CN1484660A - 异氰酸酯的缩合催化剂,包括该催化剂的组合物,使用方法,和所得组合物 - Google Patents
异氰酸酯的缩合催化剂,包括该催化剂的组合物,使用方法,和所得组合物 Download PDFInfo
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- CN1484660A CN1484660A CNA018215599A CN01821559A CN1484660A CN 1484660 A CN1484660 A CN 1484660A CN A018215599 A CNA018215599 A CN A018215599A CN 01821559 A CN01821559 A CN 01821559A CN 1484660 A CN1484660 A CN 1484660A
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- Prior art keywords
- advantageously
- isocyanate
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- 239000012948 isocyanate Substances 0.000 title claims abstract description 91
- 239000003054 catalyst Substances 0.000 title claims abstract description 79
- 150000002513 isocyanates Chemical class 0.000 title claims abstract description 73
- 238000000034 method Methods 0.000 title claims abstract description 36
- 238000009833 condensation Methods 0.000 title claims abstract description 25
- 230000005494 condensation Effects 0.000 title claims abstract description 25
- 239000000203 mixture Substances 0.000 title claims description 67
- 150000001875 compounds Chemical class 0.000 claims abstract description 112
- 239000000178 monomer Substances 0.000 claims abstract description 76
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims abstract description 65
- 238000006243 chemical reaction Methods 0.000 claims abstract description 58
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 51
- 150000003839 salts Chemical class 0.000 claims abstract description 50
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 45
- 229910052710 silicon Inorganic materials 0.000 claims abstract description 29
- 125000004429 atom Chemical group 0.000 claims abstract description 27
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 25
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 25
- 239000010703 silicon Substances 0.000 claims abstract description 10
- 230000003197 catalytic effect Effects 0.000 claims abstract description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 6
- 239000002243 precursor Substances 0.000 claims abstract description 6
- 238000006482 condensation reaction Methods 0.000 claims abstract description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 4
- -1 salt compound Chemical class 0.000 claims description 89
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 50
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical group CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 39
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 38
- 238000005829 trimerization reaction Methods 0.000 claims description 35
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 claims description 34
- 229910052799 carbon Inorganic materials 0.000 claims description 32
- 150000001768 cations Chemical class 0.000 claims description 30
- 230000008569 process Effects 0.000 claims description 29
- 239000000047 product Substances 0.000 claims description 29
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 26
- 229910052760 oxygen Inorganic materials 0.000 claims description 26
- 125000003118 aryl group Chemical group 0.000 claims description 25
- 125000001931 aliphatic group Chemical group 0.000 claims description 23
- 125000005843 halogen group Chemical group 0.000 claims description 18
- 229910052751 metal Inorganic materials 0.000 claims description 17
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 16
- 125000004185 ester group Chemical group 0.000 claims description 16
- RADWEERUPCRDRI-UHFFFAOYSA-N 4-amino-1h-1,3-diazet-2-one Chemical class N=C1NC(=O)N1 RADWEERUPCRDRI-UHFFFAOYSA-N 0.000 claims description 15
