JP6873102B2 - 開環重合生成物を製造する方法 - Google Patents
開環重合生成物を製造する方法 Download PDFInfo
- Publication number
- JP6873102B2 JP6873102B2 JP2018506880A JP2018506880A JP6873102B2 JP 6873102 B2 JP6873102 B2 JP 6873102B2 JP 2018506880 A JP2018506880 A JP 2018506880A JP 2018506880 A JP2018506880 A JP 2018506880A JP 6873102 B2 JP6873102 B2 JP 6873102B2
- Authority
- JP
- Japan
- Prior art keywords
- polyisocyanate
- diisocyanate
- opening polymerization
- ring
- polyol
- 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.)
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- 238000007151 ring opening polymerisation reaction Methods 0.000 title claims description 19
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 claims description 37
- 239000005056 polyisocyanate Substances 0.000 claims description 27
- 229920001228 polyisocyanate Polymers 0.000 claims description 27
- 229920005862 polyol Polymers 0.000 claims description 26
- 150000003077 polyols Chemical class 0.000 claims description 26
- 239000000047 product Substances 0.000 claims description 23
- 239000007795 chemical reaction product Substances 0.000 claims description 22
- 239000006260 foam Substances 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 15
- -1 aliphatic isocyanate Chemical class 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 11
- INDZWIZFONXCIY-UHFFFAOYSA-N 2-oxo-1,3-dioxolane-4-carboxylic acid Chemical compound OC(=O)C1COC(=O)O1 INDZWIZFONXCIY-UHFFFAOYSA-N 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 8
- 230000000269 nucleophilic effect Effects 0.000 claims description 8
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 7
- 239000000543 intermediate Substances 0.000 claims description 7
- 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 7
- 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 5
- 239000012948 isocyanate Substances 0.000 claims description 5
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 4
- 230000003197 catalytic effect Effects 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- KYVBNYUBXIEUFW-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine Chemical compound CN(C)C(=N)N(C)C KYVBNYUBXIEUFW-UHFFFAOYSA-N 0.000 claims description 3
- FTTATHOUSOIFOQ-UHFFFAOYSA-N 1,2,3,4,6,7,8,8a-octahydropyrrolo[1,2-a]pyrazine Chemical compound C1NCCN2CCCC21 FTTATHOUSOIFOQ-UHFFFAOYSA-N 0.000 claims description 2
- UWKQJZCTQGMHKD-UHFFFAOYSA-N 2,6-di-tert-butylpyridine Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=N1 UWKQJZCTQGMHKD-UHFFFAOYSA-N 0.000 claims description 2
- 239000011248 coating agent Substances 0.000 claims description 2
- 238000000576 coating method Methods 0.000 claims description 2
