SK283404B6 - Tris-aryl-s-triazíny, spôsob ich prípravy, kompozícia stabilizovaná týmito triazínmi, ich použitie a spôsob ochrany organického polyméru proti degradácii - Google Patents

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Publication number

SK283404B6

SK283404B6 SK935-95A SK93595A SK283404B6 SK 283404 B6 SK283404 B6 SK 283404B6 SK 93595 A SK93595 A SK 93595A SK 283404 B6 SK283404 B6 SK 283404B6

Authority

SK

Slovakia

Prior art keywords

group

carbon atoms

alkyl

phenyl

bis

Prior art date

1994-07-27

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• 239000000203 mixture Substances 0.000 title claims description 163
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 137
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 49
• 150000002367 halogens Chemical class 0.000 claims abstract description 48
• 125000003884 phenylalkyl group Chemical group 0.000 claims abstract description 18
• 239000000758 substrate Substances 0.000 claims abstract description 9
• -1 2,2,6,6-tetramethylpiperidinyl Chemical group 0.000 claims description 172
• 150000001875 compounds Chemical class 0.000 claims description 141
• 125000004432 carbon atom Chemical group C* 0.000 claims description 137
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 96
• 125000002947 alkylene group Chemical group 0.000 claims description 79
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 56
• 239000007787 solid Substances 0.000 claims description 47
• 238000000034 method Methods 0.000 claims description 41
• 239000000126 substance Substances 0.000 claims description 41
• 125000003545 alkoxy group Chemical group 0.000 claims description 34
• 238000000576 coating method Methods 0.000 claims description 34
• 229920000642 polymer Polymers 0.000 claims description 30
• 150000001412 amines Chemical class 0.000 claims description 26
• 125000003118 aryl group Chemical group 0.000 claims description 25
• 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 24
• 239000011248 coating agent Substances 0.000 claims description 23
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 22
• 125000003342 alkenyl group Chemical group 0.000 claims description 21
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 21
• VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical group Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 20
• 229920005989 resin Polymers 0.000 claims description 19
• 239000011347 resin Substances 0.000 claims description 19
• 239000003381 stabilizer Substances 0.000 claims description 17
• 230000000087 stabilizing effect Effects 0.000 claims description 16
• 230000005855 radiation Effects 0.000 claims description 14
• NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 13
• 125000005843 halogen group Chemical group 0.000 claims description 13
• 229910052751 metal Inorganic materials 0.000 claims description 13
• 239000002184 metal Substances 0.000 claims description 13
• 229920000877 Melamine resin Polymers 0.000 claims description 11
• 239000006096 absorbing agent Substances 0.000 claims description 11
• 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 11
• 125000002993 cycloalkylene group Chemical group 0.000 claims description 11
• 125000004956 cyclohexylene group Chemical group 0.000 claims description 11
• 125000006686 (C1-C24) alkyl group Chemical group 0.000 claims description 10
• 239000011230 binding agent Substances 0.000 claims description 10
