JP2021517596A - 新しいポリイソシアネート組成物 - Google Patents
新しいポリイソシアネート組成物 Download PDFInfo
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- JP2021517596A JP2021517596A JP2020546466A JP2020546466A JP2021517596A JP 2021517596 A JP2021517596 A JP 2021517596A JP 2020546466 A JP2020546466 A JP 2020546466A JP 2020546466 A JP2020546466 A JP 2020546466A JP 2021517596 A JP2021517596 A JP 2021517596A
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- Prior art keywords
- carbon atoms
- members
- compound
- phosphite
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- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 126
- 239000005056 polyisocyanate Substances 0.000 title claims abstract description 54
- 229920001228 polyisocyanate Polymers 0.000 title claims abstract description 54
- -1 monophenol alkyl compound Chemical class 0.000 claims abstract description 40
- 239000003054 catalyst Substances 0.000 claims abstract description 35
- 238000000576 coating method Methods 0.000 claims abstract description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 51
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical class OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims description 40
- 150000001875 compounds Chemical class 0.000 claims description 32
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- 125000003118 aryl group Chemical group 0.000 claims description 22
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
- 238000004132 cross linking Methods 0.000 claims description 14
- 239000000654 additive Substances 0.000 claims description 11
- 125000000623 heterocyclic group Chemical group 0.000 claims description 11
- 125000001072 heteroaryl group Chemical group 0.000 claims description 10
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical group SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 claims description 10
- 239000012948 isocyanate Substances 0.000 claims description 9
- 150000002513 isocyanates Chemical class 0.000 claims description 9
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 8
- 125000001931 aliphatic group Chemical group 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 5
- 230000000996 additive effect Effects 0.000 claims description 4
- 239000000853 adhesive Substances 0.000 claims description 4
- 230000001070 adhesive effect Effects 0.000 claims description 4
- 239000011248 coating agent Substances 0.000 claims description 4
- 239000003973 paint Substances 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 3
- 239000006096 absorbing agent Substances 0.000 claims description 2
- 150000001409 amidines Chemical class 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 150000002902 organometallic compounds Chemical class 0.000 claims description 2
- 150000003512 tertiary amines Chemical class 0.000 claims description 2
- 230000002429 anti-coagulating effect Effects 0.000 claims 1
