JP6260300B2 - 硬化性組成物 - Google Patents
硬化性組成物 Download PDFInfo
- Publication number
- JP6260300B2 JP6260300B2 JP2014013179A JP2014013179A JP6260300B2 JP 6260300 B2 JP6260300 B2 JP 6260300B2 JP 2014013179 A JP2014013179 A JP 2014013179A JP 2014013179 A JP2014013179 A JP 2014013179A JP 6260300 B2 JP6260300 B2 JP 6260300B2
- Authority
- JP
- Japan
- Prior art keywords
- curable composition
- group
- nitroxide free
- containing compound
- isocyanate group
- 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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- 239000000203 mixture Substances 0.000 title claims description 103
- 150000001875 compounds Chemical class 0.000 claims description 77
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 74
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical class ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 63
- -1 nitroxide free radical Chemical class 0.000 claims description 47
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 45
- 239000001257 hydrogen Substances 0.000 claims description 37
- 229910052739 hydrogen Inorganic materials 0.000 claims description 37
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 36
- 239000012948 isocyanate Substances 0.000 claims description 17
- 239000000463 material Substances 0.000 claims description 13
- 239000003566 sealing material Substances 0.000 claims description 13
- 239000003381 stabilizer Substances 0.000 claims description 13
- 238000003860 storage Methods 0.000 claims description 13
- 239000000853 adhesive Substances 0.000 claims description 9
- 239000000945 filler Substances 0.000 claims description 9
- 239000013008 thixotropic agent Substances 0.000 claims description 9
- 239000003960 organic solvent Substances 0.000 claims description 8
- 239000004014 plasticizer Substances 0.000 claims description 7
- 125000003386 piperidinyl group Chemical group 0.000 claims description 6
- UZFMOKQJFYMBGY-UHFFFAOYSA-N 4-hydroxy-TEMPO Chemical group CC1(C)CC(O)CC(C)(C)N1[O] UZFMOKQJFYMBGY-UHFFFAOYSA-N 0.000 claims description 5
- 150000003254 radicals Chemical class 0.000 claims description 5
- 239000000654 additive Substances 0.000 claims description 4
- 239000003086 colorant Substances 0.000 claims description 4
- 229920005862 polyol Polymers 0.000 description 52
- 150000003077 polyols Chemical class 0.000 description 47
- 238000001723 curing Methods 0.000 description 24
- 239000005056 polyisocyanate Substances 0.000 description 20
- 229920001228 polyisocyanate Polymers 0.000 description 20
- 230000015572 biosynthetic process Effects 0.000 description 18
- 238000003786 synthesis reaction Methods 0.000 description 18
- 230000000052 comparative effect Effects 0.000 description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
- 150000001412 amines Chemical class 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 13
- 238000012360 testing method Methods 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 12
- 229910052751 metal Inorganic materials 0.000 description 12
- 239000002184 metal Substances 0.000 description 12
- 239000000843 powder Substances 0.000 description 11
- 238000005227 gel permeation chromatography Methods 0.000 description 10
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- 150000002513 isocyanates Chemical class 0.000 description 7
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- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 7
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
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- 238000010998 test method Methods 0.000 description 5
