JP2022514467A - オキサゾリジンを含有する湿気硬化性ポリウレタン組成物 - Google Patents
オキサゾリジンを含有する湿気硬化性ポリウレタン組成物 Download PDFInfo
- Publication number
- JP2022514467A JP2022514467A JP2021532103A JP2021532103A JP2022514467A JP 2022514467 A JP2022514467 A JP 2022514467A JP 2021532103 A JP2021532103 A JP 2021532103A JP 2021532103 A JP2021532103 A JP 2021532103A JP 2022514467 A JP2022514467 A JP 2022514467A
- Authority
- JP
- Japan
- Prior art keywords
- group
- diisocyanate
- polyurethane composition
- composition
- oxazolidine
- 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.)
- Granted
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- 239000000203 mixture Substances 0.000 title claims abstract description 128
- 239000004814 polyurethane Substances 0.000 title claims abstract description 56
- 229920002635 polyurethane Polymers 0.000 title claims abstract description 54
- WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 title claims abstract description 46
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims abstract description 42
- 229920000642 polymer Polymers 0.000 claims abstract description 32
- 229920005862 polyol Polymers 0.000 claims abstract description 28
- 150000003077 polyols Chemical class 0.000 claims abstract description 28
- 125000005442 diisocyanate group Chemical group 0.000 claims abstract description 24
- 238000006243 chemical reaction Methods 0.000 claims abstract description 18
- 238000000576 coating method Methods 0.000 claims abstract description 14
- 239000011248 coating agent Substances 0.000 claims abstract description 10
- -1 benzodioxanyl Chemical group 0.000 claims description 46
- 239000000758 substrate Substances 0.000 claims description 23
- 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 22
- 238000000034 method Methods 0.000 claims description 15
- 238000007789 sealing Methods 0.000 claims description 13
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical group O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 12
- 239000004014 plasticizer Substances 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 125000000160 oxazolidinyl group Chemical group 0.000 claims description 9
- 239000003054 catalyst Substances 0.000 claims description 8
- 239000000945 filler Substances 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 claims description 6
- 150000004705 aldimines Chemical class 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 239000003381 stabilizer Substances 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000000962 organic group Chemical group 0.000 claims description 4
- 125000004861 4-isopropyl phenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 3
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 3
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 2
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 2
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 2
- 238000005304 joining Methods 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims description 2
- JIABEENURMZTTI-UHFFFAOYSA-N 1-isocyanato-2-[(2-isocyanatophenyl)methyl]benzene Chemical compound O=C=NC1=CC=CC=C1CC1=CC=CC=C1N=C=O JIABEENURMZTTI-UHFFFAOYSA-N 0.000 claims 1