• 239000003054 catalyst Substances 0.000 claims description 10
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 10
• 238000002360 preparation method Methods 0.000 claims description 10
• 230000008569 process Effects 0.000 claims description 10
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 10
• 229910052727 yttrium Inorganic materials 0.000 claims description 10
• 239000001257 hydrogen Substances 0.000 claims description 9
• 229910052739 hydrogen Inorganic materials 0.000 claims description 9
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 8
• 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 8
• 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims description 7
• 125000002252 acyl group Chemical group 0.000 claims description 7
• SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 claims description 7
• 229920001187 thermosetting polymer Polymers 0.000 claims description 7
• 239000004593 Epoxy Substances 0.000 claims description 6
• 150000001336 alkenes Chemical class 0.000 claims description 6
• 125000003282 alkyl amino group Chemical group 0.000 claims description 6
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
• 230000015556 catabolic process Effects 0.000 claims description 6
• 238000006731 degradation reaction Methods 0.000 claims description 6
• 125000003700 epoxy group Chemical group 0.000 claims description 6
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
• 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 5
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 5
• 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 claims description 5
• 125000001769 aryl amino group Chemical group 0.000 claims description 5
• 125000000732 arylene group Chemical group 0.000 claims description 5
• NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical group C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 5
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 5
• 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 5
• 125000002757 morpholinyl group Chemical group 0.000 claims description 5
• 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 5
• 239000003973 paint Substances 0.000 claims description 5
• 125000004193 piperazinyl group Chemical group 0.000 claims description 5
• 125000003386 piperidinyl group Chemical group 0.000 claims description 5
• FJGQBLRYBUAASW-UHFFFAOYSA-N 2-(benzotriazol-2-yl)phenol Chemical compound OC1=CC=CC=C1N1N=C2C=CC=CC2=N1 FJGQBLRYBUAASW-UHFFFAOYSA-N 0.000 claims description 4
• ONIKNECPXCLUHT-UHFFFAOYSA-N 2-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1Cl ONIKNECPXCLUHT-UHFFFAOYSA-N 0.000 claims description 4
• 238000003547 Friedel-Crafts alkylation reaction Methods 0.000 claims description 4
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
• 239000004305 biphenyl Substances 0.000 claims description 4
• 230000003197 catalytic effect Effects 0.000 claims description 4
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
• JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 claims description 4
• 229940098779 methanesulfonic acid Drugs 0.000 claims description 4
• 229920000620 organic polymer Polymers 0.000 claims description 4
• 239000001301 oxygen Substances 0.000 claims description 4
• 229910052760 oxygen Inorganic materials 0.000 claims description 4
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
• 125000005628 tolylene group Chemical group 0.000 claims description 4