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- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 4
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 4
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- RSOILICUEWXSLA-UHFFFAOYSA-N bis(1,2,2,6,6-pentamethylpiperidin-4-yl) decanedioate Chemical compound C1C(C)(C)N(C)C(C)(C)CC1OC(=O)CCCCCCCCC(=O)OC1CC(C)(C)N(C)C(C)(C)C1 RSOILICUEWXSLA-UHFFFAOYSA-N 0.000 description 4
- 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 4
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- 239000012975 dibutyltin dilaurate Substances 0.000 description 4
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- 239000003999 initiator Substances 0.000 description 4
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- 238000003756 stirring Methods 0.000 description 4
- 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 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- VLJQDHDVZJXNQL-UHFFFAOYSA-N 4-methyl-n-(oxomethylidene)benzenesulfonamide Chemical compound CC1=CC=C(S(=O)(=O)N=C=O)C=C1 VLJQDHDVZJXNQL-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 229910052797 bismuth Inorganic materials 0.000 description 3
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 3
- 239000004566 building material Substances 0.000 description 3
- 229910000019 calcium carbonate Inorganic materials 0.000 description 3
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- 239000013522 chelant Substances 0.000 description 3
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- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
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- 238000007665 sagging Methods 0.000 description 3
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- 150000003512 tertiary amines Chemical class 0.000 description 3
- 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 3
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 238000004078 waterproofing Methods 0.000 description 3
- 229910052725 zinc Inorganic materials 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- QEGNUYASOUJEHD-UHFFFAOYSA-N 1,1-dimethylcyclohexane Chemical compound CC1(C)CCCCC1 QEGNUYASOUJEHD-UHFFFAOYSA-N 0.000 description 2
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidine Chemical compound CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 2
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- IRIAEXORFWYRCZ-UHFFFAOYSA-N Butylbenzyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCC1=CC=CC=C1 IRIAEXORFWYRCZ-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
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- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
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- XQBCVRSTVUHIGH-UHFFFAOYSA-L [dodecanoyloxy(dioctyl)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCCCCCC)(CCCCCCCC)OC(=O)CCCCCCCCCCC XQBCVRSTVUHIGH-UHFFFAOYSA-L 0.000 description 2
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- XDPCFUNJJWMBFH-UHFFFAOYSA-N cesium;ethanolate Chemical compound [Cs+].CC[O-] XDPCFUNJJWMBFH-UHFFFAOYSA-N 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- SZKXDURZBIICCF-UHFFFAOYSA-N cobalt;pentane-2,4-dione Chemical compound [Co].CC(=O)CC(C)=O SZKXDURZBIICCF-UHFFFAOYSA-N 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- QNZRVYCYEMYQMD-UHFFFAOYSA-N copper;pentane-2,4-dione Chemical compound [Cu].CC(=O)CC(C)=O QNZRVYCYEMYQMD-UHFFFAOYSA-N 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 1
