EP3841137A1 - Déshydratant pour compositions durcissant à l'humidité - Google Patents
Déshydratant pour compositions durcissant à l'humiditéInfo
- Publication number
- EP3841137A1 EP3841137A1 EP19752526.4A EP19752526A EP3841137A1 EP 3841137 A1 EP3841137 A1 EP 3841137A1 EP 19752526 A EP19752526 A EP 19752526A EP 3841137 A1 EP3841137 A1 EP 3841137A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- nco
- moisture
- reactive
- polymer
- weight
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 215
- 239000002274 desiccant Substances 0.000 title claims abstract description 36
- 238000013008 moisture curing Methods 0.000 title claims description 86
- 229920000642 polymer Polymers 0.000 claims abstract description 103
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 62
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 62
- 229920013730 reactive polymer Polymers 0.000 claims abstract description 48
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims abstract description 29
- 238000000034 method Methods 0.000 claims abstract description 25
- 239000000565 sealant Substances 0.000 claims abstract description 18
- 229910000077 silane Inorganic materials 0.000 claims abstract description 18
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 17
- 239000011248 coating agent Substances 0.000 claims abstract description 13
- 239000004839 Moisture curing adhesive Substances 0.000 claims abstract description 5
- 229920005862 polyol Polymers 0.000 claims description 43
- 150000003077 polyols Chemical group 0.000 claims description 43
- 239000003054 catalyst Substances 0.000 claims description 42
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 41
- 239000000945 filler Substances 0.000 claims description 34
- 238000006243 chemical reaction Methods 0.000 claims description 27
- 239000004014 plasticizer Substances 0.000 claims description 23
- 238000004132 cross linking Methods 0.000 claims description 22
- 150000004756 silanes Chemical class 0.000 claims description 22
- 239000002318 adhesion promoter Substances 0.000 claims description 19
- 150000001875 compounds Chemical class 0.000 claims description 19
- 239000000853 adhesive Substances 0.000 claims description 18
- 230000001070 adhesive effect Effects 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 14
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 13
- 238000004519 manufacturing process Methods 0.000 claims description 13
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 12
- 238000000576 coating method Methods 0.000 claims description 10
- 239000000463 material Substances 0.000 claims description 9
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 5
- 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 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 229940008841 1,6-hexamethylene diisocyanate Drugs 0.000 claims description 3
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 3
- VNMOIBZLSJDQEO-UHFFFAOYSA-N 1,10-diisocyanatodecane Chemical compound O=C=NCCCCCCCCCCN=C=O VNMOIBZLSJDQEO-UHFFFAOYSA-N 0.000 claims description 2
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 claims description 2
- AZYRZNIYJDKRHO-UHFFFAOYSA-N 1,3-bis(2-isocyanatopropan-2-yl)benzene Chemical compound O=C=NC(C)(C)C1=CC=CC(C(C)(C)N=C=O)=C1 AZYRZNIYJDKRHO-UHFFFAOYSA-N 0.000 claims description 2
- WZZDGHUQRSGHLQ-UHFFFAOYSA-N 1,3-diisocyanato-5,7-dimethyladamantane Chemical compound C1C(C2)(C)CC3(N=C=O)CC1(C)CC2(N=C=O)C3 WZZDGHUQRSGHLQ-UHFFFAOYSA-N 0.000 claims description 2
- MLXLDKWQJYBKOH-UHFFFAOYSA-N 1,3-diisocyanatoadamantane Chemical compound C1C(C2)CC3CC1(N=C=O)CC2(N=C=O)C3 MLXLDKWQJYBKOH-UHFFFAOYSA-N 0.000 claims description 2
- AGJCSCSSMFRMFQ-UHFFFAOYSA-N 1,4-bis(2-isocyanatopropan-2-yl)benzene Chemical compound O=C=NC(C)(C)C1=CC=C(C(C)(C)N=C=O)C=C1 AGJCSCSSMFRMFQ-UHFFFAOYSA-N 0.000 claims description 2
- OVBFMUAFNIIQAL-UHFFFAOYSA-N 1,4-diisocyanatobutane Chemical compound O=C=NCCCCN=C=O OVBFMUAFNIIQAL-UHFFFAOYSA-N 0.000 claims description 2
- CDMDQYCEEKCBGR-UHFFFAOYSA-N 1,4-diisocyanatocyclohexane Chemical compound O=C=NC1CCC(N=C=O)CC1 CDMDQYCEEKCBGR-UHFFFAOYSA-N 0.000 claims description 2
- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 claims description 2
- DFPJRUKWEPYFJT-UHFFFAOYSA-N 1,5-diisocyanatopentane Chemical compound O=C=NCCCCCN=C=O DFPJRUKWEPYFJT-UHFFFAOYSA-N 0.000 claims description 2
- WXIOQJUEBPUFHH-UHFFFAOYSA-N 1-isocyanato-4-(2-isocyanatopropan-2-yl)-1-methylcyclohexane Chemical compound O=C=NC(C)(C)C1CCC(C)(N=C=O)CC1 WXIOQJUEBPUFHH-UHFFFAOYSA-N 0.000 claims description 2
- ZDKYYMRLZONTFK-UHFFFAOYSA-N 3,4-bis(isocyanatomethyl)bicyclo[2.2.1]heptane Chemical compound C1CC2(CN=C=O)C(CN=C=O)CC1C2 ZDKYYMRLZONTFK-UHFFFAOYSA-N 0.000 claims description 2
- 239000000654 additive Substances 0.000 claims description 2
- 230000000996 additive effect Effects 0.000 claims description 2
- NRYUXUHIGUILJE-UHFFFAOYSA-N bis[4-(2-isocyanatopropan-2-yl)phenyl] carbonate Chemical compound C1=CC(C(C)(N=C=O)C)=CC=C1OC(=O)OC1=CC=C(C(C)(C)N=C=O)C=C1 NRYUXUHIGUILJE-UHFFFAOYSA-N 0.000 claims description 2
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- 125000006736 (C6-C20) aryl group Chemical group 0.000 claims 1
- OHTRJOZKRSVAOX-UHFFFAOYSA-N 1,3-diisocyanato-2-methylcyclohexane Chemical compound CC1C(N=C=O)CCCC1N=C=O OHTRJOZKRSVAOX-UHFFFAOYSA-N 0.000 claims 1
- OHLKMGYGBHFODF-UHFFFAOYSA-N 1,4-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=C(CN=C=O)C=C1 OHLKMGYGBHFODF-UHFFFAOYSA-N 0.000 claims 1
- ROHUXHMNZLHBSF-UHFFFAOYSA-N 1,4-bis(isocyanatomethyl)cyclohexane Chemical compound O=C=NCC1CCC(CN=C=O)CC1 ROHUXHMNZLHBSF-UHFFFAOYSA-N 0.000 claims 1
- MZEGJNMYXWIQFF-UHFFFAOYSA-N 2,5-diisocyanato-1,1,3-trimethylcyclohexane Chemical compound CC1CC(N=C=O)CC(C)(C)C1N=C=O MZEGJNMYXWIQFF-UHFFFAOYSA-N 0.000 claims 1
- 239000007822 coupling agent Substances 0.000 claims 1
- -1 polyoxypropylene Polymers 0.000 description 52
- 229920001002 functional polymer Polymers 0.000 description 29
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical group [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 22
- 125000005442 diisocyanate group Chemical group 0.000 description 17
- 150000002009 diols Chemical class 0.000 description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 14
- 229920000570 polyether Polymers 0.000 description 14
- 229920001451 polypropylene glycol Polymers 0.000 description 14
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 13
- 238000002360 preparation method Methods 0.000 description 13
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 12
- 230000008569 process Effects 0.000 description 12
- 238000003860 storage Methods 0.000 description 12
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 11
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 10
- 239000011230 binding agent Substances 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 10
- 229910052710 silicon Inorganic materials 0.000 description 10
- 239000004721 Polyphenylene oxide Substances 0.000 description 9
- 235000014113 dietary fatty acids Nutrition 0.000 description 9
- 239000000194 fatty acid Substances 0.000 description 9
- 229930195729 fatty acid Natural products 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 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 8
- 239000003921 oil Substances 0.000 description 8
- 235000019198 oils Nutrition 0.000 description 8
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 150000004702 methyl esters Chemical class 0.000 description 7
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 7
- 229920000515 polycarbonate Polymers 0.000 description 7
- 239000004417 polycarbonate Substances 0.000 description 7
- 229920005989 resin Polymers 0.000 description 7
- 239000011347 resin Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 150000003672 ureas Chemical class 0.000 description 7
- 239000010457 zeolite Substances 0.000 description 7
- 150000001343 alkyl silanes Chemical class 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- 239000012528 membrane Substances 0.000 description 6
- UKRDPEFKFJNXQM-UHFFFAOYSA-N vinylsilane Chemical class [SiH3]C=C UKRDPEFKFJNXQM-UHFFFAOYSA-N 0.000 description 6
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 229920001577 copolymer Polymers 0.000 description 5
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 description 5
- 239000003925 fat Substances 0.000 description 5
- 239000000835 fiber Substances 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- 229920005906 polyester polyol Polymers 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- 150000003505 terpenes Chemical class 0.000 description 5
- 235000007586 terpenes Nutrition 0.000 description 5
- ZYAASQNKCWTPKI-UHFFFAOYSA-N 3-[dimethoxy(methyl)silyl]propan-1-amine Chemical compound CO[Si](C)(OC)CCCN ZYAASQNKCWTPKI-UHFFFAOYSA-N 0.000 description 4
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 4
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- 235000019484 Rapeseed oil Nutrition 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 4
- 150000001409 amidines Chemical class 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- 238000006555 catalytic reaction Methods 0.000 description 4
- 239000004927 clay Substances 0.000 description 4
- 238000001723 curing Methods 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 4
- 150000004665 fatty acids Chemical class 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 239000012948 isocyanate Substances 0.000 description 4
- 150000002513 isocyanates Chemical class 0.000 description 4
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 4
- 229920000728 polyester Polymers 0.000 description 4
- 230000009257 reactivity Effects 0.000 description 4
- 150000004072 triols Chemical class 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000006087 Silane Coupling Agent Substances 0.000 description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 3
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 3
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 238000006482 condensation reaction Methods 0.000 description 3