- 239000002184 metal Substances 0.000 claims description 15
- 229910052717 sulfur Inorganic materials 0.000 claims description 15
- 150000001450 anions Chemical class 0.000 claims description 11
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 11
- 229920006395 saturated elastomer Polymers 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 150000000917 Erbium Chemical class 0.000 claims description 9
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical class [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 9
- YSKUZVBSHIWEFK-UHFFFAOYSA-N ammelide Chemical compound NC1=NC(O)=NC(O)=N1 YSKUZVBSHIWEFK-UHFFFAOYSA-N 0.000 claims description 9
- 150000002430 hydrocarbons Chemical class 0.000 claims description 9
- UYAHIZSMUZPPFV-UHFFFAOYSA-N erbium Chemical compound [Er] UYAHIZSMUZPPFV-UHFFFAOYSA-N 0.000 claims description 8
- 125000000524 functional group Chemical group 0.000 claims description 8
- IUTCEZPPWBHGIX-UHFFFAOYSA-N tin(2+) Chemical compound [Sn+2] IUTCEZPPWBHGIX-UHFFFAOYSA-N 0.000 claims description 8
- 229910052691 Erbium Inorganic materials 0.000 claims description 7
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 7
- 150000001449 anionic compounds Chemical class 0.000 claims description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- HIMXYMYMHUAZLW-UHFFFAOYSA-N [[[dimethyl(phenyl)silyl]amino]-dimethylsilyl]benzene Chemical compound C=1C=CC=CC=1[Si](C)(C)N[Si](C)(C)C1=CC=CC=C1 HIMXYMYMHUAZLW-UHFFFAOYSA-N 0.000 claims description 6
- WYUIWUCVZCRTRH-UHFFFAOYSA-N [[[ethenyl(dimethyl)silyl]amino]-dimethylsilyl]ethene Chemical compound C=C[Si](C)(C)N[Si](C)(C)C=C WYUIWUCVZCRTRH-UHFFFAOYSA-N 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 6
- 230000000903 blocking effect Effects 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
- 230000003647 oxidation Effects 0.000 claims description 6
- 238000007254 oxidation reaction Methods 0.000 claims description 6
- 229910052761 rare earth metal Inorganic materials 0.000 claims description 6
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 6
- MHRNQQUEUYMEEH-UHFFFAOYSA-N [[[ethyl(dimethyl)silyl]amino]-dimethylsilyl]ethane Chemical compound CC[Si](C)(C)N[Si](C)(C)CC MHRNQQUEUYMEEH-UHFFFAOYSA-N 0.000 claims description 5
- 125000005442 diisocyanate group Chemical group 0.000 claims description 5
- 229910052747 lanthanoid Inorganic materials 0.000 claims description 5
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 150000002910 rare earth metals Chemical class 0.000 claims description 5
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 5
- WGGNJZRNHUJNEM-UHFFFAOYSA-N 2,2,4,4,6,6-hexamethyl-1,3,5,2,4,6-triazatrisilinane Chemical compound C[Si]1(C)N[Si](C)(C)N[Si](C)(C)N1 WGGNJZRNHUJNEM-UHFFFAOYSA-N 0.000 claims description 4
- 125000000129 anionic group Chemical group 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 150000002602 lanthanoids Chemical class 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- KDZDCBUTQIVSGK-UHFFFAOYSA-N C(C)[Si](N[Si](CC)(CC)CC)(CC)CC.C(C)[Si](N[Si](CC)(CC)CC)(CC)CC Chemical compound C(C)[Si](N[Si](CC)(CC)CC)(CC)CC.C(C)[Si](N[Si](CC)(CC)CC)(CC)CC KDZDCBUTQIVSGK-UHFFFAOYSA-N 0.000 claims description 3
- APDDLLVYBXGBRF-UHFFFAOYSA-N [diethyl-(triethylsilylamino)silyl]ethane Chemical compound CC[Si](CC)(CC)N[Si](CC)(CC)CC APDDLLVYBXGBRF-UHFFFAOYSA-N 0.000 claims description 3
- 239000000853 adhesive Substances 0.000 claims description 3
- 230000001070 adhesive effect Effects 0.000 claims description 3
- 150000001721 carbon Chemical group 0.000 claims description 3
