DE69528331T2 - Rotverschobene Tris-aryl-s-triazine und damit stabilisierte Zusammensetzungen - Google Patents

Info

Publication number

DE69528331T2

DE69528331T2 DE69528331T DE69528331T DE69528331T2 DE 69528331 T2 DE69528331 T2 DE 69528331T2 DE 69528331 T DE69528331 T DE 69528331T DE 69528331 T DE69528331 T DE 69528331T DE 69528331 T2 DE69528331 T2 DE 69528331T2

Authority

DE

Germany

Prior art keywords

carbon atoms

alkyl

phenyl

substituted

bis

Prior art date

1994-07-27

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Expired - Fee Related

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• 239000000203 mixture Substances 0.000 title claims description 134
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 107
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 57
• 150000002367 halogens Chemical class 0.000 claims abstract description 57
• 125000003884 phenylalkyl group Chemical group 0.000 claims abstract description 25
• 239000000758 substrate Substances 0.000 claims abstract description 7
• 125000004432 carbon atom Chemical group C* 0.000 claims description 244
• -1 2,2,6,6-tetramethylpiperidinyl Chemical group 0.000 claims description 116
• 150000001875 compounds Chemical class 0.000 claims description 99
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 83
• 125000002947 alkylene group Chemical group 0.000 claims description 82
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 43
• 239000007787 solid Substances 0.000 claims description 36
• 125000003545 alkoxy group Chemical group 0.000 claims description 35
• 238000000034 method Methods 0.000 claims description 33
• 125000003118 aryl group Chemical group 0.000 claims description 27
• 229920000642 polymer Polymers 0.000 claims description 26
• 239000006096 absorbing agent Substances 0.000 claims description 25
• 125000003342 alkenyl group Chemical group 0.000 claims description 23
• 239000001257 hydrogen Substances 0.000 claims description 23
• 229910052739 hydrogen Inorganic materials 0.000 claims description 23
• 150000001412 amines Chemical class 0.000 claims description 22
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 21
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 20
• NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 20
• 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 19
• 230000008569 process Effects 0.000 claims description 17
• 150000002431 hydrogen Chemical group 0.000 claims description 16
• 229920000178 Acrylic resin Polymers 0.000 claims description 15
• 239000004593 Epoxy Substances 0.000 claims description 15
• 229920000877 Melamine resin Polymers 0.000 claims description 15
• 239000003381 stabilizer Substances 0.000 claims description 15
• 229910052751 metal Inorganic materials 0.000 claims description 13
• 239000002184 metal Substances 0.000 claims description 13
• 239000011368 organic material Substances 0.000 claims description 13
• 125000002993 cycloalkylene group Chemical group 0.000 claims description 12
• 239000000463 material Substances 0.000 claims description 12
• 230000000087 stabilizing effect Effects 0.000 claims description 12
• 125000004956 cyclohexylene group Chemical group 0.000 claims description 11
• 239000004925 Acrylic resin Substances 0.000 claims description 10
• VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical group Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 10
• 239000011230 binding agent Substances 0.000 claims description 10
• 239000003054 catalyst Substances 0.000 claims description 10
• NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 10
• 239000004611 light stabiliser Substances 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
• 239000002585 base Substances 0.000 claims description 9
• 229910052727 yttrium Inorganic materials 0.000 claims description 9
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 8
• 125000006686 (C1-C24) alkyl 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
• 125000001589 carboacyl group Chemical group 0.000 claims description 7
• 230000005855 radiation Effects 0.000 claims description 7
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 6
• 239000004640 Melamine resin Substances 0.000 claims description 6
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 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
• 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
• 125000001309 chloro group Chemical group Cl* 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