- 239000012975 dibutyltin dilaurate Substances 0.000 description 3
- HMNXRLQSCJJMBT-UHFFFAOYSA-N diethyl 2-aminobutanedioate Chemical compound CCOC(=O)CC(N)C(=O)OCC HMNXRLQSCJJMBT-UHFFFAOYSA-N 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 229910021485 fumed silica Inorganic materials 0.000 description 3
- 238000005227 gel permeation chromatography Methods 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 239000005011 phenolic resin Substances 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 229920000573 polyethylene Polymers 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 230000000379 polymerizing effect Effects 0.000 description 3
- 239000011148 porous material Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- OLAQBFHDYFMSAJ-UHFFFAOYSA-L 1,2-bis(7-methyloctyl)cyclohexane-1,2-dicarboxylate Chemical compound CC(C)CCCCCCC1(C([O-])=O)CCCCC1(CCCCCCC(C)C)C([O-])=O OLAQBFHDYFMSAJ-UHFFFAOYSA-L 0.000 description 2
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
- GRWFGVWFFZKLTI-IUCAKERBSA-N 1S,5S-(-)-alpha-Pinene Natural products CC1=CC[C@@H]2C(C)(C)[C@H]1C2 GRWFGVWFFZKLTI-IUCAKERBSA-N 0.000 description 2
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical class CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- 235000019482 Palm oil Nutrition 0.000 description 2
- 239000005062 Polybutadiene Substances 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 2
- 229910018540 Si C Inorganic materials 0.000 description 2
- 229910018557 Si O Inorganic materials 0.000 description 2
- 235000011941 Tilia x europaea Nutrition 0.000 description 2
- LCKIEQZJEYYRIY-UHFFFAOYSA-N Titanium ion Chemical compound [Ti+4] LCKIEQZJEYYRIY-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- 229920004482 WACKER® Polymers 0.000 description 2
- 229910021536 Zeolite Inorganic materials 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 125000004423 acyloxy group Chemical group 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 229910000323 aluminium silicate Inorganic materials 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- HORIEOQXBKUKGQ-UHFFFAOYSA-N bis(7-methyloctyl) cyclohexane-1,2-dicarboxylate Chemical class CC(C)CCCCCCOC(=O)C1CCCCC1C(=O)OCCCCCCC(C)C HORIEOQXBKUKGQ-UHFFFAOYSA-N 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- 239000006229 carbon black Substances 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 239000004359 castor oil Substances 0.000 description 2
- 235000019438 castor oil Nutrition 0.000 description 2
- 229910052570 clay Inorganic materials 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000007857 degradation product Substances 0.000 description 2
- 150000001993 dienes Chemical class 0.000 description 2
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 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 2
- 238000000227 grinding Methods 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 238000007037 hydroformylation reaction Methods 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 238000002372 labelling Methods 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- 239000004571 lime Substances 0.000 description 2
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- 150000004706 metal oxides Chemical class 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- PHQOGHDTIVQXHL-UHFFFAOYSA-N n'-(3-trimethoxysilylpropyl)ethane-1,2-diamine Chemical compound CO[Si](OC)(OC)CCCNCCN PHQOGHDTIVQXHL-UHFFFAOYSA-N 0.000 description 1
- NHBRUUFBSBSTHM-UHFFFAOYSA-N n'-[2-(3-trimethoxysilylpropylamino)ethyl]ethane-1,2-diamine Chemical compound CO[Si](OC)(OC)CCCNCCNCCN NHBRUUFBSBSTHM-UHFFFAOYSA-N 0.000 description 1
- MQWFLKHKWJMCEN-UHFFFAOYSA-N n'-[3-[dimethoxy(methyl)silyl]propyl]ethane-1,2-diamine Chemical compound CO[Si](C)(OC)CCCNCCN MQWFLKHKWJMCEN-UHFFFAOYSA-N 0.000 description 1
- MGKYTFDYDXZTEM-UHFFFAOYSA-N n,n-dibutyl-2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepin-10-amine Chemical compound CCCCN(CCCC)C1CCCCN2CCCN=C12 MGKYTFDYDXZTEM-UHFFFAOYSA-N 0.000 description 1
- KBJFYLLAMSZSOG-UHFFFAOYSA-N n-(3-trimethoxysilylpropyl)aniline Chemical compound CO[Si](OC)(OC)CCCNC1=CC=CC=C1 KBJFYLLAMSZSOG-UHFFFAOYSA-N 0.000 description 1
- XCOASYLMDUQBHW-UHFFFAOYSA-N n-(3-trimethoxysilylpropyl)butan-1-amine Chemical compound CCCCNCCC[Si](OC)(OC)OC XCOASYLMDUQBHW-UHFFFAOYSA-N 0.000 description 1
- WUFHQGLVNNOXMP-UHFFFAOYSA-N n-(triethoxysilylmethyl)cyclohexanamine Chemical compound CCO[Si](OCC)(OCC)CNC1CCCCC1 WUFHQGLVNNOXMP-UHFFFAOYSA-N 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000006855 networking Effects 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000012766 organic filler Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000001283 organosilanols Chemical class 0.000 description 1
- HXSACZWWBYWLIS-UHFFFAOYSA-N oxadiazine-4,5,6-trione Chemical group O=C1ON=NC(=O)C1=O HXSACZWWBYWLIS-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000005949 ozonolysis reaction Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 239000013500 performance material Substances 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- UDKSLGIUCGAZTK-UHFFFAOYSA-N phenyl pentadecane-1-sulfonate Chemical compound CCCCCCCCCCCCCCCS(=O)(=O)OC1=CC=CC=C1 UDKSLGIUCGAZTK-UHFFFAOYSA-N 0.000 description 1
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920001083 polybutene Polymers 0.000 description 1
- 229920000582 polyisocyanurate Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 238000010944 pre-mature reactiony Methods 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- SCUZVMOVTVSBLE-UHFFFAOYSA-N prop-2-enenitrile;styrene Chemical compound C=CC#N.C=CC1=CC=CC=C1 SCUZVMOVTVSBLE-UHFFFAOYSA-N 0.000 description 1
- JTQPTNQXCUMDRK-UHFFFAOYSA-N propan-2-olate;titanium(2+) Chemical compound CC(C)O[Ti]OC(C)C JTQPTNQXCUMDRK-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- GRWFGVWFFZKLTI-UHFFFAOYSA-N rac-alpha-Pinene Natural products CC1=CCC2C(C)(C)C1C2 GRWFGVWFFZKLTI-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 239000006254 rheological additive Substances 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical class OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 1
- 125000005372 silanol group Chemical group 0.000 description 1
- 150000004819 silanols Chemical class 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000003707 silyl modified polymer Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 235000015424 sodium Nutrition 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 229920000638 styrene acrylonitrile Polymers 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- TXDNPSYEJHXKMK-UHFFFAOYSA-N sulfanylsilane Chemical compound S[SiH3] TXDNPSYEJHXKMK-UHFFFAOYSA-N 0.000 description 1
- 230000019635 sulfation Effects 0.000 description 1
- 238000005670 sulfation reaction Methods 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 238000009864 tensile test Methods 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- 230000009974 thixotropic effect Effects 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- 150000003609 titanium compounds Chemical class 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 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 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical compound NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000002025 wood fiber Substances 0.000 description 1
- CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 0.000 description 1
- 229910052726 zirconium Inorganic materials 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
- C08G18/70—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
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7614—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring
- C08G18/7621—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring being toluene diisocyanate including isomer mixtures
-
- 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
- C08G18/08—Processes
- C08G18/16—Catalysts
- C08G18/22—Catalysts containing metal compounds
- C08G18/24—Catalysts containing metal compounds of tin
- C08G18/244—Catalysts containing metal compounds of tin tin salts of carboxylic acids
- C08G18/246—Catalysts containing metal compounds of tin tin salts of carboxylic acids containing also tin-carbon bonds
-
- 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
- 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
- C08G18/40—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
- C08G18/70—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
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/04—Polyurethanes
- C09D175/08—Polyurethanes from polyethers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
- C09J175/08—Polyurethanes from 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
- C08G2190/00—Compositions for sealing or packing joints
Definitions
- the invention relates to polymer compositions containing silane-functional polymers, a process for their preparation and their use as drying agents for moisture-curing compositions, in particular sealants, adhesives and coating materials.
- the invention also relates to moisture-curing compositions comprising these polymer compositions and processes for their preparation.
- silane-functional polymers Polymers which are modified with at least one silane group, but preferably two or more silane groups, are referred to as silane-functional polymers.
- Such silane groups are also known to the person skilled in the art as organoalkoxysilane or organoacyloxysilane.
- Silanes have the property of hydrolyzing to organ silanols on contact with moisture, that is to say forming groups with at least one silanol group (Si-OH group), and polymerizing to organosiloxanes by subsequent condensation.
- silane-functional polymers In the case of silane-functional polymers, this polymerization leads to a wide-meshed network for crosslinking the polymers. This process is also known as curing. Because of this ability for further crosslinking, silane-functional polymers are also referred to as prepolymers.
