JP6301905B2 - シラン末端ポリマー系の組成物 - Google Patents
シラン末端ポリマー系の組成物 Download PDFInfo
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- JP6301905B2 JP6301905B2 JP2015500879A JP2015500879A JP6301905B2 JP 6301905 B2 JP6301905 B2 JP 6301905B2 JP 2015500879 A JP2015500879 A JP 2015500879A JP 2015500879 A JP2015500879 A JP 2015500879A JP 6301905 B2 JP6301905 B2 JP 6301905B2
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- silane
- polymer
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- 239000000203 mixture Substances 0.000 title claims description 106
- 239000003707 silyl modified polymer Substances 0.000 title 1
- 229920000642 polymer Polymers 0.000 claims description 59
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 50
- 229910000077 silane Inorganic materials 0.000 claims description 41
- 229920002635 polyurethane Polymers 0.000 claims description 37
- 239000004814 polyurethane Substances 0.000 claims description 37
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 36
- 150000001875 compounds Chemical class 0.000 claims description 34
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 31
- 229920001002 functional polymer Polymers 0.000 claims description 29
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 239000003054 catalyst Substances 0.000 claims description 11
- 239000003446 ligand Substances 0.000 claims description 10
- 239000000853 adhesive Substances 0.000 claims description 8
- 230000001070 adhesive effect Effects 0.000 claims description 8
- 229920000570 polyether Polymers 0.000 claims description 8
- NOKSMMGULAYSTD-UHFFFAOYSA-N [SiH4].N=C=O Chemical compound [SiH4].N=C=O NOKSMMGULAYSTD-UHFFFAOYSA-N 0.000 claims description 7
- 239000012948 isocyanate Substances 0.000 claims description 7
- 239000000565 sealant Substances 0.000 claims description 7
- 238000000576 coating method Methods 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000005842 heteroatom Chemical group 0.000 claims description 5
- 238000006459 hydrosilylation reaction Methods 0.000 claims description 4
- 239000011248 coating agent Substances 0.000 claims description 3
- 229920000193 polymethacrylate Polymers 0.000 claims description 3
- 150000003606 tin compounds Chemical class 0.000 claims description 2
- 229920000058 polyacrylate Polymers 0.000 claims 1
- -1 fumaric acid diesters Chemical class 0.000 description 45
- 229920005862 polyol Polymers 0.000 description 44
- 150000003077 polyols Chemical class 0.000 description 44
- 238000006243 chemical reaction Methods 0.000 description 18
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 18
- 150000002009 diols Chemical class 0.000 description 17
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 15
- 238000001723 curing Methods 0.000 description 14
- 229920001451 polypropylene glycol Polymers 0.000 description 14
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 12
- 239000000758 substrate Substances 0.000 description 12
- 239000005056 polyisocyanate Substances 0.000 description 11
- 229920001228 polyisocyanate Polymers 0.000 description 11
