JP2016519696A - ポリウレタンおよびそれから調製される物品およびコーティング、ならびにそれらを作製する方法。 - Google Patents
ポリウレタンおよびそれから調製される物品およびコーティング、ならびにそれらを作製する方法。 Download PDFInfo
- Publication number
- JP2016519696A JP2016519696A JP2016502645A JP2016502645A JP2016519696A JP 2016519696 A JP2016519696 A JP 2016519696A JP 2016502645 A JP2016502645 A JP 2016502645A JP 2016502645 A JP2016502645 A JP 2016502645A JP 2016519696 A JP2016519696 A JP 2016519696A
- Authority
- JP
- Japan
- Prior art keywords
- polyurethane
- polyol
- diisocyanate
- equivalent
- polyisocyanate
- 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
Links
- 229920002635 polyurethane Polymers 0.000 title claims abstract description 254
- 239000004814 polyurethane Substances 0.000 title claims abstract description 254
- 238000000034 method Methods 0.000 title abstract description 64
- 238000000576 coating method Methods 0.000 title abstract description 50
- 239000000203 mixture Substances 0.000 claims abstract description 320
- 229920005862 polyol Polymers 0.000 claims abstract description 274
- 150000003077 polyols Chemical class 0.000 claims abstract description 253
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 147
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 147
- 239000012948 isocyanate Substances 0.000 claims abstract description 118
- 150000002513 isocyanates Chemical class 0.000 claims abstract description 101
- 229920000515 polycarbonate Polymers 0.000 claims abstract description 81
- 239000004417 polycarbonate Substances 0.000 claims abstract description 81
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 68
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 42
- 239000000463 material Substances 0.000 claims description 183
- -1 lysine diisocyanate methyl ester Chemical class 0.000 claims description 162
- 238000006243 chemical reaction Methods 0.000 claims description 106
- 150000002009 diols Chemical class 0.000 claims description 85
- 239000011521 glass Substances 0.000 claims description 78
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 60
- 238000010438 heat treatment Methods 0.000 claims description 55
- 239000003795 chemical substances by application Substances 0.000 claims description 52
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 50
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 47
- 150000001412 amines Chemical class 0.000 claims description 46
- 239000000758 substrate Substances 0.000 claims description 41
- 229910052757 nitrogen Inorganic materials 0.000 claims description 39
- 238000002156 mixing Methods 0.000 claims description 38
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 33
- 239000008199 coating composition Substances 0.000 claims description 32
- 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 29
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 29
- 125000005442 diisocyanate group Chemical group 0.000 claims description 23
- 230000003287 optical effect Effects 0.000 claims description 23
- 238000007872 degassing Methods 0.000 claims description 21
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 20
- 229910052751 metal Inorganic materials 0.000 claims description 20
- 239000002184 metal Substances 0.000 claims description 20
- 238000005266 casting Methods 0.000 claims description 19
- 229920000570 polyether Polymers 0.000 claims description 19
- 239000012780 transparent material Substances 0.000 claims description 19
- 239000000047 product Substances 0.000 claims description 15
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 14
- 229920005906 polyester polyol Polymers 0.000 claims description 14
- 239000013638 trimer Substances 0.000 claims description 14
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 claims description 13
- 238000004519 manufacturing process Methods 0.000 claims description 12
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 11
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 claims description 11
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 10
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 claims description 10
- 239000000539 dimer Substances 0.000 claims description 10
- 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 10