- Silane-functional polymers can be obtained, for example, by reacting isocyanate group-containing (NCO-containing) polymers with secondary aminosilanes. Such products are mentioned for example in EP 2 952 533 A1.
- the isocyanate groups are completely reacted with the amino groups of the aminosilanes to form urea groups, so that no free isocyanate groups remain.
- the isocyanate group-containing polymers are usually obtained by reacting polyisocyanates with high molecular weight polyols. Vorzugswei se diisocyanates are reacted with diols.
- the molar ratio of NCO groups from the diisocyanates to the hydroxyl groups (OH groups) of the high molecular weight polyol determines the composition of the NCO-containing polymers.
- an NCO: OH ratio of 2: 1 is ideally selected so that, on statistical average, two diisocyanates always react with one diol and a product with exactly two free isocyanate groups is formed.
- Higher molecular weight polymers are obtained as by-products, which are formed by the reaction of two or more diols with more than two diisocyanates.
- a lower than 2: 1 ideal NCO: OH ratio favors the formation of higher molecular weight polymers, while a larger NCO: OH ratio results in a larger proportion of free diisocyanates in the product mixture.
- the former has the disadvantage that the viscosity of the uncrosslinked NCO-containing polymer and subsequently that of the silane-functional polymer produced from it Polymers increases, so that the latter is more difficult to process into a sealant or adhesive composition.
- such products have the disadvantage that excess diisocyanate has to be removed in a complex manner (for example by distillation). For this reason, the NCO-containing polymers for the production of silane-terminated polymers are usually produced with an NCO: OH ratio in the range from 1.5: 1 to 2.2: 1.
- EP 2 952 533 A1 discloses the production of silane-functional polymers by reacting polyoxypropylene diol with isophorone diisocyanate (IPDI) at an NCO: OH ratio of 2.1: 1 and then reacting the reaction product with (N- (3-triethoxysilyl -propyl) -amino-succinic acid diethyl ester or (N- (3-trimethoxysilyl-propyl) -amino-succinic acid diethyl ester.
- the NCO: OH ratio is preferably to a value of 1.5 : 1 to 2.2: 1 set.
- silane-functional polymers are used, for example, as binders for moisture-curing sealants, adhesives and coating materials. Since they are free of isocyanate groups, unlike, for example, isocyanate prepolymers for the production of moisture-curing sealant and adhesive compositions, they can be combined with formulation components which carry isocyanate-reactive groups. Examples include polyols as plasticizer components and aminosilanes as adhesion promoters.
- moisture-curing sealants adhesives and coating materials based on silane-functional polymers
- drying agents are usually added to the moisture-curing composition. This is particularly necessary because, on the one hand, many of the commonly used components of moisture-curing sealant and adhesive compositions, e.g. Fillers, even water, and inevitably moisture is introduced into the moisture-curing composition. On the other hand, the moisture-curing composition must be protected against moisture penetrating from outside by leaking packaging or diffusion.
- Monomeric vinyl silanes such as vinyl trimethoxy silane or vinyl triethoxy silane, are used as drying agents, for example. These monomeric silanes react preferentially with the water contained in the composition and thus prevent the undesired premature reaction of this water with the silane groups of the binder.
- vinyl silanes are subject to increasingly stringent labeling requirements, which is why there is an interest in ne to be replaced by other desiccants that do not require labeling and are less harmful to occupational hygiene.
- silane-functional polymers as binders in combination with drying agents is also disclosed, for example, in DE 10 2005 026 085 A1.
- This publication describes silane-modified urea derivatives and their use as rheology aids for sealants and adhesives.
- the urea derivatives are prepared by reacting a diisocyanate and an aminosilane in the presence of a silane-functional polymer.
- the disadvantage here is that the mixtures of binder and urea derivative obtained are highly viscous and can usually not be processed without further addition of plasticizers.
- water scavengers is necessary to increase the storage stability of the urea derivatives in the binder.
- Vinylsilanes are mentioned as exemplary water scavengers, in particular vinyltrimethoxy silane (VTMO). The above applies to a mixture of externally produced urea derivatives with silane-functional binders, which is also described.
- the present invention has for its object to provide new, less hygienic and easy to manufacture drying agents for moisture-curing compositions, in particular sealants, adhesives and coatings, which are suitable for monomeric vinyl silanes such as vinyl trimethoxy silane (VTMO) to replace.
- moisture-curing compositions in particular sealants, adhesives and coatings, which are suitable for monomeric vinyl silanes such as vinyl trimethoxy silane (VTMO) to replace.
- polymer compositions which contain silane-functional polymers which can be prepared by reacting an isocyanate-reactive (NCO-reactive) polymer with a polyisocyanate and subsequent reaction of the remaining isocyanate groups with an NCO-reactive silane, the ratio the amount of polyisocyanate to the amount of NCO-reactive groups of the polymer is at least 1.25.
- the polymer compositions prepared in this way can also take on the function of a drying agent in addition to their function as binders thus make the use of conventional additional drying agents such as vinyl triethoxysilane or vinyltrimethoxysilane superfluous.
- the polymer compositions produced in this way have a lower viscosity than comparable polymers which are produced from the same components but with a lower ratio of polyisocyanates to OH groups.
- the invention thus relates to a polymer composition which can be prepared by:
- step b) reaction of the remaining NCO groups in the reaction product from step a) with an NCO-reactive silane.
- the polymer composition according to the invention comprises silane-functional polymers which have resulted from the reaction of an NCO-reactive polymer, which has at least two NCO-reactive groups, with at least two polyisocyanates and a subsequent reaction with at least two NCO-reactive silanes.
- the composition may include higher molecular weight polymers resulting from the reaction of more than one NCO-reactive polymer with more than two polyisocyanates and subsequent reaction with at least two NCO-reactive silanes.
- the proportion of these higher molecular weight polymers is relatively low due to the high ratio of polyisocyanates to NCO-reactive groups compared to the silane-functional polymers produced according to the prior art, with the result that the composition as a whole has a relatively low viscosity has.
- the composition also contains so-called free silane-functional reaction products which have resulted from the reaction of a polyisocyanate (which has not reacted with the NCO-reactive polymer) with a number of NCO-reactive silanes corresponding to the number of NCO groups of the polyisocyanate.
- the molar ratios of these components in the composition according to the invention is determined for otherwise identical starting materials essentially by the molar ratio of the polyisocyanate molecules to the NCO-reactive groups of the polymer in step a).
- silane-functional reaction products contained in the polymer composition according to the invention react preferentially or at least as quickly as the terminal silane groups of the silane-functional polymers with water and thus act as drying agents.
- the silane-functional polymers contained in the polymer composition do not, or only to a minor extent, in the presence of small amounts of water. and therefore the polymer composition itself and the moisture-curing compositions that can be produced from it are extremely stable in storage.
- the silane-functional polymers are crosslinked and the composition is thus cured, as is desired, for example, when used as a moisture-curing sealant.
- the polymer composition according to the invention can thus be used as a combination of moisture-curing binder and drying agent for a moisture-curing composition, in particular a sealant or adhesive or a coating agent.
- the NCO-reactive polymer When the NCO-reactive polymer is reacted with the polyisocyanate, all of the NCO-reactive groups of the NCO-reactive polymer are preferably reacted. Likewise, in the reaction of the reaction product from step a) with the NCO-reactive silane, preferably all free NCO groups of the reaction product from step a) are reacted. The person skilled in the art can determine this by determining the isocyanate content, for example by titration according to DIN 11909 or by IR spectroscopy.
- the polymer composition according to the invention preferably has a viscosity of less than 150 Pa s, preferably 2 to 70 Pa s, particularly preferably 5 to 50 Pa s, most preferably 15 to 27 Pa s, measured according to the specification of DIN EN ISO 3219 / B3 ,
- the molar ratio of polyisocyanate to NCO-reactive groups of the NCO-reactive polymer denotes the ratio of the amount of polyisocyanate in mol to the total number of NCO-reactive groups of the NCO-reactive polymer in mol.
- the amount of polyiso cyanate results from the molecular weight of the polyisocyanate and the mass of polyisocyanate used.
- the total number of NCO-reactive groups of the NCO-reactive polymer in mol results from the mass of NCO-reactive polymer and the number of NCO-reactive groups based on the mass of the NCO-reactive polymer.
- the molar ratio of polyisocyanate molecules to NCO-reactive groups of the NCO-reactive polymer in step a) is preferably 1.25: 1 to 10: 1. Particularly preferred in step (a) the molar ratio of polyisocyanate to NCO-reactive groups of the NCO-reactive polymer is 1.5: 1 to 7: 1, most preferably it is 2: 1 to 5: 1.
- the NCO-reactive groups initially only react with one NCO group.
- the reaction products formed e.g. urethanes
- the reaction products formed can react with another NCO group under certain conditions. If this is desired or is observed, the person skilled in the art can adjust the molar ratio accordingly.
- Suitable NCO-reactive polymers have at least two NCO-reactive groups.
- An NCO-reactive group is understood to mean a functional group which enters into an addition reaction with an isocyanate group.
- Suitable NCO-reactive groups are, for example, hydroxyl, amino and mercapto groups. Mixtures of NCO-reactive polymers with different NCO-reactive groups can also be used. NCO-reactive polymers with different NCO-reactive groups can also be used.
- the NCO-reactive groups are preferably hydroxyl groups (OH groups).
- the molar amount of the NCO-reactive groups can be determined in accordance with DIN 53240-1 (2012).
- the amine number measured according to the specification DIN 53176: 2002-11
- the mass of the respective NCO-reactive polymer can be used.
- the molar amount of OH groups can be calculated from the mass of the NCO-reactive polymer and the hydroxyl number using known calculation methods. Unless otherwise stated, the hydroxyl number is determined in accordance with DIN 53240-1 (2012).