- 239000003795 chemical substances by application Substances 0.000 description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 7
- 235000014113 dietary fatty acids Nutrition 0.000 description 7
- 239000000194 fatty acid Substances 0.000 description 7
- 229930195729 fatty acid Natural products 0.000 description 7
- 239000000945 filler Substances 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 229920005906 polyester polyol Polymers 0.000 description 7
- 230000008569 process Effects 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 125000005442 diisocyanate group Chemical group 0.000 description 6
- ZVFDTKUVRCTHQE-UHFFFAOYSA-N Diisodecyl phthalate Chemical compound CC(C)CCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC(C)C ZVFDTKUVRCTHQE-UHFFFAOYSA-N 0.000 description 5
- 239000004721 Polyphenylene oxide Substances 0.000 description 5
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 5
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 5
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 5
- 239000003925 fat Substances 0.000 description 5
- 150000002430 hydrocarbons Chemical group 0.000 description 5
- 150000002513 isocyanates Chemical class 0.000 description 5
- 239000004014 plasticizer Substances 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- 150000005846 sugar alcohols Polymers 0.000 description 5
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 4
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 4
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- 238000004132 cross linking Methods 0.000 description 4
- 239000000539 dimer Substances 0.000 description 4
- 150000004665 fatty acids Chemical class 0.000 description 4
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 4
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 4
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 125000000962 organic group Chemical group 0.000 description 4
- 239000013500 performance material Substances 0.000 description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
- 229920000515 polycarbonate Polymers 0.000 description 4
- 239000004417 polycarbonate Substances 0.000 description 4
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 4
- 150000004756 silanes Chemical class 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- 235000012239 silicon dioxide Nutrition 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-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 3
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 3
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Natural products OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 3
- 239000005058 Isophorone diisocyanate Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
- 239000000370 acceptor Substances 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 3
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 3
- 239000006229 carbon black Substances 0.000 description 3
- WCRDXYSYPCEIAK-UHFFFAOYSA-N dibutylstannane Chemical compound CCCC[SnH2]CCCC WCRDXYSYPCEIAK-UHFFFAOYSA-N 0.000 description 3
- VSNLCLFPPHBFLV-UHFFFAOYSA-N diethyl 2-(3-trimethoxysilylpropylamino)butanedioate Chemical compound CCOC(=O)CC(C(=O)OCC)NCCC[Si](OC)(OC)OC VSNLCLFPPHBFLV-UHFFFAOYSA-N 0.000 description 3