- 238000001556 precipitation Methods 0.000 abstract description 13
- 238000004383 yellowing Methods 0.000 abstract description 5
- 238000010586 diagram Methods 0.000 abstract 1
- 230000003197 catalytic effect Effects 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- 229910052760 oxygen Inorganic materials 0.000 description 8
- 229920005862 polyol Polymers 0.000 description 8
- 239000004814 polyurethane Substances 0.000 description 8
- 229920002635 polyurethane Polymers 0.000 description 8
- 229910052717 sulfur Inorganic materials 0.000 description 8
- 150000003077 polyols Chemical class 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 238000004040 coloring Methods 0.000 description 6
- 125000005842 heteroatom Chemical group 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000011593 sulfur Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- 150000007942 carboxylates Chemical class 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 4
- 125000003367 polycyclic group Chemical group 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 125000005442 diisocyanate group Chemical group 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 125000001261 isocyanato group Chemical group *N=C=O 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 3
- BVUXDWXKPROUDO-UHFFFAOYSA-N 2,6-di-tert-butyl-4-ethylphenol Chemical compound CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 BVUXDWXKPROUDO-UHFFFAOYSA-N 0.000 description 2
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-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
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000005058 Isophorone diisocyanate Substances 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 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
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-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
- 125000002723 alicyclic group Chemical group 0.000 description 2
- 125000002877 alkyl aryl group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 230000002744 anti-aggregatory effect Effects 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 2
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
- AYOHIQLKSOJJQH-UHFFFAOYSA-N dibutyltin Chemical compound CCCC[Sn]CCCC AYOHIQLKSOJJQH-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- HGQSXVKHVMGQRG-UHFFFAOYSA-N dioctyltin Chemical compound CCCCCCCC[Sn]CCCCCCCC HGQSXVKHVMGQRG-UHFFFAOYSA-N 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 239000001530 fumaric acid Substances 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 2
- 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 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- MBAUOPQYSQVYJV-UHFFFAOYSA-N octyl 3-[4-hydroxy-3,5-di(propan-2-yl)phenyl]propanoate Chemical compound OC1=C(C=C(C=C1C(C)C)CCC(=O)OCCCCCCCC)C(C)C MBAUOPQYSQVYJV-UHFFFAOYSA-N 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 230000006641 stabilisation Effects 0.000 description 2