- the NCO-reactive polymer can also be reacted with a polyisocyanate with a known NCO content up to a constant NCO content in significant excess and the amount of unreacted NCO groups can be determined as described above.
- the molar amount of the remaining NCO-reactive groups in the reaction product of step (a) can then be determined from the difference between the molar amount of the NCO groups used and the unreacted NCO groups.
- the NCO-reactive polymer can be, for example, a polyacrylate, a polycarbonate, a polyester, polyurethane or a polyether which is functionalized with at least two NCO-reactive groups.
- Polyethers are particularly preferred as NCO-reactive polymers because they have a flexible and elastic structure that can be used to produce compositions that have excellent elastic properties.
- polyethers are not only flexible in their basic structure, but at the same time resistant. For example, polyethers are not attacked or decomposed by water and bacteria, in contrast to polyesters, for example.
- the NCO-reactive polymers to be used according to the invention preferably have a number average molecular weight of 2,000 to 100,000 g / mol.
- the NCO-reactive polymers to be used according to the invention have a number average molecular weight of 4,000 to 100,000 g / mol, preferably 4,000 to 50,000 g / mol, particularly preferably 8,000 to 22,000 g / mol. These molecular weights are particularly advantageous because the corresponding compositions have good film-forming properties and a balanced ratio of viscosity (easy to process), strength and elasticity.
- NCO-reactive polymers with a narrow molar mass distribution and thus a low polydispersity are used.
- the polydispersity represents the ratio of weight-average to number-average molecular weight Mw / Mn.
- the NCO-reactive polymer preferably has a polydispersity of at most 3, preferably at most 1.7, particularly preferably at most 1.5.
- the number and / or weight average molecular weight is determined by gel permeation chromatography (GPC) according to the specification of DIN 55672-1: 2016-03 with THF as an eluent against a polystyrene standard.
- the NCO-reactive polymer is preferably a polyol.
- Suitable polyols for the preparation of the composition are in particular polyether polyols, polyester polyols and polycarbonate polyols and mixtures of these polyols, polyether polyols being particularly preferred.
- Polytetramethylene polyols, polyoxyethylene polyols and polyoxypropylene polyols, in particular polyoxyethylene diols, polyoxypropylene diols, polyoxyethyl entriols and polyoxypropylene triols, are particularly suitable. Mixtures of different polyols can also be used.
- the polyols to be used according to the invention preferably have a number average molecular weight of 2,000 to 100,000 g / mol, in particular 4,000 to 50,000 g / mol, preferably 6,000 to 30,000 g / mol, particularly preferably 8,000 to 22,000 g / mol.
- Polyether polyols which can be prepared by the so-called double metal cyanide catalysis (DMC catalysis) are particularly preferred. This is described, for example, in US Pat. No. 5,158,922 (eg Example 30) and EP A 0 654 302 (page 5, line 26 to page 6, line 32). Polyether made in this way polyols are characterized by a particularly low polydispersity, by a high average molecular weight and by a very low degree of unsaturation. Corresponding products are available, for example, from Covestro Deutschland AG under the name Acclaim ® Polyol 4200 N, Acclaim ® Polyol 8200 N and Acclaim ® Polyol 12200 N.
- DMC catalysis double metal cyanide catalysis
- the polyols to be used according to the invention preferably have an average OH functionality of 1.6 to 3, particularly preferably 1.9 to 2.1.
- the OH functionality of a connection is to be understood as the mean OH functionality. It indicates the average number of hydroxyl groups per molecule.
- the average OH functionality of a compound can be calculated based on the number average molecular weight and the hydroxyl number. Unless otherwise stated, the hydroxyl number of a compound is determined according to the DIN 53240-1 (2012) standard.
- polyoxyalkylene diols or polyoxyalkylene triols with a degree of unsaturation less than 0.02 mEq / g (determined according to the specification in ASTM D4671-16) and with a number average molecular weight (determined by GPC) in the range from 2000 to 30000 g / mol
- Polyoxyethylene diols, polyoxyethylene triols, polyoxypropylene diols and polyoxypropylene triols with an average molecular weight of 2000 to 30000 g / mol So-called ethylene oxide-terminated (“oxide-endcapped”) polyoxypropylene polyols are also particularly suitable. The latter are obtained if propylene oxide is first used as the monomer in the preparation for the polymerization and then ethylene oxide is used as the monomer instead of propylene oxide before termination of the polymerization.
- hydroxyl-terminated polybutadiene polyols such as, for example, those which are prepared by polymerizing 1,3-butadiene and allyl alcohol or by oxidation of polybutadiene, and their hydrogenation products.
- styrene-acrylonitrile grafted polyether polyols such as those Lich example, under the trade name Lupranol® ® by the company Elastogran GmbH, Germany obtained commercially.
- Suitable polyester polyols are in particular polyesters which carry at least two hydroxyl groups and are prepared by known processes, in particular the polycondensation of hydroxycarboxylic acids or the polycondensation of aliphatic and / or aromatic polycarbonates with dihydric or polyhydric alcohols.
- Particularly suitable polycarbonate polyols are those such as those obtained by reacting, for example, the abovementioned alcohols used to construct the polyester polyols with dialkyl carbonates. ten such as dimethyl carbonate, diaryl carbonates such as diphenyl carbonate or phosgene are accessible. Polycarbonate diols, in particular amorphous polycarbonate diols, are particularly suitable.
- polystyrene resins are poly (meth) acrylate polyols.
- polyhydroxy-functional fats and oils for example natural fats and oils, in particular castor oil, or so-called oleochemical polyols obtained by chemical modification of natural fats and oils, which are obtained, for example, by epoxidation of unsaturated oils and subsequent ring opening with carboxylic acids or alcohols Epoxy polyester or epoxy polyether, or polyols obtained by hydroformylation and hydrogenation of unsaturated oils.
- polyols which are obtained from natural fats and oils by degradation processes such as alcoholysis or ozonolysis and subsequent chemical linkage, for example by transesterification or dimerization, of the degradation products or derivatives thereof obtained in this way.
- Suitable degradation products of natural fats and oils are in particular fatty acids and fatty alcohols and fatty acid esters, in particular the methyl esters (FAME), which can be derivatized, for example, by hydroformylation and hydrogenation to give hydroxy fatty acid esters.
- FAME methyl esters
- polycarbonate polyols also called oligohydrocarbonols
- polyhydroxy-functional ethylene-propylene, ethylene-butylene or ethylene-propylene-diene copolymers as are produced, for example, by Kraton Polymers, USA, or polyhydroxy-functional copolymers Dienes such as 1,3-butanediene or diene mixtures and vinyl monomers such as styrene, acrylonitrile or isobutylene, or polyhydroxy-functional polybutadiene polyols, for example those which are prepared by copolymerization of 1,3-butadiene and allyl alcohol and can also be hydrogenated.
- polyhydroxy-functional acrylonitrile / butadiene copolymers as they can be produced at game, from epoxides or aminoalcohols and carboxyl-terminated acrylonitrile / butadiene copolymers, which are commercially available under the name Hypro ® CTBN from the company Emerald Performance Materials, EEC, USA ,
- polyester polyols and polyether polyols in particular polyoxyethylene polyol, polyoxypropylene polyol and polyoxypropylene polyoxyethylene polyol, preferably polyoxyethylene diol, polyoxypropylene diol, polyoxyethylene triol, polyoxypropylene triol, polyoxypropylene polyoxyethylene diol and polyoxypropylene polyoxyethylene triol.
- Poly oxypropylene diol is very particularly suitable.
- Commercially available polyisocyanates, in particular diisocyanates can be used as polyisocyanates for the preparation of the polymer composition.
- polyisocyanates in general, we mean monomeric and / or oligomeric polyisocyanates.
- oligomeric polyisocyanates we mean polyisocyanates that are made up of at least two polyisocyanate molecules, i.e. they are compounds which represent or contain a reaction product containing at least two monomeric polyisocyanate molecules.
- Diisocyanates are preferably used, particularly preferably monomeric diisocyanates with a molecular weight in the range from 140 to 400 g / mol with aliphatic, cycloaliphatic, araliphatic and / or aromatically bound isocyanate groups.
- the polyisocyanate is selected from monomeric diisocyanates.
- Suitable monomeric diisocyanates are in particular those of a group of polyisocyanates comprising 1,4-diisocyanatobutane (BDI), 1,5-diisocyanatopentane (PDI), 1,6-hexamethylene diisocyanate (HDI), 2-methyl-1,5-diisocyanatopentane , l, 5-diisocyanato-2,2-dimethylpentane, 2,2,4- or 2,4,4-trimethyl-l, 6-diisocyanatohexane, 1,10-diisocyanatodecane, 1,3- and 1,4- Diisocyanato-cyclohexane, l, 4-diisocyanato-3,3,5-trimethylcyclohexane, l, 3-diisocyanato-2-methylcyclohexane, l, 3-diisocyanatocyana
- the polyisocyanate is l-isocyanato-3,3,5-trimethyl-5-isocyanatomethyl-cyclohexane (IPDI), 1,6-hexamethylene diisocyanate (HDI), 2,4- and / or 2,6-tolylene diisocyanate (TDI), or mixtures thereof.
- IPDI l-isocyanato-3,3,5-trimethyl-5-isocyanatomethyl-cyclohexane
- HDI 1,6-hexamethylene diisocyanate
- TDI 2,6-tolylene diisocyanate
- IPDI l-isocyanato-3,3,5-trimethyl-5-isocyanatomethyl-cyclohexane
- HDI high viscosity
- a mixture of HDI with other diisocyanates is preferably used.
