylation reaction Methods 0.000 description 1
- JYVATDLODMRIPD-UHFFFAOYSA-N ethyl carbamate silane Chemical compound [SiH4].CCOC(N)=O JYVATDLODMRIPD-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 235000011087 fumaric acid Nutrition 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
- 208000014674 injury Diseases 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 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
- 150000002739 metals Chemical class 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000013008 moisture curing Methods 0.000 description 1
- VIKNJXKGJWUCNN-XGXHKTLJSA-N norethisterone Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 VIKNJXKGJWUCNN-XGXHKTLJSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical class OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical class [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 229960004029 silicic acid Drugs 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000011232 storage material Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 239000012974 tin catalyst Substances 0.000 description 1
- XYJRNCYWTVGEEG-UHFFFAOYSA-N trimethoxy(2-methylpropyl)silane Chemical compound CO[Si](OC)(OC)CC(C)C XYJRNCYWTVGEEG-UHFFFAOYSA-N 0.000 description 1
- 210000001944 turbinate Anatomy 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
- C09K3/10—Materials in mouldable or extrudable form for sealing or packing joints or covers
- C09K3/1006—Materials in mouldable or extrudable form for sealing or packing joints or covers characterised by the chemical nature of one of its constituents
- C09K3/1021—Polyurethanes or derivatives thereof
-
- 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
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
-
- 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
- C08G18/4866—Polyethers having a low unsaturation value
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Polyurethanes Or Polyureas (AREA)
- Sealing Material Composition (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19849817A DE19849817A1 (de) | 1998-10-29 | 1998-10-29 | Alkoxysilan-Endgruppen aufweisende Polyurethanprepolymere, ein Verfahren zu ihrer Herstellung sowie ihre Verwendung zur Herstellung von Dichtstoffen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TWI240726B true TWI240726B (en) | 2005-10-01 |
Family
ID=7886010
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW088118634A TWI240726B (en) | 1998-10-29 | 1999-10-28 | Polyurethane prepolymers comprising alkoxysilane terminal groups, a method of producing them and their use for the production of sealing materials |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US6545087B1 (enExample) |
| EP (1) | EP1124872B1 (enExample) |
| JP (1) | JP4616992B2 (enExample) |
| KR (1) | KR100547526B1 (enExample) |
| CN (1) | CN1146609C (enExample) |
| AT (1) | ATE248872T1 (enExample) |
| AU (1) | AU743227B2 (enExample) |
| CA (1) | CA2348566C (enExample) |
| CZ (1) | CZ295160B6 (enExample) |
| DE (2) | DE19849817A1 (enExample) |
| DK (1) | DK1124872T3 (enExample) |
| ES (1) | ES2212678T3 (enExample) |
| HK (1) | HK1042101B (enExample) |