- 238000011105 stabilization Methods 0.000 description 2
- 229920001187 thermosetting polymer Polymers 0.000 description 2
- 229940071127 thioglycolate Drugs 0.000 description 2
- CWERGRDVMFNCDR-UHFFFAOYSA-M thioglycolate(1-) Chemical compound [O-]C(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-M 0.000 description 2
- 150000007944 thiolates Chemical class 0.000 description 2
- 150000003606 tin compounds Chemical class 0.000 description 2
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 2
- 229910001887 tin oxide Inorganic materials 0.000 description 2
- 125000003944 tolyl group Chemical group 0.000 description 2
- QOQNJVLFFRMJTQ-UHFFFAOYSA-N trioctyl phosphite Chemical compound CCCCCCCCOP(OCCCCCCCC)OCCCCCCCC QOQNJVLFFRMJTQ-UHFFFAOYSA-N 0.000 description 2
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 2
- WGKLOLBTFWFKOD-UHFFFAOYSA-N tris(2-nonylphenyl) phosphite Chemical compound CCCCCCCCCC1=CC=CC=C1OP(OC=1C(=CC=CC=1)CCCCCCCCC)OC1=CC=CC=C1CCCCCCCCC WGKLOLBTFWFKOD-UHFFFAOYSA-N 0.000 description 2
- QEDNBHNWMHJNAB-UHFFFAOYSA-N tris(8-methylnonyl) phosphite Chemical compound CC(C)CCCCCCCOP(OCCCCCCCC(C)C)OCCCCCCCC(C)C QEDNBHNWMHJNAB-UHFFFAOYSA-N 0.000 description 2
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical compound NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 1
- ZBBLRPRYYSJUCZ-GRHBHMESSA-L (z)-but-2-enedioate;dibutyltin(2+) Chemical compound [O-]C(=O)\C=C/C([O-])=O.CCCC[Sn+2]CCCC ZBBLRPRYYSJUCZ-GRHBHMESSA-L 0.000 description 1
- VCMZIKKVYXGKCI-UHFFFAOYSA-N 1,1-bis(2,4-ditert-butyl-6-methylphenyl)-2,2-bis(hydroxymethyl)propane-1,3-diol dihydroxyphosphanyl dihydrogen phosphite Chemical compound OP(O)OP(O)O.C(C)(C)(C)C1=C(C(=CC(=C1)C(C)(C)C)C)C(O)(C(CO)(CO)CO)C1=C(C=C(C=C1C)C(C)(C)C)C(C)(C)C VCMZIKKVYXGKCI-UHFFFAOYSA-N 0.000 description 1
- QXRRAZIZHCWBQY-UHFFFAOYSA-N 1,1-bis(isocyanatomethyl)cyclohexane Chemical compound O=C=NCC1(CN=C=O)CCCCC1 QXRRAZIZHCWBQY-UHFFFAOYSA-N 0.000 description 1
- VNMOIBZLSJDQEO-UHFFFAOYSA-N 1,10-diisocyanatodecane Chemical compound O=C=NCCCCCCCCCCN=C=O VNMOIBZLSJDQEO-UHFFFAOYSA-N 0.000 description 1
- SSUJUUNLZQVZMO-UHFFFAOYSA-N 1,2,3,4,8,9,10,10a-octahydropyrimido[1,2-a]azepine Chemical compound C1CCC=CN2CCCNC21 SSUJUUNLZQVZMO-UHFFFAOYSA-N 0.000 description 1
- 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 1
- ZTNJGMFHJYGMDR-UHFFFAOYSA-N 1,2-diisocyanatoethane Chemical compound O=C=NCCN=C=O ZTNJGMFHJYGMDR-UHFFFAOYSA-N 0.000 description 1
- TYWNQLNRLUVYTH-UHFFFAOYSA-N 1,3,5-oxadiazinane-2,4,6-trione Chemical compound O=C1NC(=O)OC(=O)N1 TYWNQLNRLUVYTH-UHFFFAOYSA-N 0.000 description 1
- BLWNLYFYKIIZKR-UHFFFAOYSA-N 1,3,7,9-tetratert-butyl-11-(6-methylheptoxy)-5h-benzo[d][1,3,2]benzodioxaphosphocine Chemical compound C1C2=CC(C(C)(C)C)=CC(C(C)(C)C)=C2OP(OCCCCCC(C)C)OC2=C1C=C(C(C)(C)C)C=C2C(C)(C)C BLWNLYFYKIIZKR-UHFFFAOYSA-N 0.000 description 1