- 238000000576 coating method Methods 0.000 claims description 3
- VURPSIJHXNVCNZ-UHFFFAOYSA-N isocyanic acid;urea Chemical compound N=C=O.NC(N)=O VURPSIJHXNVCNZ-UHFFFAOYSA-N 0.000 claims description 3
- 229910052744 lithium Inorganic materials 0.000 claims description 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 3
- 239000003973 paint Substances 0.000 claims description 3
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- 239000002966 varnish Substances 0.000 claims description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 2
- 229910021626 Tin(II) chloride Inorganic materials 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 239000003139 biocide Substances 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims description 2
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 239000003599 detergent Substances 0.000 claims description 2
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 claims description 2
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 2
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 2
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 125000005347 halocycloalkyl group Chemical group 0.000 claims description 2
- 150000002466 imines Chemical class 0.000 claims description 2
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 2
- 239000000976 ink Substances 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 229910052746 lanthanum Inorganic materials 0.000 claims description 2
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 claims description 2
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 2
- 229910052749 magnesium Inorganic materials 0.000 claims description 2
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 2
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 229910052723 transition metal Inorganic materials 0.000 claims description 2
- 150000003624 transition metals Chemical class 0.000 claims description 2
- WVMSIBFANXCZKT-UHFFFAOYSA-N triethyl(hydroxy)silane Chemical compound CC[Si](O)(CC)CC WVMSIBFANXCZKT-UHFFFAOYSA-N 0.000 claims description 2
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims description 2
- 229920002554 vinyl polymer Polymers 0.000 claims description 2
- 125000005023 xylyl group Chemical group 0.000 claims description 2
- 239000011248 coating agent Substances 0.000 claims 1
- AXCGWVYNDXPANP-UHFFFAOYSA-N ethyl-hydroxy-dimethylsilane Chemical compound CC[Si](C)(C)O AXCGWVYNDXPANP-UHFFFAOYSA-N 0.000 claims 1
- 125000003106 haloaryl group Chemical group 0.000 claims 1
- 230000000737 periodic effect Effects 0.000 abstract description 5
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 1
- 239000011707 mineral Substances 0.000 abstract 1
- 230000009466 transformation Effects 0.000 abstract 1
- 239000013638 trimer Substances 0.000 description 69
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 24
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 24
- 239000012429 reaction media Substances 0.000 description 24
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 238000004458 analytical method Methods 0.000 description 17
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 14
- 239000007788 liquid Substances 0.000 description 14
- 239000002253 acid Substances 0.000 description 12
- 238000004519 manufacturing process Methods 0.000 description 12
- JYFHYPJRHGVZDY-UHFFFAOYSA-N Dibutyl phosphate Chemical compound CCCCOP(O)(=O)OCCCC JYFHYPJRHGVZDY-UHFFFAOYSA-N 0.000 description 11
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 10
- 230000000694 effects Effects 0.000 description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 239000002981 blocking agent Substances 0.000 description 8
