DK3202816T3 - Alkoxysilylholdige klæbetætningsstoffer med forbedret rivestyrke - Google Patents
Alkoxysilylholdige klæbetætningsstoffer med forbedret rivestyrke Download PDFInfo
- Publication number
- DK3202816T3 DK3202816T3 DK16154170.1T DK16154170T DK3202816T3 DK 3202816 T3 DK3202816 T3 DK 3202816T3 DK 16154170 T DK16154170 T DK 16154170T DK 3202816 T3 DK3202816 T3 DK 3202816T3
- Authority
- DK
- Denmark
- Prior art keywords
- group
- groups
- alkoxysilyl
- anhydride
- formula
- Prior art date
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- 239000000853 adhesive Substances 0.000 title claims description 24
- 230000001070 adhesive effect Effects 0.000 title claims description 24
- 239000000203 mixture Substances 0.000 claims description 122
- -1 methyl - Chemical class 0.000 claims description 109
- 238000000034 method Methods 0.000 claims description 106
- 229920000642 polymer Polymers 0.000 claims description 88
- 229920000570 polyether Polymers 0.000 claims description 69
- 125000005370 alkoxysilyl group Chemical group 0.000 claims description 65
- 150000001875 compounds Chemical class 0.000 claims description 54
- 239000012634 fragment Substances 0.000 claims description 51
- 239000007858 starting material Substances 0.000 claims description 50
- 125000004432 carbon atom Chemical group C* 0.000 claims description 46
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 44
- 230000008569 process Effects 0.000 claims description 43
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- 125000002947 alkylene group Chemical group 0.000 claims description 34
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- 239000000178 monomer Substances 0.000 claims description 26
- 125000005442 diisocyanate group Chemical group 0.000 claims description 24
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 21
- 239000000126 substance Substances 0.000 claims description 20
- 239000000758 substrate Substances 0.000 claims description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
- 150000001298 alcohols Chemical class 0.000 claims description 18
- 125000003118 aryl group Chemical group 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 16
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 14
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- 150000008064 anhydrides Chemical class 0.000 claims description 11
- 238000009826 distribution Methods 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
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- 239000000565 sealant Substances 0.000 claims description 11
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- 229910052710 silicon Inorganic materials 0.000 claims description 10
- YPIFGDQKSSMYHQ-UHFFFAOYSA-N 7,7-dimethyloctanoic acid Chemical compound CC(C)(C)CCCCCC(O)=O YPIFGDQKSSMYHQ-UHFFFAOYSA-N 0.000 claims description 9
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- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 9
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 8
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 8
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 8
- 125000000853 cresyl group Chemical group C1(=CC=C(C=C1)C)* 0.000 claims description 8
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 8
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- 238000002360 preparation method Methods 0.000 claims description 8
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 229940014800 succinic anhydride Drugs 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 239000011248 coating agent Substances 0.000 claims description 6
- 238000000576 coating method Methods 0.000 claims description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
- 238000007789 sealing Methods 0.000 claims description 6