- the ratio of polyisocyanates to NCO-reactive groups is particularly preferably at least 2.5: 1.
- polyisocyanates preference is given to a polyisocyanate with differently reactive isocyanate groups, such as l-isocyanato-3,3,5-trimethyl-5-isocyanatomethyl-cyclohexane (IPDI), 2,4- and / or 2,6 -Toluylene diisocyanate (TDI) used to achieve a low viscosity.
- IPDI l-isocyanato-3,3,5-trimethyl-5-isocyanatomethyl-cyclohexane
- TDI 2,6 -Toluylene diisocyanate
- Suitable NCO-reactive silanes have at least one NCO-reactive group, such as a hydroxyl, amino and mercapto group. Mixtures of different NCO-reactive silanes can also be used.
- a compound is used as the NCO-reactive silane which has at least one silicon atom, at least one organic radical bonded to the silicon atom via an Si-O bond and at least one organic radical bonded to the silicon atom via an Si-C bond, which has at least one NCO-reactive group.
- the NCO-reactive silane is an aminosilane, mercaptosilane or hydroxysilane.
- the NCO-reactive silane is preferably an aminosilane.
- the aminosilane for the preparation of the composition a compound is used which has at least one silicon atom, at least one organic radical bonded to the silicon atom via an Si-O bond and at least one organic radical bonded to the silicon atom via an Si-C bond , which has at least one primary or secondary amino group. It is preferably the one bonded to the silicon atom via an Si — O bond organic residue around an alkoxy or acyloxy group.
- the amino group is preferably a secondary amino group. Such aminosilanes which have a secondary amino group are also referred to as secondary aminosilanes.
- suitable aminosilanes are primary aminosilanes such as 3-aminopropyltrimethoxysilane, 3-aminopropyldimethoxymethylsilane; secondary aminosilanes such as N-butyl-3-aminopropyltrimethoxysilane, N-phenyl-3-aminopropyltrimethoxysilane; the products from the Michael-like addition of primary aminosilanes such as 3-aminopropyltrimethoxysilane or 3-aminopropyldimethoxymethylsilane to Michael acceptors such as acrylonitrile, (meth) acrylic acid esters, (meth) acrylic acid amides, maleic and fumaric acid diesters, citraconic acid diesters and itaconic acid diesters tern, e.g.
- primary aminosilanes such as 3-aminopropyltrimethoxysilane, 3-aminopropyldimethoxymethylsilane
- EP-A 0 807 649 can lead to cyclocondensation which further reduces the viscosity of the prepolymers containing alkoxysilane groups according to the invention can. Accordingly, this hydantoin formation can also be intentionally brought about in a preferred embodiment of the present invention.
- This cyclocondensation can be brought about by simply stirring the polyether-based polyurethane prepolymer capped with an isocyanate-reactive alkoxysilane of the formula (III) at from 70 ° C. to 180 ° C., preferably from 80 ° C. to 150 ° C.
- the reaction can be carried out without further catalysis, or, preferably, accelerated by catalysis.
- Suitable catalysts are both basic and acidic organic compounds, for example N, N, N, N-benzyltrimethylammonium hydroxide, other hydroxides soluble in organic media, DBN, DBU, other amidines, tin octoate, dibutyltin dilaurate, other organic tin compounds, zinc octoate, Acetic acid, other alkanoic acids, benzoic acid, benzoyl chloride, other acid chlorides or dibutyl phosphate, or other derivatives of phosphoric acid.
- the catalyst is added in amounts of 0.005% by weight to 5% by weight, preferably 0.05% by weight to 1% by weight.
- NCO-reactive silane is a compound of the formula (I):
- R 1 each radical is selected independently of one another from (Y (Yalkyl, C6-C2o-aryl, Ci- (Yalkoxy or (Y (Yacyloxy and at least one of the radicals R 1 is a (Y (Yalkoxy or (Y (Yacyloxy radical,
- n is an integer between 1 and 4,
- X is selected from -OH, -SH or -NHR 2 ;
- R 2 is selected from H, Ci-C2o-alkyl, -CH2CH2CN or -CHR 3 CH2COOR 4 ,
- R 3 is selected from H and -COOR 4 .
- R 4 is in each case Ci-C 2 o-alkyl.
- Ci-Cs-alkoxy radical here denotes a radical of the general formula R-O-, where an R is an alkyl radical with 1 to 8 carbon atoms.
- R Y acyloxy radical, a radical of the general formula R-CO-O- is referred to, where R is hydrogen or an alkyl radical having 1 to 7 carbon atoms.
- radicals R 1 are each C i (VAIkoxy tendency and the optionally remaining radical R 1 is a Cj-Cs alkyl group.
- Each R 1 radical is particularly preferably selected independently of one another from methyl, ethyl, methoxy and ethoxy.
- the number n is preferably 1 or 3.
- X is preferably -NHR 2 .
- R 2 is preferably selected from (Y (Y alkyl, -CH2CH2CN or -CHR 3 CH2COOR 4 , where R 3 is selected from H and -COOR 4 , and R 4 is each (YCe alkyl.
- R 2 is particularly preferably selected from (YCe-alkyl, or -CHR 3 CH2COOR 4 , where R 3 is -COOR 4 , and R 4 is in each case (YCe-alkyl.
- R 2 has the meaning -CHR 3 CH2COOR 4 , where R 3 is a group -COOR 4 , and R 4 is in each case (YCe-alkyl.
- the present invention also relates to a moisture curing composition containing the polymer composition described above.
- the moisture-curing composition according to the invention is preferably an adhesive, sealant or coating material. It is particularly preferably a sealing or adhesive.
- the moisture-curing composition according to the invention generally contains, in addition to the polymer composition described above, at least one additive selected from one or more fillers, one or more crosslinking catalysts, one or more adhesion promoters and / or one or more plasticizers.
- the moisture-curing composition contains the polymer composition described above and at least one crosslinking catalyst. In one embodiment, the moisture-curing composition contains the polymer composition described above and at least one filler. In a further embodiment, the moisture-curing composition contains the polymer composition described above, at least one crosslinking catalyst and at least one filler.
- the moisture-curing composition is preferably produced and stored in the absence of moisture.
- the moisture-curing composition is stable in storage, ie it can be stored in a suitable packaging or arrangement, for example a barrel, a bag or a cartridge, in the absence of moisture for a period of from several months to a year and longer, without changing their application properties or their properties after curing to an extent relevant to their use.
- the storage stability is usually determined by measuring the viscosity or the pressing force.
- the silane groups contained in the polymer composition according to the invention come into contact with moisture.
- the silane groups have the property of hydrolyzing on contact with moisture.
- Organosilanols are formed and, through subsequent condensation reactions, organosiloxanes.
- organosiloxanes As a result of these reactions, which can be accelerated by using a crosslinking catalyst, the moisture-curing composition finally hardens. This process is also called networking.
- the water required for curing can either come from the air (atmospheric humidity) or be present in the coated substrates in the presence of moisture, or else the moisture-curing composition can be brought into contact with a water-containing component, for example by brushing, for example with a smoothing agent, or by spraying, or a water-containing component can be added to the moisture-curing composition during application, for example in the form of a water-containing paste.
- a water-containing component for example by brushing, for example with a smoothing agent, or by spraying, or a water-containing component can be added to the moisture-curing composition during application, for example in the form of a water-containing paste.
- the moisture-curing composition according to the invention preferably has a particularly low water content after production.
- the water content of the moisture-curing composition is preferably up to 0.1% by weight, preferably up to 0.05% by weight, particularly preferably up to 0.01% by weight, based on the total weight of the composition.
- the water content is determined in accordance with DIN EN ISO 15512: 2017-03, method B2.
- drying agents that is to say compounds which react with the water present in the moisture-curing composition.
- drying agents in particular reactive drying agents
- Reactive drying agents are those whose drying effect is due to a reaction with water. It is preferred not to add in particular reactive drying agents which do not meet the OECD polymer definition valid on 01/01/2017, in particular alkylsilanes and silanes containing vinyl groups, such as, for example, vinyltrimethoxysilane or vinyltriethoxysilane.
- this term includes vinyltrialkoxy silanes and the reaction products which result from the reaction of these silanes with water, or partial hydrolyzates of these compounds.
- a reactive desiccant is generally understood to be a desiccant that undergoes a chemical reaction with water.
- physical desiccants bind water so that it is not available for a chemical reaction.
- Examples of a physical desiccant are special fillers such as zeolites or molecular sieves.
- a moisture-curing composition according to the invention comprises only up to 1% by weight, preferably up to 0.8% by weight, particularly preferably up to 0.5% by weight, of silane-containing vinyl groups and after preparation and before application / or alkylsilanes, based on the total weight of the moisture-curing composition.
- the moisture-curing composition preferably comprises only up to 1% by weight, preferably up to 0.8% by weight, particularly preferably up to 0.5% by weight of vinyltrimethoxysilane and vinyltriethoxysilane.
- the amount of the silane and / or alkylsilanes containing vinyl groups used to prepare the moisture-curing composition can be limited to the weight percentages specified, or it is even possible to dispense entirely with the use of silanes containing vinyl groups.
- the moisture-curing composition contains no vinyl group-containing silanes and / or alkylsilanes or no reaction products formed during the reaction of these silanes with water. “None” here means that the individual concentrations of the vinyl group-containing silanes and / or alkylsilanes in each case not exceed ⁇ 0.1% by weight, based on the moisture-curing composition.
- the moisture-curing composition preferably has a viscosity at 23 ° C. of less than 100 Pa s measured according to the specification of DIN EN ISO 3219 / B3 at a shear rate of 40 / s.
- the viscosity of the moisture-curing composition is largely determined by the mixing ratio of silane-functional polymer and filler and the type of filler and can be modified if necessary by adding a plasticizer.