- 229920000642 polymer Polymers 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 238000001228 spectrum Methods 0.000 description 8
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- 238000006068 polycondensation reaction Methods 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- 239000001257 hydrogen Substances 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 239000003446 ligand Substances 0.000 description 6
- 239000005056 polyisocyanate Substances 0.000 description 6
- 229920001228 polyisocyanate Polymers 0.000 description 6
- 150000003746 yttrium Chemical class 0.000 description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 5
- 230000008901 benefit Effects 0.000 description 5
- 239000004202 carbamide Substances 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 239000000539 dimer Substances 0.000 description 4
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical group OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- XMKLTEGSALONPH-UHFFFAOYSA-N 1,2,4,5-tetrazinane-3,6-dione Chemical compound O=C1NNC(=O)NN1 XMKLTEGSALONPH-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 229910052772 Samarium Inorganic materials 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
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- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- NMGFRGWSRHOQOP-UHFFFAOYSA-N carbamic acid;urea Chemical class NC(N)=O.NC(O)=O NMGFRGWSRHOQOP-UHFFFAOYSA-N 0.000 description 3
- 150000001767 cationic compounds Chemical class 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 238000006006 cyclotrimerization reaction Methods 0.000 description 3
- 238000002845 discoloration Methods 0.000 description 3
- 238000010494 dissociation reaction Methods 0.000 description 3
- 230000005593 dissociations Effects 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 150000002892 organic cations Chemical class 0.000 description 3
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 3
- 239000013589 supplement Substances 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
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- 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
- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
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- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
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- 239000002585 base Substances 0.000 description 2
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- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
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- 229910001411 inorganic cation Inorganic materials 0.000 description 2
- 150000003951 lactams Chemical class 0.000 description 2
- 229910003002 lithium salt Inorganic materials 0.000 description 2
- 159000000002 lithium salts Chemical class 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 238000006384 oligomerization reaction Methods 0.000 description 2
- 235000021317 phosphate Nutrition 0.000 description 2
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- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 2
- 238000004445 quantitative analysis Methods 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
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- 125000005207 tetraalkylammonium group Chemical group 0.000 description 2
- 125000005497 tetraalkylphosphonium group Chemical group 0.000 description 2
- AATYKEFFPLPLST-UHFFFAOYSA-N trimethylsilylurea Chemical compound C[Si](C)(C)NC(N)=O AATYKEFFPLPLST-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 2