• 229920001187 thermosetting polymer Polymers 0.000 claims description 6
• 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 claims description 5
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
• 125000003282 alkyl amino group Chemical group 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
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
• 230000015556 catabolic process Effects 0.000 claims description 5
• 230000003197 catalytic effect Effects 0.000 claims description 5
• 238000009500 colour coating Methods 0.000 claims description 5
• 238000006731 degradation reaction Methods 0.000 claims description 5
• 125000002757 morpholinyl group Chemical group 0.000 claims description 5
• 239000001301 oxygen Substances 0.000 claims description 5
• 229910052760 oxygen Inorganic materials 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
• 229920002803 thermoplastic polyurethane Polymers 0.000 claims description 5
• 125000006839 xylylene group Chemical group 0.000 claims description 5
• 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 4
• 238000004070 electrodeposition Methods 0.000 claims description 4
• 229920000620 organic polymer Polymers 0.000 claims description 4
• 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 3
• WDSZRYWCOPYDJE-UHFFFAOYSA-N 2-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-5-(2-hydroxy-3-nonoxypropoxy)-4-(2-phenylpropan-2-yl)phenol Chemical compound CCCCCCCCCOCC(O)COC1=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 WDSZRYWCOPYDJE-UHFFFAOYSA-N 0.000 claims description 3
• 238000003547 Friedel-Crafts alkylation reaction Methods 0.000 claims description 3
• 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
• 229940098779 methanesulfonic acid Drugs 0.000 claims description 3
• 229920006254 polymer film Polymers 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
• KINCBELNIUTKJP-UHFFFAOYSA-N 2-(4,6-diphenyl-1,3,5-triazin-2-yl)-5-octoxy-4-(2-phenylpropan-2-yl)phenol Chemical compound CCCCCCCCOC1=CC(O)=C(C=2N=C(N=C(N=2)C=2C=CC=CC=2)C=2C=CC=CC=2)C=C1C(C)(C)C1=CC=CC=C1 KINCBELNIUTKJP-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
• JVTFIMKVCNGACA-UHFFFAOYSA-N 4-(benzenesulfinyl)-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)c1ccccc1)-c1ccc(C)cc1C JVTFIMKVCNGACA-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
• TXDXQEUCTLNDBH-UHFFFAOYSA-N 4-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-6-(2-phenylpropan-2-yl)benzene-1,3-diol Chemical compound CC1=CC(C)=CC=C1C1=NC(C=2C(=CC(C)=CC=2)C)=NC(C=2C(=CC(O)=C(C=2)C(C)(C)C=2C=CC=CC=2)O)=N1 TXDXQEUCTLNDBH-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
• 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
• 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
• AKIUXKFWYRSMKX-UHFFFAOYSA-N 4-chloro-6-(4,6-diphenyl-1,3,5-triazin-2-yl)benzene-1,3-diol Chemical compound C1=C(Cl)C(O)=CC(O)=C1C1=NC(C=2C=CC=CC=2)=NC(C=2C=CC=CC=2)=N1 AKIUXKFWYRSMKX-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
• SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 claims description 2
• 230000000694 effects Effects 0.000 claims description 2
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
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• 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 2
• VITJZARSNITWFI-UHFFFAOYSA-N 4-(4,6-diphenyl-1,3,5-triazin-2-yl)-6-(2-phenylpropan-2-yl)benzene-1,3-diol Chemical compound C=1C(C=2N=C(N=C(N=2)C=2C=CC=CC=2)C=2C=CC=CC=2)=C(O)C=C(O)C=1C(C)(C)C1=CC=CC=C1 VITJZARSNITWFI-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• 230000002411 adverse Effects 0.000 claims 1
• 125000005628 tolylene group Chemical group 0.000 claims 1
• GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 abstract description 38
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• 238000011105 stabilization Methods 0.000 abstract description 4
• 238000002211 ultraviolet spectrum Methods 0.000 abstract description 3
• 125000000446 sulfanediyl group Chemical group *S* 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
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• JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical group C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 25
• 238000006467 substitution reaction Methods 0.000 description 25
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• QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 10
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