- the moisture-curing composition preferably comprises at least one filler, which in particular serves to influence the rheological properties and mechanical properties of the composition in the uncured and in the cured state.
- Suitable fillers are, for example, chalk, lime powder, precipitated and / or pyrogenic silica, zeolites, bentonites, magnesium carbonate, diatomaceous earth, clay, clay, tallow, titanium oxide, iron oxide, zinc oxide, sand, quartz, flint, mica, glass powder and other ground minerals .
- Organic fillers can also be used, in particular carbon black, graphite, wood fibers, wood flour, sawdust, cellulose, cotton, pulp, wood chips, chopped chaff, chaff, ground walnut shells and other fiber short cuts.
- short fibers such as glass fiber, glass filament, polyacrylonitrile, carbon fiber, kevlar fiber or polyethylene fibers can also be added.
- Aluminum powder is also suitable as a filler.
- hollow spheres with a mineral shell or a plastic shell are suitable as fillers.
- This may for example be hollow glass beads, which are commercially available under the trade names Glass Bubbles ®.
- Hollow spheres based on plastics are commercially available, for example under the names Expancel or Dualite® ®. These are composed of inorganic or organic substances, each with a diameter of 1 mm or less, preferably 500 ⁇ m or less.
- a highly disperse silica with a BET surface area of 10 to 500 m 2 / g is used as the filler.
- a silica does not significantly increase the viscosity of the composition according to the invention, but does contribute to a strengthening of the hardened preparation.
- This reinforcement improves, for example, the initial strengths, tensile shear strengths and the adhesion of the adhesives, sealants or coating materials in which the composition according to the invention is used.
- the pore opening of the zeolite or zeolites used is preferably just large enough to take up water molecules. Accordingly, an effective pore opening of the zeolites of less than 0.4 nm is preferred. The effective pore opening is particularly preferably 0.3 nm ⁇ 0.02 nm.
- the zeolite (s) is / are preferably used in the form of a powder.
- the filler comprises naturally occurring silicates (for example clay, clay, talc, mica, kaolin), carbonates (for example chalk, dolomite), sulfates (for example barite), quartz sand, silica (in particular precipitated pyrogenic silica), metal hydroxides (for example aluminum hydroxide, magnesium hydroxide), metal oxides (for example zinc oxide, calcium oxide, aluminum oxide) and / or carbon black.
- silicates for example clay, clay, talc, mica, kaolin
- carbonates for example chalk, dolomite
- sulfates for example barite
- quartz sand silica (in particular precipitated pyrogenic silica)
- metal hydroxides for example aluminum hydroxide, magnesium hydroxide
- metal oxides for example zinc oxide, calcium oxide, aluminum oxide
- Chalk is preferably used as the filler. Cubic, non-cubic, amorphous and other modifications of magnesium and / or calcium carbonate can be used as chalk.
- the chalks used are preferably surface-treated or coated. Fatty acids, fatty acid soaps and fatty acid esters are preferably used as coating agents for this, for example lauric acid, palmitic acid or stearic acid, sodium or potassium salts of such acids or their alkyl esters.
- other surface-active substances such as sulfate esters of long-chain alcohols or alkylbenzenesulfonic acids or their sodium or potassium salts or coupling reagents based on silanes or titanates are also suitable.
- the surface treatment of the chalks is often associated with an improvement in the workability and the adhesive strength and also the weather resistance of the compositions.
- the coating agent for this is usually used in a proportion of 0.1 to 20% by weight, preferably 1 to 5% by weight, based on the total weight of the raw chalk.
- ground chalks can, for example, be made from natural lime, limestone or marble by mechanical grinding, whereby dry or moist methods can be used. Depending on the grinding process, fractions with obtained different average particle size.
- Advantageous specific surface values (BET) are between 1.5 m 2 / g and 50 m 2 / g.
- the fillers used to prepare the composition usually have a certain proportion of water.
- this is disadvantageous since the water present in the filler leads to a pre-crosslinking of the silane-functional polymers even during the storage of the composition. For this reason, either additional drying agents are added to the composition in the prior art, or only anhydrous fillers are used.
- the silane-functional polymer according to the invention also acts as a drying agent, a filler which contains a certain proportion of water can also be used to produce the composition according to the invention, without this having a negative effect on the resistance of the composition to fager.
- the filler used for the preparation of the composition therefore comprises water.
- the filler preferably comprises water in an amount of up to 1% by weight, preferably 0.01 to 0.5% by weight, particularly preferably 0.1 to 0.3% by weight, based on the mass of the filler , measured according to the regulation in / DIN EN ISO 15512: 2017-03, procedure B2.
- the proportion of filler in the moisture-curing composition is preferably 10 to 80% by weight, preferably 20 to 70% by weight, particularly preferably 40 to 70% by weight, based on the total weight of the moisture-curing composition.
- the moisture-curing composition preferably comprises at least one adhesion promoter.
- An adhesion promoter is a substance that improves the adhesion properties of adhesive layers on surfaces.
- Conventional tackifiers known to those skilled in the art can be used alone or as a combination of several compounds. Suitable, for example, are resins, terpene oligomers, coumarone / indene resins, aliphatic, petrochemical resins and modified phenolic resins.
- Suitable for the purposes of the present invention are, for example, hydrocarbon resins such as those obtained by polymerizing terpenes, mainly ⁇ - or ⁇ -pinene, dipentene or fimone.
- the terpene resins also include copolymers of terpenes and other monomers, for example styrene, ⁇ -methylstyrene, isoprene and the like.
- the resins mentioned are used, for example, as adhesion promoters for pressure-sensitive adhesives and coating materials.
- the terpene-phenol resins which are obtained by acid-catalyzed addition of phenols to terpenes or Rosin are made.
- Terpene-phenol resins are soluble in most organic solvents and oils and are miscible with other resins, waxes and rubber.
- the rosin resins and their derivatives for example their esters or alcohols, are also suitable as adhesion promoters in the context of the present invention.
- Silane coupling agents in particular aminosilanes, are particularly suitable.
- the moisture-curing composition comprises, as an adhesion promoter, a compound of the general formula (II)
- R 1 each radical is selected independently of one another from Ci-Cs-alkyl, Cj-Cs-alkoxy or (YCVAcyloxy and at least one radical R 1 is a Ci-Cs-alkoxy or Cj-Cs-acyloxy radical,
- R 2 is a double-bonded and optionally one or more heteroatoms containing hydrocarbon radicals having 1 to 12 carbon atoms, and
- R 3 each radical is independently selected from H and Cj-Cs-alkyl.
- Such compounds naturally have a high affinity for the binding polymer components of the moisture-curing composition, but also for a wide range of polar and non-polar surfaces, and therefore contribute to the formation of a particularly stable adhesion between the sealant or adhesive and the substrates to be connected at.
- the group R 2 can be, for example, a straight-chain, branched or cyclic, substituted or unsubstituted alkylene radical. If necessary, nitrogen (N) or oxygen (O) is contained as a hetero atom.
- the group R 2 can in particular comprise an acetoxy group -O-CO-R, where R is a divalent hydrocarbon radical.
- an oligomer of an aminosilane is used as the adhesion promoter; oligomers of aminosilanes in which the silicon atoms are connected via siloxane bonds are particularly suitable.
- oligomeric diaminosilanes such as Dynasylan ® 1146 from Evonik are. Partial hydrolyzates of aminosilanes or other silanes are also suitable. Oligomeric silanes are preferably used.
- the proportion of adhesion promoter in the moisture-curing composition is preferably 0.1 to 5% by weight, preferably 0.2 to 3% by weight, particularly preferably 0.5 to 1.5% by weight, based on the total weight of the moisture-curing composition. If compounds with reactive silane groups are used as adhesion promoters, these can additionally influence the storage stability of the moisture-curing compound, but are not absolutely necessary to achieve storage stability.
- the moisture-curing compositions each contain less than 0.1% by weight of silane coupling agents and drying agents which do not meet the OECD polymer definition valid on 01/01/2017 and which do not meet the OECD polymer definition valid on 01/01/2017.
- the moisture-curing composition also comprises at least one catalyst for the crosslinking of silane-functional polymers (crosslinking catalyst).
- crosslinking catalyst facilitates the reaction of silane-functional polymer with water and the subsequent condensation reaction to form cross-linked polysiloxanes.
- the catalysts known in the prior art can be used as the crosslinking catalyst. For example, these are Lewis and / or Bronstedt acids or bases.
- the catalyst can be, for example, a metal catalyst or a nitrogen-containing compound.
- Suitable metal catalysts are in particular organotin compounds, organotitanates, organozirconates and organoaluminates.
- the organotitanates, organozirconates and organoaluminates preferably have ligands which are selected from an alkoxy group, sulfonate group, carboxylate group, dialkyl phosphate group, dialkyl pyrophosphate group and acetylacetonate group, where all ligands can be identical or different from one another.
- Suitable nitrogen-containing compounds are, for example, amidines; Amines such as, in particular, N-ethyl-diisopropylamine, N, N, N ', N'-tetramethylalkylene diamines, polyoxyalkylene amines, 1,4-diazabicyclo [2.2.2] octane; Aminosilanes such as 3-aminopropyltrimethoxysilane, 3-aminopropyldimethoxymethylsilane, N- (2-aminoethyl) -3-aminopropyltrimethoxysilane, N- (2-aminoethyl) -3-aminopropylmethyldimethoxysilane, N- (2 -Aminoethyl) -N '- [3- (trimethoxysilyl) propyl] ethylenediamine as well as their analogues with ethoxy or isopropoxy instead of the methoxy groups on the
- crosslinking catalysts are organotitanates and amidines.