- LFSYUSUFCBOHGU-UHFFFAOYSA-N 1-isocyanato-2-[(4-isocyanatophenyl)methyl]benzene Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=CC=C1N=C=O LFSYUSUFCBOHGU-UHFFFAOYSA-N 0.000 claims 1
- 238000003860 storage Methods 0.000 abstract description 30
- 239000000853 adhesive Substances 0.000 abstract description 15
- 230000001070 adhesive effect Effects 0.000 abstract description 15
- 239000000565 sealant Substances 0.000 abstract description 11
- 239000000463 material Substances 0.000 abstract description 7
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 20
- 150000001412 amines Chemical class 0.000 description 12
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 12
- 229920001451 polypropylene glycol Polymers 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 150000001299 aldehydes Chemical class 0.000 description 10
- 229920001971 elastomer Polymers 0.000 description 10
- 239000012948 isocyanate Substances 0.000 description 10
- 239000007788 liquid Substances 0.000 description 10
- 229910052751 metal Inorganic materials 0.000 description 10
- 239000002184 metal Substances 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 9
- 150000002009 diols Chemical class 0.000 description 9
- 239000000806 elastomer Substances 0.000 description 9
- 239000000178 monomer Substances 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- 239000004721 Polyphenylene oxide Substances 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- WTWBUQJHJGUZCY-UHFFFAOYSA-N cuminaldehyde Chemical compound CC(C)C1=CC=C(C=O)C=C1 WTWBUQJHJGUZCY-UHFFFAOYSA-N 0.000 description 8
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 8
- 229920000570 polyether Polymers 0.000 description 8
- 229920001577 copolymer Polymers 0.000 description 7
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 7
- 239000000835 fiber Substances 0.000 description 7
- 150000004072 triols Chemical class 0.000 description 7
- 239000001431 2-methylbenzaldehyde Substances 0.000 description 6
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 6
- 125000001931 aliphatic group Chemical group 0.000 description 6
- 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 6
- 150000002513 isocyanates Chemical class 0.000 description 6
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 6
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 6
- 150000001414 amino alcohols Chemical class 0.000 description 5
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000000470 constituent Substances 0.000 description 5
- 238000010276 construction Methods 0.000 description 5
- 239000003925 fat Substances 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 150000002739 metals Chemical class 0.000 description 5
- 150000002917 oxazolidines Chemical class 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical group CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 4
- 239000005058 Isophorone diisocyanate Substances 0.000 description 4
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 4
- 239000004952 Polyamide Substances 0.000 description 4
