DE69528331T2 - Rotverschobene Tris-aryl-s-triazine und damit stabilisierte Zusammensetzungen - Google Patents
Rotverschobene Tris-aryl-s-triazine und damit stabilisierte ZusammensetzungenInfo
- 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
- 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
Links
- 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
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- 230000008569 process Effects 0.000 claims description 17
- 150000002431 hydrogen Chemical group 0.000 claims description 16
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- 239000004593 Epoxy Substances 0.000 claims description 15
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- 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
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- 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
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- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 6
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- 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
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- 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
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- 238000004070 electrodeposition Methods 0.000 claims description 4
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- 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
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- 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
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- FHAFFFSIDLDWQA-UHFFFAOYSA-N n-hexadecyloctadecan-1-imine oxide Chemical compound CCCCCCCCCCCCCCCCCC=[N+]([O-])CCCCCCCCCCCCCCCC FHAFFFSIDLDWQA-UHFFFAOYSA-N 0.000 description 1
- LVZUNTGFCXNQAF-UHFFFAOYSA-N n-nonyl-n-phenylaniline Chemical class C=1C=CC=CC=1N(CCCCCCCCC)C1=CC=CC=C1 LVZUNTGFCXNQAF-UHFFFAOYSA-N 0.000 description 1
- ZXGDIORKSOYRMQ-UHFFFAOYSA-N n-octadecylheptadecan-1-imine oxide Chemical compound CCCCCCCCCCCCCCCCCC[N+]([O-])=CCCCCCCCCCCCCCCCC ZXGDIORKSOYRMQ-UHFFFAOYSA-N 0.000 description 1
- HORBOHJHQGXXOR-UHFFFAOYSA-N n-octadecyloctadecan-1-imine oxide Chemical compound CCCCCCCCCCCCCCCCCC[N+]([O-])=CCCCCCCCCCCCCCCCCC HORBOHJHQGXXOR-UHFFFAOYSA-N 0.000 description 1
- QXJGVICBAANVMZ-UHFFFAOYSA-N n-octyloctan-1-imine oxide Chemical compound CCCCCCCC[N+]([O-])=CCCCCCCC QXJGVICBAANVMZ-UHFFFAOYSA-N 0.000 description 1
- MHJCZOMOUCUAOI-UHFFFAOYSA-N n-tert-butyl-n-phenylaniline Chemical class C=1C=CC=CC=1N(C(C)(C)C)C1=CC=CC=C1 MHJCZOMOUCUAOI-UHFFFAOYSA-N 0.000 description 1
- SLYJXPKHTZCZOG-UHFFFAOYSA-N n-tetradecyltetradecan-1-imine oxide Chemical compound CCCCCCCCCCCCCC[N+]([O-])=CCCCCCCCCCCCCC SLYJXPKHTZCZOG-UHFFFAOYSA-N 0.000 description 1
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- MGFYIUFZLHCRTH-UHFFFAOYSA-K nitrilotriacetate(3-) Chemical compound [O-]C(=O)CN(CC([O-])=O)CC([O-])=O MGFYIUFZLHCRTH-UHFFFAOYSA-K 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
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- 239000012994 photoredox catalyst Substances 0.000 description 1
- 125000005498 phthalate group Chemical class 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
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- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
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- 229920002312 polyamide-imide Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920002480 polybenzimidazole Polymers 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
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- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- MQOCIYICOGDBSG-UHFFFAOYSA-M potassium;hexadecanoate Chemical compound [K+].CCCCCCCCCCCCCCCC([O-])=O MQOCIYICOGDBSG-UHFFFAOYSA-M 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 238000007342 radical addition reaction Methods 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000000979 retarding effect Effects 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- IJRHDFLHUATAOS-DPMBMXLASA-M sodium ricinoleate Chemical compound [Na+].CCCCCC[C@@H](O)C\C=C/CCCCCCCC([O-])=O IJRHDFLHUATAOS-DPMBMXLASA-M 0.000 description 1
- 229940074404 sodium succinate Drugs 0.000 description 1
- ZDQYSKICYIVCPN-UHFFFAOYSA-L sodium succinate (anhydrous) Chemical compound [Na+].[Na+].[O-]C(=O)CCC([O-])=O ZDQYSKICYIVCPN-UHFFFAOYSA-L 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