- XBZSBBLNHFMTEB-UHFFFAOYSA-N cyclohexane-1,3-dicarboxylic acid Chemical compound OC(=O)C1CCCC(C(O)=O)C1 XBZSBBLNHFMTEB-UHFFFAOYSA-N 0.000 description 1
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000007033 dehydrochlorination reaction Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 description 1
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- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 229940043237 diethanolamine Drugs 0.000 description 1
- OTARVPUIYXHRRB-UHFFFAOYSA-N diethoxy-methyl-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](C)(OCC)CCCOCC1CO1 OTARVPUIYXHRRB-UHFFFAOYSA-N 0.000 description 1
- HQWPLXHWEZZGKY-UHFFFAOYSA-N diethylzinc Chemical compound CC[Zn]CC HQWPLXHWEZZGKY-UHFFFAOYSA-N 0.000 description 1
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- 125000005442 diisocyanate group Chemical group 0.000 description 1
- HBGGXOJOCNVPFY-UHFFFAOYSA-N diisononyl phthalate Chemical compound CC(C)CCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCC(C)C HBGGXOJOCNVPFY-UHFFFAOYSA-N 0.000 description 1
- JFHGLVIOIANSIN-UHFFFAOYSA-N dimethyl butanedioate;1-(2-hydroxyethyl)-2,2,6,6-tetramethylpiperidin-4-ol Chemical compound COC(=O)CCC(=O)OC.CC1(C)CC(O)CC(C)(C)N1CCO JFHGLVIOIANSIN-UHFFFAOYSA-N 0.000 description 1
- HGQSXVKHVMGQRG-UHFFFAOYSA-N dioctyltin Chemical compound CCCCCCCC[Sn]CCCCCCCC HGQSXVKHVMGQRG-UHFFFAOYSA-N 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 1
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- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
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- 238000006266 etherification reaction Methods 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
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- 235000011187 glycerol Nutrition 0.000 description 1
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- 239000010438 granite Substances 0.000 description 1
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- 229910002804 graphite Inorganic materials 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
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- 239000004312 hexamethylene tetramine Substances 0.000 description 1
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- ANJPRQPHZGHVQB-UHFFFAOYSA-N hexyl isocyanate Chemical compound CCCCCCN=C=O ANJPRQPHZGHVQB-UHFFFAOYSA-N 0.000 description 1
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- 238000006460 hydrolysis reaction Methods 0.000 description 1
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- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 description 1
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- 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 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000005453 ketone based solvent Substances 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- QIJRBQDGQLSRLG-UHFFFAOYSA-N magnesium;pentane-2,4-dione Chemical compound [Mg].CC(=O)CC(C)=O QIJRBQDGQLSRLG-UHFFFAOYSA-N 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- SQZZGEUJERGRIN-UHFFFAOYSA-N manganese;pentane-2,4-dione Chemical compound [Mn].CC(=O)CC(C)=O SQZZGEUJERGRIN-UHFFFAOYSA-N 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 239000004579 marble Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000007769 metal material Substances 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- AYLRODJJLADBOB-QMMMGPOBSA-N methyl (2s)-2,6-diisocyanatohexanoate Chemical compound COC(=O)[C@@H](N=C=O)CCCCN=C=O AYLRODJJLADBOB-QMMMGPOBSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- PHQOGHDTIVQXHL-UHFFFAOYSA-N n'-(3-trimethoxysilylpropyl)ethane-1,2-diamine Chemical compound CO[Si](OC)(OC)CCCNCCN PHQOGHDTIVQXHL-UHFFFAOYSA-N 0.000 description 1