- Preferred organotitanates are, in particular, bis (ethylacetoacetato) diisobutoxy titanium (IV), bis (ethylacetoacetato) diisopropoxy titanium (IV), bis (acetylacetonato) diisopropoxy titanium (IV), bis (acetyl ylacetonato) diisobutoxy titanium (IV), tris (oxyethyl) amine isopropoxy titanium (IV), bis [tris (oxyethyl) amine] diisopropoxy titanium (IV), bis (2-ethylhexane-l, 3-dioxy) titanium (IV ), Bis (neopentyl (diallyl) oxy-di-ethoxytitan (IV), tris [2 - ((2-aminoethyl) amino) ethoxy] -ethoxy-titanium (IV), titanium (IV) tetrabutanolate, tetra- (2 -ethyl
- Preferred amidines are in particular 1,8-diazabicyclo [5.4.0] undec-7-ene (DBU), 1,5-diazabicyclo [4.3.0] non-5-ene (DBN), 6-dibutylamino-1, 8-diazabicyclo [5.4.0] undec-7-ene; Methyltriazabicyclodecene, guanidines such as tetramethylguanidine, 2-guanidinobenzimidazole, acetylacetoneguanidine, 1,3-di-o-tolylguanidine, 1,3-diphenylguanidine, tolylbiguanidine, 2-tert-butyl-l, l, 3,3-tetra- methyl guanidine; and imidazoles such as N- (3-trimethoxysilylpropyl) -4,5-dihydroimidazole and N- (3-triethoxysilylpropyl) -4,5-dihydroimidazo
- catalysts can be used, in particular mixtures of metal catalysts and non-metal catalysts which contain a nitrogen atom, the metal catalysts preferably not containing tin and the non-metal catalysts being amines.
- the moisture-curing composition therefore contains less than 0.1% tin (calculated on the weight fraction of tin atoms).
- the tin content of the composition is less than 0.06% by weight, in particular less than 0.01% by weight.
- the catalyst used for the production of the polymer composition according to the invention is preferably selected or omitted accordingly, so that this is ensured.
- the proportion of crosslinking catalyst in the moisture-curing composition is preferably 0.001 to 5% by weight, preferably 0.005 to 1% by weight, particularly preferably 0.01 to 0.5% by weight, based on the total weight of the composition.
- the moisture-curing composition also comprises at least one plasticizer.
- plasticizers examples include esters of organic carboxylic acids or their anhydrides, such as fatty acid alkyl esters, phthalates, e.g. Dioctyl phthalate, diisononyl phthalate or diisodecyl phthalate, adipates, e.g. Dioctyl adipate, azelates and sebacates, polyols, e.g. Polyoxyalkylene polyols or polyester polyols, organic phosphoric and sulfonic acid esters, mineral oils or polybutenes.
- the use of plasticizers containing phthalates is preferably avoided.
- Preferred plasticizers are fatty acid alkyl esters, alkyl sulfonic acid esters of phenol, mineral oils, plasticizers based on renewable raw materials, which may also be fatty acid real alkyl esters, or combinations thereof.
- plasticizers based on renewable raw materials are vegetable oils, such as rapeseed oil, soybean oil and palm oil, and esters, in particular methyl esters, of vegetable oils, such as rapeseed oil methyl ester, soy methyl ester and palm oil methyl ester.
- plasticizers which are not based on renewable raw materials but are phthalate-free are 1,2-cyclohexanedicarboxylic acid diisononyl esters, alkyl sulfonic acid esters of phenol and polyethers with an average molecular weight of less than 4000 g / mol, such as Desmophen 2061 BD from Covestro Deutschland AG ,
- the plasticizer particularly preferably comprises 1,2-cyclohexane-dicarboxylic acid diisononyl ester (DINCH), alkyl sulfonic acid ester of phenol, rapeseed oil methyl ester or a combination thereof, preferably a combination of 1,2-cyclohexanedicarboxylic acid diisononyl ester and rapeseed oil methyl ester being used.
- DICH 1,2-cyclohexane-dicarboxylic acid diisononyl ester
- alkyl sulfonic acid ester of phenol rapeseed oil methyl ester or a combination thereof, preferably a combination of 1,2-cyclohexanedicarboxylic acid diisononyl ester and rapeseed oil methyl ester being used.
- the proportion of plasticizer in the moisture-curing composition is preferably 1 to 50% by weight, preferably 5 to 30% by weight, particularly preferably 5 to 25% by weight, based on the total weight of the moisture-curing composition.
- the moisture-curing composition can additionally contain further constituents.
- constituents of this type are solvents; Fibers, for example made of polyethylene; dyes; pigments; Rheology modifiers such as thickeners or thixotropic agents, for example urea compounds of the type described as thixotropic endowning agents in WO 2002/048228 A2 on pages 9 to 11, polyamide waxes, hydrogenated castor oil or swellable plastics such as PVC, stabilizers, for example against heat, light and UV radiation; flame-retardant substances; surface-active substances such as wetting agents, leveling agents, deaerating agents or defoamers; biocides such as algicides, fungicides or antifungal substances; as well as other substances commonly used in moisture-curing compositions.
- so-called reactive diluents can optionally be used, which are incorporated into the polymer matrix during the curing of the composition, in particular by reaction with the silane groups.
- silane-functional polymers can also be contained as part of the moisture-curing composition according to the invention.
- Those silane-functional polymers which have silane groups with less reactivity to water can be added particularly preferably. These are, for example, those polymers which have resulted from the reaction of polyols with isocyanatosilanes and those which are obtainable by a hydrosilylation reaction of polymers with terminal double bonds, for example poly (meth) acrylate polymers or polyether polymers, in particular of allyl-terminated polyoxyalkylene polymers, described, for example, in US Pat. A 3,971,751 and US-B 6,207,766, the entire disclosure of which is hereby incorporated.
- silane-functional polymers are commercially available under the trade names MS Polymer TM S203H, S303H, S227, S327, MS Silyl TM SAX220, SAX 260, SAX350, SAX400, SAX 510, SAX 520, SAX 530, SAX 580, SAX 590, SAX725 MAX 602 MAX 923 MAX 951, silyl TM SAT350 and SAT400, XMAP TM SA100S and SA310S from the company Kaneka Corp., Japan, and sold under the trade name Excestar ® S2410, S2420, S3430, S3630, W2450 and MSX931 by the company Asahi Glass Co, Ftd., Japan.
- the moisture curing composition comprises
- the moisture-curing composition comprises
- silane-functional polymer without urethane groups with lower reactivity to water selected from the products MS Polymer TM S203H, S303H, S227, S327, MS Silyl TM SAX220, SAX 260, SAX350, SAX400, SAX 510, SAX 520, SAX 530, SAX 580, SAX 590, SAX725, MAX 602, MAX 923, MAX 951, Silyl TM SAT350 and SAT400, XMAP TM SA100S and SA310S from Kaneka Corp., Japan, as well as under the trade names Excestar ® S2410, S2420, S3430, S3630, W2450 and MSX931 from Asahi
- the moisture-curing composition comprises
- a further silane-functional polymer with urethane groups selected from the products Geniosil ® STPE-15 and STPE-35 from Wacker, Desmoseal ® S XP 2636, XP 2774, XP 2479 (Covestro)
- the invention further relates to a process for the preparation of the polymer composition according to the invention, comprising the steps of: a) reacting an NCO-reactive polymer which has at least two NCO-reactive groups per molecule with a polyisocyanate, the molar ratio of the polymer isocyanate molecules to the NCO-reactive groups of the NCO-reactive polymer is at least 1.25: 1; and b) reaction of the reaction product from step a) with an NCO-reactive silane.
- the molar ratio of the polyisocyanate molecules to the NCO-reactive groups of the polymer in step a) of the production process is preferably 1.25 to 10, particularly preferably 1.5 to 7, most preferably 2 to 5.
- the reaction of the polyisocyanate with the NCO-reactive polymer takes place, for example, at a temperature of 20 to 100 ° C, optionally with the addition of a suitable catalyst, in particular a urethanization catalyst, such as dibutyltin dilaurate.
- a suitable catalyst in particular a urethanization catalyst, such as dibutyltin dilaurate.
- the reaction product formed is reacted with the NCO-reactive silane, for example, at a temperature of 30 to 100 ° C.
- a rapid reaction can be carried out in many cases even without the addition of a tin-containing catalyst, especially when aromatic NCO groups, such as those of toluyl diisocyanates, react. Therefore, in a preferred embodiment, no tin-containing catalyst is used, but tin-free catalysts such as bismuth, zirconium and / or titanium compounds known from the prior art. In a further embodiment, the implementation is carried out without a catalyst. In one embodiment, at least one step a) and or b) is carried out in the presence of a plasticizer or solvent. However, the addition of plasticizer and / or solvent is preferably dispensed with.
- the invention also relates to a process for producing the moisture-curing composition according to the invention, a polymer composition according to the invention being mixed with at least one filler, at least one adhesion promoter, at least one crosslinking catalyst and / or at least one plasticizer.
- the polymer composition according to the invention is mixed with at least one filler which has a water content of up to 1% by weight, preferably 0.01 to 0.5% by weight, particularly preferably 0.1 to 0.3% by weight, based on the total weight of the filler.
- the vinyl group-containing silane is not added to the moisture-curing composition.
- at most 1% by weight, preferably up to 0.8% by weight, particularly preferably up to 0.5% by weight, of vinyl groups-containing silanes are added to the moisture-curing composition, based on the total weight the moisture-curing composition.
- the composition contains less than 1.0% by weight of vinyltrimethoxy silane and vinyltriethoxysilane.