- ZXHZWRZAWJVPIC-UHFFFAOYSA-N 1,2-diisocyanatonaphthalene Chemical compound C1=CC=CC2=C(N=C=O)C(N=C=O)=CC=C21 ZXHZWRZAWJVPIC-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
- 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 1
- MKZPMOFOBNHBSL-UHFFFAOYSA-N 1-isocyanato-1-methylcyclohexane Chemical compound O=C=NC1(C)CCCCC1 MKZPMOFOBNHBSL-UHFFFAOYSA-N 0.000 description 1
- USXSCBCCYNVIPN-UHFFFAOYSA-N 1-isocyanato-2,2-dimethylpropane Chemical group CC(C)(C)CN=C=O USXSCBCCYNVIPN-UHFFFAOYSA-N 0.000 description 1
- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical class C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 description 1
- 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 1
- SSPYSWLZOPCOLO-UHFFFAOYSA-N 6-azauracil Chemical compound O=C1C=NNC(=O)N1 SSPYSWLZOPCOLO-UHFFFAOYSA-N 0.000 description 1
- RREANTFLPGEWEN-MBLPBCRHSA-N 7-[4-[[(3z)-3-[4-amino-5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidin-2-yl]imino-5-fluoro-2-oxoindol-1-yl]methyl]piperazin-1-yl]-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(\N=C/3C4=CC(F)=CC=C4N(CN4CCN(CC4)C=4C(=CC=5C(=O)C(C(O)=O)=CN(C=5C=4)C4CC4)F)C\3=O)=NC=2)N)=C1 RREANTFLPGEWEN-MBLPBCRHSA-N 0.000 description 1
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 1
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
- GXGJIOMUZAGVEH-UHFFFAOYSA-N Chamazulene Chemical group CCC1=CC=C(C)C2=CC=C(C)C2=C1 GXGJIOMUZAGVEH-UHFFFAOYSA-N 0.000 description 1
- 239000005046 Chlorosilane Substances 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-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
- 239000002841 Lewis acid Substances 0.000 description 1
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 1
- NAUBYZNGDGDCHH-UHFFFAOYSA-N N=C=O.N=C=O.CCCC(C)C Chemical compound N=C=O.N=C=O.CCCC(C)C NAUBYZNGDGDCHH-UHFFFAOYSA-N 0.000 description 1
- 229910018954 NaNH2 Inorganic materials 0.000 description 1
- 229910052779 Neodymium Inorganic materials 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 150000001216 Samarium Chemical class 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- VYGUBTIWNBFFMQ-UHFFFAOYSA-N [N+](#[C-])N1C(=O)NC=2NC(=O)NC2C1=O Chemical group [N+](#[C-])N1C(=O)NC=2NC(=O)NC2C1=O VYGUBTIWNBFFMQ-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001341 alkaline earth metal compounds Chemical class 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- KXDAEFPNCMNJSK-UHFFFAOYSA-M benzenecarboximidate Chemical compound [NH-]C(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-M 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- JGCWKVKYRNXTMD-UHFFFAOYSA-N bicyclo[2.2.1]heptane;isocyanic acid Chemical compound N=C=O.N=C=O.C1CC2CCC1C2 JGCWKVKYRNXTMD-UHFFFAOYSA-N 0.000 description 1
- AUCYFJHDJZKXFM-UHFFFAOYSA-N butane-2,3-dione;urea Chemical compound NC(N)=O.CC(=O)C(C)=O AUCYFJHDJZKXFM-UHFFFAOYSA-N 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical class Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000006352 cycloaddition reaction Methods 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- SEGLCEQVOFDUPX-UHFFFAOYSA-N di-(2-ethylhexyl)phosphoric acid Chemical compound CCCCC(CC)COP(O)(=O)OCC(CC)CCCC SEGLCEQVOFDUPX-UHFFFAOYSA-N 0.000 description 1
- RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 description 1