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 claims description 5
- MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 claims description 5
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 claims description 5
- 125000001118 alkylidene group Chemical group 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- OFNISBHGPNMTMS-UHFFFAOYSA-N 3-methylideneoxolane-2,5-dione Chemical compound C=C1CC(=O)OC1=O OFNISBHGPNMTMS-UHFFFAOYSA-N 0.000 claims description 4
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 claims description 4
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 125000004398 2-methyl-2-butyl group Chemical group CC(C)(CC)* 0.000 claims description 3
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 claims description 3
- 125000004917 3-methyl-2-butyl group Chemical group CC(C(C)*)C 0.000 claims description 3
- AYKYXWQEBUNJCN-UHFFFAOYSA-N 3-methylfuran-2,5-dione Chemical compound CC1=CC(=O)OC1=O AYKYXWQEBUNJCN-UHFFFAOYSA-N 0.000 claims description 3
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000000524 functional group Chemical group 0.000 claims description 3
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- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 238000010348 incorporation Methods 0.000 claims description 3
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 3
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- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 230000003014 reinforcing effect Effects 0.000 claims description 3
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 2
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- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
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- NBJODVYWAQLZOC-UHFFFAOYSA-L [dibutyl(octanoyloxy)stannyl] octanoate Chemical compound CCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCC NBJODVYWAQLZOC-UHFFFAOYSA-L 0.000 description 1
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- SPTWMADJBWWWPW-UHFFFAOYSA-N methyl(3-trimethoxysilylpropyl)carbamic acid Chemical compound CO[Si](OC)(OC)CCCN(C)C(O)=O SPTWMADJBWWWPW-UHFFFAOYSA-N 0.000 description 1
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- QQWAKSKPSOFJFF-UHFFFAOYSA-N oxiran-2-ylmethyl 2,2-dimethyloctanoate Chemical compound CCCCCCC(C)(C)C(=O)OCC1CO1 QQWAKSKPSOFJFF-UHFFFAOYSA-N 0.000 description 1
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- UKODFQOELJFMII-UHFFFAOYSA-N pentamethyldiethylenetriamine Chemical compound CN(C)CCN(C)CCN(C)C UKODFQOELJFMII-UHFFFAOYSA-N 0.000 description 1
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- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical class O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
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- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical class [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 1
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
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- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- WOZZOSDBXABUFO-UHFFFAOYSA-N tri(butan-2-yloxy)alumane Chemical compound [Al+3].CCC(C)[O-].CCC(C)[O-].CCC(C)[O-] WOZZOSDBXABUFO-UHFFFAOYSA-N 0.000 description 1
- 125000005369 trialkoxysilyl group Chemical group 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- DNOKYIVCEOPUSL-UHFFFAOYSA-N triethoxy-[6-(oxiran-2-ylmethoxy)hexyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCCCCOCC1CO1 DNOKYIVCEOPUSL-UHFFFAOYSA-N 0.000 description 1
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 description 1
- NYGMEPURWGJPNA-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)hexyl]silane Chemical compound CO[Si](OC)(OC)CCC(CCC)OCC1CO1 NYGMEPURWGJPNA-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- UKRDPEFKFJNXQM-UHFFFAOYSA-N vinylsilane Chemical class [SiH3]C=C UKRDPEFKFJNXQM-UHFFFAOYSA-N 0.000 description 1