- MYMKXVFDVQUQLG-UHFFFAOYSA-N 1,3,7,9-tetratert-butyl-11-fluoro-5-methyl-5h-benzo[d][1,3,2]benzodioxaphosphocine Chemical compound CC1C2=CC(C(C)(C)C)=CC(C(C)(C)C)=C2OP(F)OC2=C1C=C(C(C)(C)C)C=C2C(C)(C)C MYMKXVFDVQUQLG-UHFFFAOYSA-N 0.000 description 1
- RTTZISZSHSCFRH-UHFFFAOYSA-N 1,3-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC(CN=C=O)=C1 RTTZISZSHSCFRH-UHFFFAOYSA-N 0.000 description 1
- XXNMTDJPGAIKPD-UHFFFAOYSA-N 1,3-diazetidin-2-one Chemical compound O=C1NCN1 XXNMTDJPGAIKPD-UHFFFAOYSA-N 0.000 description 1
- PCHXZXKMYCGVFA-UHFFFAOYSA-N 1,3-diazetidine-2,4-dione Chemical compound O=C1NC(=O)N1 PCHXZXKMYCGVFA-UHFFFAOYSA-N 0.000 description 1
- OHTRJOZKRSVAOX-UHFFFAOYSA-N 1,3-diisocyanato-2-methylcyclohexane Chemical compound CC1C(N=C=O)CCCC1N=C=O OHTRJOZKRSVAOX-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OVBFMUAFNIIQAL-UHFFFAOYSA-N 1,4-diisocyanatobutane Chemical compound O=C=NCCCCN=C=O OVBFMUAFNIIQAL-UHFFFAOYSA-N 0.000 description 1
- CDMDQYCEEKCBGR-UHFFFAOYSA-N 1,4-diisocyanatocyclohexane Chemical compound O=C=NC1CCC(N=C=O)CC1 CDMDQYCEEKCBGR-UHFFFAOYSA-N 0.000 description 1
- DFPJRUKWEPYFJT-UHFFFAOYSA-N 1,5-diisocyanatopentane Chemical compound O=C=NCCCCCN=C=O DFPJRUKWEPYFJT-UHFFFAOYSA-N 0.000 description 1
- 229940008841 1,6-hexamethylene diisocyanate Drugs 0.000 description 1
- ICLCCFKUSALICQ-UHFFFAOYSA-N 1-isocyanato-4-(4-isocyanato-3-methylphenyl)-2-methylbenzene Chemical group 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
- JEWLAPHZCZBXJS-UHFFFAOYSA-N 1-isocyanato-4-(4-isocyanato-3-phenylphenyl)-2-phenylbenzene Chemical group O=C=NC1=CC=C(C=2C=C(C(N=C=O)=CC=2)C=2C=CC=CC=2)C=C1C1=CC=CC=C1 JEWLAPHZCZBXJS-UHFFFAOYSA-N 0.000 description 1
- RQBUVIFBALZGPC-UHFFFAOYSA-N 1-isocyanato-4-(4-isocyanatophenyl)benzene Chemical group C1=CC(N=C=O)=CC=C1C1=CC=C(N=C=O)C=C1 RQBUVIFBALZGPC-UHFFFAOYSA-N 0.000 description 1
- AXFVIWBTKYFOCY-UHFFFAOYSA-N 1-n,1-n,3-n,3-n-tetramethylbutane-1,3-diamine Chemical compound CN(C)C(C)CCN(C)C AXFVIWBTKYFOCY-UHFFFAOYSA-N 0.000 description 1
- UUAIOYWXCDLHKT-UHFFFAOYSA-N 2,4,6-tricyclohexylphenol Chemical compound OC1=C(C2CCCCC2)C=C(C2CCCCC2)C=C1C1CCCCC1 UUAIOYWXCDLHKT-UHFFFAOYSA-N 0.000 description 1
- UESGEYFCYSJZSZ-UHFFFAOYSA-N 2,4,8,10-tetratert-butyl-6-hydroxybenzo[d][1,3,2]benzodioxaphosphepine Chemical compound O1P(O)OC2=C(C(C)(C)C)C=C(C(C)(C)C)C=C2C2=CC(C(C)(C)C)=CC(C(C)(C)C)=C21 UESGEYFCYSJZSZ-UHFFFAOYSA-N 0.000 description 1
- FRAQIHUDFAFXHT-UHFFFAOYSA-N 2,6-dicyclopentyl-4-methylphenol Chemical compound OC=1C(C2CCCC2)=CC(C)=CC=1C1CCCC1 FRAQIHUDFAFXHT-UHFFFAOYSA-N 0.000 description 1
- JBYWTKPHBLYYFJ-UHFFFAOYSA-N 2,6-ditert-butyl-4-(2-methylpropyl)phenol Chemical compound CC(C)CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 JBYWTKPHBLYYFJ-UHFFFAOYSA-N 0.000 description 1