- WCRDXYSYPCEIAK-UHFFFAOYSA-N dibutylstannane Chemical compound CCCC[SnH2]CCCC WCRDXYSYPCEIAK-UHFFFAOYSA-N 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- HDGGAKOVUDZYES-UHFFFAOYSA-K erbium(iii) chloride Chemical compound Cl[Er](Cl)Cl HDGGAKOVUDZYES-UHFFFAOYSA-K 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 150000002222 fluorine compounds Chemical class 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 238000000265 homogenisation Methods 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 150000002443 hydroxylamines Chemical class 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 125000002632 imidazolidinyl group Chemical group 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- DUDXQIXWPJMPRQ-UHFFFAOYSA-N isocyanatomethylcyclohexane Chemical compound O=C=NCC1CCCCC1 DUDXQIXWPJMPRQ-UHFFFAOYSA-N 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 1
- OXOZHAWWRPCVGL-UHFFFAOYSA-N lithium;trimethyl(oxido)silane Chemical compound [Li+].C[Si](C)(C)[O-] OXOZHAWWRPCVGL-UHFFFAOYSA-N 0.000 description 1
- 150000002690 malonic acid derivatives Chemical class 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- WHIVNJATOVLWBW-UHFFFAOYSA-N n-butan-2-ylidenehydroxylamine Chemical compound CCC(C)=NO WHIVNJATOVLWBW-UHFFFAOYSA-N 0.000 description 1
- QEFYFXOXNSNQGX-UHFFFAOYSA-N neodymium atom Chemical compound [Nd] QEFYFXOXNSNQGX-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 150000003961 organosilicon compounds Chemical class 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-O oxonium Chemical compound [OH3+] XLYOFNOQVPJJNP-UHFFFAOYSA-O 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000003009 phosphonic acids Chemical class 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- IUBQJLUDMLPAGT-UHFFFAOYSA-N potassium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([K])[Si](C)(C)C IUBQJLUDMLPAGT-UHFFFAOYSA-N 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 125000003072 pyrazolidinyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229910052706 scandium Inorganic materials 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical class [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000011593 sulfur Chemical group 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical group S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 150000005621 tetraalkylammonium salts Chemical class 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 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
- 125000001425 triazolyl group Chemical group 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- XGCPRKZQVACHIU-UHFFFAOYSA-N urea Chemical compound NC(N)=O.NC(N)=O.NC(N)=O XGCPRKZQVACHIU-UHFFFAOYSA-N 0.000 description 1
- AVWRKZWQTYIKIY-UHFFFAOYSA-M urea-1-carboxylate Chemical compound NC(=O)NC([O-])=O AVWRKZWQTYIKIY-UHFFFAOYSA-M 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/40—Nitrogen atoms
- C07D251/42—One nitrogen atom
- C07D251/46—One nitrogen atom with oxygen or sulfur atoms attached to the two other ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D229/00—Heterocyclic compounds containing rings of less than five members having two nitrogen atoms as the only ring hetero atoms
-
- 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
- C08G18/02—Polymeric products of isocyanates or isothiocyanates of isocyanates or isothiocyanates only
-
- 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
- C08G18/09—Processes comprising oligomerisation of isocyanates or isothiocyanates involving reaction of a part of the isocyanate or isothiocyanate groups with each other in the reaction mixture
-
- 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
- C08G18/16—Catalysts
- C08G18/22—Catalysts containing metal compounds
- C08G18/24—Catalysts containing metal compounds of tin
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Polyurethanes Or Polyureas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