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- 238000003466 welding Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- NHXVNEDMKGDNPR-UHFFFAOYSA-N zinc;pentane-2,4-dione Chemical compound [Zn+2].CC(=O)[CH-]C(C)=O.CC(=O)[CH-]C(C)=O NHXVNEDMKGDNPR-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
- C08G18/50—Polyethers having heteroatoms other than oxygen
- C08G18/5096—Polyethers having heteroatoms other than oxygen 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
- 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
- C08G18/2805—Compounds having only one group containing active hydrogen
- 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
-
- 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
-
- 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
- C08G18/4829—Polyethers containing at least three 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
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
- C08G18/751—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring
- C08G18/752—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group
- C08G18/753—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group
- C08G18/755—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate
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- C08G65/32—Polymers modified by chemical after-treatment
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- C08G65/33348—Polymers modified by chemical after-treatment with organic compounds containing nitrogen containing isocyanate group
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Claims (15)
1. Alkoxysilyl-modificerede polymerer med formel (I) MiDjURuAPv formel (I) idet fragmenterne M og D ikke er forbundet indbyrdes, men derimod via grupperne UR og/eller AP, og grupperne UR og AP ikke er forbundet indbyrdes, men derimod på tilsvarende måde via fragmenterne M og D, og det for indicierne gælder: i = 1 til 2, fortrinsvis større end 1 til 2, særligt foretrukket 2, j = 1 til 10, fortrinsvis 1 til 8, særligt foretrukket 2 til 6, fortrinsvis foretrukket > 1, u = 0 til 11, fortrinsvis 1 til 8, mere foretrukket 2 til 6, navnlig 2 til 4, v = 0 til 6, fortrinsvis større end 0 til 4, navnlig 0,1 til 2, på den betingelse at u + v > 1, idet M uafhængigt af hinanden er en alkoxysilyl-modificeret polyethergruppe, fortrinsvis med 8 til 400 carbonatomer, M særligt foretrukket er en gruppe med formel (la) , idet
Formel (la) med a = 0,1 til 100, fortrinsvis 0,5 til 50, mere foretrukket 1 til 10, særligt foretrukket større end 1 til 5, b = 2 til 1.000, fortrinsvis 2 til 500, mere foretrukket større end 2 til 400, særligt foretrukket 10 til 100, c = 0 til 200, fortrinsvis 0 til 100, mere foretrukket større end 0 til 80, særligt foretrukket > 0 til 50, d = 0 til 200, fortrinsvis 0 til 100, mere foretrukket større end 0 til 80, særligt foretrukket > 0 til 50, w = 0 til 200, fortrinsvis 0 til 100, mere foretrukket større
end O til 80, særligt foretrukket > 0 til 50, y = 0 til 500, fortrinsvis 0 til 300, særligt foretrukket 0 til 200 og særligt foretrukket > 0 til 100, e = 1 til 10, f = 0 til 2, g = 1 til 3, på den betingelse at g + f = 3, h = 0 til 10, fortrinsvis 1 til 6, særligt foretrukket 1, 2 eller 3, på den betingelse at grupperne med indicierne a, b, c, d, w og y frit kan permuteres via molekylekæden, idet grupperne med indicierne w og y hver især ikke må følge efter sig selv eller efter de respektive andre grupper, og på den betingelse at de forskellige monomerenheder i både fragmenterne med indicierne a, b, c, d, w og y og den i givet fald eksisterende polyoxyalkylenkæde i substituenten RI indbyrdes kan være opbygget blokvist, idet enkelte blokke også kan forekomme flere gange og indbyrdes