| NO (1) | NO20012033D0 (enExample) |
| PL (1) | PL347426A1 (enExample) |
| PT (1) | PT1124872E (enExample) |
| TW (1) | TWI240726B (enExample) |
| WO (1) | WO2000026271A1 (enExample) |
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| DE19914879A1 (de) * | 1999-04-01 | 2000-10-05 | Bayer Ag | Polyurethanlösungen mit Alkoxysilanstruktureinheiten |
| US6265517B1 (en) | 1999-09-07 | 2001-07-24 | Bostik, Inc. | Silylated polyether sealant |
| DE10139132A1 (de) | 2001-08-09 | 2003-02-27 | Consortium Elektrochem Ind | Alkoxyvernetzende einkomponentige feuchtigkeitshärtende Massen |
| EP1421129B1 (de) | 2001-08-28 | 2005-06-15 | Consortium für elektrochemische Industrie GmbH | Einkomponentige alkoxysilanterminierte polymere enthaltende schnell härtende abmischungen |
| DE10201703A1 (de) | 2002-01-17 | 2003-08-07 | Consortium Elektrochem Ind | Alkoxysilanterminierte Polymere enthaltende vernetzbare Polymerabmischungen |
| DE10204523A1 (de) | 2002-02-05 | 2003-08-07 | Bayer Ag | Alkoxysilan- und OH-Endgruppen aufweisende Polyurethanprepolymere mit erniedrigter Funktionalität, ein Verfahren zu ihrer Herstellung sowie ihre Verwendung |
| US7115696B2 (en) * | 2002-05-31 | 2006-10-03 | Bayer Materialscience Llc | Moisture-curable, polyether urethanes with reactive silane groups and their use as sealants, adhesives and coatings |
| US6809170B2 (en) * | 2002-05-31 | 2004-10-26 | Bayer Materialscience Llc | Moisture-curable, polyether urethanes with reactive silane groups and their use as sealants, adhesive and coatings |
| US6887964B2 (en) * | 2002-05-31 | 2005-05-03 | Bayer Materialscience Llc | Moisture-curable, polyether urethanes with reactive silane groups and their use as sealants, adhesives and coatings |
| US6844413B2 (en) * | 2002-06-18 | 2005-01-18 | Bayer Materialscience Llc | Moisture-curable, polyether urethanes with reactive silane groups and their use as sealants, adhesives and coatings |
| 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 |
| US6998459B2 (en) * | 2002-06-18 | 2006-02-14 | Bayer Materialscience Llc | Polyether urethanes containing one reactive silane group and their use in moisture-curable polyether urethanes |
| JP4101632B2 (ja) | 2002-11-01 | 2008-06-18 | 株式会社カネカ | 硬化性組成物および復元性、クリープ性改善方法 |
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| AU2003298940A1 (en) | 2002-12-20 | 2004-07-29 | Bayer Materialscience Llc | Moisture-curable, polyether urethanes with terminal cyclic urea/reactive silane groups and their use as sealants, adhesives and coatin |
| US20050112273A1 (en) * | 2003-05-19 | 2005-05-26 | Stenzel Eric B. | Method of improving the quality and performance of a coating on a coated medical device using a solvent to reflow the coating |
| DE10328844A1 (de) * | 2003-06-26 | 2005-02-03 | Consortium für elektrochemische Industrie GmbH | Alkoxysilanterminierte Prepolymere |
| US20050091304A1 (en) * | 2003-10-27 | 2005-04-28 | Advanced Premise Technologies, Llc | Telecommunications device and method |
| DE10351804A1 (de) | 2003-11-06 | 2005-06-09 | Wacker-Chemie Gmbh | Verfahren zur Erhöhung der Elastizität von feuchtigkeitsgehärteten Elastomeren |