产物/组分 | 实施例1 | 实施例2 | 实施例3 | 实施例4 | 实施例5 | 实施例6 | 实施例7 | 实施例8 | 实施例9 |
IPDI(%) | 39.3 | 91.5 | 53.0 | 45.4 | 49.1 | 67.8 | 73.7 | - | 28.0 |
HDI | 76.4 | ||||||||
催化剂(1) | K,HMDZ(0.1) | K,HMDZ(0.04) | K,HMDZ(0.04) | K,HMDZ(0.03) | K,HMDZ(0.03) | Li.GMIDZ(0.5) | Li,HMDZ(0.4) | K,HMIDZ(0.04) | Li8(Me)3SiO(5) |
温度 | 60℃ | 60℃ | 60℃ | 120℃ | 150℃ | 60℃ | 60℃ | 90℃ | 60℃ |
氩气喷射 | 无 | 无 | 有 | 有 | 有 | 无 | 无 | 有 | 无 |
三聚体+二聚体(%) | 33.1 | 5.6 | 27.7 | 33.9 | 33.8 | 20.1 | 16.4 | - | 37.9 |
双-三聚体(%) | 15.9 | 2.1 | 12.4 | 13.7 | 11.8 | 8.6 | 7.0 | - | 20.9 |
重质产物(三-三聚体)(%) | 11.7 | 0.8 | 6.9 | 7.0 | 5.2 | 3.5 | 2.9 | - | 13.2 |
产物/组分 | 相对于异氰酸酯重量的wt% |
IPDI(%) | 76.8% |
IPDI三甲基甲硅烷基脲 | 2.0% |
真二聚体(单脲丁啶二酮) | 痕量 |
未确认的脲或二脲 | |
三聚体(+氮尿嘧啶+缩二脲) | 15.9% |
重质产物 | 5.4% |
产物/组分 | 相对于异氰酸酯重量的wt% |
IPDI(%) | 74.5% |
IPDI三甲基甲硅烷基脲 | 4.7%* |
IUT** | 16.3% |
双-IUT | 4.3% |
催化剂 | 质量% | 溶剂 | 粗产物的外观 | 所发现的三聚体谱带,cm-1 |
Y(N(SiMe3)2)3 | 1% | 无 | 灰白色膏状物和不透明固体 | 16901464.5 |
Y(N(SiMe3)2)3 | 1% | 有 | 灰白色膏状物 | 16861466.5 |
金属中心 | RM的外观 | 三聚体谱带,cm-1 | 所存在的实体(GPC/FTIR分析) | ||||
Y | 灰白色膏状物 | 16861466.5 | 重质产物 | 三-三聚体 | 双-三聚体 | 三聚体 | HDI |
Nd | 灰白色膏状物 | 1689.51463.5 | 重质产物 | 三-三聚体 | 双-三聚体 | 三聚体 | HDI |
Sm | 黄色膏状物 | 16891463.5 | 重质产物 | 三-三聚体 | 双-三聚体 | 三聚体 | HDI |
催化剂质量% | RM的外观 | 三聚体谱带,cm-1 | 所存在的实体和它们的量(GPC/FTIR分析) | DC | ||||
1% | 灰白色膏状物 | 16861466.5 | 重质产物 | 三-三聚体 | 双-三聚体 | 三聚体 | HDI | |
0.2% | 黄色粘性液体 | 1686.51465 | 重质产物1.2% | 三-三聚体0.9% | 双-三聚体2.9% | 三聚体+缩二脲12.3% | HDI40.5% | Ov:31%T+B:21% |
0.1% | 黄色粘性液体 | 16861460 | 双-三聚体0.7% | 三聚体+缩二脲6.3% | HDI83.3% | 0v:8%T+B:7% |
T.℃ | RM的外观 | 三聚体谱带,cm-1 | 所存在的实体和它们的量(GPC/FTIR分析) | DC | ||||
60 | 黄色粘性液体 | 1686.51465 | 双-三聚体0.7% | 三聚体+缩二脲6.3% | HDI83.3% | Ov:8%T+B:7% | ||
100 | 黄色粘性液体 | 16891464.5 | 重质产物0.8% | 聚体0.4% | 双-三聚体2.1% | 三聚体13% | HDI64.3% | 0v:25%T:20% |
催化剂 | 质量% | 粗产物的外观 | 所发现的三聚体谱带,cm-1 |
Sm(Siam)3PhCN | 1% | 不透明膏状物 | 1688.51464 |
NaSiam | 1% | 不透明固体 | 16861465.5 |
LiSiam | 1% | 不透明固体 | 16891465 |
金属中心 | RM的外观 | 三聚体谱带,cm-1 | 所存在的实体(GPC/FTIR分析) | ||||
Sm | 不透明膏状物 | 1688.51464 | 重质产物 | 三-三聚体 | 双-三聚体 | 三聚体 | HDI |
Yb | 不透明膏状物 | 1688.51463 | 重质产物 | 三-三聚体 | 双-三聚体 | 三聚体 | HDI |
Y | 灰白色膏状物 | 1688.51463 | 重质产物 | 三-三聚体 | 双-三聚体 | 三聚体 | HDI |
催化剂质量% | RM的外观 | 三聚体谱带,cm-1 | 所存在的实体和它们的量(GPC/FTIR分析) | DC | ||||
1% | 灰白色膏状物 | 1688.51463 | 重质产物 | 聚体 | 双-三聚体 | 三聚体 | HDI | |
0.2% | 黄色粘性液体 | 16861460 | 重质产物2.7% | 聚体1.7% | 双-三聚体4.3% | 三聚体+缩二脲13.4% | HDI41.3% | 0v:35%T+B:21% |
催化剂 | RM的外观 | 三聚体谱带,cm-1 | 所存在的实体和它们的量(GPC/FTIR分析) | ||||
Y(N(SiMe3)2)3(1质量%) | 淡黄色液体 | 不非常明显 | 重质产物 | 缩二脲-三聚体 | 脲 | 氨基甲酸酯 | IPDI |
NaN(SiMe3)2(1质量%) | 淡黄色膏状物 | 16921446.5 | 重质产物 | 三-三聚体 | 双-三聚体 | 三聚体 | IPDI |
金属中心 | RM的外观 | 三聚体谱带,cm-1 | 所存在的实体和它们的量(GPC/FTIR分析) | DC | |||
Y | 淡黄色不太粘的液体 | 弱 | 三聚体+缩二脲 | 脲 | 氨基甲酸酯 | IPDI | |
Sm | 淡黄色不太粘的液体 | 弱 | 三聚体+缩二脲1.5% | 脲4.3% | 二聚体0.4% | IPDI76% | Ov:0.1% |
T,℃ | RM的外观 | 三聚体谱带,cm-1 | 所存在的实体和它们的量(GPC/FTIR分析) | DC | |||
60 | 黄色不太粘的液体 | 弱 | 缩二脲+三聚体 | 脲 | 氨基甲酸酯 | IPDI | |
100 | 黄色不太粘的液体 | 有 | 缩二脲+三聚体2.2% | 脲5% | 氨基甲酸酯 | IPDI53% | 0v:14%T+B:4% |
催化剂 | 质量% | 粗产物的外观 | 所发现的三聚体谱带,cm-1 |
Sm(Siam)3PhCN | 1% | 黄色不太粘的液体 | 不显著 |
NaSiam | 1% | 黄色膏状物 | 16901445 |
质量% | RM的外观 | 所存在的实体(GPC/FTIR分析) | |||
1% | 黄色不太粘的液体 | 缩二脲 | 脲 | 氨基甲酸酯 | IPDI |
5% | 淡黄色不太粘的液体 | 缩二脲+三聚体 | 脲 | 氨基甲酸酯 | IPDI |
Claims (42)
Applications Claiming Priority (8)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR00/17315 | 2000-12-29 | ||
FR0017323A FR2818976B1 (fr) | 2000-12-29 | 2000-12-29 | Procede de (cyclo) condensation au moyen d'un sel de silazane d'erbium |
FR0017317A FR2818975B1 (fr) | 2000-12-29 | 2000-12-29 | Nouveau procede de (cyclo) condensation, notamment de (cyclo) trimerisation catalytique d'isocyanates |