- 239000004698 Polyethylene Substances 0.000 description 4
- 229920002367 Polyisobutene Polymers 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- 150000001735 carboxylic acids Chemical class 0.000 description 4
- 239000004359 castor oil Substances 0.000 description 4
- 235000019438 castor oil Nutrition 0.000 description 4
- 239000004568 cement Substances 0.000 description 4
- 239000002274 desiccant Substances 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- 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 4
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 4
- BTFQKIATRPGRBS-UHFFFAOYSA-N o-tolualdehyde Chemical compound CC1=CC=CC=C1C=O BTFQKIATRPGRBS-UHFFFAOYSA-N 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- 229920002647 polyamide Polymers 0.000 description 4
- 229920000573 polyethylene Polymers 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- HIKRJHFHGKZKRI-UHFFFAOYSA-N 2,4,6-trimethylbenzaldehyde Chemical compound CC1=CC(C)=C(C=O)C(C)=C1 HIKRJHFHGKZKRI-UHFFFAOYSA-N 0.000 description 3
- XNIOWJUQPMKCIJ-UHFFFAOYSA-N 2-(benzylamino)ethanol Chemical compound OCCNCC1=CC=CC=C1 XNIOWJUQPMKCIJ-UHFFFAOYSA-N 0.000 description 3
- MIJDSYMOBYNHOT-UHFFFAOYSA-N 2-(ethylamino)ethanol Chemical compound CCNCCO MIJDSYMOBYNHOT-UHFFFAOYSA-N 0.000 description 3
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- ADWNZPLMYDAHNM-UHFFFAOYSA-N 3-methylbenzaldehyde Chemical compound CC1=CC=CC(C=O)=C1.CC1=CC=CC(C=O)=C1 ADWNZPLMYDAHNM-UHFFFAOYSA-N 0.000 description 3
- DNYVKUCAEGCQRE-UHFFFAOYSA-N 4-methylbenzaldehyde Chemical compound CC1=CC=C(C=O)C=C1.CC1=CC=C(C=O)C=C1 DNYVKUCAEGCQRE-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 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 2
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- 229910052618 mica group Inorganic materials 0.000 description 1
- 239000011490 mineral wool Substances 0.000 description 1
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- 239000002808 molecular sieve Substances 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
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- 239000000025 natural resin Substances 0.000 description 1
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- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
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- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000006353 oxyethylene group Chemical group 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- RUOPINZRYMFPBF-UHFFFAOYSA-N pentane-1,3-diol Chemical compound CCC(O)CCO RUOPINZRYMFPBF-UHFFFAOYSA-N 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- 239000013500 performance material Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
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- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N phthalic anhydride Chemical class C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- SATCULPHIDQDRE-UHFFFAOYSA-N piperonal Chemical compound O=CC1=CC=C2OCOC2=C1 SATCULPHIDQDRE-UHFFFAOYSA-N 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