- 239000004035 construction material Substances 0.000 claims description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 2
- 239000011810 insulating material Substances 0.000 claims description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 2
- 229920000233 poly(alkylene oxides) Polymers 0.000 claims description 2
- OVBFMUAFNIIQAL-UHFFFAOYSA-N 1,4-diisocyanatobutane Chemical compound O=C=NCCCCN=C=O OVBFMUAFNIIQAL-UHFFFAOYSA-N 0.000 claims 1
- DFPJRUKWEPYFJT-UHFFFAOYSA-N 1,5-diisocyanatopentane Chemical compound O=C=NCCCCCN=C=O DFPJRUKWEPYFJT-UHFFFAOYSA-N 0.000 claims 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims 1
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 claims 1
- JXCHMDATRWUOAP-UHFFFAOYSA-N diisocyanatomethylbenzene Chemical group O=C=NC(N=C=O)C1=CC=CC=C1 JXCHMDATRWUOAP-UHFFFAOYSA-N 0.000 claims 1
- 239000000539 dimer Substances 0.000 claims 1
- 238000007789 sealing Methods 0.000 claims 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
- 239000011230 binding agent Substances 0.000 description 16
- 239000011541 reaction mixture Substances 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- 239000004721 Polyphenylene oxide Substances 0.000 description 8
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 8
- 150000005676 cyclic carbonates Chemical class 0.000 description 8
- 239000012975 dibutyltin dilaurate Substances 0.000 description 8
- 229920000570 polyether Polymers 0.000 description 8
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 7
- 239000004033 plastic Substances 0.000 description 7
- 229920003023 plastic Polymers 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 239000012299 nitrogen atmosphere Substances 0.000 description 6
- JFMGYULNQJPJCY-UHFFFAOYSA-N 4-(hydroxymethyl)-1,3-dioxolan-2-one Chemical compound OCC1COC(=O)O1 JFMGYULNQJPJCY-UHFFFAOYSA-N 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 238000005187 foaming Methods 0.000 description 5
- 239000011572 manganese Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- 229920005906 polyester polyol Polymers 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- VGEWEGHHYWGXGG-UHFFFAOYSA-N ethyl n-hydroxycarbamate Chemical compound CCOC(=O)NO VGEWEGHHYWGXGG-UHFFFAOYSA-N 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000004814 polyurethane Substances 0.000 description 3
- 229920002635 polyurethane Polymers 0.000 description 3
- 238000007142 ring opening reaction Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 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 description 2
- KCZQSKKNAGZQSZ-UHFFFAOYSA-N 1,3,5-tris(6-isocyanatohexyl)-1,3,5-triazin-2,4,6-trione Chemical compound O=C=NCCCCCCN1C(=O)N(CCCCCCN=C=O)C(=O)N(CCCCCCN=C=O)C1=O KCZQSKKNAGZQSZ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- CDMDQYCEEKCBGR-UHFFFAOYSA-N 1,4-diisocyanatocyclohexane Chemical compound O=C=NC1CCC(N=C=O)CC1 CDMDQYCEEKCBGR-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