FR00/17317 | 2000-12-29 | ||
FR0017315A FR2818973B1 (fr) | 2000-12-29 | 2000-12-29 | Nouveau procede de (cyclo) condensation d'isocyanates au moyen d'un sel de silazane d'etain |
FR00/17323 | 2000-12-29 | ||
FR0116723A FR2833864A1 (fr) | 2001-12-21 | 2001-12-21 | Catalyseur de condensation pour isocyanate, composition en contenant, procede d'utilisation, et compositions obtenues |
FR01/16723 | 2001-12-21 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1484660A true CN1484660A (zh) | 2004-03-24 |
CN1215100C CN1215100C (zh) | 2005-08-17 |
Family
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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CNB018215599A Expired - Fee Related CN1215100C (zh) | 2000-12-29 | 2001-12-28 | 异氰酸酯的缩合催化剂,包括该催化剂的组合物,使用方法,和所得组合物 |
Country Status (8)
Country | Link |
---|---|
US (1) | US6946538B2 (zh) |
EP (1) | EP1358238B1 (zh) |
CN (1) | CN1215100C (zh) |
AT (1) | ATE463522T1 (zh) |
BR (1) | BR0116559A (zh) |
CA (1) | CA2432960A1 (zh) |
DE (1) | DE60141771D1 (zh) |
WO (1) | WO2002053614A1 (zh) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN109071762A (zh) * | 2015-04-21 | 2018-12-21 | 科思创德国股份有限公司 | 包含硅氧烷基团的聚异氰脲酸酯塑料及其制造方法 |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2818974B1 (fr) * | 2000-12-29 | 2003-10-24 | Rhodia Chimie Sa | (cyclo) condensation de composes isocyanates |
CN107531876B (zh) * | 2015-04-21 | 2021-02-09 | 科思创德国股份有限公司 | 具有高热稳定性的聚异氰脲酸酯塑料 |
EP3715396A1 (de) * | 2019-03-26 | 2020-09-30 | PolyU GmbH | Zusammensetzung und verfahren zur herstellung silylierter polymere und deren verwendung |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4003859A (en) * | 1974-01-30 | 1977-01-18 | The Upjohn Company | Novel process for trimerizing polyisocyanates |
FR2572402B1 (fr) * | 1984-10-30 | 1988-03-11 | Rhone Poulenc Spec Chim | Procede de preparation de polyisocyanates polyisocyanurates par cyclotrimerisation catalytique de polyisocyanates |
GB2203159B (en) * | 1987-04-03 | 1990-12-12 | Asahi Chemical Ind | An isocyanurate polyisocyanate and its use as a curing agent for a two-component polyurethane composition |
US5017695A (en) * | 1987-12-03 | 1991-05-21 | Rhone-Poulenc, Inc. | Ceric hydrocarbyl silyloxides and process for their preparation |
-
2001
- 2001-12-28 BR BR0116559-3A patent/BR0116559A/pt active Pending
- 2001-12-28 AT AT01989673T patent/ATE463522T1/de not_active IP Right Cessation
- 2001-12-28 DE DE60141771T patent/DE60141771D1/de not_active Expired - Lifetime
- 2001-12-28 US US10/450,261 patent/US6946538B2/en not_active Expired - Lifetime
- 2001-12-28 CA CA002432960A patent/CA2432960A1/fr not_active Abandoned
- 2001-12-28 WO PCT/FR2001/004228 patent/WO2002053614A1/fr not_active Application Discontinuation
- 2001-12-28 EP EP01989673A patent/EP1358238B1/fr not_active Expired - Lifetime
- 2001-12-28 CN CNB018215599A patent/CN1215100C/zh not_active Expired - Fee Related
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN109071762A (zh) * | 2015-04-21 | 2018-12-21 | 科思创德国股份有限公司 | 包含硅氧烷基团的聚异氰脲酸酯塑料及其制造方法 |
CN109071762B (zh) * | 2015-04-21 | 2022-03-11 | 科思创德国股份有限公司 | 包含硅氧烷基团的聚异氰脲酸酯塑料及其制造方法 |
Also Published As
Publication number | Publication date |
---|---|
DE60141771D1 (de) | 2010-05-20 |
US20040024212A1 (en) | 2004-02-05 |
US6946538B2 (en) | 2005-09-20 |
EP1358238B1 (fr) | 2010-04-07 |
BR0116559A (pt) | 2004-02-17 |
ATE463522T1 (de) | 2010-04-15 |
CN1215100C (zh) | 2005-08-17 |
EP1358238A1 (fr) | 2003-11-05 |
WO2002053614A1 (fr) | 2002-07-11 |
CA2432960A1 (fr) | 2002-07-11 |
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