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- 229920001083 polybutene Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
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- 229920001228 polyisocyanate Polymers 0.000 description 1
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- 229920005594 polymer fiber Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 229940088417 precipitated calcium carbonate Drugs 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 229960004063 propylene glycol Drugs 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
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- 238000010079 rubber tapping Methods 0.000 description 1
- 229940116351 sebacate Drugs 0.000 description 1
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 1
- 238000000526 short-path distillation Methods 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 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
- 238000005507 spraying Methods 0.000 description 1
- 239000010421 standard material Substances 0.000 description 1
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- 125000001424 substituent group Chemical group 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- WMOVHXAZOJBABW-UHFFFAOYSA-N tert-butyl acetate Chemical compound CC(=O)OC(C)(C)C WMOVHXAZOJBABW-UHFFFAOYSA-N 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 229920002397 thermoplastic olefin Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 230000009974 thixotropic effect Effects 0.000 description 1
- SYRHIZPPCHMRIT-UHFFFAOYSA-N tin(4+) Chemical class [Sn+4] SYRHIZPPCHMRIT-UHFFFAOYSA-N 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- 125000005591 trimellitate group Chemical group 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
- ASLWPAWFJZFCKF-UHFFFAOYSA-N tris(1,3-dichloropropan-2-yl) phosphate Chemical compound ClCC(CCl)OP(=O)(OC(CCl)CCl)OC(CCl)CCl ASLWPAWFJZFCKF-UHFFFAOYSA-N 0.000 description 1
- HQUQLFOMPYWACS-UHFFFAOYSA-N tris(2-chloroethyl) phosphate Chemical compound ClCCOP(=O)(OCCCl)OCCCl HQUQLFOMPYWACS-UHFFFAOYSA-N 0.000 description 1
- XKCQNWLQCXDVOP-UHFFFAOYSA-N tris(2-chloropropan-2-yl) phosphate Chemical compound CC(C)(Cl)OP(=O)(OC(C)(C)Cl)OC(C)(C)Cl XKCQNWLQCXDVOP-UHFFFAOYSA-N 0.000 description 1
- LIPMRGQQBZJCTM-UHFFFAOYSA-N tris(2-propan-2-ylphenyl) phosphate Chemical compound CC(C)C1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C(C)C)OC1=CC=CC=C1C(C)C LIPMRGQQBZJCTM-UHFFFAOYSA-N 0.000 description 1
- GRXOWOKLKIZFNP-UHFFFAOYSA-N undecane-1,1-diol Chemical compound CCCCCCCCCCC(O)O GRXOWOKLKIZFNP-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
- 150000003672 ureas Chemical class 0.000 description 1
- 239000002966 varnish Substances 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
- 239000000080 wetting agent Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
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- C08L75/08—Polyurethanes from polyethers
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- C08G18/12—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step using two or more compounds having active hydrogen in the first polymerisation step