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 3
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 239000010703 silicon Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 150000004072 triols Chemical class 0.000 description 3
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 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 description 2
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 2
- WMRCTEPOPAZMMN-UHFFFAOYSA-N 2-undecylpropanedioic acid Chemical compound CCCCCCCCCCCC(C(O)=O)C(O)=O WMRCTEPOPAZMMN-UHFFFAOYSA-N 0.000 description 2
- ZYAASQNKCWTPKI-UHFFFAOYSA-N 3-[dimethoxy(methyl)silyl]propan-1-amine Chemical compound CO[Si](C)(OC)CCCN ZYAASQNKCWTPKI-UHFFFAOYSA-N 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 238000006834 Hetero-Michael addition reaction Methods 0.000 description 2
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 2
- 239000004472 Lysine Substances 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical class CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000005062 Polybutadiene Substances 0.000 description 2
- 229920002396 Polyurea Polymers 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 229910018540 Si C Inorganic materials 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 2
- JJLKTTCRRLHVGL-UHFFFAOYSA-L [acetyloxy(dibutyl)stannyl] acetate Chemical compound CC([O-])=O.CC([O-])=O.CCCC[Sn+2]CCCC JJLKTTCRRLHVGL-UHFFFAOYSA-L 0.000 description 2
- 239000002318 adhesion promoter Substances 0.000 description 2
- 239000001361 adipic acid Substances 0.000 description 2
- 235000011037 adipic acid Nutrition 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 2
- HUCVOHYBFXVBRW-UHFFFAOYSA-M caesium hydroxide Chemical compound [OH-].[Cs+] HUCVOHYBFXVBRW-UHFFFAOYSA-M 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 238000010276 construction Methods 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- INSRQEMEVAMETL-UHFFFAOYSA-N decane-1,1-diol Chemical compound CCCCCCCCCC(O)O INSRQEMEVAMETL-UHFFFAOYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 239000002274 desiccant Substances 0.000 description 2
- 150000001991 dicarboxylic acids Chemical class 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
- HGQSXVKHVMGQRG-UHFFFAOYSA-N dioctyltin Chemical compound CCCCCCCC[Sn]CCCCCCCC HGQSXVKHVMGQRG-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 230000007717 exclusion Effects 0.000 description 2
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- 239000003063 flame retardant Substances 0.000 description 2
- 239000001530 fumaric acid Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- MHIBEGOZTWERHF-UHFFFAOYSA-N heptane-1,1-diol Chemical compound CCCCCCC(O)O MHIBEGOZTWERHF-UHFFFAOYSA-N 0.000 description 2
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 2
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 2
- 150000004677 hydrates Chemical class 0.000 description 2
- 238000007037 hydroformylation reaction Methods 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 2
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 2