kan være statistisk fordelte, men dog er underlagt en statistisk fordeling og endvidere skal placeres, så de indbyrdes frit kan permuteres ud fra en vilkårlig rækkefølge, med den begrænsning at grupperne med indicierne w og y hver især ikke må følge efter sig selv eller de respektive andre grupper, og R1 = uafhængigt af hinanden er en mættet eller umættet, lineær eller forgrenet organisk carbonhydridgruppe, der som heteroatomer kan indeholde O, S og/eller N, carbonhydridgruppen fortrinsvis indeholder 1 til 400 carbonatomer, fortrinsvis 2, 3 eller 4 til 200 carbonatomer, R2 = uafhængigt af hinanden en alkylgruppe med 1 til 8 carbonatomer, navnlig methyl-, ethyl-, propyl-, eller isopropyl-, R3 = uafhængigt af hinanden en alkylgruppe med 1 til 8 carbonatomer, navnlig methyl-, ethyl-, propyl- eller isopropyl-, R4 = uafhængigt af hinanden en hydrogenradikal, en alkylgruppe med 1 til 20 carbonatomer, en aryl- eller alkarylgruppe, fortrinsvis hydrogen, methyl-, ethyl-, octyl-, decyl-, dodecyl-, phenyl-, benzyl-, særligt foretrukket hydrogen, methyl- eller ethyl-, R5 = uafhængigt af hinanden en hydrogenradikal eller en alkylgruppe med 1 til 8 carbonatomer, fortrinsvis hydrogen, methyl- eller ethyl-, særligt foretrukket hydrogen, eller R4 og en af grupperne R5 i fællesskab kan danne en ring, som inkluderer de atomer, som R4 og R5 er bundet til, fortrinsvis indeholder denne ring 5 til 8 carbonatomer, R6 og R7 = uafhængigt af hinanden en hydrogenradikal, en alkylgruppe med 1 til 20 carbonatomer, en aryl- eller alkarylgruppe og/eller en alkoxygruppe, fortrinsvis en methylgruppe, R11 = uafhængigt af hinanden en mættet eller umættet, alifatisk eller aromatisk carbonhydridgruppe med 2 til 30 C-atomer, navnlig til 24 C-atomer, som i givet fald er substitueret, fortrinsvis drejer det sig om en alkylgruppe med 1 til 16 carbonatomer, særligt foretrukket med 6 til 12 carbonatomer, hvis kæde kan være afbrudt af oxygen og kan bære yderligere funktionelle grupper som f.eks. carboxylgrupper i givet fald foresteret med alkoholer som f.eks. methanol, ethanol, propanol, butanol eller hexanol, hydroxygrupper i givet fald foresteret med syrer, såsom eddikesyre, smørsyre, neodecansyre eller (meth)acrylssyre eller polymerisaterne af (meth)acrylsyre, eller en arylgruppe med 6 til 20 carbonatomer eller en alkarylgruppe med 7 til 30, fortrinsvis 7 til 20 carbonatomer, fortrinsvis udvalgt af methyl-, ethyl-, propyl-, butyl-, iso-butyl-, tert-butyl-, 2-pentyl-, 3-pentyl-, 2-methylbutyl-, 3-methylbutyl-, 2-methyl-2-butyl-, 3-methyl-2-butyl-, 2,2-dimethylpropyl-, hexyl-, heptyl-, octyl-, 2-ethylhexyl-, 2-propylheptyl-, 2-butyloctanyl-, 2-methylundecyl-, 2-propylnonyl-, 2-ethyldecyl-, 2-pentylheptyl-, 2-hexyldecyl-, 2-butyltetradecyl-, 2-dodecylhexadecyl-, 2-tetradecyloctadecyl-, 3,5,5-trimethylhexyl-, isononanyl-, isotridecyl-, isomyristyl-, isostearyl-, 2-octyldodecyl-triphenylmethyl-, C(O)-(CH2)5-C-(CH3)3- (gruppe af neodecansyre), Ci2/Ci4-alkyl-, phenyl-, kresyl-, tert-butylphenyl- eller benzylgruppe, særligt foretrukket en 2-ethylhexyl-, C(O)-(CH2)5-C-(CH3)3- (gruppe af neodecansyre) , Ci2/Ci4-alkyl-, phenyl-, kresyl-, tert-butylphenylgruppe, ganske særligt foretrukket en tert-butylphenyl- eller 2-ethylhexylgruppe, R13, R14 = uafhængigt af hinanden hydrogen og/eller en organisk gruppe, fortrinsvis alkyl-, alkenyl-, alkyliden, alkoxy-, aryl-og/eller aralkylgrupper, eller i givet fald kan R13 og/eller R14 heller ikke være til stede, idet der, hvis R13 og R14 ikke er til stede, findes en C=C dobbeltbinding i stedet for grupperne R13 og R14, det omførende fragment Z kan være til stede eller ikke være til stede, er det omførende fragment Z ikke til stede, er R15 og R16 = uafhængigt af hinanden hydrogen og/eller en organisk gruppe, fortrinsvis