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 229920005877 Lupranol® 2095 Polymers 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000001450 anions Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 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 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 239000013065 commercial product Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 125000004435 hydrogen atom Chemical group [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
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 2
- 229920002521 macromolecule Polymers 0.000 description 2
- HNHHKYXWATVPLU-UHFFFAOYSA-N methyl 2-oxo-1,3-dioxolane-4-carboxylate Chemical compound COC(=O)C1COC(=O)O1 HNHHKYXWATVPLU-UHFFFAOYSA-N 0.000 description 2
- YKNYRRVISWJDSR-UHFFFAOYSA-N methyl oxirane-2-carboxylate Chemical compound COC(=O)C1CO1 YKNYRRVISWJDSR-UHFFFAOYSA-N 0.000 description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 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 description 2
- 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 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
- 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
- VGHSXKTVMPXHNG-UHFFFAOYSA-N 1,3-diisocyanatobenzene Chemical compound O=C=NC1=CC=CC(N=C=O)=C1 VGHSXKTVMPXHNG-UHFFFAOYSA-N 0.000 description 1
- LAACLQLJWIQDEE-UHFFFAOYSA-N 1,3-dioxolane-4-carboxamide Chemical compound NC(=O)C1COCO1 LAACLQLJWIQDEE-UHFFFAOYSA-N 0.000 description 1
- ROHUXHMNZLHBSF-UHFFFAOYSA-N 1,4-bis(isocyanatomethyl)cyclohexane Chemical compound O=C=NCC1CCC(CN=C=O)CC1 ROHUXHMNZLHBSF-UHFFFAOYSA-N 0.000 description 1
- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 description 1
- ICLCCFKUSALICQ-UHFFFAOYSA-N 1-isocyanato-4-(4-isocyanato-3-methylphenyl)-2-methylbenzene Chemical compound C1=C(N=C=O)C(C)=CC(C=2C=C(C)C(N=C=O)=CC=2)=C1 ICLCCFKUSALICQ-UHFFFAOYSA-N 0.000 description 1
- ZMBQZWCDYKGVLW-UHFFFAOYSA-N 1-methylcyclohexa-3,5-diene-1,2-diamine Chemical compound CC1(N)C=CC=CC1N ZMBQZWCDYKGVLW-UHFFFAOYSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 1
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- MZEGJNMYXWIQFF-UHFFFAOYSA-N 2,5-diisocyanato-1,1,3-trimethylcyclohexane Chemical compound CC1CC(N=C=O)CC(C)(C)C1N=C=O MZEGJNMYXWIQFF-UHFFFAOYSA-N 0.000 description 1
- GKJYRYGNJQHVSQ-UHFFFAOYSA-N 2-oxo-1,3-dioxolane-4-carboxamide Chemical compound NC(=O)C1COC(=O)O1 GKJYRYGNJQHVSQ-UHFFFAOYSA-N 0.000 description 1