- 150000002596 lactones Chemical class 0.000 description 2
- 229920002521 macromolecule Polymers 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 description 2
- 150000001283 organosilanols Chemical class 0.000 description 2
- 150000003961 organosilicon compounds Chemical class 0.000 description 2
- 125000005375 organosiloxane group Chemical group 0.000 description 2
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
- UWJJYHHHVWZFEP-UHFFFAOYSA-N pentane-1,1-diol Chemical compound CCCCC(O)O UWJJYHHHVWZFEP-UHFFFAOYSA-N 0.000 description 2
- 229920002857 polybutadiene Polymers 0.000 description 2
- 238000006068 polycondensation reaction Methods 0.000 description 2
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- 229910010271 silicon carbide Inorganic materials 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 2
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 2
- GRXOWOKLKIZFNP-UHFFFAOYSA-N undecane-1,1-diol Chemical compound CCCCCCCCCCC(O)O GRXOWOKLKIZFNP-UHFFFAOYSA-N 0.000 description 2
- 150000003672 ureas Chemical class 0.000 description 2
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 2
- PLFFHJWXOGYWPR-HEDMGYOXSA-N (4r)-4-[(3r,3as,5ar,5br,7as,11as,11br,13ar,13bs)-5a,5b,8,8,11a,13b-hexamethyl-1,2,3,3a,4,5,6,7,7a,9,10,11,11b,12,13,13a-hexadecahydrocyclopenta[a]chrysen-3-yl]pentan-1-ol Chemical compound C([C@]1(C)[C@H]2CC[C@H]34)CCC(C)(C)[C@@H]1CC[C@@]2(C)[C@]4(C)CC[C@@H]1[C@]3(C)CC[C@@H]1[C@@H](CCCO)C PLFFHJWXOGYWPR-HEDMGYOXSA-N 0.000 description 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- MHYXPAGFFCSTCJ-UHFFFAOYSA-N 1,2-bis(2-isocyanatopropan-2-yl)naphthalene Chemical compound C1=CC=CC2=C(C(C)(C)N=C=O)C(C(C)(N=C=O)C)=CC=C21 MHYXPAGFFCSTCJ-UHFFFAOYSA-N 0.000 description 1
- RTTZISZSHSCFRH-UHFFFAOYSA-N 1,3-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC(CN=C=O)=C1 RTTZISZSHSCFRH-UHFFFAOYSA-N 0.000 description 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 description 1
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- 230000003068 static effect Effects 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- TXDNPSYEJHXKMK-UHFFFAOYSA-N sulfanylsilane Chemical class S[SiH3] TXDNPSYEJHXKMK-UHFFFAOYSA-N 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- VXUYXOFXAQZZMF-UHFFFAOYSA-N tetraisopropyl titanate Substances CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 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
- 238000004448 titration Methods 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000000811 xylitol Substances 0.000 description 1
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
- 235000010447 xylitol Nutrition 0.000 description 1
- 229960002675 xylitol Drugs 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
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4825—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
- C08G18/70—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
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0091—Complexes with metal-heteroatom-bonds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/56—Organo-metallic compounds, i.e. organic compounds containing a metal-to-carbon bond