alkyl-, alkenyl-, alkyliden, alkoxy-, aryl-og/eller aralkylgrupper, idet i det tilfælde, at en af grupperne R13 eller R14 ikke er til stede, den pågældende geminale gruppe (altså R15, hvis R13 ikke er til stede, og R16, hvis R14 ikke er til stede) en alkylidengruppe, fortrinsvis methyliden (=CH2), er det omførende fragment Z til stede, er R15 og R16 = carbonhydridgrupper, som er omført cycloalifatisk eller aromatisk via fragment Z, idet Z er en divalent alkylen- eller alkenylengruppe, som kan være substitueret yderligere, fragmentet med index y kan eksempelvis opnås ved hjælp af indbygning af cykliske anhydrider, foretrukne cykliske anhydrider er succinanhydrid, maleinsyreanhydrid, itaconanhydrid, glutaranhydrid, adipinanhydrid, citraconanhydrid, phthalsyreanhydrid, hexahydrophthalsyreanhydrid og trimellitanhydrid samt polyfunktionelle syreanhydrider som pyromellit-dianhydrid, benzophenon-3,3',4,4'-tetracarboxylsyredianhydrid, 1,2,3,4- butantetracarboxylsyredianhydrid eller radikalisk polymeriserede homo- eller copolymerisater af maleinsyreanhydrid med ethylen, isobutylene, acrylnitril, vinylacetat eller styren, særligt foretrukne anhydrider er succinanhydrid, maleinsyreanhydrid, itaconanhydrid, glutaranhydrid, adipinanhydrid, citraconanhydrid, phthalsyreanhydrid, hexahydrophthalsyreanhydrid, og idet det for fragmentet D gælder: D er en polyethergruppe -(DA)t_Dx med t lig med 2, idet Dx er en t-valent funktionel, mættet eller umættet, lineær eller forgrenet organisk carbonhydridgruppe, der som heteroatomer kan indeholde 0, S, Si og/eller N, idet hver af grupperne DA er bundet kovalent til gruppen Dx, fortrinsvis indeholder carbonhydridgruppen 8 til 1.500 carbonatomer, fortrinsvis er carbonkæden i carbonhydridgruppen afbrudt af oxygenatomer, fortrinsvis indeholder carbonhydridgruppen siliciumatom-holdige substituenter, fortrinsvis er de siliciumatom-holdige substituenter alkoxysilylgrupper, fortrinsvis er den af oxygenatomer afbrudte carbonhydridgruppe en polyoxyalkylengruppe, polyethergruppe og/eller polyetheralkoxygruppe, eller Dx kan være en en eller flere gange anelleret phenolisk gruppe, eller særligt foretrukket kan Dx være en t-valent gruppe af en t-gange hydroxyleret alkohol, polyetherol, polyesterol, siloxan, perfluoreret polyetherol eller (poly)-urethan, fortrinsvis OH-funktionelle polyethere, polyestere, polycarbonater, polyetherestere eller perfluorerede polyethere og blandingspolymerer heraf, særligt foretrukket OH-funktionelle polyethere eller polyestere, og idet DA er et fragment med formel (II)
Formel (II) med a til h, w og y, R2 til R16 og Z uafhængigt af hinanden defineret som i formel (la), på den betingelse at summen af alle indicier b i formlerne (la) og (II) giver i det mindste 5, fortrinsvis i det mindste 10, særligt foretrukket i det mindste 15, og summen af alle indicier a i formlerne (la) og (II) skal være større end 2,
UR er uafhængigt af hinanden ens eller forskellige divalente grupper af formen -U-Dc-U-, idet U er en -C(0)-NH-gruppe, som er bundet til Dc via nitrogenet, og Dc er uafhængigt af hinanden en divalent substitueret eller usubstitueret, lineær eller forgrenet, mættet eller umættet carbonhydridgruppe med 1 til 30 carbonatomer udvalgt af alkyl-, alkenyl-, aryl- eller alkarylgrupper, som i givet fald kan være afbrudt af heteroatomer som 0, N og/eller S, en aryl- eller alkarylgruppe, fortrinsvis er DC en divalent carbonhydridgruppe med 6-30 carbonatomer, særligt foretrukket er Dc lig med en isophorongruppe, AP er uafhængigt af hinanden ens eller forskellige grupper med de almene formler (Illa) eller (Hib)
Formel (Illa) Formel (IIIb)
2. Alkoxysilyl-modificerede polymerer ifølge krav 1, kendetegnet ved, at forholdet i formel (I) mellem indicierne a i fragmenterne M og D adlyder den følgende ligning: a (M) > 2 * a (D) .