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- C08G18/2805—Compounds having only one group containing active hydrogen
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- C08G18/40—High-molecular-weight compounds
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- C08G18/4804—Two or more polyethers of different physical or chemical nature
- C08G18/4812—Mixtures of polyetherdiols with polyetherpolyols having at least three hydroxy groups
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08G18/40—High-molecular-weight compounds
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- C08G18/4825—Polyethers containing two hydroxy groups
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- C08G18/40—High-molecular-weight compounds
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- C08G18/00—Polymeric products of isocyanates or isothiocyanates
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- C08G18/50—Polyethers having heteroatoms other than oxygen
- C08G18/5021—Polyethers having heteroatoms other than oxygen having nitrogen
- C08G18/5036—Polyethers having heteroatoms other than oxygen having nitrogen containing -N-C=O groups
- C08G18/5048—Products of hydrolysis of polyether-urethane prepolymers containing isocyanate groups
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- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
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- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
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Abstract
Description
少なくとも一種のポリオールと、少なくとも一種のジイソシアネートとの反応から得られる、イソシアネート基を含有する少なくとも一種のポリマー、及び
少なくとも一種の下記式(I)のオキサゾリジン
を含むポリウレタン組成物を提供する:
R1は、1~8個の炭素原子を有するアルキル、シクロアルキル、又はアリールアルキル基であり、
R2は、H又はメチルであり、
Gは、フラニル、チオフェニル、ピリジニル、インデニル、インダニル、ベンゾジオキソリル、ベンゾジオキサニル、ナフチル、テトラヒドロナフチル、アントラセニル、及び下記式の基からなる群から選択される芳香族基であり、
R3は、フルオロ、クロロ、ブロモ、ニトロ、シアノ、フェニル、フェノキシ、(C1~C5)-アルキル、又は(C1~C5)-アルコキシであり、
nは、0、1、2又は3である]。
- ポリエーテルポリオール、特に、ポリオキシアルキレンジオール及び/又はポリオキシアルキレントリオール、特に、エチレンオキシド又は1,2-プロピレンオキシド又は1,2-若しくは2,3-ブチレンオキシド又はオキセタン又はテトラヒドロフラン又はこれらの混合物の重合生成物であり、ここで、これらは、2個若しくは3個の活性水素原子を有するスターター分子、特に、水、アンモニア、又は複数のOH若しくはNH基を有する化合物のようなスターター分子、例えば、エタン-1,2-ジオール、プロパン-1,2-若しくは-1,3-ジオール、ネオペンチルグリコール、ジエチレングリコール、トリエチレングリコール、異性体のジプロピレングリコール又はトリプロピレングリコール、異性体のブタンジオール、ペンタンジオール、ヘキサンジオール、ヘプタンジオール、オクタンジオール、ノナンジオール、デカンジオール、ウンデカンジオール、シクロヘキサン-1,3-若しくは-1,4-ジメタノール、ビスフェノールA、水素化ビスフェノールA、1,1,1-トリメチロールエタン、1,1,1-トリメチロールプロパン、グリセロール又はアニリン、又は上記の化合物の混合物の助けで重合し得る。同様に適切であるのは、その中に分散したポリマー粒子を有するポリエーテルポリオール、特に、スチレン/アクリロニトリル(SAN)粒子又はポリ尿素又はポリヒドラゾジカーボンアミド(PHD)粒子を有するものである。
- 公知のプロセス、特に、ヒドロキシカルボン酸若しくはラクトンの重縮合、又は脂肪族及び/若しくは芳香族ポリカルボン酸と二価若しくは多価アルコールとの重縮合によって調製される、オリゴエステロールとまた称されるポリエステルポリオール。
- ポリカーボネートポリオール。
- ポリエーテルポリエステルポリオール。
- ポリアクリレート又はポリメタクリレートポリオール。
- ポリヒドロキシ官能性脂肪若しくは油、例えば、天然油脂、特に、ヒマシ油、又は天然油脂の化学修飾によって得られるポリオール-オレオケミカルポリオールと称される。