- C08K5/57—Organo-tin compounds
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
- C08L75/04—Polyurethanes
Description
特に有機スズ化合物は、水の存在下で、シラン官能性ポリマーを含有する組成物の架橋のための触媒又は促進剤システムとして使用される。この目的のためにチタネート(titanate)を使用することも知られている。
チタネートで硬化された系は、一般的に顕著な利点を示す有機スズ化合物で硬化された系と比較して、優れた機械的性質を示すことが見出された。
有機スズ化合物とチタネートとの正確に規定された重量部での使用が、適用プロセス及び加工プロセスで調整を必要とさせるようなスキン形成時間の変化を発生させずに、硬化した状態で改善された機械的特性を与える組成物を提供することを可能にする。
すなわち本発明の実施態様としては以下の態様を挙げることができる:
《態様1》
a)少なくとも1つのシラン官能性ポリマーP;
b)少なくとも1つの有機スズ化合物;及び
c)少なくとも1つのチタネート
を含み、
それぞれ組成物全体に基づいて、有機スズ化合物の割合が、0.01〜0.15wt%であり、チタネートの割合が0.05〜1wt%である、組成物。
《態様2》
前記シラン官能性ポリウレタンポリマーPが、以下から選択される、態様1に記載の組成物:
− イソシアネート基に対して反応性がある少なくとも1つの基を含む少なくとも1つのシランと、イソシアネート基を含有するポリウレタンポリマーとを反応させることにより得られうる、シラン官能性ポリウレタンポリマーP1;
− イソシアナートシランISと、イソシアネート基に対して反応性がある官能性末端基を含むポリマーとを反応させることにより得られうる、シラン官能性ポリウレタンポリマーP2;又は
− 末端2重結合を有するポリマーのヒドロシリル化反応によって得られうる、シラン官能性ポリマーP3。
《態様3》
前記有機スズ化合物が、ジアルキルスズ化合物である、態様1又は2に記載の組成物。
《態様4》
前記有機スズ化合物の割合が、組成物全体に基づいて0.05〜0.1wt%である、態様1〜3のいずれか一項に記載の組成物。
《態様5》
前記チタネートの割合が、組成物全体に基づいて0.1〜0.6wt%、特に0.1〜0.3wt%である、態様1〜4のいずれか一項に記載の組成物。
《態様6》
前記チタネートが、少なくとも一つの多座リガンドを有する、態様1〜5のいずれか一項に記載の組成物。
《態様7》
前記チタネートが、次の式(VI)のチタネートである、態様5に記載の組成物:
R 21 は、水素原子、又は1〜8個の炭素原子を有する直鎖の又は分岐したアルキル基を表し、
R 22 は、水素原子、又はヘテロ原子を含有していてもよい、1〜8個の炭素原子を有する直鎖の又は分岐したアルキル基を表し、
R 23 は、水素原子、又は1〜8個の炭素原子を有するアルキル基、又は1〜8個の炭素原子を有する直鎖の又は分岐したアルコキシ基を表し、
R 24 は、2〜20個の炭素原子を有する直鎖の又は分岐したアルキル基を表し、
nは、1又は2の値である)。
《態様8》
シラン官能性ポリマーを含有する組成物を水の存在下で架橋するための、触媒又は促進剤系としての、少なくとも一つのチタネートと少なくとも一つの有機スズ化合物とを共に用いる使用であって、それぞれ組成物全体に基づいて、有機スズ化合物の割合が0.01〜0.15wt%であり、チタネートの割合が0.05〜1wt%である、使用。
《態様9》
接着剤、封止剤、又はコーティングとしての、態様1〜7のいずれか一項に記載の組成物の使用。
《態様10》
態様1〜7のいずれか1項に記載の組成物から水で硬化した後に得られる、硬化した組成物。
a)少なくとも1つのシラン官能性ポリマーPと、
b)少なくとも1つの有機スズ化合物と、
c)少なくとも1つのチタネートと、
を含む組成物であって、
それぞれ組成物全体に基づいて、有機スズ化合物の割合が0.01〜0.15wt%であり、チタネートの割合が0.05〜1wt%である組成物である。
本明細書において「室温」は、23℃の温度として定義される。
R2基は、1〜5個の炭素原子を有するアシル基、又は直鎖の又は分岐した1価炭化水素基、特にメチル基、エチル基又はイソプロピル基を表す。
添え字aは、0又は1又は2の値を表し、特に0の値を表す。
有機スズ化合物の割合は、組成物全体に基づいて、0.01〜0.15wt%、特に0.05〜0.1wt%になる。
R22基は、水素原子、又は随意にヘテロ原子を有し、1〜8個の炭素原子を有する直鎖の又は分岐したアルキル基を表し、特に水素原子を表す。
R23基は、水素原子、又は1〜8個、特に1〜3個の炭素原子を有するアルキル基、又は1〜8個、特に1〜3個の炭素原子を有する直鎖の又は分岐したアルコキシ基を表す。
R24基は、2〜20個の炭素原子を有する直鎖の又は分岐したアルキル基、特にイソブチル−又はイソプロピル基を表す。
nは、1又は2の値、特に2を表す。
チタネートの割合は、組成物全体に基づいて、0.05〜1wt%、好ましくは0.1〜0.6wt%、特に0.1〜0.3wt%になる。
充填剤の適切な量は、組成物全体に基づいて、例えば20〜60wt%、好ましくは30〜60wt%の範囲である。
示された値のための測定方法は、態様の枠組みの中で説明されている。
i)基質S1及び/又は基質S2に上記組成物を塗布する工程と、
ii)組成物のオープン時間内に、塗布された組成物上で、基質S1とS2とを接触させる工程と、
iii)組成物を水で硬化させる工程と、
を含み、基質S1とS2は互いに同じか又は異なる、方法で使用される。
i)基質S1上に、及び/又は2つの基質S1とS2との間に、前記組成物を塗布する工程と、
ii)組成物を、特に湿度の形態の水で硬化する工程と、
を含み、基質S1とS2は互いに同じか又は異なる、方法で使用することもできる。
記載された発明をさらに説明するために、以下に例が提示される。当然ながら、本発明は記載されたこれらの例に限定されるものではない。
0〜5%伸びでの弾性率、引張強度、及び破壊伸び率は、DIN53504(クロスヘッド速度:200mm/分)に従って、23℃で相対湿度50%で7日間硬化させた2mmの層厚さを有する膜で測定した。
窒素雰囲気下で、1000gのポリオールAcclaim(商標)12200(Bayer MaterialScience AG,Germany;低モノールポリオキシプロピレンジオール;OH価11.0mgKOH/g;含水量約0.02wt%)、46.17gのイソホロンジイソシアネート(Vestanat(商標)IPDI)、261.72gのフタル酸ジイソデシル(Palatinol(商標)Z)、及び0.14gのジ−n−ブチルスズジラウレート(Metatin(商標)K712、Acima AG、Switzerland)を、絶えず攪拌しながら90℃に加熱し、この温度で保持した。1時間の反応時間の後、0.70%(滴定)の遊離イソシアネート基含量が達成された。次に69.88gのN−(3−トリメトキシシリル−プロピル)−アミノ−コハク酸ジエチルエステルを添加し、90℃でさらに撹拌を2〜3時間続けた。赤外分光法(2275〜2230cm−1)によってそれ以上の遊離イソシアネートを測定することができなくなると、直ちに反応を止めた。生成物を室温(23℃)まで冷却し、水分の排除下で保存した(理論的ポリマー含量=90%)。このようにして製造したシラン官能性ポリウレタンポリマーSHは、室温で液体である。