3. Alkoxysilyl-modificerede polymerer ifølge krav 1 eller 2, kendetegnet ved, at det i formel (I) gælder, at 1 = 1 til 2, fortrinsvis større end 1 til 2, særligt foretrukket 2 j = 1 til 6, fortrinsvis 1, 2, 3 eller 4 u = j +1 v = 0,
idet M svarer til formel (la) med a = 0,1 til 50, fortrinsvis 0,5 til 20, yderligere foretrukket 1 til 4, b = 10 til 500, yderligere foretrukket 12 til 100 c = 0 til 20, fortrinsvis 0 til 4 d = 0 til 20, fortrinsvis 0 w = 0 til 20, fortrinsvis 0 y = 0 til 20, fortrinsvis 0, e = 1 til 10, f = 0 til 2 g = 1 til 3, på den betingelse at g + f = 3, samt h = 1, 2 eller 3, og idet D svarer til formel (II) med a = 0 til 10, fortrinsvis større end 0,1 til 5, yderligere foretrukket 0,2 til 2, særligt 0,25 til 1, b = 10 til 700, yderligere foretrukket 12 til 350, c = 0 til 20, fortrinsvis 0 til 10 d = 0 til 20, fortrinsvis 0 w = 0 til 20, fortrinsvis 0 y = 0 til 20, fortrinsvis 0, e = 1 til 10, f = 0 til 2 g = 1 til 3, på den betingelse at g + f = 3, samt h = 1, 2 eller 3, og idet definitionerne af de ikke eksplicit nævnte grupper gælder som defineret tidligere i krav 2, og idet det for UR gælder: UR er uafhængigt af hinanden ens eller forskellige divalente grupper af formen -U-Dc-U-, med Dc uafhængigt af hinanden en divalent substitueret eller usubstitueret, lineær eller forgrenet, mættet eller umættet carbonhydridgruppe med 1 til 30 carbonatomer, særligt foretrukket er Dc lig med en isophorongruppe.
4. Fremgangsmåde til fremstilling af de alkoxysilyl-modificerede polymerer ifølge krav 1 til 3, omfattende trinnene (1) omsætning af i det mindste en dihydroxy-funktionel starter (A) udvalgt af gruppen af alkoholerne eller polyetherolerne med i det mindste et alkylenoxid og i det mindste et epoxid bærende en alkoxysilylgruppe, (2) omsætning af i det mindste en monohydroxy-funktionel starter (B) udvalgt af gruppen af alkoholerne eller polyetherolerne med i det mindste et alkylenoxid og i det mindste et epoxid bærende en alkoxysilylgruppe, og (3) omsætning af produkterne fra fremgangsmådetrinnene (1) og (2) med i det mindste et diisocyanat og i givet fald yderligere reaktander.
5. Fremgangsmåde ifølge krav 4 kendetegnet ved, at fremgangsmådetrin (3) gennemføres i to trin, idet det i det første trin (3a) først er alkoxyleringsproduktet H-D-H fra fremgangsmådetrin (1), som bringes således til reaktion med et diisocyanat, at der dannes et NCO-funktionelt intermediat, som efterfølgende omsættes i det andet trin (3b) med det monohydroxy-funktionelle alkoxyleringsprodukt H-M fra fremgangsmådetrin (2) til den endelige polymer.
6. Fremgangsmåde ifølge et af kravene 4 og 5, kendetegnet ved, at der i fremgangsmådetrin (3) i det andet trin (3b) ud over alkoxysilyl-modificerede monohydroxy-funktionelle alkoxyleringsprodukter H-M også anvendes ikke-alkoxysilyl-modificerede forbindelser H-M.
7. Fremgangsmåde ifølge et af kravene 4 til 6 til fremstilling af alkoxysilyl-modificerede polymerer ifølge formel (I), kendetegnet ved, at der i trinnene (1) og (2) omsættes i det mindste en forbindelse med den almene formel (V) Formel (V) med f, g, h, R2 og R3 ifølge formel (la) og (II) og i det mindste et alkylenoxid, fortrinsvis propylenoxid, og i givet fald ethylenoxid.
8. Fremgangsmåde ifølge et af kravene 4 til 7, kendetegnet
ved, at den dihydroxy-funktionelle starter fra fremgangsmådetrin (1) er udvalgt af polyetheroler, polycarbonatpolyoler og polyethercarbonater, og den monohydroxy-funktionelle starter fra fremgangsmådetrin (2) fortrinsvis er udvalgt af butanol, ethanol eller polyetherol.