- WJIOHMVWGVGWJW-UHFFFAOYSA-N 3-methyl-n-[4-[(3-methylpyrazole-1-carbonyl)amino]butyl]pyrazole-1-carboxamide Chemical compound N1=C(C)C=CN1C(=O)NCCCCNC(=O)N1N=C(C)C=C1 WJIOHMVWGVGWJW-UHFFFAOYSA-N 0.000 description 1
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- PHOOZFDRVFBOBV-UHFFFAOYSA-N CCCC1(COC(=O)OC1C)C2COC(=O)O2 Chemical compound CCCC1(COC(=O)OC1C)C2COC(=O)O2 PHOOZFDRVFBOBV-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 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 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 229920005863 Lupranol® Polymers 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- VUKCPUAOPNOVKC-UHFFFAOYSA-N OCC1OC(OC1)=O.OCC1OC(OC1)=O Chemical compound OCC1OC(OC1)=O.OCC1OC(OC1)=O VUKCPUAOPNOVKC-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
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Images
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Description
a)少なくとも1種のポリイソシアネートと2−オキソ−1,3−ジオキソラン−4−カルボン酸との反応生成物を用意する工程;および
b)前記反応生成物を、触媒量の少なくとも1種の非求核塩基の存在下で40〜150℃の範囲内にある温度に曝す工程
を含む、開環重合生成物を製造する方法である。
反応生成物を調製するためのポリイソシアネートは、ポリウレタンの調製で知られている、NCO官能価(分子内のNCO基の数)が、2以上、好ましくは2〜6、より好ましくは2〜3の全ての脂肪族、芳香族または脂環式のイソシアネート、またはこれらの組み合わせ、つまり脂肪族/芳香族/脂環式の混合型のイソシアネートを含む。
(1)ポリイソシアネートを等モル量の2−オキソ−1,3−ジオキソラン−4−カルボン酸と反応させることができる。「等モル」という用語は、本明細書で使用されるように、2−オキソ−1,3−ジオキソラン−4−カルボン酸のCOOH基に対するポリイソシアネートのNCO基のモル比率が、「実質的に」1(つまり0.95〜1.05)に等しいことを意味する。得られる反応生成物は、式(I):
の反応生成物である。
工程(a)の反応生成物を、触媒量の非求核塩基の存在下で、約40〜約150℃、好ましくは60〜150℃の範囲にある温度に曝すことで反応させて、開環重合により生成物をもたらす。
の繰り返し単位から構成されている。
本実施例では、以下の略語および製品を使用する:
CYCA:2−オキソ−1,3−ジオキソラン−4−カルボン酸
IPDI:イソホロンジイソシアネート
DBTL:ジブチル錫ジラウレート
DMAP:4−ジメチルアミノピリジン
THF:テトラヒドロフラン
RT:室温
Lupranol(登録商標)2032:BASF SEの市販品;55mgKOH/gのOH価およびMn=3060g/モルを有する三官能性ポリエーテルポリオール
Lupranol(登録商標)2095:BASF SEの市販品;35mgKOH/gのOH価およびMn=4800g/モルを有する三官能性ポリエーテルポリオール
DBU:1,8−ジアザビシクロ[5.4.0]ウンデカ−7−エン
TGA:熱重量分析
TDI:トルイレン−2,4−ジイソシアネート
HDI:ヘキサメチレン−1,6−ジイソシアネート
Arcol(登録商標)ポリオール1374:Bayerの市販品;25〜29mgKOH/gのOH価およびMeq=2078g/モルを有する三官能性ポリエーテルポリオール
Desmodur(登録商標)N3600:Bayerの市販品;多官能脂肪族ポリイソシアネート、つまりHDIトリマー;NCO含量23.5±0.5%。
N2雰囲気のもと、250mLの無水THF中の91.80gのLupranol2032(0.03モル)、20.01gのIPDI(0.09モル)および0.022gのDBTLを60℃に加熱して、3.0%の所望のNCO値が達成されるまで1.25時間にわたり撹拌した。この反応混合物を室温に冷却し、10.70gのCYCA(3.0%の最終的なNCO値によるもの)および0.10gのDMAPを添加し、この反応混合物を、残留NCOがこれ以上検出できなくなるまで、12時間にわたり撹拌した(IR制御)。溶媒を真空で除去し、バインダーが、高粘度の黄色がかった油として定量的収率で得られた。
12.0gのCYCA−I2032および0.36g(3重量%)のDBUをプラスチックビーカー内で激しく混合し、乾燥機内で1時間にわたり100℃に加熱した。黄色がかった軟質発泡体が得られた。この発泡体は、ほとんどの一般的な有機溶媒、例えばTHF、ジメチルスルホキシド、アセトン、トルエンおよび水に不溶であった。いくつかの場合では、膨潤が観察された。
N2雰囲気のもと、584.76gのLupranol2095(0.36モルのOH)、100.0gのTDI−CYCA中間体(15.35%のNCO、0.36モルのNCO;国際公開第2014/118268号(WO2014/118268)の例11または12と同様にして得られる)および0.09gのDBTLをフラスコ内で混合し、60℃に加熱し、残留NCOが検出されなくなるまで撹拌した(およそ6時間、IR制御)。この反応混合物を室温に冷却し、バインダーが、黄色がかった高粘度の油として定量的収率で得られた。