- UWJJYHHHVWZFEP-UHFFFAOYSA-N pentane-1,1-diol Chemical compound CCCCC(O)O UWJJYHHHVWZFEP-UHFFFAOYSA-N 0.000 claims description 10
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 9
- OYQYHJRSHHYEIG-UHFFFAOYSA-N ethyl carbamate;urea Chemical compound NC(N)=O.CCOC(N)=O OYQYHJRSHHYEIG-UHFFFAOYSA-N 0.000 claims description 9
- 239000002861 polymer material Substances 0.000 claims description 9
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 8
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 8
- ORLQHILJRHBSAY-UHFFFAOYSA-N [1-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1(CO)CCCCC1 ORLQHILJRHBSAY-UHFFFAOYSA-N 0.000 claims description 8
- 229920002451 polyvinyl alcohol Polymers 0.000 claims description 8
- 239000004372 Polyvinyl alcohol Substances 0.000 claims description 7
- 229920000620 organic polymer Polymers 0.000 claims description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 6
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 6
- 239000004305 biphenyl Substances 0.000 claims description 6
- 235000010290 biphenyl Nutrition 0.000 claims description 6
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims description 6
- 229940059574 pentaerithrityl Drugs 0.000 claims description 6
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 6
- 239000008096 xylene Substances 0.000 claims description 6
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 5
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 claims description 5
- 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 4
- PQHKQOSECWTIJQ-UHFFFAOYSA-N 2-(2,2-dihydroxyethyl)benzene-1,4-diol Chemical compound OC(O)CC1=CC(O)=CC=C1O PQHKQOSECWTIJQ-UHFFFAOYSA-N 0.000 claims description 4
- 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
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims description 4
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims description 4
- 239000000919 ceramic Substances 0.000 claims description 4
- KQWGXHWJMSMDJJ-UHFFFAOYSA-N cyclohexyl isocyanate Chemical compound O=C=NC1CCCCC1 KQWGXHWJMSMDJJ-UHFFFAOYSA-N 0.000 claims description 4
- 239000004744 fabric Substances 0.000 claims description 4
- TUDHHJQPQZFEIH-UHFFFAOYSA-N piperidine-4,4-diol Chemical compound OC1(O)CCNCC1 TUDHHJQPQZFEIH-UHFFFAOYSA-N 0.000 claims description 4
- 239000000600 sorbitol Substances 0.000 claims description 4
- 235000010356 sorbitol Nutrition 0.000 claims description 4
- 239000002023 wood Substances 0.000 claims description 4
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 claims description 3
- FAZUWMOGQKEUHE-UHFFFAOYSA-N 1,2-bis(2-isocyanatoethyl)benzene Chemical compound O=C=NCCC1=CC=CC=C1CCN=C=O FAZUWMOGQKEUHE-UHFFFAOYSA-N 0.000 claims description 3
- YCFNKSOIDNKUIO-UHFFFAOYSA-N 1,2-bis(4-isocyanatobutyl)benzene Chemical compound O=C=NCCCCC1=CC=CC=C1CCCCN=C=O YCFNKSOIDNKUIO-UHFFFAOYSA-N 0.000 claims description 3
- WZROIUBWZBSCSE-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)naphthalene Chemical compound C1=CC=CC2=C(CN=C=O)C(CN=C=O)=CC=C21 WZROIUBWZBSCSE-UHFFFAOYSA-N 0.000 claims description 3
- 239000005059 1,4-Cyclohexyldiisocyanate Substances 0.000 claims description 3
- VZXPHDGHQXLXJC-UHFFFAOYSA-N 1,6-diisocyanato-5,6-dimethylheptane Chemical compound O=C=NC(C)(C)C(C)CCCCN=C=O VZXPHDGHQXLXJC-UHFFFAOYSA-N 0.000 claims description 3
- KYZJYDSSXRSBDB-UHFFFAOYSA-N 1-isocyanato-2-(2-isocyanatophenoxy)benzene Chemical compound O=C=NC1=CC=CC=C1OC1=CC=CC=C1N=C=O KYZJYDSSXRSBDB-UHFFFAOYSA-N 0.000 claims description 3
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 claims description 3
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims description 3
- 239000004386 Erythritol Substances 0.000 claims description 3
- UNXHWFMMPAWVPI-UHFFFAOYSA-N Erythritol Natural products OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 claims description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
- 229930195725 Mannitol Natural products 0.000 claims description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 3
- JTDWCIXOEPQECG-UHFFFAOYSA-N N=C=O.N=C=O.CCCCCC(C)(C)C Chemical compound N=C=O.N=C=O.CCCCCC(C)(C)C JTDWCIXOEPQECG-UHFFFAOYSA-N 0.000 claims description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 3