| DE10351802A1 (de) * | 2003-11-06 | 2005-06-09 | Consortium für elektrochemische Industrie GmbH | alpha-Alkoxysilane sowie ihre Anwendung in alkoxysilanterminierten Prepolymeren |
| US20050137374A1 (en) * | 2003-12-17 | 2005-06-23 | Roesler Richard R. | Two-component water-borne adhesive |
| US7465778B2 (en) * | 2003-12-19 | 2008-12-16 | Bayer Materialscience Llc | Silante terminated polyurethane |
| US7482420B2 (en) | 2004-03-24 | 2009-01-27 | Construction Research & Technology Gmbh | Silane-terminated polyurethanes with high strength and high elongation |
| US7060750B2 (en) * | 2004-04-28 | 2006-06-13 | Bayer Materialscience Llc | Moisture-curable, polyether urethanes and their use in sealant, adhesive and coating compositions |
| EP2546308B1 (en) * | 2004-11-10 | 2014-07-16 | Kaneka Corporation | Curable composition |
| DE102004062653A1 (de) * | 2004-12-24 | 2006-07-06 | Bayer Materialscience Ag | Feuchthärtende Zusammensetzung und Schmelzklebstoff |
| EP1717254A1 (de) | 2005-04-29 | 2006-11-02 | Sika Technology AG | Feuchtigkeitshärtende Zusammensetzung mit erhöhter Dehnbarkeit |
| DE102005029169A1 (de) | 2005-06-23 | 2006-12-28 | Wacker Chemie Ag | Kontinuierliche polymeranaloge Umsetzung von reaktiven Silanmonomeren mit funktionalisierten Polymeren |
| DE102005041953A1 (de) * | 2005-09-03 | 2007-03-08 | Bayer Materialscience Ag | Niedrigviskose alkoxysilangruppenaufweisende Prepolymere, ein Verfahren zu ihrer Herstellung sowie ihre Verwendung |
| DE102005041954A1 (de) * | 2005-09-03 | 2007-03-08 | Bayer Materialscience Ag | Alkoxysilan- und spezielle Allophanat-und/oder Biuretgruppen aufweisende Prepolymere, ein Verfahren zu ihrer Herstellung sowie ihre Verwendung |
| ES2332246T3 (es) * | 2006-02-14 | 2010-01-29 | Bostik Sa | Composicion de recubrimiento anhidra de un solo componente para sellado de estructuras construidas y techos planos. |
| DE102006022095A1 (de) | 2006-05-11 | 2007-11-15 | Wacker Chemie Ag | Alkoxysilanterminierte Polymere enthaltende transparente Polymerabmischungen |
| DE102006022834A1 (de) * | 2006-05-16 | 2007-11-22 | Wacker Chemie Ag | Verbesserung der elastischen Rückstellung bei alkoxysilanvernetzten Polymeren |
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| DE102006059473A1 (de) | 2006-12-14 | 2008-06-19 | Henkel Kgaa | Silylgruppen enthaltende Mischung von Prepolymeren und deren Verwendung |
| US8029854B2 (en) * | 2007-07-26 | 2011-10-04 | Bayer Materialscience Llc | Concrete repair process |
| WO2009065654A1 (de) * | 2007-11-21 | 2009-05-28 | Sika Technology Ag | Feuchtigkeitshärtende zusammensetzung umfassend mindestens zwei silangruppen-aufweisende polymere |
| DE102007058344A1 (de) | 2007-12-03 | 2009-06-04 | Henkel Ag & Co. Kgaa | Härtbare Zusammensetzungen enthaltend silylierte Polyurethane |
| DE102007058483A1 (de) | 2007-12-04 | 2009-06-10 | Henkel Ag & Co. Kgaa | Härtbare Zusammensetzungen enthaltend silylierte Polyurethane |
| DE102008003743A1 (de) | 2008-01-10 | 2009-07-16 | Henkel Ag & Co. Kgaa | Härtbare Zusammensetzungen enthaltend weichelastische silylierte Polyurethane |