9. Fremgangsmåde ifølge et af kravene 4 til 8, kendetegnet ved, at der i fremgangsmådetrin (3) anvendes isophorondiisocyanat som diisocyanat.
10. Fremgangsmåde ifølge et af kravene 4 til 9 til fremstilling af alkoxysilyl-modificerede polymerer med forbedret rivestyrke.
11. Hærdelig sammensætning indeholdende i det mindste en alkoxysilyl-modificeret polymer ifølge krav 1 til 3, fortrinsvis fremstillet ifølge en fremgangsmåde ifølge et af kravene 4 til 10, og i det mindste en hærdningskatalysator.
12. Hærdelig sammensætning ifølge krav 11, kendetegnet ved, at sammensætningen endvidere indeholder et eller flere vedhæftningsmidler og/eller et eller flere kemiske fugt-tørremidler, idet der som vedhæftningsmiddel fortrinsvis er indeholdt 3-aminopropyltriethoxysilan, 3-aminopropyltrimethoxysilan, N-(2-aminoethyl)-3-aminopropyltrimethoxysilan eller oligomere amino/alkyl-alkoxysilaner og som kemisk fugt-tørremiddel fortrinsvis anvendes vinyltriethoxysilan eller vinyltrimethoxysilan.
13. Anvendelse af sammensætninger ifølge krav 11 og/eller 12 til klæbe- og/eller tætningsmiddelanvendelser.
14. Anvendelse af alkoxysilyl-modificerede polymerer ifølge krav 1 til 3 til forstærkning, nivellering, modifikation, sammenklæbning, tætning og/eller belægning af substrater.
15. Anvendelse af alkoxysilyl-modificerede polymerer ifølge krav 1 til 3, navnlig ifølge krav 2, i hærdelige sammensætninger, fortrinsvis ifølge krav 11 eller 12 til forbedring af rivestyrken .
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| DK16154170.1T DK3202816T3 (da) | 2016-02-04 | 2016-02-04 | Alkoxysilylholdige klæbetætningsstoffer med forbedret rivestyrke |
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| US (1) | US10087278B2 (da) |
| EP (1) | EP3202816B1 (da) |
| JP (1) | JP2017206673A (da) |
| CN (1) | CN107099027B (da) |
| CA (1) | CA2957108A1 (da) |
| DK (1) | DK3202816T3 (da) |
| ES (1) | ES2703012T3 (da) |
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| EP3461864B1 (de) | 2017-09-28 | 2025-10-29 | Evonik Operations GmbH | Härtbare zusammensetzung auf basis von polysiloxanen |
| EP3467006B1 (de) | 2017-10-09 | 2022-11-30 | Evonik Operations GmbH | Mischungen zyklischer-verzweigter siloxane vom d/t-typ und deren folgeprodukte |
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| EP3611215A1 (de) | 2018-08-15 | 2020-02-19 | Evonik Operations GmbH | Verfahren zur herstellung acetoxygruppen-tragender siloxane |
| CA3116908C (en) | 2018-11-02 | 2025-03-18 | H.B. Fuller Company | HUMIDITY-CURABLE THERMAL SEALANT COMPOSITION |
| US10968371B2 (en) | 2018-11-02 | 2021-04-06 | H.B. Fuller Company | Moisture curable hot melt sealant composition including silane functional polyurethane |
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| EP3744774B1 (de) | 2019-05-28 | 2021-09-01 | Evonik Operations GmbH | Verfahren zum recycling von silikonen |
| EP3744753B1 (de) | 2019-05-28 | 2022-04-06 | Evonik Operations GmbH | Verfahren zur aufreinigung von acetoxysiloxanen |
| PL3744762T3 (pl) | 2019-05-28 | 2025-03-31 | Evonik Operations Gmbh | Sposób wytwarzania polimerów blokowych polioksyalkilen-polisiloksan |
| ES2986717T3 (es) | 2019-05-28 | 2024-11-12 | Evonik Operations Gmbh | Procedimiento para la producción de polietersiloxanos enlazados a SiOC ramificados en la parte de siloxano |