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
• 239000008199 coating composition Substances 0.000 claims description 3
• 150000001925 cycloalkenes Chemical class 0.000 claims description 3
• 125000006839 xylylene group Chemical group 0.000 claims description 3
• XIIJQVXWEHBGTQ-UHFFFAOYSA-N 1-[5-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-2,4-dihydroxyphenyl]propan-1-one Chemical compound C1=C(O)C(C(=O)CC)=CC(C=2N=C(N=C(N=2)C=2C(=CC(C)=CC=2)C)C=2C(=CC(C)=CC=2)C)=C1O XIIJQVXWEHBGTQ-UHFFFAOYSA-N 0.000 claims description 2
• BYTDJFWMBNWPHB-UHFFFAOYSA-N 2-(4,6-diphenyl-1,3,5-triazin-2-yl)-4-hexyl-5-(2-hydroxy-3-nonoxypropoxy)phenol Chemical compound C1=C(CCCCCC)C(OCC(O)COCCCCCCCCC)=CC(O)=C1C1=NC(C=2C=CC=CC=2)=NC(C=2C=CC=CC=2)=N1 BYTDJFWMBNWPHB-UHFFFAOYSA-N 0.000 claims description 2
• ZUKRRNURZPMYFF-UHFFFAOYSA-N 2-(4,6-diphenyl-1,3,5-triazin-2-yl)-4-hexyl-5-methoxyphenol Chemical compound C1=C(OC)C(CCCCCC)=CC(C=2N=C(N=C(N=2)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1O ZUKRRNURZPMYFF-UHFFFAOYSA-N 0.000 claims description 2
• VYBOVBLHRYWRDU-UHFFFAOYSA-N 2-(4,6-diphenyl-1,3,5-triazin-2-yl)-5-hexoxy-4-hexylphenol Chemical compound C1=C(CCCCCC)C(OCCCCCC)=CC(O)=C1C1=NC(C=2C=CC=CC=2)=NC(C=2C=CC=CC=2)=N1 VYBOVBLHRYWRDU-UHFFFAOYSA-N 0.000 claims description 2
• WATQWOIVOVTGAU-UHFFFAOYSA-N 2-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-5-(3-dodecoxy-2-hydroxypropoxy)-4-hexylphenol Chemical compound C1=C(CCCCCC)C(OCC(O)COCCCCCCCCCCCC)=CC(O)=C1C1=NC(C=2C(=CC(C)=CC=2)C)=NC(C=2C(=CC(C)=CC=2)C)=N1 WATQWOIVOVTGAU-UHFFFAOYSA-N 0.000 claims description 2
• XOEDSKNCBPKBJK-UHFFFAOYSA-N 2-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-5-hexoxy-4-(2-phenylpropan-2-yl)phenol Chemical compound CCCCCCOC1=CC(O)=C(C=2N=C(N=C(N=2)C=2C(=CC(C)=CC=2)C)C=2C(=CC(C)=CC=2)C)C=C1C(C)(C)C1=CC=CC=C1 XOEDSKNCBPKBJK-UHFFFAOYSA-N 0.000 claims description 2
• ROJJGXXZFGBZBA-UHFFFAOYSA-N 2-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-5-hexoxy-4-hexylphenol Chemical compound CCCCCCOc1cc(O)c(cc1CCCCCC)-c1nc(nc(n1)-c1ccc(C)cc1C)-c1ccc(C)cc1C ROJJGXXZFGBZBA-UHFFFAOYSA-N 0.000 claims description 2
• JQYYVSXZAIWYSF-UHFFFAOYSA-N 2-[4,6-bis(4-methylphenyl)-1,3,5-triazin-2-yl]-5-hexoxy-4-hexylphenol Chemical compound C1=C(CCCCCC)C(OCCCCCC)=CC(O)=C1C1=NC(C=2C=CC(C)=CC=2)=NC(C=2C=CC(C)=CC=2)=N1 JQYYVSXZAIWYSF-UHFFFAOYSA-N 0.000 claims description 2
• FIWCBWRTLBJGOE-UHFFFAOYSA-N 3-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-5-phenylthiophene-2,4-diol Chemical compound OC=1SC(=C(C1C1=NC(=NC(=N1)C1=C(C=C(C=C1)C)C)C1=C(C=C(C=C1)C)C)O)C1=CC=CC=C1 FIWCBWRTLBJGOE-UHFFFAOYSA-N 0.000 claims description 2
• CKKYBCOKWOYIPX-UHFFFAOYSA-N 4-(4,6-diphenyl-1,3,5-triazin-2-yl)-6-hexylbenzene-1,3-diol Chemical compound C1=C(O)C(CCCCCC)=CC(C=2N=C(N=C(N=2)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1O CKKYBCOKWOYIPX-UHFFFAOYSA-N 0.000 claims description 2
• KBMCOOMAMATYHQ-UHFFFAOYSA-N 4-(benzenesulfonyl)-6-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]benzene-1,3-diol Chemical compound Cc1ccc(c(C)c1)-c1nc(nc(n1)-c1cc(c(O)cc1O)S(=O)(=O)c1ccccc1)-c1ccc(C)cc1C KBMCOOMAMATYHQ-UHFFFAOYSA-N 0.000 claims description 2
• LNWQRUNTXDGNLU-UHFFFAOYSA-N 4-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-6-(1-hydroxypropyl)benzene-1,3-diol Chemical compound C1=C(O)C(C(O)CC)=CC(C=2N=C(N=C(N=2)C=2C(=CC(C)=CC=2)C)C=2C(=CC(C)=CC=2)C)=C1O LNWQRUNTXDGNLU-UHFFFAOYSA-N 0.000 claims description 2