| DE102008020979A1 (de) | 2008-04-25 | 2009-10-29 | Henkel Ag & Co. Kgaa | Härtbare Zusammensetzungen enthaltend silylierte Polyurethane |
| DE102008020980A1 (de) * | 2008-04-25 | 2009-10-29 | Henkel Ag & Co. Kgaa | Härtbare Zusammensetzungen enthaltend silylierte Polyurethane auf Basis von Polyetherblockpolymeren |
| DE102008021221A1 (de) * | 2008-04-28 | 2009-10-29 | Henkel Ag & Co. Kgaa | Härtbare Zusammensetzung auf Basis silylierter Polyurethane |
| DE102008021222A1 (de) | 2008-04-28 | 2009-12-24 | Henkel Ag & Co. Kgaa | Härtbare Zusammensetzungen auf Basis silylierter Polyurethane |
| DE102008038399A1 (de) | 2008-08-19 | 2010-02-25 | Henkel Ag & Co. Kgaa | Härtbare Zusammensetzungen auf Basis silylierter Polyurethane |
| DE102008038488A1 (de) | 2008-08-20 | 2010-02-25 | Henkel Ag & Co. Kgaa | Feuchtigkeitshärtende wasserfeste Beschichtung |
| KR101088786B1 (ko) | 2009-09-02 | 2011-12-01 | (주)삼중 | 실록산 변성 이소시아네이트 알콕시 실란 화합물, 이의 제조방법, 및 이의 용도 |
| DE102009046269A1 (de) | 2009-10-30 | 2011-05-05 | Henkel Ag & Co. Kgaa | Harnstoffgebundende Alkoxysilane zum Einsatz in Dicht- und Klebstoffen |
| CN102261000B (zh) * | 2011-05-12 | 2012-12-05 | 四川大学 | 一种溶胶-凝胶法制备水性聚氨酯/SiO2纳米杂化皮革涂饰剂的方法 |
| EP2861642B1 (de) * | 2012-06-15 | 2018-10-17 | Sika Technology AG | Silangruppen-haltiges polymer |
| DE102012223422A1 (de) * | 2012-12-17 | 2014-06-18 | Henkel Ag & Co. Kgaa | Niedermodulige silanterminierte PU-Präpolymere |
| WO2015088764A1 (en) | 2013-12-12 | 2015-06-18 | Dow Global Technologies Llc | Aminosilane adhesion promoter for urethane system |
| PL3067375T3 (pl) | 2015-03-11 | 2018-01-31 | Henkel Ag & Co Kgaa | Sililowane poliuretany, ich wytwarzanie i zastosowanie |
| EP3526285B1 (de) | 2016-10-17 | 2024-07-17 | Covestro Deutschland AG | Stabilisatoren für klebstoff-, dichtstoff- und beschichtungszusammensetzungen |
| KR102078767B1 (ko) * | 2018-06-25 | 2020-04-07 | 한국생산기술연구원 | 화학작용제 제거용 자기가교형 수분산성 폴리우레탄 조성물 및 그의 제조방법 |
| KR102164674B1 (ko) * | 2019-03-28 | 2020-10-12 | 한국생산기술연구원 | 화학작용제 제거용 자기가교형 수분산성 폴리우레탄 적층 필름 및 그의 제조방법 |
| US20220411631A1 (en) | 2020-02-03 | 2022-12-29 | Ddp Specialty Electronic Materials Us, Llc | Polyurethane based thermal interface material comprising silane terminated urethane prepolymers |
| WO2021160493A1 (de) | 2020-02-10 | 2021-08-19 | Sika Technology Ag | Verzweigtes silangruppen-haltiges polymer |
| EP4103633A1 (de) | 2020-02-10 | 2022-12-21 | Sika Technology AG | Silangruppen-haltiges polymer |
| DE102021107569A1 (de) | 2021-03-25 | 2022-09-29 | Franken Systems Gmbh | 2-Komponenten-Beschichtungszusammensetzung zur Bauwerksabdichtung mit Katalysator-Cokatalysator-System |
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| US4645816A (en) * | 1985-06-28 | 1987-02-24 | Union Carbide Corporation | Novel vulcanizable silane-terminated polyurethane polymers |
| US5068304A (en) * | 1988-12-09 | 1991-11-26 | Asahi Glass Company, Ltd. | Moisture-curable resin composition |
| JPH0749576B2 (ja) * | 1989-10-20 | 1995-05-31 | アドコ・プロダクツ・インコーポレーテッド | 水分にて硬化可能な一剤式シーリング材組成物 |
| DE4237468A1 (de) * | 1992-11-06 | 1994-05-11 | Bayer Ag | Alkoxysilan- und Aminogruppen aufweisende Verbindungen |