- オリゴヒドロカルボノールとまた称されるポリ炭化水素ポリオール、例えば、特に、ポリヒドロキシ官能性ポリオレフィン、ポリイソブチレン、ポリイソプレン;ポリヒドロキシ官能性エチレン/プロピレン、エチレン/ブチレン又はエチレン/プロピレン/ジエンコポリマー(例えば、Kraton Polymersによって生産されているような);特に、またアニオン重合から調製することができる、ジエン、特に、1,3-ブタジエンのポリヒドロキシ官能性ポリマー;ジエン、例えば、1,3-ブタジエン、又はジエン混合物及びビニルモノマー、例えば、スチレン、アクリロニトリル、塩化ビニル、酢酸ビニル、ビニルアルコール、イソブチレン又はイソプレンのポリヒドロキシ官能性コポリマー、特に、エポキシド又はアミノアルコール及びカルボキシル末端アクリロニトリル/ブタジエンコポリマーから調製することができる、特に、ポリヒドロキシ官能性アクリロニトリル/ブタジエンコポリマー(例えば、Emerald Performance MaterialsからのHypro(登録商標)CTBN若しくはCTBNX若しくはETBN名で市販されている);又はジエンの水素化ポリヒドロキシ官能性ポリマー若しくはコポリマー。
式中、
R4は、H、又は1~17個の炭素原子を有するアルキル基、特に、1~11個の炭素原子を有する直鎖状アルキル基であり、
G、A及びyは、既に示した定義を有する。
- 無機若しくは有機顔料、特に、二酸化チタン、酸化クロム又は酸化鉄;
- 繊維、特に、ガラス繊維、炭素繊維、金属繊維、セラミック繊維、ポリマー繊維、例えば、ポリアミド繊維若しくはポリエチレン繊維、又は天然繊維、例えば、ウール、セルロース、ヘンプ若しくはサイザル;
- ナノ充填剤、例えば、グラフェン又はカーボンナノチューブ;
- 染料;
- さらなる潜在型硬化剤、特に、さらなるオキサゾリジン、アルジミン、ケチミン又はエナミン;
- さらなるイソシアネート、特に、MDIの室温液体形態、特に、カルボジイミド化若しくはウレトンイミン形成若しくはポリオールとの付加体形成によって液化した4,4’-MDI、又はMDIモノマーとMDIホモログとの混合物(ポリマーMDI若しくはPMDI);
- さらなるデシカント、特に、分子篩粉末、酸化カルシウム、高度に反応性のイソシアネート、例えば、p-トシルイソシアネート、又はオルトギ酸エステル;
- 接着促進剤、特に、オルガノアルコキシシラン、特に、エポキシシラン、例えば、特に、3-グリシドキシプロピルトリメトキシシラン若しくは3-グリシドキシプロピルトリエトキシシラン、(メタ)アクリロシラン、アンヒドリドシラン、カルバマトシラン、アルキルシラン若しくはイミノシラン、又はこれらのシランのオリゴマー形態、又はチタネート;
- イソシアネート基の反応を促進するさらなる触媒;
- レオロジーモディファイヤー、特に、増粘剤、特に、シート状ケイ酸塩、例えば、ベントナイト、ヒマシ油の誘導体、水添ヒマシ油、ポリアミド、ポリアミドワックス、ポリウレタン、尿素化合物、ヒュームドシリカ、セルロースエーテル又は疎水的に修飾したポリオキシエチレン;
- 溶媒、特に、アセトン、酢酸メチル、tert-ブチルアセテート、1-メトキシ-2-プロピルアセテート、エチル3-エトキシプロピオネート、ジイソプロピルエーテル、ジエチレングリコールジエチルエーテル、エチレングリコールジエチルエーテル、エチレングリコールモノブチルエーテル、エチレングリコールモノ-2-エチルヘキシルエーテル、アセタール、例えば、プロピラール、ブチラール、2-エチルヘキシラール、ジオキソラン、グリセロールホルマール又は2,5,7,10-テトラオキサウンデカン(TOU)、トルエン、キシレン、ヘプタン、オクタン、ナフサ、ホワイトスピリット、石油エーテル又はガソリン、特に、Solvesso(商標)グレード(ExxonMobil Chemical Co.から)、及び炭酸プロピレン、炭酸ジメチル、ブチロラクトン、N-メチルピロリドン、N-エチルピロリドン、p-クロロベンゾトリフルオリド又はベンゾトリフルオリド;
- 天然樹脂、脂肪若しくは油、例えば、ロジン、セラック、亜麻仁油、ヒマシ油又はダイズ油;
- 非反応性ポリマー、特に、エチレン、プロピレン、ブチレン、イソブチレン、イソプレン、酢酸ビニル又は(メタ)アクリル酸アルキルを含む群からの不飽和モノマーのホモ若しくはコポリマー、特に、ポリエチレン(PE)、ポリプロピレン(PP)、ポリイソブチレン、エチレン/酢酸ビニルコポリマー(EVA)又はアタクチックポリ-α-オレフィン(APAO);
- 難燃性物質、特に、既に記述した水酸化アルミニウム若しくは水酸化マグネシウム充填剤、及びまた特に、有機リン酸エステル、例えば、特に、リン酸トリエチル、リン酸トリクレシル、リン酸トリフェニル、リン酸ジフェニルクレシル、イソデシルジフェニルホスフェート、トリス(1,3-ジクロロ-2-プロピル)ホスフェート、トリス(2-クロロエチル)ホスフェート、トリス(2-エチルヘキシル)ホスフェート、トリス(クロロイソプロピル)ホスフェート、トリス(クロロプロピル)ホスフェート、イソプロピル化リン酸トリフェニル、異なる程度のイソプロピル化のモノ、ビス若しくはトリス(イソプロピルフェニル)ホスフェート、レソルシノールビス(ジフェニルホスフェート)、ビスフェノールAビス(ジフェニルホスフェート)又はポリリン酸アンモニウム;
- 添加物、特に、湿潤剤、レベリング剤、消泡剤、脱泡剤、さらなる安定剤又は殺生物剤;
或いは湿気硬化性ポリウレタン組成物中で通例使用されるさらなる物質
を含有し得る。
- 10重量%~50重量%のポリマーであって、少なくとも1種のポリオールと、HDI、H12MDI、TDI及びMDIからなる群から選択される少なくとも1種のジイソシアネートとの反応から得られる、イソシアネート基を含有し、且つ0.5重量%~5重量%の範囲のNCO含量を有するポリマー、
- 0.1重量%~5重量%の式(I)のオキサゾリジン、
- 20重量%~60重量%の充填剤、
- 10重量%~40重量%の可塑剤、及び
任意選択で、さらなる構成成分、特に、アルジミン、ジイソシアネートオリゴマー、触媒又は安定剤
を含有する。
- ガラス、ガラスセラミック、コンクリート、モルタル、セメントスクリード、繊維セメント、特に、繊維セメントボード、れんが、タイル、石膏、特に、石膏ボード、又は天然石、例えば、花崗岩若しくは大理石;
- PCC(ポリマー変性セメントモルタル)又はECC(エポキシ樹脂変性セメントモルタル)をベースとする修復又はレベリング化合物;
- 表面仕上げ金属又は合金、例えば、亜鉛めっき金属若しくはクロムめっき金属を含めた金属又は合金、例えば、アルミニウム、銅、鉄、鋼、非鉄金属;
- アスファルト又はビチューメン;
- 革、織物、紙、木、樹脂、例えば、フェノール樹脂、メラミン樹脂若しくはエポキシ樹脂によって結合した木質材料、樹脂/織物複合材料、又はポリマー複合材料と称されるさらなる材料;
- いずれの場合にも、未処理、又は例えば、プラズマ、コロナ若しくは火炎を用いて表面処理された、プラスチック、例えば、剛性及び可撓性のPVC、ポリカーボネート、ポリスチレン、ポリエステル、ポリアミド、PMMA、ABS、SAN、エポキシ樹脂、フェノール樹脂、PUR、POM、TPO、PE、PP、EPM又はEPDM;
- 繊維強化プラスチック、例えば、炭素繊維強化プラスチック(CFP)、ガラス繊維強化プラスチック(GFP)及びシート成形化合物(SMC);
- 特に、EPS、XPS、PUR、PIR、ロックウール、グラスウール又は発砲ガラスでできている絶縁フォーム;