真空ミキサー中で、表1〜3に示した重量部に対応して、シラン官能性ポリマーSH、ジイソデシルフタレート(DIDP)、及びビニルトリメトキシシラン(乾燥剤、Momentive Performance Materials Inc.、USAからのSilquest(商標)A−171)を5分間よく混合した。その後乾燥させ、沈殿したチョーク(Socal(商標)U1S2、Solvay SA、Belgium)を60℃で15分間混練した。ヒーターをオフにし、N−(2−アミノエチル)−(3−アミノプロピル)トリメトキシシラン(接着促進剤、Momentive Performance Materials Inc.からのSilquest(商標)A−1120)、ジ−n−ブチル−スズジラウレート(DBTDL、Metatin(商標)K712、10%のDIDP溶液として加えられた)、及び/又はチタネート(Dorf KetalからTyzor(商標)IBAY)を、真空下で10分間処理して、均質なペーストを作成した。次に、これを内部にラッカー塗装したアルミニウム拡大プランジャーカートリッジ(internally lacquered aluminum expanding plunger cartridge)に充填した。
Claims (10)
- a)少なくとも1つのシラン官能性ポリマーP;
b)少なくとも1つの有機スズ化合物;及び
c)少なくとも1つのチタネート
を含み、
それぞれ組成物全体に基づいて、有機スズ化合物の割合が、0.01〜0.15wt%であり、チタネートの割合が0.05〜1wt%であり、かつ
前記シラン官能性ポリマーPが、以下から選択される、組成物:
− イソシアネート基に対して反応性がある少なくとも1つの基を含む少なくとも1つのシランと、イソシアネート基を含有するポリウレタンポリマーとを反応させることにより得られうる、シラン官能性ポリウレタンポリマーP1;
− イソシアナートシランISと、イソシアネート基に対して反応性がある官能性末端基を含むポリマーとを反応させることにより得られうる、シラン官能性ポリウレタンポリマーP2;又は
− 末端2重結合を有するポリ(メタ)アクリレートポリマー又はポリエーテルポリマーのヒドロシリル化反応によって得られうる、シラン官能性ポリマーP3。 - 前記シラン官能性ポリマーPが、以下から選択される、請求項1に記載の組成物:
− イソシアネート基に対して反応性がある少なくとも1つの基を含む少なくとも1つのシランと、イソシアネート基を含有するポリウレタンポリマーとを反応させることにより得られうる、シラン官能性ポリウレタンポリマーP1;又は
− イソシアナートシランISと、イソシアネート基に対して反応性がある官能性末端基を含むポリマーとを反応させることにより得られうる、シラン官能性ポリウレタンポリマーP2。 - 前記有機スズ化合物が、ジアルキルスズ化合物である、請求項1又は2に記載の組成物。
- 前記有機スズ化合物の割合が、組成物全体に基づいて0.05〜0.1wt%である、請求項1〜3のいずれか一項に記載の組成物。
- 前記チタネートの割合が、組成物全体に基づいて0.1〜0.6wt%である、請求項1〜4のいずれか一項に記載の組成物。
- 前記チタネートが、少なくとも一つの多座リガンドを有する、請求項1〜5のいずれか一項に記載の組成物。
- シラン官能性ポリマーを含有する組成物を水の存在下で架橋するための、触媒又は促進剤系としての、少なくとも一つのチタネートと少なくとも一つの有機スズ化合物との使用であって、それぞれ組成物全体に基づいて、有機スズ化合物の割合が0.01〜0.15wt%であり、チタネートの割合が0.05〜1wt%であり、かつ前記シラン官能性ポリマーPが、以下から選択される、使用:
− イソシアネート基に対して反応性がある少なくとも1つの基を含む少なくとも1つのシランと、イソシアネート基を含有するポリウレタンポリマーとを反応させることにより得られうる、シラン官能性ポリウレタンポリマーP1;
− イソシアナートシランISと、イソシアネート基に対して反応性がある官能性末端基を含むポリマーとを反応させることにより得られうる、シラン官能性ポリウレタンポリマーP2;又は
− 末端2重結合を有するポリ(メタ)アクリレートポリマー又はポリエーテルポリマーのヒドロシリル化反応によって得られうる、シラン官能性ポリマーP3。 - 接着剤、封止剤、又はコーティングとしての、請求項1〜7のいずれか一項に記載の組成物の使用。
- 請求項1〜7のいずれか一項に記載の組成物から水で硬化した後に得られる、硬化した組成物。
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EP12160128.0A EP2641935A1 (de) | 2012-03-19 | 2012-03-19 | Zusammensetzung auf Basis von silanterminierten Polymeren |
EP12160128.0 | 2012-03-19 | ||
PCT/EP2013/055624 WO2013139759A1 (de) | 2012-03-19 | 2013-03-19 | Zusammensetzung auf basis von silanterminierten polymeren |
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US (1) | US20150045519A1 (ja) |
EP (2) | EP2641935A1 (ja) |
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CN (1) | CN104169353B (ja) |
AU (1) | AU2013237539B2 (ja) |
BR (1) | BR112014020592B1 (ja) |
WO (1) | WO2013139759A1 (ja) |
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CN107603551B (zh) * | 2017-08-22 | 2021-11-02 | 山西省建筑科学研究院 | 硅烷改性聚脲及其制备方法 |
CA3162641C (en) | 2019-12-23 | 2023-02-14 | Maude DESROCHES | Sealant composition |
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US3971751A (en) | 1975-06-09 | 1976-07-27 | Kanegafuchi Kagaku Kogyo Kabushiki Kaisha | Vulcanizable silylether terminated polymer |