- MQWFLKHKWJMCEN-UHFFFAOYSA-N n'-[3-[dimethoxy(methyl)silyl]propyl]ethane-1,2-diamine Chemical compound CO[Si](C)(OC)CCCNCCN MQWFLKHKWJMCEN-UHFFFAOYSA-N 0.000 description 1
- HNHVTXYLRVGMHD-UHFFFAOYSA-N n-butyl isocyanate Chemical compound CCCCN=C=O HNHVTXYLRVGMHD-UHFFFAOYSA-N 0.000 description 1
- WIBFFTLQMKKBLZ-SEYXRHQNSA-N n-butyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCCCC WIBFFTLQMKKBLZ-SEYXRHQNSA-N 0.000 description 1
- LKTCWOYIQVKYIV-UHFFFAOYSA-N n-butyl-4-chloro-n-(1,2,2,6,6-pentamethylpiperidin-4-yl)-1,3,5-triazin-2-amine Chemical compound N=1C=NC(Cl)=NC=1N(CCCC)C1CC(C)(C)N(C)C(C)(C)C1 LKTCWOYIQVKYIV-UHFFFAOYSA-N 0.000 description 1
- KYTZHLUVELPASH-UHFFFAOYSA-N naphthalene-1,2-dicarboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 KYTZHLUVELPASH-UHFFFAOYSA-N 0.000 description 1
- 235000013557 nattō Nutrition 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- FLESAADTDNKLFJ-UHFFFAOYSA-N nickel;pentane-2,4-dione Chemical compound [Ni].CC(=O)CC(C)=O FLESAADTDNKLFJ-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229950002083 octabenzone Drugs 0.000 description 1
- OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 description 1
- 125000005447 octyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- WATYAKBWIQTPDE-UHFFFAOYSA-N pentane-2,4-dione;zinc Chemical compound [Zn].CC(=O)CC(C)=O WATYAKBWIQTPDE-UHFFFAOYSA-N 0.000 description 1
- 125000005498 phthalate group Chemical class 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 1
- 239000011120 plywood Substances 0.000 description 1
- 229920002647 polyamide Chemical group 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920006149 polyester-amide block copolymer Polymers 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 150000008442 polyphenolic compounds Chemical class 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 229920006389 polyphenyl polymer Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000007870 radical polymerization initiator Substances 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 230000003014 reinforcing effect Effects 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- 238000007790 scraping Methods 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 230000009974 thixotropic effect Effects 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 238000005809 transesterification reaction Methods 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
- 235000020234 walnut Nutrition 0.000 description 1
- 239000008096 xylene Chemical group 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Sealing Material Composition (AREA)
- Polyurethanes Or Polyureas (AREA)
- Adhesives Or Adhesive Processes (AREA)
Description
ニトロキシド遊離基を有するイソシアネート基含有化合物は、本発明の硬化性組成物において硬化成分として働くとともに、硬化後の組成物に被着面との良好な接着性を与え、揺変性を損なわずに長期にわたって良好な耐候性を付与するものである。
攪拌機、温度計、窒素導入管および加熱冷却装置の付いた反応容器に、窒素ガスを流しながら、ポリオキシプロピレンジオール(旭硝子社製、製品名EL−3021、水酸基価34.68mgKOH/g)を587.8g、ポリオキシプロピレントリオール(旭硝子社製、製品名EL−4030、水酸基価41.47mgKOH/g)を172.9g、4−ヒドロキシ−2,2,6,6−テトラメチルピペリジン1−オキシル(和光純薬工業社製)を7.2g、トルエンを157.7g仕込み、攪拌しながらキシリレンジイソシアネート(三井化学社製、製品名タケネート500)を74.3g、反応触媒としてジブチル錫ジラウレートを0.1g加え、加温して70〜80℃で2時間反応させ、イソシアネート基含有量が理論値(1.08質量%)以下となった時点で反応を終了し、ニトロキシド遊離基を有するイソシアネート基含有ウレタンプレポリマーPU−1を含有する組成物Aを得た。得られた組成物Aの25℃における粘度は、3,600mPa・sであった。また、得られた組成物Aは、滴定による実測のイソシアネート基含有量が1.06質量%であった。そして、得られたニトロキシド遊離基を有するイソシアネート基含有ウレタンプレポリマーPU−1は、ゲルパーミエーションクロマトグラフィー(GPC)測定のポリスチレン換算による数平均分子量が3,500であった。