- コーティング若しくは塗装された基材、特に、塗装されたタイル、コーティングされたコンクリート、粉体コーティングされた金属若しくは合金又は塗装された金属シート;
- 塗料又はニス、特に、自動車のトップコート
である。
(i)記載したポリウレタン組成物を
- 第1の基材に適用し、組成物のオープンタイム内で組成物と少なくとも一種の第2の基材とを接触させること、又は
- 第1及び第2の基材に適用し、組成物のオープンタイム内で2つの基材を接合すること、又は
- 少なくとも2つの基材の間に適用すること、
(ii)湿気と接触させることによって上記組成物を硬化させること。
(i)記載したポリウレタン組成物を少なくとも一種の基材に適用すること、
(ii)湿気と接触させることによって上記組成物を硬化させること。
アミン値(ブロックされたアミノ基を含めた)は、滴定を用いて決定した(クリスタルバイオレットに対して酢酸中の0.1NのHClO4による)。
水分離器(Dean-Stark装置)を有する丸底フラスコ中の26.29gのN-メチルエタノールアミンの最初の投入に、37.88gのベンズアルデヒド、65mlのシクロヘキサン及び1.25gのサリチル酸を加え、全ての水が分離するまで反応混合物を還流させながら120℃にて沸騰させた。それに続いて、反応混合物を冷却し、濾過し、揮発性構成物質をロータリーエバポレーター上で80℃にて減圧下で除去した。得られたものは、20℃にて5.6mPa・sの粘度、333mg KOH/gのアミン値及び163.2g/eqの計算されたオキサゾリジン当量を有する黄色がかった液体であった。
FT-IR:3030、2974、2947、2885、2843、2792、2709、1702、1595、1491、1456、1419、1380、1339、1308、1292、1249、1220、1205、1160、1101、1052、1036、1026、975、956、922、887、860、843、754、698。
31.20gのN-エチルエタノールアミンを、オキサゾリジンOx-1について記載したように、37.88gのベンズアルデヒドと反応させた。得られたものは、20℃にて6.1mPa・sの粘度、308mg KOH/gのアミン値及び177.3g/eqの計算されたオキサゾリジン当量を有する黄色がかった液体であった。
41.02gのN-n-ブチルエタノールアミンを、オキサゾリジンOx-1について記載したように、37.88gのベンズアルデヒドと反応させた。得られたものは、20℃にて8.6mPa・sの粘度、267mg KOH/gのアミン値及び205.3g/eqの計算されたオキサゾリジン当量を有する黄色がかった液体であった。
FT-IR:2955、2931、2872、2801、2714、1704、1593、1492、1456、1377、1342、1307、1292、1248、1215、1203、1178、1152、1086、1063、956、924、912、844、756、736、695。
52.92gのN-ベンジルエタノールアミンを、オキサゾリジンOx-1について記載したように、37.88gのベンズアルデヒドと反応させた。得られたものは、20℃にて71mPa・sの粘度、230mg KOH/gのアミン値及び239.3g/eqの計算されたオキサゾリジン当量を有する黄色がかった液体であった。
FT-IR:3061、3028、2942、2884、2801、2713、1952、1882、1811、1703、1604、1586、1494、1454、1385、1371、1340、1307、1292、1252、1215、1203、1161、1127、1101、1056、1025、1001、957、922、912、889、847、757、737、696。
48.01gのN-フェニルエタノールアミン(アニリン-エタノール)を、オキサゾリジンOx-1について記載したように、37.88gのベンズアルデヒドと反応させた。得られたものは、250mg KOH/gのアミン値及び225.3g/eqの計算されたオキサゾリジン当量を有する黄色がかった液体であったが、これは室温にて徐々に結晶化した。
63.09gのジエタノールアミンを、オキサゾリジンOx-1について記載したように、37.88gのベンズアルデヒドと反応させることによって、3-(2-ヒドロキシエチル)-2-フェニル-1,3-オキサゾリジンを最初に調製した。288.2mg KOH/gのアミン値を有する暗い黄色の液体を得た。
ポリマーP1:
1300gのポリオキシプロピレンジオール(Acclaim(登録商標)4200、Covestroから;OH数28.5mg KOH/g)、2600gのポリオキシプロピレントリオール(Caradol(登録商標)MD34-02、Shellから;OH数35.0mg KOH/g)、600gのジフェニルメタン4,4’-ジイソシアネート(Desmodur(登録商標)44MC L、Covestroから)及び500gのフタル酸ジイソデシルを、80℃にて反応させ、2.1重量%の含量の遊離イソシアネート基を有するNCO-末端ポリウレタンポリマーを得た。
組成物Z1~Z14:
各組成物について、表1~3において特定した成分を、湿気を排除して3000rpmにて1分間遠心ミキサー(SpeedMixer(商標)DAC150、FlackTek Inc.)を用いて特定した量で(重量部で)混合し、湿気を排除して貯蔵した。各組成物を、下記のように試験した。
Claims (15)
- 少なくとも一種のポリオールと、少なくとも一種のジイソシアネートとの反応から得られる、イソシアネート基を含有する少なくとも一種のポリマー、及び
少なくとも一種の下記式(I)のオキサゾリジン
を含むポリウレタン組成物:
R1は、1~8個の炭素原子を有するアルキル、シクロアルキル、又はアリールアルキル基であり、
R2は、H又はメチルであり、
Gは、フラニル、チオフェニル、ピリジニル、インデニル、インダニル、ベンゾジオキソリル、ベンゾジオキサニル、ナフチル、テトラヒドロナフチル、アントラセニル、及び下記式の基からなる群から選択される芳香族基であり、
R3は、フルオロ、クロロ、ブロモ、ニトロ、シアノ、フェニル、フェノキシ、(C1~C5)-アルキル、又は(C1~C5)-アルコキシであり、
nは、0、1、2又は3である]。 - イソシアネート基を含有する前記ポリマーが、0.5重量%~5重量%の範囲のNCO値を有することを特徴とする、請求項1に記載のポリウレタン組成物。
- 前記ジイソシアネートが、ヘキサメチレン1,6-ジイソシアネート、ペルヒドロ(ジフェニルメタン4,4’-ジイソシアネート)、トリレン2,4-ジイソシアネート、又はトリレン2,6-ジイソシアネートとこれらの混合物、及びジフェニルメタン2,4’-ジイソシアネート及び/又はジフェニルメタン2,2’-ジイソシアネートの画分を任意選択で伴うジフェニルメタン4,4’-ジイソシアネートからなる群から選択されることを特徴とする、請求項1又は2に記載のポリウレタン組成物。
- 前記ポリオールが、少なくとも一種のトリオールを含有することを特徴とする、請求項1~3のいずれか一項に記載のポリウレタン組成物。