| ES2988517T3 (es) | 2019-05-28 | 2024-11-20 | Evonik Operations Gmbh | Sistemas acetoxi |
| EP3744745A1 (de) | 2019-05-28 | 2020-12-02 | Evonik Operations GmbH | Herstellung von pu-schaumstoffen |
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| DE112023002011T5 (de) * | 2022-04-22 | 2025-02-20 | AGC Inc. | Aushärtbare zusammensetzung und ausgehärtetes produkt |
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| US12435514B2 (en) | 2023-06-06 | 2025-10-07 | Bmic Llc | Adhesive-less roofing systems and related methods |
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| DE69831518T2 (de) | 1997-04-21 | 2006-06-22 | Asahi Glass Co., Ltd. | Bei Raumtemperatur härtende Zusammensetzung |
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| DE102009028636A1 (de) * | 2009-08-19 | 2011-02-24 | Evonik Goldschmidt Gmbh | Neuartige Urethangruppen enthaltende silylierte Präpolymere und Verfahren zu deren Herstellung |
| US8822606B2 (en) | 2010-06-30 | 2014-09-02 | Dow Global Technologies Llc | Low viscosity silyl-terminated polymers |
| DE102010038774A1 (de) * | 2010-08-02 | 2012-02-02 | Evonik Goldschmidt Gmbh | Modifizierte Alkoxylierungsprodukte, die zumindest eine nicht-terminale Alkoxysilylgruppe aufweisen, mit erhöhter Lagerstabilität und erhöhter Dehnbarkeit der unter deren Verwendung hergestellten Polymere |
| DE102010038768A1 (de) | 2010-08-02 | 2012-02-02 | Evonik Goldschmidt Gmbh | Modifizierte Alkoxylierungsprodukte mit mindestens einer nicht-terminalen Alkoxysilylgruppe mit erhöhter Lagerstabilität und erhöhter Dehnbarkeit der unter deren Verwendung hergestellten Polymere |
| DE102012203737A1 (de) | 2012-03-09 | 2013-09-12 | Evonik Goldschmidt Gmbh | Modifizierte Alkoxylierungsprodukte, die zumindest eine nicht-terminale Alkoxysilylgruppe aufweisen und mehrere Urethangruppen enthalten und deren Verwendung |
| DE102013206883A1 (de) * | 2013-04-17 | 2014-10-23 | Evonik Industries Ag | Alkoxysilylhaltige Klebdichtstoffe mit intrinsisch reduzierter Viskosität |
| DE102013216751A1 (de) | 2013-08-23 | 2015-02-26 | Evonik Industries Ag | Modifizierte Alkoxylierungsprodukte, die Alkoxysilylgruppen aufweisen und Urethangruppen enthalten und deren Verwendung |
| DE102013224708A1 (de) | 2013-12-03 | 2015-06-03 | Evonik Industries Ag | Alkoxysilylhaltige Klebdichtstoffe mit intrinsisch reduzierter Viskosität |
-
2016
- 2016-02-04 DK DK16154170.1T patent/DK3202816T3/da active
- 2016-02-04 ES ES16154170T patent/ES2703012T3/es active Active
- 2016-02-04 EP EP16154170.1A patent/EP3202816B1/de active Active
- 2016-12-30 US US15/395,449 patent/US10087278B2/en active Active
-
2017
- 2017-02-02 CA CA2957108A patent/CA2957108A1/en not_active Abandoned
- 2017-02-03 JP JP2017018252A patent/JP2017206673A/ja active Pending
- 2017-02-03 CN CN201710063513.0A patent/CN107099027B/zh not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US10087278B2 (en) | 2018-10-02 |
| CA2957108A1 (en) | 2017-08-04 |
| CN107099027A (zh) | 2017-08-29 |
| EP3202816B1 (de) | 2018-09-19 |
| CN107099027B (zh) | 2021-07-13 |
| JP2017206673A (ja) | 2017-11-24 |
| US20170226285A1 (en) | 2017-08-10 |
| EP3202816A1 (de) | 2017-08-09 |
| ES2703012T3 (es) | 2019-03-06 |
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