• BINPLUADTPSKCM-UHFFFAOYSA-N 4-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-6-[3-(2-methylpropylamino)propyl]benzene-1,3-diol Chemical compound C1=C(O)C(CCCNCC(C)C)=CC(C=2N=C(N=C(N=2)C=2C(=CC(C)=CC=2)C)C=2C(=CC(C)=CC=2)C)=C1O BINPLUADTPSKCM-UHFFFAOYSA-N 0.000 claims description 2
• LGXTZRACBVFXPU-UHFFFAOYSA-N 4-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-6-[3-(2-methylpropylimino)propyl]benzene-1,3-diol Chemical compound C1=C(O)C(CCC=NCC(C)C)=CC(C=2N=C(N=C(N=2)C=2C(=CC(C)=CC=2)C)C=2C(=CC(C)=CC=2)C)=C1O LGXTZRACBVFXPU-UHFFFAOYSA-N 0.000 claims description 2
• IDNMOCZVCKKPQW-UHFFFAOYSA-N 4-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-6-chlorobenzene-1,3-diol Chemical compound CC1=CC(C)=CC=C1C1=NC(C=2C(=CC(C)=CC=2)C)=NC(C=2C(=CC(O)=C(Cl)C=2)O)=N1 IDNMOCZVCKKPQW-UHFFFAOYSA-N 0.000 claims description 2
• DGJDPVINDQRXKS-UHFFFAOYSA-N 4-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-6-hexylbenzene-1,3-diol Chemical compound C1=C(O)C(CCCCCC)=CC(C=2N=C(N=C(N=2)C=2C(=CC(C)=CC=2)C)C=2C(=CC(C)=CC=2)C)=C1O DGJDPVINDQRXKS-UHFFFAOYSA-N 0.000 claims description 2
• APXVALWQCJACEN-UHFFFAOYSA-N 4-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-6-prop-1-enylbenzene-1,3-diol Chemical compound CC=Cc1cc(c(O)cc1O)-c1nc(nc(n1)-c1ccc(C)cc1C)-c1ccc(C)cc1C APXVALWQCJACEN-UHFFFAOYSA-N 0.000 claims description 2
• CQYHODPINUKJFS-UHFFFAOYSA-N 4-[4,6-bis(4-methylphenyl)-1,3,5-triazin-2-yl]-6-hexylbenzene-1,3-diol Chemical compound C1=C(O)C(CCCCCC)=CC(C=2N=C(N=C(N=2)C=2C=CC(C)=CC=2)C=2C=CC(C)=CC=2)=C1O CQYHODPINUKJFS-UHFFFAOYSA-N 0.000 claims description 2
• ROMOVEOVEAWFBS-UHFFFAOYSA-N 4-chloro-2-(4,6-diphenyl-1,3,5-triazin-2-yl)-5-hexoxyphenol Chemical compound C1=C(Cl)C(OCCCCCC)=CC(O)=C1C1=NC(C=2C=CC=CC=2)=NC(C=2C=CC=CC=2)=N1 ROMOVEOVEAWFBS-UHFFFAOYSA-N 0.000 claims description 2
• IRVMGEAXNIMINM-UHFFFAOYSA-N 4-hexyl-6-[4-(5-hexyl-2,4-dihydroxyphenyl)-6-phenyl-1,3,5-triazin-2-yl]benzene-1,3-diol Chemical compound C1=C(O)C(CCCCCC)=CC(C=2N=C(N=C(N=2)C=2C=CC=CC=2)C=2C(=CC(O)=C(CCCCCC)C=2)O)=C1O IRVMGEAXNIMINM-UHFFFAOYSA-N 0.000 claims description 2
• RNPMCTYVUSAJCK-UHFFFAOYSA-N 5-hexoxy-2-[4-(4-hexoxy-5-hexyl-2-hydroxyphenyl)-6-phenyl-1,3,5-triazin-2-yl]-4-hexylphenol Chemical compound C1=C(CCCCCC)C(OCCCCCC)=CC(O)=C1C1=NC(C=2C=CC=CC=2)=NC(C=2C(=CC(OCCCCCC)=C(CCCCCC)C=2)O)=N1 RNPMCTYVUSAJCK-UHFFFAOYSA-N 0.000 claims description 2
• QNBMOSPYOAEHDK-UHFFFAOYSA-N [5-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-2,4-dihydroxyphenyl]-phenylmethanone Chemical compound CC1=CC(C)=CC=C1C1=NC(C=2C(=CC(C)=CC=2)C)=NC(C=2C(=CC(O)=C(C(=O)C=3C=CC=CC=3)C=2)O)=N1 QNBMOSPYOAEHDK-UHFFFAOYSA-N 0.000 claims description 2
• 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 2
• 125000004429 atom Chemical group 0.000 claims description 2
• SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 claims description 2
• 239000001023 inorganic pigment Substances 0.000 claims description 2
• 239000012860 organic pigment Substances 0.000 claims description 2
• 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 2
• IGSZLCRLLROOEG-UHFFFAOYSA-N 2-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-4-hexyl-5-(2-hydroxy-3-phenoxypropoxy)phenol Chemical compound CCCCCCC1=CC(C=2N=C(N=C(N=2)C=2C(=CC(C)=CC=2)C)C=2C(=CC(C)=CC=2)C)=C(O)C=C1OCC(O)COC1=CC=CC=C1 IGSZLCRLLROOEG-UHFFFAOYSA-N 0.000 claims 1