- R1が、メチル、エチル、n-ブチル、又はベンジルであることを特徴とする、請求項1~4のいずれか一項に記載のポリウレタン組成物。
- Gが、フェニル、2-メチルフェニル、3-メチルフェニル、4-メチルフェニル、4-イソプロピルフェニル、又は4-メトキシフェニルであることを特徴とする、請求項1~6のいずれか一項に記載のポリウレタン組成物。
- オキサゾリジン基のイソシアネート基に対する数比が、0.2~0.45の範囲であることを特徴とする、請求項1~7のいずれか一項に記載のポリウレタン組成物。
- オキサゾリジン基のイソシアネート基に対する数比が、0.1~0.3の範囲であり、オキサゾリジン基とアルジミン基とを加えた合計のイソシアネート基に対する数比が、0.3~0.8の範囲であることを特徴とする、請求項9に記載のポリウレタン組成物。
- 充填剤、可塑剤、ジイソシアネートオリゴマー、触媒、及び安定剤からなる群から選択される少なくとも一種のさらなる構成成分が存在することを特徴とする、請求項1~10のいずれか一項に記載のポリウレタン組成物。
- 一成分湿気硬化性組成物であることを特徴とする、請求項1~11のいずれか一項に記載のポリウレタン組成物。
- 以下の工程を含む、結合及び/又はシーリングの方法:
(i)請求項1~12のいずれか一項に記載のポリウレタン組成物を、
- 第1の基材に適用し、かつ前記組成物のオープンタイム内で前記組成物と少なくとも一種の第2の基材とを接触させること、又は
- 第1及び第2の基材に適用し、かつ前記組成物のオープンタイム内で前記2つの基材を接合すること、又は
- 少なくとも2つの基材の間に適用すること、
(ii)湿気と接触させることによって前記組成物を硬化させること。 - 以下の工程を含む、コーティング及び/又はシーリングの方法:
(i)請求項1~12のいずれか一項に記載のポリウレタン組成物を少なくとも一種の基材に適用すること、
(ii)湿気と接触させることによって前記組成物を硬化させること。 - 請求項13又は14に記載の方法から得られる物品。
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EP18213019.5 | 2018-12-17 | ||
EP18213019 | 2018-12-17 | ||
PCT/EP2019/084940 WO2020126841A1 (de) | 2018-12-17 | 2019-12-12 | Feuchtigkeitshärtende polyurethan-zusammensetzung enthaltend oxazolidin |
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JP7431236B2 JP7431236B2 (ja) | 2024-02-14 |
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US (1) | US11952493B2 (ja) |
EP (1) | EP3898619B1 (ja) |
JP (1) | JP7431236B2 (ja) |
CN (1) | CN113272299B (ja) |
AU (1) | AU2019409054A1 (ja) |
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US6255433B1 (en) | 1998-06-19 | 2001-07-03 | Takeda Chemical Industries, Ltd. | One-package thixotropic polyurethane resin composition |
JP4027762B2 (ja) | 2002-09-13 | 2007-12-26 | 横浜ゴム株式会社 | 一液湿気硬化型ポリウレタン樹脂組成物およびその製造方法 |
EP1876196A1 (de) * | 2006-06-30 | 2008-01-09 | Sika Technology AG | VOC-freie oder VOC-arme Polyurethanbeschichtung |
EP2072550A1 (de) | 2007-12-21 | 2009-06-24 | Sika Technology AG | Härtbare Zusammensetzungen mit verminderter Ausgasung |
DE102008020979A1 (de) * | 2008-04-25 | 2009-10-29 | Henkel Ag & Co. Kgaa | Härtbare Zusammensetzungen enthaltend silylierte Polyurethane |
JP5446152B2 (ja) | 2008-07-16 | 2014-03-19 | 横浜ゴム株式会社 | 1液湿気硬化型ポリウレタン樹脂組成物 |
JP6348913B2 (ja) | 2013-01-22 | 2018-06-27 | シーカ・テクノロジー・アーゲー | オキサゾリジン及びアルジミンを含む液体塗布防水膜 |
KR20220004227A (ko) | 2013-01-22 | 2022-01-11 | 시카 테크놀러지 아게 | 장쇄 알디민을 포함하는 지붕을 위한 액체 도포된 방수막 |
CN108431067B (zh) * | 2015-12-21 | 2021-11-23 | Sika技术股份公司 | 羟基醛亚胺和具有低单体异氰酸酯含量的可固化聚氨酯组合物 |
US11535694B2 (en) * | 2017-06-19 | 2022-12-27 | Sika Technology Ag | Latent curing agent and curable polyurethane composition |
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- 2019-12-12 AU AU2019409054A patent/AU2019409054A1/en not_active Abandoned
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US20220025176A1 (en) | 2022-01-27 |
JP7431236B2 (ja) | 2024-02-14 |
CN113272299B (zh) | 2023-07-07 |
CN113272299A (zh) | 2021-08-17 |
AU2019409054A1 (en) | 2021-07-01 |
BR112021009141A2 (pt) | 2021-08-10 |
EP3898619B1 (de) | 2023-02-08 |
EP3898619A1 (de) | 2021-10-27 |
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