攪拌機、温度計、窒素導入管および加熱冷却装置の付いた反応容器に、窒素ガスを流しながら、ポリオキシプロピレンジオール(旭硝子社製、製品名EL−3021、水酸基価34.68mgKOH/g)を595.8g、ポリオキシプロピレントリオール(旭硝子社製、製品名EL−4030、水酸基価41.47mgKOH/g)を175.2g、トルエンを157.7g仕込み、攪拌しながらキシリレンジイソシアネート(三井化学社製、製品名タケネート500)を71.2g、反応触媒としてジブチル錫ジラウレートを0.1g加え、加温して70〜80℃で2時間反応させ、イソシアネート基含有量が理論値(1.09質量%)以下となった時点で反応を終了し、ニトロキシド遊離基を有さないイソシアネート基含有ウレタンプレポリマーPU−2を含有する組成物Bを得た。得られた組成物Bの25℃における粘度は、3,800mPa・sであった。また、得られた組成物Bは、滴定による実測のイソシアネート基含有量が1.06質量%であった。そして、得られたニトロキシド遊離基を有さないイソシアネート基含有ウレタンプレポリマーPU−2は、ゲルパーミエーションクロマトグラフィー(GPC)測定のポリスチレン換算による数平均分子量が3,600であった。
合成例1で得たニトロキシド遊離基を有するイソシアネート基含有ウレタンプレポリマーPU−1を含有する組成物A 1,000gを、実施例1の硬化性組成物とした。
攪拌機および窒素導入管付混合容器に窒素ガスを流しながら合成例1で得たニトロキシド遊離基を有するイソシアネート基含有ウレタンプレポリマーPU−1を含有する組成物Aを1,000g、ヒンダードアミン系光安定剤(BASF社製、Tinuvin292)を11.8g仕込み、内容物が均一になるまで攪拌し硬化性組成物を製造した。
実施例2において、Tinuvin292に替えて2,2,6,6−テトラメチルピペリジン1−オキシル(和光純薬工業社製)を6.5g仕込んだ以外は同様の操作をして硬化性組成物を製造した。
合成例2で得たニトロキシド遊離基を有さないイソシアネート基含有ウレタンプレポリマーPU−2を含有する組成物B 1,000gを、比較例1の硬化性組成物とした。
実施例2において、合成例1で得たニトロキシド遊離基を有するイソシアネート基含有ウレタンプレポリマーPU−1を含有する組成物Aを、合成例2で得たニトロキシド遊離基を有さないイソシアネート基含有ウレタンプレポリマーPU−2を含有する組成物Bに替えた以外は、同様の操作をして硬化性組成物を製造した。
実施例3において、合成例1で得たニトロキシド遊離基を有するイソシアネート基含有ウレタンプレポリマーPU−1を含有する組成物Aを、合成例2で得たニトロキシド遊離基を有さないイソシアネート基含有ウレタンプレポリマーPU−2を含有する組成物Bに替えた以外は、同様の操作をして硬化性組成物を製造した。
攪拌機、減圧装置および窒素導入管付混練容器に、窒素ガスを流しながら、合成例1で得たニトロキシド遊離基を有するイソシアネート基含有ウレタンプレポリマーPU−1を含有する組成物Aを1,000g仕込み、攪拌しながら重質炭酸カルシウム(白石カルシウム社製、製品名ホワイトンB)を690g、有機溶剤(ジャパンエナジー社製、製品名カクタスソルベントP−20)を136g仕込み内容物が均一になるまで混練した。次いでジメチルカーボネートを35g、p−トルエンスルホニルイソシアネートを5g、揺変性付与剤として微粉末シリカ(トクヤマ社製、製品名レオロシールQS−102S)を64g仕込み、内容物が均一になるまで混練した。さらに、20〜50hPaで減圧脱泡し一液型湿気硬化性シーリング材組成物S−1を製造した。一液型湿気硬化型シーリング材S−1は室温でペースト状であった。
実施例4において、合成例1で得たニトロキシド遊離基を有するイソシアネート基含有ウレタンプレポリマーPU−1を含有する組成物Aを、合成例2で得たニトロキシド遊離基を有さないイソシアネート基含有ウレタンプレポリマーPU−2を含有する組成物Bに替えた以外は同様の操作を行い一液型湿気硬化型シーリング材組成物S−2を製造した。一液型湿気硬化性シーリング材S−2は室温でペースト状であった。
比較例4において、さらにヒンダードアミン系光安定剤(BASF社製、Tinuvin292)を11.8gを添加した以外は同様にして一液型湿気硬化性シーリング材組成物S−3を製造した。一液型湿気硬化性シーリング材S−3は室温でペースト状であった。
実施例1〜3の硬化性組成物および比較例1〜3の硬化性組成物を用いて、下記の試験を行った。その結果を表1に示す。
厚さ5mmのスレート板(セメント系板状建材)の表面に厚さ2mm×幅12mmの発泡ポリエチレン製バックアップ材を四角枠状に貼り、この枠内に硬化性組成物を打設し、余分のものをヘラでかきとり表面を平らにし、厚さ2mm×幅30mm×長さ100mmに硬化したものを試験体とした。
試験体をJIS A 1415(1999)「高分子系建築材料の実験室光源による暴露試験方法」の6.3オープンフレームカーボンアークランプによる暴露試験方法のWS−A法(サンシャインウエザオメーター、ブラックパネル温度63℃、102分間照射後、18分照射及び水噴射)で1,000時間後、1,300時間後、1,500時間後それぞれの試験体表面の外観変化を目視により観察し、耐候性を下記の判定基準により評価した。
判定基準
○:試験体表面にクラックがない
△:試験体表面に微細なクラックがある
×:試験体表面にクラックが多数ある
厚さ5mmのスレート板の表面に厚さ5mm×幅12mmの発泡ポリエチレン製バックアップ材を四角枠状に貼り、この枠内に硬化性組成物(一液型湿気硬化性シーリング材)を打設し、余分のものをヘラでかきとり表面を平らにし、厚さ5mm×幅30mm×長さ100mmに硬化したものを試験体とした。
試験体をJIS A 1415(1999)「高分子系建築材料の実験室光源による暴露試験方法」の6.3オープンフレームカーボンアークランプによる暴露試験方法のWS−A法(サンシャインウエザオメーター、ブラックパネル温度63℃、102分間照射後、18分照射及び水噴射)で1,000時間後、1,300時間後、1,500時間後それぞれの試験体表面の外観変化を目視により観察し、耐候性を下記の判定基準により評価した。
判定基準
○:試験体表面にクラックがない
△:試験体表面に微細なクラックがある
×:試験体表面にクラックが多数ある
JIS A 1439(2010)「建築用シーリング材の試験方法」の5.1スランプ試験により23℃におけるスランプ縦試験を行った。
空気が入らないように紙管のカートリッジに一液型湿気硬化性シーリング材を詰め密封し、50℃の恒温器中に入れた。10日後にカートリッジを取り出して室温に3時間置き、手動のシーリングガンを用いて押出した。押出しの状況から下記の判断により貯蔵安定性を評価した。
○:押出しすれば内容物が容易に出る
×:かなり強く押出さないと内容物が出ない
Claims (4)
- ニトロキシド遊離基を有するイソシアネート基含有化合物を含有し、
前記ニトロキシド遊離基を有するイソシアネート基含有化合物が、有機イソシアネート化合物と活性水素含有化合物とを反応させて得られ、
前記活性水素含有化合物の少なくとも1つがニトロキシド遊離基およびピペリジン環を有する活性水素含有化合物であるイソシアネート基含有ウレタンプレポリマーであることを特徴とする硬化性組成物。 - 前記ニトロキシド遊離基およびピペリジン環を有する活性水素含有化合物が4−ヒドロキシ−2,2,6,6−テトラメチルピペリジン1−オキシルであることを特徴とする請求項1に記載の硬化性組成物。
- さらに硬化促進触媒、可塑剤、耐候安定剤、充填剤、揺変性付与剤、接着性向上剤、貯蔵安定性向上剤、着色剤および有機溶剤からなる群から選ばれる添加剤を1種または2種以上含有することを特徴とする請求項1または2に記載の硬化性組成物。
- シーリング材、防水材または接着剤であ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硬化性組成物。
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