- SCXYLTWTWUGEAA-UHFFFAOYSA-N 2,6-ditert-butyl-4-(methoxymethyl)phenol Chemical compound COCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SCXYLTWTWUGEAA-UHFFFAOYSA-N 0.000 description 1
- VQQLTEBUMLSLFJ-UHFFFAOYSA-N 2,6-ditert-butyl-4-nonylphenol Chemical compound CCCCCCCCCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 VQQLTEBUMLSLFJ-UHFFFAOYSA-N 0.000 description 1
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 1
- MMGVVYCBXBYXRR-UHFFFAOYSA-L 2-acetyl-3-oxobutanoate;dibutyltin(2+) Chemical compound CCCC[Sn+2]CCCC.CC(=O)C(C(C)=O)C([O-])=O.CC(=O)C(C(C)=O)C([O-])=O MMGVVYCBXBYXRR-UHFFFAOYSA-L 0.000 description 1
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- 239000012974 tin catalyst Substances 0.000 description 1
- DZXKSFDSPBRJPS-UHFFFAOYSA-N tin(2+);sulfide Chemical class [S-2].[Sn+2] DZXKSFDSPBRJPS-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
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- XTTGYFREQJCEML-UHFFFAOYSA-N tributyl phosphite Chemical compound CCCCOP(OCCCC)OCCCC XTTGYFREQJCEML-UHFFFAOYSA-N 0.000 description 1
- PWBHRVGYSMBMIO-UHFFFAOYSA-M tributylstannanylium;acetate Chemical compound CCCC[Sn](CCCC)(CCCC)OC(C)=O PWBHRVGYSMBMIO-UHFFFAOYSA-M 0.000 description 1
- LHHPEAQVCCPLBC-UHFFFAOYSA-N tributyltin;hydrate Chemical compound O.CCCC[Sn](CCCC)CCCC LHHPEAQVCCPLBC-UHFFFAOYSA-N 0.000 description 1
- IVIIAEVMQHEPAY-UHFFFAOYSA-N tridodecyl phosphite Chemical compound CCCCCCCCCCCCOP(OCCCCCCCCCCCC)OCCCCCCCCCCCC IVIIAEVMQHEPAY-UHFFFAOYSA-N 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- CNUJLMSKURPSHE-UHFFFAOYSA-N trioctadecyl phosphite Chemical compound CCCCCCCCCCCCCCCCCCOP(OCCCCCCCCCCCCCCCCCC)OCCCCCCCCCCCCCCCCCC CNUJLMSKURPSHE-UHFFFAOYSA-N 0.000 description 1
- XATCWUIVPWOLDP-UHFFFAOYSA-N trioctyl(trioctylstannyloxy)stannane Chemical compound CCCCCCCC[Sn](CCCCCCCC)(CCCCCCCC)O[Sn](CCCCCCCC)(CCCCCCCC)CCCCCCCC XATCWUIVPWOLDP-UHFFFAOYSA-N 0.000 description 1
- QYRVVCYHGWGULA-UHFFFAOYSA-N tris(1,3-dichloropropyl) phosphite Chemical compound ClCCC(Cl)OP(OC(Cl)CCCl)OC(Cl)CCCl QYRVVCYHGWGULA-UHFFFAOYSA-N 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
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- C08G18/792—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates
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Abstract
Description
a)一般式(I):O=C=N−Y−(N=C=O)n[式中、
Yは、イソシアネート官能基を除去した後のイソシアネート又はポリイソシアネートの残部であり、
nは、少なくとも1に等しい]を有する少なくとも1つのポリイソシアネートと、
b)少なくとも1つのモノフェノールアルキル化合物と、
c)全ホスファイトのモル数に対してモルで最大17%のトリアルキルホスファイトを含む、ホスファイト化合物の混合物と、
d)任意選択的に、少なくとも1つの架橋触媒と、
e)任意選択的に、1つ以上の添加剤と、を含む、組成物である。
Yは、芳香族、脂肪族、芳香脂肪族、複素環式又は脂環式基であり、
nは、少なくとも1に等しい]を有する。
97.9%〜99.98%の一般式(I)のポリイソシアネート、
0.01%〜1%、好ましくは0.01%〜0.5%のモノフェノールアルキル化合物、
0.01%及び1%のホスファイト化合物の混合物、
0%〜0.1%の架橋触媒。
a)一般式(I):O=C=N−Y−(N=C=O)n[式中、
Yは、イソシアネート官能基を除去した後のイソシアネート又はポリイソシアネートの残部であり、
nは、少なくとも1に等しい]を有する少なくとも1つのポリイソシアネートと、
b)少なくとも1つのモノフェノールアルキル化合物、