- AMEDKBHURXXSQO-UHFFFAOYSA-N azonous acid Chemical compound ONO AMEDKBHURXXSQO-UHFFFAOYSA-N 0.000 claims description 3
- NSKYMLWGJWRTQE-UHFFFAOYSA-N bis(2-isocyanatoethyl) benzene-1,2-dicarboxylate Chemical compound O=C=NCCOC(=O)C1=CC=CC=C1C(=O)OCCN=C=O NSKYMLWGJWRTQE-UHFFFAOYSA-N 0.000 claims description 3
- UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 claims description 3
- 235000019414 erythritol Nutrition 0.000 claims description 3
- 229940009714 erythritol Drugs 0.000 claims description 3
- 239000004973 liquid crystal related substance Substances 0.000 claims description 3
- 239000000594 mannitol Substances 0.000 claims description 3
- 235000010355 mannitol Nutrition 0.000 claims description 3
- OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 claims description 3
- 239000000123 paper Substances 0.000 claims description 3
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 claims description 3
- 239000004575 stone Substances 0.000 claims description 3
- QXRRAZIZHCWBQY-UHFFFAOYSA-N 1,1-bis(isocyanatomethyl)cyclohexane Chemical compound O=C=NCC1(CN=C=O)CCCCC1 QXRRAZIZHCWBQY-UHFFFAOYSA-N 0.000 claims description 2
- NNOZGCICXAYKLW-UHFFFAOYSA-N 1,2-bis(2-isocyanatopropan-2-yl)benzene Chemical compound O=C=NC(C)(C)C1=CC=CC=C1C(C)(C)N=C=O NNOZGCICXAYKLW-UHFFFAOYSA-N 0.000 claims description 2
- ZTNJGMFHJYGMDR-UHFFFAOYSA-N 1,2-diisocyanatoethane Chemical group O=C=NCCN=C=O ZTNJGMFHJYGMDR-UHFFFAOYSA-N 0.000 claims description 2
- IKYNWXNXXHWHLL-UHFFFAOYSA-N 1,3-diisocyanatopropane Chemical compound O=C=NCCCN=C=O IKYNWXNXXHWHLL-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
- QGLRLXLDMZCFBP-UHFFFAOYSA-N 1,6-diisocyanato-2,4,4-trimethylhexane Chemical compound O=C=NCC(C)CC(C)(C)CCN=C=O QGLRLXLDMZCFBP-UHFFFAOYSA-N 0.000 claims description 2
- 229940008841 1,6-hexamethylene diisocyanate Drugs 0.000 claims description 2
- FELBNCXDZSNTIX-UHFFFAOYSA-N 1,8-diisocyanato-4-(isocyanatomethyl)-2,4,7-trimethyloctane Chemical compound O=C=NCC(C)CCC(C)(CN=C=O)CC(C)CN=C=O FELBNCXDZSNTIX-UHFFFAOYSA-N 0.000 claims description 2
- RHNNQENFSNOGAM-UHFFFAOYSA-N 1,8-diisocyanato-4-(isocyanatomethyl)octane Chemical compound O=C=NCCCCC(CN=C=O)CCCN=C=O RHNNQENFSNOGAM-UHFFFAOYSA-N 0.000 claims description 2
- QUPKOUOXSNGVLB-UHFFFAOYSA-N 1,8-diisocyanatooctane Chemical compound O=C=NCCCCCCCCN=C=O QUPKOUOXSNGVLB-UHFFFAOYSA-N 0.000 claims description 2
- GHSZVIPKVOEXNX-UHFFFAOYSA-N 1,9-diisocyanatononane Chemical compound O=C=NCCCCCCCCCN=C=O GHSZVIPKVOEXNX-UHFFFAOYSA-N 0.000 claims description 2
- PAUHLEIGHAUFAK-UHFFFAOYSA-N 1-isocyanato-1-[(1-isocyanatocyclohexyl)methyl]cyclohexane Chemical compound C1CCCCC1(N=C=O)CC1(N=C=O)CCCCC1 PAUHLEIGHAUFAK-UHFFFAOYSA-N 0.000 claims description 2
- QLOQTKGUQKAAAB-UHFFFAOYSA-N 1-isocyanato-2-(2-isocyanatoethoxy)ethane Chemical compound O=C=NCCOCCN=C=O QLOQTKGUQKAAAB-UHFFFAOYSA-N 0.000 claims description 2
- YXODMIMTGATJKD-UHFFFAOYSA-N 2,5-bis(isocyanatomethyl)furan Chemical compound O=C=NCC1=CC=C(CN=C=O)O1 YXODMIMTGATJKD-UHFFFAOYSA-N 0.000 claims description 2
- VARKIGWTYBUWNT-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanol Chemical compound OCCN1CCN(CCO)CC1 VARKIGWTYBUWNT-UHFFFAOYSA-N 0.000 claims description 2
- PTJWCLYPVFJWMP-UHFFFAOYSA-N 2-[[3-hydroxy-2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)COCC(CO)(CO)CO PTJWCLYPVFJWMP-UHFFFAOYSA-N 0.000 claims description 2
- HJHZRZFONUPQAA-UHFFFAOYSA-N 2-isocyanato-1,3,5-trimethylbenzene Chemical compound CC1=CC(C)=C(N=C=O)C(C)=C1 HJHZRZFONUPQAA-UHFFFAOYSA-N 0.000 claims description 2
- BCBHDSLDGBIFIX-UHFFFAOYSA-N 4-[(2-hydroxyethoxy)carbonyl]benzoic acid Chemical compound OCCOC(=O)C1=CC=C(C(O)=O)C=C1 BCBHDSLDGBIFIX-UHFFFAOYSA-N 0.000 claims description 2
- VBGAVNKWFCSKSE-UHFFFAOYSA-N 5-(2-isocyanatoethyl)-3-(isocyanatomethyl)-2-(3-isocyanatopropyl)bicyclo[2.2.1]heptane Chemical compound C1C(CCN=C=O)C2C(CN=C=O)C(CCCN=C=O)C1C2 VBGAVNKWFCSKSE-UHFFFAOYSA-N 0.000 claims description 2
- ZMRNTPSLQDZXBU-UHFFFAOYSA-N N=C=O.N=C=O.C12=CC=CC=C2NC2=C1C=CC=C2CC Chemical compound N=C=O.N=C=O.C12=CC=CC=C2NC2=C1C=CC=C2CC ZMRNTPSLQDZXBU-UHFFFAOYSA-N 0.000 claims description 2