• PQSSARCHBGYLPE-UHFFFAOYSA-N 2-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-5-(3-butoxy-2-hydroxypropoxy)-4-hexylphenol Chemical compound C1=C(OCC(O)COCCCC)C(CCCCCC)=CC(C=2N=C(N=C(N=2)C=2C(=CC(C)=CC=2)C)C=2C(=CC(C)=CC=2)C)=C1O PQSSARCHBGYLPE-UHFFFAOYSA-N 0.000 claims 1
• ZOQBTWAAZMIHRQ-UHFFFAOYSA-N 2-[4,6-bis(4-methylphenyl)-1,3,5-triazin-2-yl]-5-(3-butoxy-2-hydroxypropoxy)-4-hexylphenol Chemical compound C1=C(OCC(O)COCCCC)C(CCCCCC)=CC(C=2N=C(N=C(N=2)C=2C=CC(C)=CC=2)C=2C=CC(C)=CC=2)=C1O ZOQBTWAAZMIHRQ-UHFFFAOYSA-N 0.000 claims 1
• KLKCGQRWVCBXEA-UHFFFAOYSA-N 4-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-6-[hydroxy(phenyl)methyl]benzene-1,3-diol Chemical compound Cc1ccc(c(C)c1)-c1nc(nc(n1)-c1cc(C(O)c2ccccc2)c(O)cc1O)-c1ccc(C)cc1C KLKCGQRWVCBXEA-UHFFFAOYSA-N 0.000 claims 1
• PFSDKNGWYYIJGH-UHFFFAOYSA-N 5-(3-butoxy-2-hydroxypropoxy)-2-[4-[4-(3-butoxy-2-hydroxypropoxy)-5-hexyl-2-hydroxyphenyl]-6-phenyl-1,3,5-triazin-2-yl]-4-hexylphenol Chemical compound C1=C(OCC(O)COCCCC)C(CCCCCC)=CC(C=2N=C(N=C(N=2)C=2C=CC=CC=2)C=2C(=CC(OCC(O)COCCCC)=C(CCCCCC)C=2)O)=C1O PFSDKNGWYYIJGH-UHFFFAOYSA-N 0.000 claims 1
• 125000001589 carboacyl group Chemical group 0.000 claims 1
• 230000009931 harmful effect Effects 0.000 claims 1
• GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 abstract description 35
• 230000006641 stabilisation Effects 0.000 abstract description 2
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 abstract description 2
• 230000002939 deleterious effect Effects 0.000 abstract 1
• 125000000446 sulfanediyl group Chemical group *S* 0.000 abstract 1
• 238000002211 ultraviolet spectrum Methods 0.000 abstract 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 195
• 239000000047 product Substances 0.000 description 60
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
• PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 42
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 38
• 229920001577 copolymer Polymers 0.000 description 37
• 229910052757 nitrogen Inorganic materials 0.000 description 35
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 30
• JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical group C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 28
• 238000001819 mass spectrum Methods 0.000 description 27
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 24
• 239000000243 solution Substances 0.000 description 24
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 23
• 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 23
• 238000006467 substitution reaction Methods 0.000 description 23
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
• 238000001914 filtration Methods 0.000 description 19
• 150000003918 triazines Chemical class 0.000 description 19
• 239000012043 crude product Substances 0.000 description 18
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 17
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 17
• 238000002844 melting Methods 0.000 description 17
• 230000008018 melting Effects 0.000 description 17
• 239000012299 nitrogen atmosphere Substances 0.000 description 17
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
• 230000002829 reductive effect Effects 0.000 description 16
• 239000002904 solvent Substances 0.000 description 16
• ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 15
• 229940093475 2-ethoxyethanol Drugs 0.000 description 15
• VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 15
• 239000005977 Ethylene Substances 0.000 description 15
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