c)全ホスファイトのモルに対してモルで最大17%のトリアルキルホスファイトを含む、ホスファイト化合物の混合物、
d)任意選択的に、少なくとも1つの架橋触媒と、
e)任意選択的に、1つ以上の添加剤と、を含む、組成物である。
20〜98%、好ましくは20%〜90%、好ましくは70%〜30%、好ましくは40%〜60%の一般式(I)のポリイソシアネート
0.01%〜1%、好ましくは0.01%〜0.5%のモノフェノールアルキル化合物、
0.01%及び1%のホスファイト化合物の混合物、
0%〜0.05%、好ましくは0%〜0.1%の架橋触媒
9.98%〜77.9%、好ましくは20〜77.9%、好ましくは30%〜70%、好ましくは40%〜60%の添加剤。
実施例に記載される組成物を製造するために、異なる市販製品が使用される。
25℃で2400mPa.sに等しい粘度及び22.5%に等しいNCO力価を有する、Vencorex製のTolonate(登録商標)HDT
Irganox1135(登録商標):BASF製のベンゼンプロパン酸、分枝状3,5−ビス(1,1−ジメチル−エチル)4−ヒドロキシ−C7〜C9アルキルエステル
Doverphos6(登録商標)(Dov6):Dover製のトリイソデシルホスファイト
Doverphos7(登録商標)(Dov7):Dover製のフェニルジイソデシルホスファイト
Doverphos8(登録商標)(Dov8):Dover製のジフェニルイソデシルホスファイト
ADEKA135A(登録商標):Adeka Palmerole製のジフェニルイソデシルホスファイト
組成物A〜Iは、実施例1に記載の市販製品から以下のように調製される。
着色試験を行うために、異なるポリイソシアネート組成物を有するために、実施例2と同じ組成物を製造する。組成物A〜Iから、組成物1〜9を製造し、異なる生成物を125mlのバイアル瓶に添加して混合し、ポットローラー上に一晩放置して、これらの製造された新たな組成物を均質化する。
異なる組成物が沈殿したかどうかを確認するために、組成物A〜Iを、実施例3のように製造し、次いで50℃で7日間オーブン内に配置する。次いで、組成物A〜Iから組成物10〜18をオーブン内で製造し、異なる生成物を125mlのバイアル瓶に添加して混合し、ポットローラー上に一晩放置して、これらの製造された新たな組成物を均質化する。次いで、組成物10〜18を、HACH比濁度計の濁度測定管に移す。
Claims (12)
- a)一般式(I):O=C=N−Y−(N=C=O)n[式中、
Yは、イソシアネート官能基を除去した後のイソシアネート又はポリイソシアネートの残部であり、
nは、少なくとも1に等しい]を有する少なくとも1つのポリイソシアネートと、
b)少なくとも1つのモノフェノールアルキル化合物と、
c)全ホスファイトのモルに対してモルで最大17%のトリアルキルホスファイトを含む、ホスファイト化合物の混合物と、
d)任意選択的に、少なくとも1つの架橋触媒と、
e)任意選択的に、1つ以上の添加剤と、を含む、ポリイソシアネート組成物。 - 一般式(I)において、
Yが、6〜15個の炭素原子を含むアリール、5〜15員を含むヘテロアリール、2〜15個の炭素原子を含む直鎖若しくは分枝鎖アルキル、6〜15個の炭素原子を含む芳香脂肪族、3〜15員を含む複素環、又は3〜15個の炭素原子を含むシクロアルキルの基であり、優先的には、6〜12個の炭素原子を含むアリール、5〜12員を含むヘテロアリール、2〜12個の炭素原子を含む直鎖若しくは分枝鎖アルキル、6〜12個の炭素原子を含む芳香脂肪族、3〜12員を含む複素環、又は3〜12個の炭素原子を含むシクロアルキルの基であり、優先的には、6〜10個の炭素原子を含むアリール、5〜10員を含むヘテロアリール、4〜10個の炭素原子を含む直鎖若しくは分枝鎖アルキル、4〜10個の炭素原子を含む芳香脂肪族、4〜10員を含む複素環、又は4〜10個の炭素原子を含むシクロアルキルの基であり、
nが、少なくとも1に等しい、請求項1に記載の組成物。 - 前記モノフェノールアルキル化合物が、少なくとも1つのヒンダードフェノール又はヒンダードチオフェノール官能基を含む、請求項1又は2に記載の組成物。
- 前記トリアルキルホスファイトが、一般式(II):(R1O)3P[式中、各R1は、独立して、ハロゲンを含有する基によって任意選択的に置換されていてもよい1〜20個の炭素原子のアルキル基、又はハロゲンを含有する基によって任意選択的に置換されていてもよい5〜20個の炭素原子のアラルキル基を表す]に従う化合物である、請求項1〜3のいずれか一項に記載の組成物。
- 前記ホスファイト化合物の混合物が、全ホスファイトのモルに対してモルで最大15%のトリアルキルホスファイトを含む、請求項1〜4のいずれか一項に記載の組成物。
- 前記架橋触媒が、三級アミン、アミジン、有機金属化合物、又はこれらの混合物を含む、請求項1〜5のいずれか一項に記載の組成物。
- 添加される前記添加剤が、溶媒、抗凝集効果を有する化合物及び/又は湿度吸収剤である、請求項1〜6のいずれか一項に記載の組成物。
- 前記化合物が、以下の質量百分率:
97.9%〜99.98%の一般式(I)のポリイソシアネート
0.01%〜1%のモノフェノールアルキル化合物
0.01%及び1%のホスファイト化合物の混合物
0%〜0.1%の架橋触媒
で存在する、請求項1〜7のいずれか一項に記載の組成物。 - 前記化合物が、以下の質量百分率:
20%〜90%の一般式(I)のポリイソシアネート
0.01%〜1%のモノフェノールアルキル化合物
0.01%及び1%のホスファイト化合物の混合物
0%〜0.1%の架橋触媒
9.98%〜77.9%の添加剤
で存在する、請求項8に記載の組成物。 - 請求項1〜9のいずれか一項に記載の組成物の調製方法であって、以下の化合物:
a)一般式(I):O=C=N−Y−(N=C=O)n[式中、
Yは、6〜15個の炭素原子を含むアリール、5〜15員を含むヘテロアリール、2〜15個の炭素原子を含む直鎖若しくは分枝鎖アルキル、6〜15個の炭素原子を含む芳香脂肪族、3〜15員を含む複素環、又は3〜15個の炭素原子を含むシクロアルキルの基であり、優先的には、6〜12個の炭素原子を含むアリール、5〜12員を含むヘテロアリール、2〜12個の炭素原子を含む直鎖若しくは分枝鎖アルキル、6〜12個の炭素原子を含む芳香脂肪族、3〜12員を含む複素環、又は3〜12個の炭素原子を含むシクロアルキルの基であり、好ましくは、6〜10個の炭素原子を含むアリール、5〜10員を含むヘテロアリール、4〜10個の炭素原子を含む直鎖若しくは分枝鎖アルキル、4〜10個の炭素原子を含む芳香脂肪族、4〜10員を含む複素環、又は4〜10個の炭素原子を含むシクロアルキルの基であり、