- OGTYCYGFMVPCCV-UHFFFAOYSA-N N=C=O.N=C=O.C1=CC=C2C3=CC=CC=C3NC2=C1 Chemical compound N=C=O.N=C=O.C1=CC=C2C3=CC=CC=C3NC2=C1 OGTYCYGFMVPCCV-UHFFFAOYSA-N 0.000 claims description 2
- OMRDSWJXRLDPBB-UHFFFAOYSA-N N=C=O.N=C=O.C1CCCCC1 Chemical compound N=C=O.N=C=O.C1CCCCC1 OMRDSWJXRLDPBB-UHFFFAOYSA-N 0.000 claims description 2
- ZTCFKBWDKVMLMM-UHFFFAOYSA-N N=C=O.N=C=O.C=1C=CC=CC=1C(=O)C1=CC=CC=C1 Chemical compound N=C=O.N=C=O.C=1C=CC=CC=1C(=O)C1=CC=CC=C1 ZTCFKBWDKVMLMM-UHFFFAOYSA-N 0.000 claims description 2
- WMTLVUCMBWBYSO-UHFFFAOYSA-N N=C=O.N=C=O.C=1C=CC=CC=1OC1=CC=CC=C1 Chemical compound N=C=O.N=C=O.C=1C=CC=CC=1OC1=CC=CC=C1 WMTLVUCMBWBYSO-UHFFFAOYSA-N 0.000 claims description 2
- HDONYZHVZVCMLR-UHFFFAOYSA-N N=C=O.N=C=O.CC1CCCCC1 Chemical compound N=C=O.N=C=O.CC1CCCCC1 HDONYZHVZVCMLR-UHFFFAOYSA-N 0.000 claims description 2
- OQSSNGKVNWXYOE-UHFFFAOYSA-N N=C=O.N=C=O.CCC(C)CC(C)(C)C Chemical compound N=C=O.N=C=O.CCC(C)CC(C)(C)C OQSSNGKVNWXYOE-UHFFFAOYSA-N 0.000 claims description 2
- UWHCKJMYHZGTIT-UHFFFAOYSA-N Tetraethylene glycol, Natural products OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 claims description 2
- BWVAOONFBYYRHY-UHFFFAOYSA-N [4-(hydroxymethyl)phenyl]methanol Chemical compound OCC1=CC=C(CO)C=C1 BWVAOONFBYYRHY-UHFFFAOYSA-N 0.000 claims description 2
- DZYFUUQMKQBVBY-UHFFFAOYSA-N bis(2-isocyanatoethyl) carbonate Chemical compound O=C=NCCOC(=O)OCCN=C=O DZYFUUQMKQBVBY-UHFFFAOYSA-N 0.000 claims description 2
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 claims description 2
- PMMYEEVYMWASQN-IMJSIDKUSA-N cis-4-Hydroxy-L-proline Chemical compound O[C@@H]1CN[C@H](C(O)=O)C1 PMMYEEVYMWASQN-IMJSIDKUSA-N 0.000 claims description 2
- UYDJAHJCGZTTHB-UHFFFAOYSA-N cyclopentane-1,1-diol Chemical compound OC1(O)CCCC1 UYDJAHJCGZTTHB-UHFFFAOYSA-N 0.000 claims description 2
- INSRQEMEVAMETL-UHFFFAOYSA-N decane-1,1-diol Chemical compound CCCCCCCCCC(O)O INSRQEMEVAMETL-UHFFFAOYSA-N 0.000 claims description 2
- GTZOYNFRVVHLDZ-UHFFFAOYSA-N dodecane-1,1-diol Chemical compound CCCCCCCCCCCC(O)O GTZOYNFRVVHLDZ-UHFFFAOYSA-N 0.000 claims description 2
- MHIBEGOZTWERHF-UHFFFAOYSA-N heptane-1,1-diol Chemical compound CCCCCCC(O)O MHIBEGOZTWERHF-UHFFFAOYSA-N 0.000 claims description 2
- AJUOPYIBDGGQOL-UHFFFAOYSA-N n',n'-bis(2-hydroxyethyl)oxamide Chemical compound NC(=O)C(=O)N(CCO)CCO AJUOPYIBDGGQOL-UHFFFAOYSA-N 0.000 claims description 2
- CQRYARSYNCAZFO-UHFFFAOYSA-N o-hydroxybenzyl alcohol Natural products OCC1=CC=CC=C1O CQRYARSYNCAZFO-UHFFFAOYSA-N 0.000 claims description 2
- BVJSUAQZOZWCKN-UHFFFAOYSA-N p-hydroxybenzyl alcohol Chemical compound OCC1=CC=C(O)C=C1 BVJSUAQZOZWCKN-UHFFFAOYSA-N 0.000 claims description 2
- 239000001294 propane Substances 0.000 claims description 2
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 claims description 2
- DRZOELSSQWENBA-UHFFFAOYSA-N benzene-1,2-dicarboperoxoic acid Chemical compound OOC(=O)C1=CC=CC=C1C(=O)OO DRZOELSSQWENBA-UHFFFAOYSA-N 0.000 claims 2
- KQYAPILZYZQRQJ-UHFFFAOYSA-N n',n'-dihydroxyoxamide Chemical compound NC(=O)C(=O)N(O)O KQYAPILZYZQRQJ-UHFFFAOYSA-N 0.000 claims 2
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- XLAIWHIOIFKLEO-OWOJBTEDSA-N trans-stilbene-4,4'-diol Chemical compound C1=CC(O)=CC=C1\C=C\C1=CC=C(O)C=C1 XLAIWHIOIFKLEO-OWOJBTEDSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 230000007723 transport mechanism Effects 0.000 description 1
- WOZZOSDBXABUFO-UHFFFAOYSA-N tri(butan-2-yloxy)alumane Chemical compound [Al+3].CCC(C)[O-].CCC(C)[O-].CCC(C)[O-] WOZZOSDBXABUFO-UHFFFAOYSA-N 0.000 description 1
- 238000005829 trimerization reaction Methods 0.000 description 1
- MNMVKGDEKPPREK-UHFFFAOYSA-N trimethyl(prop-2-enoxy)silane Chemical compound C[Si](C)(C)OCC=C MNMVKGDEKPPREK-UHFFFAOYSA-N 0.000 description 1
- MDDPTCUZZASZIQ-UHFFFAOYSA-N tris[(2-methylpropan-2-yl)oxy]alumane Chemical compound [Al+3].CC(C)(C)[O-].CC(C)(C)[O-].CC(C)(C)[O-] MDDPTCUZZASZIQ-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 229940124543 ultraviolet light absorber Drugs 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 239000003190 viscoelastic substance Substances 0.000 description 1