- a plurality of alkylsilanes and / or vinylsilanes are added, the proportion of each one based on the total weight of the moisture-curing composition not exceeding 1.0%, in particular 0.1% by weight.
- the invention also relates to the use of the polymer composition according to the invention as a drying agent for moisture-curing adhesives, sealants and coating materials.
- this also relates to the use of the polymer composition according to the invention as a combination of drying agent and binder for moisture-curing adhesives, sealants and coating materials.
- the polymer compositions according to the invention are particularly suitable as drying agents for moisture-curing adhesives for fastening floor coverings; they can be used particularly well for use in parquet adhesives. Examples
- the addition of catalyst was dispensed with and the reaction temperature was increased to 80 ° C. (Examples P4 and P5).
- the amounts of / V- (3-trimethoxysilylpropyl) aspartic acid diethyl ester prepared in accordance with EP-A 0 596 360, Example 5) given in Table 1 under “Amount of NCO-reactive silane”
- the mixture was stirred further until no more isocyanate band was visible in the IR spectrum.
- the amount of substance of NCO-reactive groups in the NCO-reactive polymer was calculated as follows: OH number in mg KOH / g polymer determined according to DIN 53240-1 divided by 1000 (mg / g) and the molar mass KOH (56.1 g / mol) multiplied by the mass of NCO-reactive polymer.
- the amount of the polyisocyanate was calculated as follows:
- the ratio of the amounts of the polyisocyanate to the amount of NCO-reactive groups was calculated as follows: the amount of the polyisocyanate in mol divided by the amount of NCO-reactive groups in the NCO-reactive polymer.
- the polymer composition produced with a low ratio of polyisocyanate to NCO-reactive groups has a higher viscosity than the polymer compositions PI and P2 according to the invention.
- the comparative composition P5 shows that with a low ratio of polyisocyanate to NCO-reactive groups, the catalyst cannot be dispensed with, because without the use of a catalyst, the reaction time until the NCO-reactive groups of the NCO-reactive group is fully implemented Polymer is significantly longer. With a high ratio of polyisocyanate to NCO-reactive groups, however, the NCO-reactive groups of the NCO-reactive polymer are reacted in a relatively short time even without the addition of a catalyst.
- the amounts of IPDI and / V- (3-trimethoxysilyl propyl) aspartic acid diethyl ester used were chosen such that the relative amounts of the raw materials used, including the raw materials used for the preparation of the polymer composition P3, correspond exactly to those of the polymer composition P2 according to the invention corresponded.
- the ratio of IPDI to NCO-reactive groups in the polyol thus corresponded to that of the polymer composition P2 according to the invention.
- the polymer composition thus obtained had a high viscosity of 45 Pa ⁇ s.
- This example shows that the polymer composition according to the invention has a lower viscosity than a composition produced from the same starting materials according to the teaching of DE 10 2005 026 085 A1.
- a moisture-curing composition based on the polymer composition PI was prepared according to the following procedure: 578.8 g of above 16 hours at 100 ° C in a convection oven to a water content of 0.08 wt .-% of dried filler Omyalite 95 T ® (calcium carbonate, Omya) are mixed with 136.2 g plasticizer (Mesamoll ®, Lanxess, water content 0.03 wt .-%), 275.5 g of polymer composition PI (Table 3), 8.4 g Cab-O-Sil ® TS 720 ( hydrophobic fumed silica, Cabot, water content 0.11% by weight) and 3 g of 1,8-diazabicyclo [5.4.0] undec-7-ene (Sigma-Aldrich Co.
- Static vacuum is understood here to mean that the apparatus is evacuated to a pressure of 200 mbar (dynamic vacuum) and then the connection to the vacuum pump is disconnected. The cooling was chosen so that a temperature of 65 ° C was not exceeded during the entire production.
- Composition FC 3 was prepared analogously to FZ-2, with the addition of vinyltrimethoxysilane as a drying agent (Dynasilan ® VTMO, Evonik) and an adhesion promoter (Dynasilan ® 1146, Evonik) were added.
- the compositions FZ-1 to FZ-3 were examined as described below for their storage stability (viscosity increase) and reactivity (skin formation time). The results are shown in the table below.
- the moisture-curing compositions were applied after 7 days in a cartridge using a doctor blade to form membranes with a uniform layer thickness of 2 mm on a polyethylene film and cured for 14 days at 23 ° C. and 50% atmospheric humidity, the membranes after 7 days were removed from the film and turned.
- the properties of these membranes were then determined using the following methods.
- the viscosity was determined after seven or 60 days of storage in accordance with the specification in DIN DIN EN ISO 3219 / B3 at a shear rate of 40 / s.
- the Shore A hardness was tested on the membranes in accordance with the specification in DIN ISO 7619-1. To determine the Shore A hardness, three membranes were placed on top of one another to ensure a layer thickness of 6 mm.
- the elongation at break and the tensile strength were determined by means of a tensile test in accordance with the specification in DIN 53 504 on S2 shoulder bars, which were punched out of the membranes produced as described above using a shaping punch.
- the test speed was 200 mm / min.
- a film of the adhesive was applied to a glass plate previously cleaned with ethyl acetate and immediately placed in a drying recorder (BK 3 drying recorder, BYK-Gardner).
- the needle was loaded with 10 g and moved over a distance of 35 cm over a period of 24 hours.
- the drying recorder was in a climate room at 23 ° C and 50% rel. Humidity. The time of disappearance of the permanent trace of the needle from the film was specified as the skin formation time.
- the water content was determined in accordance with DIN EN ISO 15512: 2017-03, method B2.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Polyurethanes Or Polyureas (AREA)
- Sealing Material Composition (AREA)
- Paints Or Removers (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
Applications Claiming Priority (2)
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EP18189953.5A EP3613785A1 (fr) | 2018-08-21 | 2018-08-21 | Agent de séchage pour compositions durcissant à l'humidité |
PCT/EP2019/071838 WO2020038803A1 (fr) | 2018-08-21 | 2019-08-14 | Déshydratant pour compositions durcissant à l'humidité |
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EP18189953.5A Ceased EP3613785A1 (fr) | 2018-08-21 | 2018-08-21 | Agent de séchage pour compositions durcissant à l'humidité |
EP19752526.4A Pending EP3841137A1 (fr) | 2018-08-21 | 2019-08-14 | Déshydratant pour compositions durcissant à l'humidité |
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EP18189953.5A Ceased EP3613785A1 (fr) | 2018-08-21 | 2018-08-21 | Agent de séchage pour compositions durcissant à l'humidité |
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US (1) | US20210309793A1 (fr) |
EP (2) | EP3613785A1 (fr) |
CN (1) | CN112638978B (fr) |
WO (1) | WO2020038803A1 (fr) |
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EP3715396A1 (fr) * | 2019-03-26 | 2020-09-30 | PolyU GmbH | Composition et procédé de fabrication de polymères silylées et son utilisation |
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US3971751A (en) | 1975-06-09 | 1976-07-27 | Kanegafuchi Kagaku Kogyo Kabushiki Kaisha | Vulcanizable silylether terminated polymer |
US5158922A (en) | 1992-02-04 | 1992-10-27 | Arco Chemical Technology, L.P. | Process for preparing metal cyanide complex catalyst |
DE4237468A1 (de) | 1992-11-06 | 1994-05-11 | Bayer Ag | Alkoxysilan- und Aminogruppen aufweisende Verbindungen |
US5470813A (en) | 1993-11-23 | 1995-11-28 | Arco Chemical Technology, L.P. | Double metal cyanide complex catalysts |
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 |
WO1998047939A1 (fr) | 1997-04-21 | 1998-10-29 | Asahi Glass Company Ltd. | Compositions durcissant a la temperature ambiante |
DE19952089C1 (de) * | 1999-10-29 | 2001-04-05 | Henkel Kgaa | Verwendung von thermoplastischen Polymerzusammensetzungen als Trockenmittel |
JP2002179753A (ja) | 2000-12-13 | 2002-06-26 | Nippon Shiika Kk | 高耐候性ポリウレタン系一液型湿気硬化性組成物 |
JP2006002008A (ja) * | 2004-06-16 | 2006-01-05 | Toagosei Co Ltd | 湿気硬化性組成物および接着剤組成物 |
DE102005026085A1 (de) | 2005-06-07 | 2006-12-14 | Construction Research & Technology Gmbh | Silan-modifizierte Harnstoff-Derivate, Verfahren zu ihrer Herstellung und deren Verwendung als Rheologiehilfsmittel |
US20070129527A1 (en) * | 2005-12-06 | 2007-06-07 | Griswold Roy M | Silylated polyurethane-polyurea protective coating compositions |
DE102008020979A1 (de) * | 2008-04-25 | 2009-10-29 | Henkel Ag & Co. Kgaa | Härtbare Zusammensetzungen enthaltend silylierte Polyurethane |
EP2952533A1 (fr) | 2014-06-04 | 2015-12-09 | Sika Technology AG | Matériau d'étanchéité sans étain ni phtalate à base de polymères à terminaisons silane |
CN109476804B (zh) * | 2016-07-21 | 2022-03-01 | Sika技术股份公司 | 具有改善的机械性能的阻燃粘合剂和密封剂 |
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2018
- 2018-08-21 EP EP18189953.5A patent/EP3613785A1/fr not_active Ceased
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- 2019-08-14 WO PCT/EP2019/071838 patent/WO2020038803A1/fr unknown
- 2019-08-14 US US17/267,524 patent/US20210309793A1/en active Pending
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- 2019-08-14 EP EP19752526.4A patent/EP3841137A1/fr active Pending
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EP3613785A1 (fr) | 2020-02-26 |
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CN112638978B (zh) | 2023-05-16 |
US20210309793A1 (en) | 2021-10-07 |
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