nは、少なくとも1に等しい]を有する少なくとも1つのポリイソシアネート、
b)少なくとも1つのモノフェノールアルキル化合物、
c)全ホスファイトのモル数に対してモルで最大17%のトリアルキルホスファイトを含む、ホスファイト化合物の混合物、
d)任意選択的に、少なくとも1つの架橋触媒、及び
e)任意選択的に、1つ以上の添加剤、
が任意の順序で混合される、方法。 - コーティング、接着剤、又は塗料を製造するための、請求項1〜10のいずれか一項に記載の組成物の使用。
- 請求項1〜10のいずれか一項に記載の組成物の実装を含むコーティング、接着剤、又は塗料の製造方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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FR1851926 | 2018-03-06 | ||
FR1851926A FR3078707B1 (fr) | 2018-03-06 | 2018-03-06 | Composition de polyisocyanates |
PCT/EP2019/055446 WO2019170674A1 (fr) | 2018-03-06 | 2019-03-05 | Nouvelles compositions de polyisocyanates |
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JP2021517596A true JP2021517596A (ja) | 2021-07-26 |
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ID=62067726
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JP2020546466A Pending JP2021517596A (ja) | 2018-03-06 | 2019-03-05 | 新しいポリイソシアネート組成物 |
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US (1) | US11667768B2 (ja) |
EP (1) | EP3762452A1 (ja) |
JP (1) | JP2021517596A (ja) |
KR (1) | KR102615930B1 (ja) |
CN (1) | CN111868156A (ja) |
BR (1) | BR112020018071A2 (ja) |
CA (1) | CA3093088A1 (ja) |
FR (1) | FR3078707B1 (ja) |
MX (1) | MX2020009227A (ja) |
RU (1) | RU2020130914A (ja) |
WO (1) | WO2019170674A1 (ja) |
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EP4263648A1 (en) * | 2020-12-18 | 2023-10-25 | Basf Se | Color-stable curing agent compositions comprising polyisocyanates of (cyclo)aliphatic diisocyanates |
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- 2019-03-05 RU RU2020130914A patent/RU2020130914A/ru unknown
- 2019-03-05 CN CN201980017519.1A patent/CN111868156A/zh active Pending
- 2019-03-05 JP JP2020546466A patent/JP2021517596A/ja active Pending
- 2019-03-05 WO PCT/EP2019/055446 patent/WO2019170674A1/fr unknown
- 2019-03-05 MX MX2020009227A patent/MX2020009227A/es unknown
- 2019-03-05 KR KR1020207026550A patent/KR102615930B1/ko active IP Right Grant
- 2019-03-05 CA CA3093088A patent/CA3093088A1/en active Pending
- 2019-03-05 BR BR112020018071-8A patent/BR112020018071A2/pt unknown
- 2019-03-05 EP EP19707825.6A patent/EP3762452A1/fr active Pending
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Also Published As
Publication number | Publication date |
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FR3078707A1 (fr) | 2019-09-13 |
CA3093088A1 (en) | 2019-09-12 |
RU2020130914A (ru) | 2022-03-21 |
BR112020018071A2 (pt) | 2020-12-22 |
CN111868156A (zh) | 2020-10-30 |
FR3078707B1 (fr) | 2020-12-25 |
EP3762452A1 (fr) | 2021-01-13 |
US11667768B2 (en) | 2023-06-06 |
MX2020009227A (es) | 2021-01-08 |
KR102615930B1 (ko) | 2023-12-19 |
US20200399439A1 (en) | 2020-12-24 |
WO2019170674A1 (fr) | 2019-09-12 |
KR20210002460A (ko) | 2021-01-08 |
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