- 238000001429 visible spectrum Methods 0.000 description 1
- 238000011179 visual inspection Methods 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000002166 wet spinning Methods 0.000 description 1
- RUDFQVOCFDJEEF-UHFFFAOYSA-N yttrium(III) oxide Inorganic materials [O-2].[O-2].[O-2].[Y+3].[Y+3] RUDFQVOCFDJEEF-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229910052984 zinc sulfide Inorganic materials 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
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 1
- XJUNLJFOHNHSAR-UHFFFAOYSA-J zirconium(4+);dicarbonate Chemical compound [Zr+4].[O-]C([O-])=O.[O-]C([O-])=O XJUNLJFOHNHSAR-UHFFFAOYSA-J 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
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- 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
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/44—Polycarbonates
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- 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
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
- 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
-
- 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
- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
- C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
- C08G18/6603—Compounds of groups C08G18/42, C08G18/48, or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38
- C08G18/6607—Compounds of groups C08G18/42, C08G18/48, or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3203
-
- 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
- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
- C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
- C08G18/6603—Compounds of groups C08G18/42, C08G18/48, or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38
- C08G18/6607—Compounds of groups C08G18/42, C08G18/48, or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3203
- C08G18/6611—Compounds of groups C08G18/42, C08G18/48, or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3203 having at least three hydroxy groups
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- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
- C08G18/758—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing two or more cycloaliphatic rings
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Abstract
Description
本出願は、2013年3月14日に出願された米国仮特許出願第61/783,197号からの優先権に対する利益を主張する。また、本出願は、2012年12月12日に出願された米国特許出願第13/712,110号の継続一部出願であり、これは2009年3月24日に出願された米国特許出願第12/410,102号の継続出願であり、これは2006年12月14日に出願された米国特許出願第11/639,058号の継続一部出願であり、これは2004年9月1日に出願された米国特許出願第10/932,641号、ならびに米国特許出願第11/303,670号、米国特許出願第11/303,422号、米国特許出願第11/303,892号および米国特許出願第11/303,671号(これらのそれぞれは2005年12月16日に出願された)の継続一部出願である。上記出願のそれぞれは参考として本明細書に援用される。
I.発明の分野
本発明は、ポリオールおよびポリイソシアネートから調製されるポリウレタンおよびポリ(ウレアウレタン)、それらから調製される物品、鋳造物、積層体およびコーティング、ならびにそれらを作製する方法に関する。
光学レンズ、光ファイバー、ウィンドウ、ならびに自動車用、船舶用および航空機産業用の透明材料などの用途においてガラスの代替物および代用物として、多くの有機ポリマー材料、例えば、ポリカーボネートおよびアクリルなどのプラスチックが開発されてきた。例えば、航空機用のグレイジング(glazing)においては、LEXAN(登録商標)などのポリカーボネートとアクリルとの両方が、広く受け入れられてきた。これらのポリマー材料は、ガラスに対して、耐破砕性または耐貫入性、所与の用途に対してより軽量であること、可撓性、成形の容易さおよび染色性を含めた利点をもたらすことができる。残念ながら、ポリカーボネートとアクリルとの両方に関連した、いくつかの深刻な不利な点が存在する。ポリカーボネートは傷がつきやすく、日光および苛酷な環境に直接曝露されると、すぐに見通しにくくなる。アクリルは、ポリカーボネートほどは傷がつきやすくないものの、熱歪み温度および耐衝撃性などの、ポリカーボネートの物理特性を有していない。一部の「高衝撃」強度ポリカーボネートは、経時的に劣化し得る一貫性のない衝撃強度、劣った耐亀裂伝搬性(K係数)、劣った光学品質、劣った耐溶剤性および劣った耐候性を有し得る。ポリカーボネートは低速で衝撃を受けたときに良好な衝撃強度を示し得るものの、弾道学的用途において示されるような約1100ft/sec(335.3m/sec)を超える大きな衝撃速度では、約20フィート(6.1m)から約1350ft/sec(411m/sec)の速度で発射された9mm弾(125グレイン)は、1インチ(2.5cm)の厚さのポリカーボネートプラスチックを容易に貫入する可能性がある。
の硫黄含有イソシアネートを使用してもよい。
で表されるジオールが含まれる。
によって表されるポリオールが含まれる。
HO−(CHR1CHR2−O)a−(CHR3CHR4−O)b−(CHR5CHR6−O)c−H
[式中、R1〜R6は、それぞれ独立に、水素またはメチルを表していてもよく;a、bおよびcは、それぞれ独立に、0〜300の整数から選択されてもよく、ここでa、bおよびcは、GPCによって決定したとき、ポリオールの数平均分子量が、約32,000グラム/モル未満、または約10,000グラム/モル未満となるように選択される。他の非限定的な実施形態では、a、bおよびcは、それぞれ独立に、1〜300の整数であってもよい。他の非限定的な実施形態では、R1、R2、R5およびR6は、水素であってもよく、R3およびR4は、それぞれ独立に、水素およびメチルから選択されてもよく、ただし、R3およびR4は、互いに異なる。他の非限定的な実施形態では、R3およびR4は、水素であってもよく、R1およびR2は、それぞれ独立に、水素およびメチルから選択されてもよく、ただし、R1およびR2は、互いに異なり、R5およびR6は、それぞれ独立に、水素およびメチルから選択されてもよく、ただし、R5およびR6は、互いに異なる]
のブロックコポリマーを含む。