12.0gのCYCA−T2095および0.12g(1重量%)のDBUをプラスチックビーカー内で混合し、80℃で1時間にわたり硬化させた。黄色がかった安定した弾性発泡体が得られた。
N2雰囲気のもと、211.38gのArcolポリオール1374(0.10モルのOH)を、750mLの無水THF中に溶解させた。27.98gのTDI−CYCA中間体(15.27%のNCO、0.10モルのNCO;国際公開第2014/118268号(WO2014/118268)の例11または12と同様にして得られる)および0.06gのDBTLを添加した。この反応混合物を、残留NCOが検出されなくなるまで60℃に加熱した(およそ6時間、IR制御)。この反応混合物を室温に冷却し、溶媒を真空で除去した。純粋なバインダーが、高粘度の黄色がかった油として定量的収率で得られた。
12.0gのCYCA−T1374および0.36g(3重量%)のDBUをプラスチックビーカー内で混合し、40℃で1時間にわたり硬化させた。黄色がかった安定した弾性フィルムが得られた。
N2雰囲気のもと、78.21gのDesmodur N3600(0.43molのNCO)、57.28gの環状カーボネートカルボン酸(CYCA)(0.43モル)および0.52gの4−DMAPを、400mLの無水THFで希釈し、この反応混合物を、残留NCOが検出されなくなるまで撹拌した(およそ6時間、IR制御)。溶媒を真空で除去し、純粋なバインダーが、黄色がかった粘稠な油として定量的収率で得られた。
12.0gのCYCA−H9046および0.12g(1重量%)のDBUをプラスチックビーカー内で混合し、80℃で1時間にわたり硬化させた。茶色がかった硬質かつ脆性の多孔質材料が得られた。
N2雰囲気のもと、320.39gのDesmodur N3600(1.72モルのNCO)、202.78gのグリセリンカーボネート(1.72モル)および0.1gのDBTLを、600mLの無水THFで希釈し、この反応混合物を、残留NCOが検出されなくなるまで60℃に加熱した(およそ6時間、IR制御)。この反応混合物を室温に冷却し、溶媒を真空で除去した。純粋なバインダーが、透明で粘稠な液体として定量的収率で得られた。
12.0gのN3600−GCおよび0.12g(1重量%)のDBUをプラスチックビーカー内で混合し、80℃で1時間にわたり反応させた。硬化および発泡は観察されず、透明で粘稠な液体が得られた。
N2雰囲気のもと、211.2gのLupranol2095(Meq=1600g/mol、0.13molのOH)を、350mLの無水THFで希釈し、23.00gのTDI(48.2%のNCO、0.13モル)を添加し、この反応混合物を20分間にわたり50℃に加熱した。NCO含量を特定し、相応量のグリセリンカーボネート(16.92g、0.14モル)、ならびに0.04g(0.02重量%)のDBTLを添加した。この反応混合物を室温で8時間にわたり撹拌し、溶媒を除去した後に、バインダーが、粘稠で透明な油として定量的収率で得られた。
12.0gのT−2095−GCおよび0.12g(1重量%)のDBUをプラスチックビーカー内で混合し、80℃で3日間にわたり反応させた。硬化および発泡は観察されず、不透明な茶色がかった液体が得られた。
Claims (14)
- 開環重合生成物を製造する方法であって、
a)少なくとも1種のポリイソシアネートと2−オキソ−1,3−ジオキソラン−4−カルボン酸との反応生成物を用意する工程;および
b)前記反応生成物を、触媒量の少なくとも1種の非求核塩基の存在下で40〜150℃の範囲内にある温度に曝す工程
を含む、前記方法。 - 前記ポリイソシアネートが、NCO官能価2以上を有する、脂肪族イソシアネート、芳香族イソシアネート、脂環式イソシアネートまたはこれらの組み合わせから選択される、請求項1記載の方法。
- 前記ポリイソシアネートが、トルイレンジイソシアネート、イソホロ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、4,4’−ジイソシアナトジシクロヘキシルメタン、テトラメチレンジイソシアネート、ペンタ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、これらの異性体、ダイマー、トリマー、オリゴマーおよび混合物から選択される、請求項1記載の方法。
- 前記ポリイソシアネートが、モル過剰の請求項2または3で定義されるポリイソシアネートとポリオールとを反応させることにより得られるポリイソシアネートプレポリマーである、請求項1記載の方法。
- 前記ポリオールが、平均OH官能価2〜8を有する、請求項4記載の方法。
- 前記ポリオールが、数平均分子量Mnを400〜10000の範囲で有するC2〜4ポリアルキレンオキシドである、請求項5記載の方法。
- 工程a)の反応生成物が、
(1)ポリイソシアネートを等モル量の2−オキソ−1,3−ジオキソラン−4−カルボン酸と反応させることにより;または
(2)第一の工程でモル過剰のポリイソシアネートを2−オキソ−1,3−ジオキソラン−4−カルボン酸と反応させて中間体を得て、第二の工程で前記中間体を、ここで先に定義されたポリオールと反応させることにより
得られる、請求項5又は6に記載の方法。 - 工程b)が、40〜150℃の範囲にある温度で実施される、請求項1から8までのいずれか1項記載の方法。
- 前記非求核塩基が、1,8−ジアザビシクロ[5.4.0]ウンデカ−7−エン、1,5−ジアゾビシクロ[4.3.0]ノン−5−エン、1,4−ジアザビシクロ[2.2.2]オクタン、2,6−ジ−tert−ブチルピリジン、ジイソプロピルエチルアミン、テトラメチルグアニジンまたはこれらの混合物から選択される、請求項1から9までのいずれか1項記載の方法。
- 請求項1から10までのいずれか1項記載の方法により得られる、開環重合生成物。
- 発泡体の形態にある請求項11記載の開環重合生成物。
- 建設材料、絶縁材料、封止剤もしくは被覆としての、またはこれらを製造するための、請求項11もしくは12記載の開環重合生成物の使用。
- マットレスまたは創傷パッドを製造するための、請求項11もしくは12記載の開環重合生成物の使用。
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