| JP2594024B2 (ja) * | 1994-04-08 | 1997-03-26 | オーエスアイ・スペシヤルテイーズ・インコーポレーテツド | アリールアミノシラン末端キヤツプドウレタンのシーラント |
| DE19619538A1 (de) * | 1996-05-15 | 1997-11-20 | Bayer Ag | Alkoxysilan- und Hydantoingruppen aufweisende Polyurethanprepolymere, ein Verfahren zu ihrer Herstellung sowie ihre Verwendung zur Herstellung von Dichtstoffen |
| US6001946A (en) * | 1996-09-23 | 1999-12-14 | Witco Corporation | Curable silane-encapped compositions having improved performances |
| US6265517B1 (en) * | 1999-09-07 | 2001-07-24 | Bostik, Inc. | Silylated polyether sealant |
-
1998
- 1998-10-29 DE DE19849817A patent/DE19849817A1/de not_active Withdrawn
-
1999
- 1999-10-18 DE DE59906898T patent/DE59906898D1/de not_active Expired - Lifetime
- 1999-10-18 WO PCT/EP1999/007883 patent/WO2000026271A1/de not_active Ceased
- 1999-10-18 CZ CZ20011504A patent/CZ295160B6/cs not_active IP Right Cessation
- 1999-10-18 CN CNB998127841A patent/CN1146609C/zh not_active Expired - Fee Related
- 1999-10-18 AT AT99971433T patent/ATE248872T1/de active
- 1999-10-18 EP EP99971433A patent/EP1124872B1/de not_active Expired - Lifetime
- 1999-10-18 AU AU11523/00A patent/AU743227B2/en not_active Ceased
- 1999-10-18 PT PT99971433T patent/PT1124872E/pt unknown
- 1999-10-18 US US09/830,307 patent/US6545087B1/en not_active Expired - Lifetime
- 1999-10-18 JP JP2000579654A patent/JP4616992B2/ja not_active Expired - Lifetime
- 1999-10-18 CA CA002348566A patent/CA2348566C/en not_active Expired - Fee Related
- 1999-10-18 DK DK99971433T patent/DK1124872T3/da active
- 1999-10-18 HK HK02103792.2A patent/HK1042101B/zh not_active IP Right Cessation
- 1999-10-18 KR KR1020017005392A patent/KR100547526B1/ko not_active Expired - Fee Related
- 1999-10-18 PL PL99347426A patent/PL347426A1/xx not_active Application Discontinuation
- 1999-10-18 ES ES99971433T patent/ES2212678T3/es not_active Expired - Lifetime
- 1999-10-28 TW TW088118634A patent/TWI240726B/zh not_active IP Right Cessation
-
2001
- 2001-04-25 NO NO20012033A patent/NO20012033D0/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| NO20012033L (no) | 2001-04-25 |
| HK1042101B (zh) | 2005-02-18 |
| CZ20011504A3 (cs) | 2001-08-15 |
| AU1152300A (en) | 2000-05-22 |
| ATE248872T1 (de) | 2003-09-15 |
| ES2212678T3 (es) | 2004-07-16 |
| DK1124872T3 (da) | 2003-12-08 |
| AU743227B2 (en) | 2002-01-24 |
| US6545087B1 (en) | 2003-04-08 |
| CA2348566C (en) | 2008-04-29 |
| CN1146609C (zh) | 2004-04-21 |
| CZ295160B6 (cs) | 2005-06-15 |
| NO20012033D0 (no) | 2001-04-25 |
| PL347426A1 (en) | 2002-04-08 |
| JP2002528612A (ja) | 2002-09-03 |
| EP1124872B1 (de) | 2003-09-03 |
| DE19849817A1 (de) | 2000-05-04 |
| HK1042101A1 (en) | 2002-08-02 |
| KR100547526B1 (ko) | 2006-01-31 |
| JP4616992B2 (ja) | 2011-01-19 |
| EP1124872A1 (de) | 2001-08-22 |
| DE59906898D1 (de) | 2003-10-09 |
| CN1325413A (zh) | 2001-12-05 |
| PT1124872E (pt) | 2003-12-31 |
| CA2348566A1 (en) | 2000-05-11 |
| WO2000026271A1 (de) | 2000-05-11 |
| KR20010075668A (ko) | 2001-08-09 |
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| MM4A | Annulment or lapse of patent due to non-payment of fees |