によって表され得る。ポリアルコキシル化ポリオールは、当技術分野で公知の方法によって調製することができる。非限定的な実施形態では、4,4’−イソプロピリデンジフェノールなどのポリオールを、エチレンオキシド、プロピレンオキシドまたはブチレンオキシドなどのオキシラン含有物質と反応させて、ヒドロキシル官能性を有する、一般にエトキシル化、プロポキシル化またはブトキシル化ポリオールと称されるものを形成することができる。ポリアルコキシル化ポリオールを調製する際に使用するのに適したポリオールの非限定的な例には、参照により本明細書に組み込まれる、米国特許第6,187,444B1号、10欄、1〜20行に記載されているポリオールが含まれ得る。
を有する化合物が含まれる。
ポリ(ウレアウレタン)は、1種または複数のアミン硬化剤を反応成分中に含めることにより、上記のポリウレタンのいずれかから調製することができる。アミン硬化剤のアミン官能基は、イソシアネート基と反応して、ポリウレタンマトリックス中にウレア連結またはウレア単位を形成することができる。アミン硬化剤の好適な量および反応条件は、上記で詳細に論じられている。
代替的には、またはさらに、ポリイソシアネートのイソシアネート官能基を水と反応させることによって、ウレア連結またはウレア単位を所望の程度までポリウレタンマトリックス中に形成することができる。以下のポリ(ウレアウレタン)合成Aの反応スキームのステップ1に示されるように、イソシアネート官能基を、水との反応によってカルバメート官能基に変換する。一部の非限定的な実施形態では、NCO:水当量比は、約10:1〜約2:1、または約5:1〜約2:1、または約3:1〜約2:1の範囲である。
以下のポリ(ウレアウレタン)合成Bに全体として示されるように、他の非限定的な実施形態では、ポリイソシアネートとポリオールの一部分とを反応させて少なくとも1種のイソシアネート官能性ウレタンプレポリマーを形成し、次いで、イソシアネート官能性ウレタンプレポリマーを水と反応させることによって、ウレア連結またはウレア単位を所望の程度までポリウレタンマトリックス中に形成することができる。以下のポリ(ウレアウレタン)合成Bの反応スキームのステップ1に示されるように、ポリオールおよび/またはジオールの一部分をポリイソシアネートと反応させて、少なくとも1種のイソシアネート官能性ウレタンプレポリマーを形成することができる。一部の非限定的な実施形態では、NCO:OH官能基当量比は、約1:0.05〜約1:0.7、または約1:0.05〜約1:0.5、または約1:0.05〜約1:0.3の範囲である。ヒドロキシル基をウレタン基に本質的に完全に変換することを確実とするためには、過剰なイソシアネートを使用することが望ましい。
配合19、21〜25、58〜65、86〜109および115のポリウレタンを、表1〜18に列挙した量の成分から調製した。
6”×6”×1”(15.2cm×15.2cm×2.5cm)の上記実施例Aからの配合93の厚い試料を、290°F(143℃)で48時間加熱することによって硬化させた。20フィート(6.1m)から1350ft/sec(411m/sec)の速度で発射した3発の9mm弾を試料に撃ち込んだ。試験試料の正面図の写真を図1に示す。
6”×6”×1”(15.2cm×15.2cm×2.5cm)の上記実施例Aからの配合94の厚い試料を、290°F(143℃)で48時間加熱することによって硬化させた。20フィート(6.1m)から1350ft/sec(411m/sec)の初速度で発射した9mm弾を試料に撃ち込んだ。試験試料の写真を図2および3に示す。図2は、試料表面に埋没した弾丸を示す、試料の透視図である。図3は、試料中への弾丸の入射を示す、試料の側面図である。
6”×6”×1”(15.2cm×15.2cm×2.5cm)の上記実施例Aからの配合2の厚い試料を、290°F(143℃)で48時間加熱することによって硬化させた。6”×6”×1”の上記実施例Aからの配合9調製の厚い試料を、290°F(143℃)で48時間加熱することによって硬化させた。6”×6”×0.5”(15.2cm×15.2cm×1.75cm)の上記実施例Aからの配合58の厚い試料を、290°F(143℃)で48時間加熱することによって硬化させた。配合2の層がライフルに向かうように、配合2の試料の厚さ1”(2.5cm)の層と、配合9の試料の厚さ1”(2.5cm)の層と、配合58の試料の厚さ0.5”(1.25cm)の層とをアセンブルすることにより、複合材を調製した。
上記実施例Aの配合58および89〜97から調製された試料は、同様の挙動を示した、すなわち、すべてが弾丸を「捕らえた」。配合94から調製された試料は、最少量の試料貫入を示し、弾丸の後部の約1/8”が表面から突き出た。配合94から調製された試料の後方において、延性の隆起は観察されなかった。配合58および89〜92から調製された試料と比較して、貫入は大きく低減した。
本発明によるポリウレタンポリマーを、以下の表23において列挙した成分から調整した:
本発明によるポリウレタンポリマーを、以下の表26において列挙した成分から調整した:
弾塑性ポリウレタンの実施例
(実施例G1)
以下の成分の重量を比例的に増加させて、十分な量の材料を準備した。以下の反応物:131.2グラムのDESMODUR W、13.41グラムのトリメチロールプロパン、26.015グラムの1,5ペンタンジオール、および81.712グラムのStahl KM−1733(分子量1000のヘキサンジオールを基礎とするポリカーボネートジオール)を一緒に混合し、80℃に加熱して脱ガスした。10ppmの二酢酸ジブチルスズを添加し、溶液が均一になるまで混合した。混合物をガラス型に注ぎ入れ、290°F(143℃)で48時間硬化させた。硬化後、セルを室温(25℃)に冷却し、ポリマーを型から離型させた。ポリマーは、215,000psi(約1482MPa)のヤング率を有していた。重量%ウレタン含有量は、23.4%であった。1架橋当たり分子量は、2548グラム/モルであった。重量%環状含有量は、32%であった。
以下の成分の重量を比例的に増加させて、十分な量の材料を準備した。以下の反応物:131.2グラムのDESMODUR W、13.41グラムのトリメチロールプロパン、28.096グラムの1,5 ペンタンジオール、および65.370グラムのStahl KM−1733(分子量1000のヘキサンジオールを基礎とするポリカーボネートジオール)を一緒に混合し、80℃に加熱して脱ガスした。10ppmの二酢酸ジブチルスズを添加し、溶液が均一になるまで混合した。混合物をガラス型に注ぎ入れ、290°F(143℃)で48時間硬化させた。硬化後、セルを室温(25℃)に冷却し、ポリマーを型から離型させた。ポリマーは、215,000psi(約1482MPa)のヤング率を有していた。重量%ウレタン含有量は、24.8%であった。1架橋当たり分子量は、2404グラム/モルであった。重量%環状含有量は、34%であった。
以下の成分の重量を比例的に増加させて、十分な量の材料を準備した。以下の反応物:131.2グラムのDESMODUR W、13.41グラムのトリメチロールプロパン、28.617グラムの1,5−ペンタンジオール、および61.284グラムのStahl KM−1733(分子量1000のヘキサンジオールを基礎とするポリカーボネートジオール)を一緒に混合し、80℃に加熱して脱ガスした。10ppmの二酢酸ジブチルスズを添加し、溶液が均一になるまで混合した。混合物をガラス型に注ぎ入れ、290°F(143℃)で48時間硬化させた。硬化後、セルを室温(25℃)に冷却し、ポリマーを型から離型させた。ポリマーは、215,000psi(約1482MPa)のヤング率を有していた。重量%ウレタン含有量は、25.15%であった。1架橋当たり分子量は、2369グラム/モルであった。重量%環状含有量は、34.53%であった。
試料J
ポリウレタンを、以下の成分から調製した:
ポリウレタンを、以下の成分から調製した:
ポリウレタンを、以下の成分から調製した:
ポリウレタンを、以下の成分から調製した:
ガラス製ケトルに、窒素ブランケット下で撹拌しながら、28.29重量%の1,10−デカンジオール(101.2等価重量);5.69重量%のTMP(44.0等価重量);ならびに80℃の温度に予備加熱した56.54%のDESMODUR W(131.2等価重量)および9.48重量%のPC−1733またはKM−1733(ICIから市販されている、ヘキサンジオールおよびジエチルカーボネートから作製された1000MWのカーボネートジオール)(428等価重量)を投入した。混合物を115℃の温度に加熱した。
ポリウレタンを、以下の成分から調製した:
ポリ(ウレアウレタン)を以下のように調製した:
弾性係数=269,800psi
破断時引張強度=9,311psi
破断時伸び=7%
Tg=82℃
ガードナー衝撃試験における平均破壊エネルギー=89in−lb
K係数=3,810lb×インチ−3/2
ポリウレタンを以下のように調製した:
ポリウレタンを以下の成分から調製した:
ポリウレタンを以下のように調製した:
ポリウレタンを以下のように調製した:
室温で3日間放置した後、いくつかの試料に対してガードナー衝撃を行い、11日目に再び行った。結果は、「高通過(high pass)」としては、3日目で48インチ・ポンドであり、11日目では352インチ・ポンドであった。経時的なガードナー衝撃における改善は、ポリマー中に硬質ドメインと軟質ドメインとが形成されていることを示している可能性が非常に高い。
ポリウレタンを以下のように調製した:
室温で3日間放置した後、数個の試料に対してガードナー衝撃を行い、11日目に再び行った。結果は、「高通過」としては、3日目で44インチ・ポンドであり、11日目では352インチ・ポンドであった。経時的なガードナー衝撃における改善は、ポリマー中に硬質ドメインと軟質ドメインとが形成されていることを示している可能性が非常に高い。
ポリウレタンを以下のように調製した:
試料を、室温でエージングさせた。3日のエージング後、および22日のエージング後に再び、4つの2”×2”の試料を、数個の試料のみを用いるスクリーニング法を使用して、ガードナー衝撃について試験した。3日のエージングにおける試料は、224インチ・ポンドの最大通過(Maximum pass)を有した。22日後では、試料は192インチ・ポンドの最大通過を有した。
ポリウレタンを以下のように調製した:
仮説的な実施例
以下の実施例は、仮説的な実施例である。
(実施例A)
本発明のポリウレタンを、以下の方法に従って調製することができる。最初に、以下の成分からプレポリマーを調製することができる:
Claims (50)
- (a)
(1)約1当量の少なくとも1種のポリイソシアネートと;
(2)該約1当量の該少なくとも1種のポリイソシアネートに対して約0.01〜約0.5当量の少なくとも1種のポリカーボネートポリオールと
の反応生成物を含む、少なくとも1種のイソシアネート官能性プレポリマー;および
(b)該約1当量の該少なくとも1種のポリイソシアネートに対して約0.01〜約1当量の少なくとも1種のポリオールであって、少なくとも3つのヒドロキシル基を有するポリオール
を含む成分の反応生成物を含むポリウレタン。 - 前記ポリイソシアネートが、ジイソシアネート、トリイソシアネート、これらのダイマー、トリマーおよび混合物からなる群から選択される、請求項1に記載のポリウレタン。
- 前記ポリイソシアネートが、エチレンジイソシアネート、トリメチレンジイソシアネート、1,6−ヘキサメチレンジイソシアネート、テトラメチレンジイソシアネート、ヘキサメチレンジイソシアネート、オクタメチレンジイソシアネート、ノナメチレンジイソシアネート、デカメチレンジイソシアネート、イソホロンジイソシアネート、1,6,11−ウンデカン−トリイソシアネート、1,3,6−ヘキサメチレントリイソシアネート、ビス(イソシアナトエチル)−カーボネート、ビス(イソシアナトエチル)エーテル、トリメチルヘキサンジイソシアネート、トリメチルヘキサメチレンジイソシアネート、2,2’−ジメチルペンタンジイソシアネート、2,2,4−トリメチルヘキサンジイソシアネート、2,4,4−トリメチルヘキサメチレンジイソシアネート、1,8−ジイソシアナト−4−(イソシアナトメチル)オクタン、2,5,7−トリメチル−1,8−ジイソシアナト−5−(イソシアナトメチル)オクタン、2−イソシアナトプロピル−2,6−ジイソシアナトヘキサノエート、リシンジイソシアネートメチルエステル、4,4’−メチレン−ビス−(シクロヘキシルイソシアネート)、4,4’−イソプロピリデン−ビス−(シクロヘキシルイソシアネート)、1,4−シクロヘキシルジイソシアネート、4,4’−ジシクロヘキシルメタンジイソシアネート、3−イソシアナトメチル−3,5,5−トリメチルシクロヘキシルイソシアネート、メタ−テトラメチルキシリレンジイソシアネート、ジフェニルメタンジイソシアネート、ジフェニルイソプロピリデンジイソシアネート、ジフェニレンジイソシアネート、ブテンジイソシアネート、1,3−ブタジエン−1,4−ジイソシアネート、シクロヘキサンジイソシアネート、メチルシクロヘキサンジイソシアネート、ビス(イソシアナトメチル)シクロヘキサン、ビス(イソシアナトシクロヘキシル)メタン、ビス(イソシアナトシクロヘキシル)−2,2−プロパン、ビス(イソシアナトシクロヘキシル)−1,2−エタン、2−イソシアナトメチル−3−(3−イソシアナトプロピル)−5−イソシアナトメチル−ビシクロ[2.2.1]−ヘプタン、2−イソシアナトメチル−3−(3−イソシアナトプロピル)−6−イソシアナトメチル−ビシクロ[2.2.1]−ヘプタン、2−イソシアナトメチル−2−(3−イソシアナトプロピル)−5−イソシアナトメチル−ビシクロ[2.2.1]−ヘプタン、2−イソシアナト−メチル−2−(3−イソシアナトプロピル)−6−イソシアナトメチル−ビシクロ[2.2.1]−ヘプタン、2−イソシアナトメチル−3−(3−イソシアナトプロピル)−6−(2−イソシアナトエチル)−ビシクロ[2.2.1]−ヘプタン、2−イソシアナトメチル−2−(3−イソシアナトプロピル)−5−(2−イソシアナトエチル)−ビシクロ−[2.2.1]−ヘプタン、2−イソシアナトメチル−2−(3−イソシアナトプロピル)−6−(2−イソシアナトエチル)−ビシクロ[2.2.1]−ヘプタン、α,α’−キシレンジイソシアネート、ビス(イソシアナトエチル)ベンゼン、α,α,α’,α’−テトラメチルキシレンジイソシアネート、1,3−ビス(1−イソシアナト−1−メチルエチル)ベンゼン、ビス(イソシアナトブチル)ベンゼン、ビス(イソシアナトメチル)ナフタレン、ビス(イソシアナトメチル)ジフェニルエーテル、ビス(イソシアナトエチル)フタレート、メシチレントリイソシアネート、2,5−ジ(イソシアナトメチル)フラン、α,α’−キシレンジイソシアネート、ビス(イソシアナトエチル)ベンゼン、α,α,α’,α’−テトラメチルキシレンジイソシアネート、1,3−ビス(1−イソシアナト−1−メチルエチル)ベンゼン、ビス(イソシアナトブチル)ベンゼン、ビス(イソシアナトメチル)ナフタレン、ビス(イソシアナトメチル)ジフェニルエーテル、ビス(イソシアナトエチル)フタレート、2,5−ジ(イソシアナトメチル)フラン、ジフェニルエーテルジイソシアネート、ビス(イソシアナトフェニルエーテル)エチレングリコール、ビス(イソシアナトフェニルエーテル)−1,3−プロピレングリコール、ベンゾフェノンジイソシアネート、カルバゾールジイソシアネート、エチルカルバゾールジイソシアネート、ジクロロカルバゾールジイソシアネート、ならびにこれらのダイマー、トリマーおよび混合物からなる群から選択される、請求項2に記載のポリウレタン。
- 前記ポリイソシアネートが、4,4’−メチレン−ビス−(シクロヘキシルイソシアネート)である、請求項3に記載のポリウレタン。
- 前記ポリイソシアネートが、ヘキサメチレンジイソシアネート、イソホロンジイソシアネート、テトラメチルキシリレンジイソシアネート、およびこれらの混合物からなる群から選択されるジイソシアネートのトリマーである、請求項2に記載のポリウレタン。
- 前記ポリカーボネートポリオールが、ヘキサンジオールおよびジアルキルカーボネートから調製される、請求項1に記載のポリウレタン。
- 前記ポリオール(b)が、グリセロール、テトラメチロールメタン、トリメチロールエタン、トリメチロールプロパン、エリスリトール、ジペンタエリスリトール、トリペンタエリスリトール、ソルビタン、これらのアルコキシル化誘導体およびこれらの混合物からなる群から選択される、請求項1に記載のポリウレタン。
- 前記ポリオール(b)が、トリメチロールプロパンである、請求項7に記載のポリウレタン。
- 前記成分が、少なくとも3つのヒドロキシル基を有する約0.4〜約1当量の前記少なくとも1種のポリオール(b)を含む、請求項1に記載のポリウレタン。
- 前記成分が、少なくとも3つのヒドロキシル基を有する約0.6〜約0.7当量の前記少なくとも1種のポリオール(b)を含む、請求項1に記載のポリウレタン。
- 前記成分が、前記約1当量の前記少なくとも1種のポリイソシアネートに対して約0.001〜約0.5当量の少なくとも1種のポリオール(c)であって、前記ポリオール(b)と異なるポリオール(c)をさらに含む、請求項1に記載のポリウレタン。
- 前記成分が、前記約1当量の前記少なくとも1種のポリイソシアネートに対して約0.01〜約0.3当量の少なくとも1種のポリオール(c)であって、前記ポリオール(b)と異なるポリオール(c)をさらに含む、請求項1に記載のポリウレタン。
- 前記成分が、前記約1当量の前記少なくとも1種のポリイソシアネートに対して約0.1当量の少なくとも1種のポリオール(c)であって、前記ポリオール(b)と異なるポリオール(c)をさらに含む、請求項1に記載のポリウレタン。
- 前記ポリオール(c)が、ジオールである、請求項11に記載のポリウレタン。
- 前記ポリオール(c)が、エチレングリコール、ジエチレングリコール、トリエチレングリコール、テトラエチレングリコール、1,2−エタンジオール、プロパンジオール、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、ドデカンジオール、ソルビトール、マンニトール、シクロペンタンジオール、1,4−シクロヘキサンジオール、シクロヘキサンジメタノール、1,4−ベンゼンジメタノール、キシレングリコール、ヒドロキシベンジルアルコール、ジヒドロキシトルエンビス(2−ヒドロキシエチル)テレフタレート、1,4−ビス(ヒドロキシエチル)ピペラジン、N,N’,ビス(2−ヒドロキシエチル)オキサミドおよびこれらの混合物からなる群から選択される、請求項11に記載のポリウレタン。
- 前記ポリオール(c)が、ペンタンジオール、ブタンジオールまたはシクロヘキサンジメタノールである、請求項15に記載のポリウレタン。