US4526930A (en) * | 1983-09-23 | 1985-07-02 | Union Carbide Corporation | Production of water-curable, silane modified thermoplastic polymers |
JPH05311063A (ja) * | 1992-05-07 | 1993-11-22 | Sekisui Chem Co Ltd | シーリング材組成物 |
TW252146B (ja) * | 1992-08-25 | 1995-07-21 | Dow Corning | |
US5733960A (en) * | 1996-04-04 | 1998-03-31 | Dow Corning Corporation | Enhanced longevity of surface drying oil on a sealant modified by incorporation of zinc oxide |
JP2837658B2 (ja) * | 1996-08-30 | 1998-12-16 | 東芝シリコーン株式会社 | 室温硬化性ポリオルガノシロキサン組成物 |
DE69821722T2 (de) | 1997-04-21 | 2004-12-02 | Asahi Glass Co., Ltd. | Bei raumtemperatur härtende zusammensetzungen |
ES2209914T3 (es) * | 1999-06-25 | 2004-07-01 | Bayer Aktiengesellschaft | Masas de poliuretano especiales, reticulables por condensacion, que contienen aminosilanos, un procedimiento para su fabricacion y su uso. |
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 |
ATE370179T1 (de) * | 2001-02-23 | 2007-09-15 | Henkel Corp | Gemischte alkoxysilyl-funktionalisierte polymere |
DE10139132A1 (de) * | 2001-08-09 | 2003-02-27 | Consortium Elektrochem Ind | Alkoxyvernetzende einkomponentige feuchtigkeitshärtende Massen |
US7307134B2 (en) * | 2002-02-22 | 2007-12-11 | Henkel Corporation | Mixed alkoxysilyl functional polymers |
WO2005108493A1 (ja) * | 2004-05-07 | 2005-11-17 | Kaneka Corporation | 硬化性組成物 |
JP2006316212A (ja) * | 2005-05-16 | 2006-11-24 | Ge Toshiba Silicones Co Ltd | 室温硬化性ポリオルガノシロキサン組成物 |
DE102005051921A1 (de) * | 2005-10-29 | 2007-05-03 | Henkel Kgaa | α-Ethoxysilan modifizierte Polymere, deren Herstellung und Verwendung |
DE102006041464A1 (de) * | 2006-09-02 | 2008-03-06 | Lanxess Deutschland Gmbh | Vulkanisierbare Zusammensetzung auf Basis von Ethylen-Vinylacetat Copolymeren, deren Herstellung und Verwendung zur Herstellung von Artikeln mit gummielastomeren Eigenschaften |
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2012
- 2012-03-19 EP EP12160128.0A patent/EP2641935A1/de not_active Withdrawn
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2013
- 2013-03-19 CN CN201380012431.3A patent/CN104169353B/zh active Active
- 2013-03-19 AU AU2013237539A patent/AU2013237539B2/en active Active
- 2013-03-19 BR BR112014020592-2A patent/BR112014020592B1/pt active IP Right Grant
- 2013-03-19 WO PCT/EP2013/055624 patent/WO2013139759A1/de active Application Filing
- 2013-03-19 JP JP2015500879A patent/JP6301905B2/ja active Active
- 2013-03-19 US US14/384,642 patent/US20150045519A1/en not_active Abandoned
- 2013-03-19 EP EP13709931.3A patent/EP2828331B1/de active Active
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BR112014020592B1 (pt) | 2020-12-15 |
AU2013237539B2 (en) | 2016-05-19 |
CN104169353A (zh) | 2014-11-26 |
EP2641935A1 (de) | 2013-09-25 |
WO2013139759A1 (de) | 2013-09-26 |
EP2828331B1 (de) | 2016-07-06 |
EP2828331A1 (de) | 2015-01-28 |
AU2013237539A1 (en) | 2014-09-18 |
US20150045519A1 (en) | 2015-02-12 |
JP2015512452A (ja) | 2015-04-27 |
CN104169353B (zh) | 2017-03-22 |
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