- 前記成分が、1つまたは複数の、ポリウレタンポリオール、アクリルアミド、ポリビニルアルコール、ヒドロキシ官能性アクリレート、ヒドロキシ官能性メタクリレート、アリルアルコール、ジヒドロキシオキサミド、ジヒドロキシアミド、ジヒドロキシピペリジン、ジヒドロキシフタレート、ジヒドロキシエチルヒドロキノンおよびこれらの混合物をさらに含む、請求項1に記載のポリウレタン。
- 前記成分が、前記約1当量の前記少なくとも1種のポリイソシアネートに対して約0.01〜約0.5当量の水をさらに含む、請求項1に記載のポリウレタン。
- 前記水が、前記ポリイソシアネートおよびポリカーボネートポリオールと反応してイソシアネート官能性ウレアウレタンプレポリマーを形成する、請求項18に記載のポリウレタン。
- 前記成分が、ポリエーテルポリオールを本質的に含まない、請求項1に記載のポリウレタン。
- 前記成分が、前記ポリカーボネートポリオール以外のポリエステルポリオールを本質的に含まない、請求項1に記載のポリウレタン。
- 前記成分が、アミン硬化剤を本質的に含まない、請求項1に記載のポリウレタン。
- 混合の際、前記成分が、脱ガスの前に少なくとも約10分間少なくとも約100℃の温度に維持され、少なくとも約6時間少なくとも約110℃の温度で反応させられる、請求項1に記載のポリウレタン。
- 混合の際、前記成分が、脱ガスの前に少なくとも約10分間少なくとも約110℃の温度に維持され、少なくとも約6時間少なくとも約120℃の温度で反応させられる、請求項23に記載のポリウレタン。
- (a)
(i)約1当量の少なくとも1種のポリイソシアネートと;
(ii)該約1当量の該少なくとも1種のポリイソシアネートに対して約0.1〜約0.4当量のポリカーボネートジオールと
を含む成分の反応生成物を含む、イソシアネート官能性ウレタンプレポリマー;
(b)該約1当量の該少なくとも1種のポリイソシアネートに対して約0.5〜約0.8当量のトリメチロールプロパン;および
(c)該約1当量の該少なくとも1種のポリイソシアネートに対して約0.1〜約0.5当量のブタンジオール、ペンタンジオールまたはシクロヘキサンジメタノール
を含む成分の反応生成物を含む、請求項1に記載のポリウレタン。 - (a)
(i)約1当量の少なくとも1種のポリイソシアネートと;
(ii)該約1当量の該少なくとも1種のポリイソシアネートに対して約0.2当量のポリカーボネートジオールと
を含む成分の反応生成物を含む、イソシアネート官能性ウレタンプレポリマー;
(b)該約1当量の該少なくとも1種のポリイソシアネートに対して約0.7当量のトリメチロールプロパン;および
(c)該約1当量の該少なくとも1種のポリイソシアネートに対して約0.1当量のブタンジオール、ペンタンジオールまたはシクロヘキサンジメタノール
を含む成分の反応生成物を含む、請求項1に記載のポリウレタン。 - 請求項1に記載のポリウレタンを含む物品。
- 成形品である、請求項27に記載の物品。
- 光学物品、光学レンズ、フォトクロミック物品、フォトクロミックレンズ、ウィンドウ、透明材料、風よけ、サイドライト、バックライト、航空機用透明材料、弾道学的抵抗性物品、ウインドミル部品、グレイジング、液晶ディスプレイの外部表示面、陰極線管、フィルム、シート、伝導性フィルム、マイクロ波吸収フィルム、低抵抗フィルム、防爆パネル、防弾パネル、およびレードームからなる群から選択される、請求項27に記載の物品。
- 航空機用透明材料である、請求項1に記載のポリウレタンを含む物品。
- 湾曲した物品である、請求項27に記載の物品。
- 平坦な物品である、請求項27に記載の物品。
- 請求項1に記載のポリウレタンの少なくとも1つの層と、ポリカーボネートの少なくとも1つの層とを含む物品。
- (a)請求項1に記載のポリウレタンの少なくとも1つの層と、
(b)紙、ガラス、セラミック、木材、石材、織物、金属または有機ポリマー材料、およびこれらの組合せからなる群から選択される基材の少なくとも1つの層と
を含む積層体。 - 請求項1に記載のポリウレタンを含むコーティング組成物。
- (a)約1当量の少なくとも1種のポリイソシアネートと;
(b)該約1当量の該少なくとも1種のポリイソシアネートに対して約0.01〜約0.5当量の少なくとも1種のポリカーボネートポリオールと;
(c)該約1当量の該少なくとも1種のポリイソシアネートに対して約0.01〜約1当量の少なくとも1種のポリオールであって、少なくとも3つのヒドロキシル基を有するポリオールと
を含む成分の反応生成物を含むポリウレタン。 - 前記成分が、前記約1当量の前記少なくとも1種のポリイソシアネートに対して約0.001〜約0.5当量の少なくとも1種のポリオール(d)であって、前記ポリカーボネートポリオール(b)とも前記ポリオール(c)とも異なるポリオール(d)をさらに含む、請求項36に記載のポリウレタン。
- 前記成分が、1つまたは複数の、ポリウレタンポリオール、アクリルアミド、ポリビニルアルコール、ヒドロキシ官能性アクリレート、ヒドロキシ官能性メタクリレート、アリルアルコール、ジヒドロキシオキサミド、ジヒドロキシアミド、ジヒドロキシピペリジン、ジヒドロキシフタレート、ジヒドロキシエチルヒドロキノンおよびこれらの混合物をさらに含む、請求項36に記載のポリウレタン。
- 前記成分が、前記約1当量の前記少なくとも1種のポリイソシアネートに対して約0.01〜約0.5当量の水をさらに含む、請求項36に記載のポリウレタン。
- 前記成分が、ポリエーテルポリオールを本質的に含まない、請求項36に記載のポリウレタン。
- 前記成分が、前記ポリカーボネートポリオール以外のポリエステルポリオールを本質的に含まない、請求項36に記載のポリウレタン。
- 前記成分が、アミン硬化剤を本質的に含まない、請求項36に記載のポリウレタン。
- 請求項36に記載のポリウレタンを含む物品。
- 光学物品、光学レンズ、フォトクロミック物品、フォトクロミックレンズ、ウィンドウ、透明材料、風よけ、サイドライト、バックライト、航空機用透明材料、弾道学的抵抗性物品、ウインドミル部品、グレイジング、液晶ディスプレイの外部表示面、陰極線管、フィルム、シート、伝導性フィルム、マイクロ波吸収フィルム、低抵抗フィルム、防爆パネル、防弾パネル、およびレードームからなる群から選択される、請求項43に記載の物品。
- 湾曲した物品である、請求項43に記載の物品。
- 平坦な物品である、請求項43に記載の物品。
- 請求項36に記載のポリウレタンの少なくとも1つの層と、ポリカーボネートの少なくとも1つの層とを含む物品。
- (a)請求項36に記載のポリウレタンの少なくとも1つの層と、
(b)紙、ガラス、セラミック、木材、石材、織物、金属または有機ポリマー材料、およびこれらの組合せからなる群から選択される基材の少なくとも1つの層と
を含む積層体。 - 請求項36に記載のポリウレタンを含むコーティング組成物。
- ポリウレタン物品を調製するプロセスであって、
(a)約1当量の少なくとも1種のポリイソシアネートと、該約1当量の該少なくとも1種のポリイソシアネートに対して約0.01〜約0.5当量の少なくとも1種のポリカーボネートポリオールとの混合物を、少なくとも約1時間約110℃〜約130℃の温度に加熱して、反応生成物を形成させる工程;
(b)該反応生成物(a)を、該約1当量の該少なくとも1種のポリイソシアネートに対して約0.01〜約1当量の少なくとも1種のポリオールと混合する工程であって、該少なくとも1種のポリオールは少なくとも3つのヒドロキシル基を有し、該混合物が少なくとも約110℃〜約130℃の温度に到達するまで、必要であれば任意選択で加熱することによって到達するまで混合する工程;
(c)該反応生成物を、少なくとも約100℃〜約130℃の温度に予備加熱した型に注型する工程;および
(d)該反応生成物を、少なくとも約0.5時間約100℃〜約120℃の第1の所定の温度で、次いで、約15〜約30時間約140℃〜約180℃の第2の所定の温度で硬化させる工程
を含むプロセス。
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CN105164175A (zh) | 2015-12-16 |
CN105164175B (zh) | 2019-06-04 |
RU2018135975A (ru) | 2018-12-10 |
BR112015022913A2 (pt) | 2017-07-18 |
WO2014152819A1 (en) | 2014-09-25 |
EP2970554A1 (en) | 2016-01-20 |
JP6316928B2 (ja) | 2018-04-25 |
JP2017066422A (ja) | 2017-04-06 |
WO2014153054A1 (en) | 2014-09-25 |
RU2015143632A (ru) | 2017-04-26 |
ES2964231T3 (es) | 2024-04-05 |
WO2014153046A3 (en) | 2014-12-11 |
RU2018135975A3 (ja) | 2019-06-26 |
WO2014153046A2 (en) | 2014-09-25 |
RU2726363C2 (ru) | 2020-07-13 |
EP2970554B1 (en) | 2023-09-20 |
RU2671860C2 (ru) | 2018-11-07 |
CA2904414A1 (en) | 2014-09-25 |
CA2904414C (en) | 2019-01-15 |
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