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- 238000009987 spinning Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 230000003019 stabilising effect Effects 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920000638 styrene acrylonitrile Polymers 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- WWJZWCUNLNYYAU-UHFFFAOYSA-N temephos Chemical compound C1=CC(OP(=S)(OC)OC)=CC=C1SC1=CC=C(OP(=S)(OC)OC)C=C1 WWJZWCUNLNYYAU-UHFFFAOYSA-N 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- WUPCFMITFBVJMS-UHFFFAOYSA-N tetrakis(1,2,2,6,6-pentamethylpiperidin-4-yl) butane-1,2,3,4-tetracarboxylate Chemical compound C1C(C)(C)N(C)C(C)(C)CC1OC(=O)CC(C(=O)OC1CC(C)(C)N(C)C(C)(C)C1)C(C(=O)OC1CC(C)(C)N(C)C(C)(C)C1)CC(=O)OC1CC(C)(C)N(C)C(C)(C)C1 WUPCFMITFBVJMS-UHFFFAOYSA-N 0.000 description 1
- NZNAAUDJKMURFU-UHFFFAOYSA-N tetrakis(2,2,6,6-tetramethylpiperidin-4-yl) butane-1,2,3,4-tetracarboxylate Chemical compound C1C(C)(C)NC(C)(C)CC1OC(=O)CC(C(=O)OC1CC(C)(C)NC(C)(C)C1)C(C(=O)OC1CC(C)(C)NC(C)(C)C1)CC(=O)OC1CC(C)(C)NC(C)(C)C1 NZNAAUDJKMURFU-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
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- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 235000010215 titanium dioxide Nutrition 0.000 description 1
- YONPGGFAJWQGJC-UHFFFAOYSA-K titanium(iii) chloride Chemical compound Cl[Ti](Cl)Cl YONPGGFAJWQGJC-UHFFFAOYSA-K 0.000 description 1
- 229960000984 tocofersolan Drugs 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- 235000019149 tocopherols Nutrition 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- INNSFNJTGFCSRN-UHFFFAOYSA-N tridecyl 2-[(3,5-ditert-butyl-4-hydroxyphenyl)methylsulfanyl]acetate Chemical compound CCCCCCCCCCCCCOC(=O)CSCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 INNSFNJTGFCSRN-UHFFFAOYSA-N 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- IVIIAEVMQHEPAY-UHFFFAOYSA-N tridodecyl phosphite Chemical compound CCCCCCCCCCCCOP(OCCCCCCCCCCCC)OCCCCCCCCCCCC IVIIAEVMQHEPAY-UHFFFAOYSA-N 0.000 description 1
- 125000005591 trimellitate group Chemical group 0.000 description 1
- CNUJLMSKURPSHE-UHFFFAOYSA-N trioctadecyl phosphite Chemical compound CCCCCCCCCCCCCCCCCCOP(OCCCCCCCCCCCCCCCCCC)OCCCCCCCCCCCCCCCCCC CNUJLMSKURPSHE-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 229920000785 ultra high molecular weight polyethylene Polymers 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
- 229920006163 vinyl copolymer Polymers 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
- 239000002076 α-tocopherol Substances 0.000 description 1
- 235000004835 α-tocopherol Nutrition 0.000 description 1
- 239000011590 β-tocopherol Substances 0.000 description 1
- 235000007680 β-tocopherol Nutrition 0.000 description 1
- 239000002478 γ-tocopherol Substances 0.000 description 1
- QUEDXNHFTDJVIY-UHFFFAOYSA-N γ-tocopherol Chemical class OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-UHFFFAOYSA-N 0.000 description 1
- QUEDXNHFTDJVIY-DQCZWYHMSA-N γ-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-DQCZWYHMSA-N 0.000 description 1
- 239000002446 δ-tocopherol Substances 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
- C07D251/14—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 hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/24—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 hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
- C08K5/3477—Six-membered rings
- C08K5/3492—Triazines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Paints Or Removers (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Epoxy Resins (AREA)
- Medicinal Preparation (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/281,381 US5556973A (en) | 1994-07-27 | 1994-07-27 | Red-shifted tris-aryl-s-triazines and compositions stabilized therewith |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69528331D1 DE69528331D1 (de) | 2002-10-31 |
| DE69528331T2 true DE69528331T2 (de) | 2003-05-15 |
Family
ID=23077052
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69528331T Expired - Fee Related DE69528331T2 (de) | 1994-07-27 | 1995-07-18 | Rotverschobene Tris-aryl-s-triazine und damit stabilisierte Zusammensetzungen |
Country Status (12)
| Country | Link |
|---|---|
| US (7) | US5556973A (OSRAM) |
| EP (1) | EP0704437B1 (OSRAM) |
| JP (1) | JP3965603B2 (OSRAM) |
| KR (1) | KR100346064B1 (OSRAM) |
| AT (1) | ATE224880T1 (OSRAM) |
| BR (1) | BR9503460A (OSRAM) |
| CA (1) | CA2154626A1 (OSRAM) |
| CZ (1) | CZ192595A3 (OSRAM) |
| DE (1) | DE69528331T2 (OSRAM) |
| ES (1) | ES2181760T3 (OSRAM) |
| SK (1) | SK283404B6 (OSRAM) |
| TW (1) | TW308602B (OSRAM) |
Families Citing this family (212)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2879756B2 (ja) * | 1993-12-02 | 1999-04-05 | カシオ計算機株式会社 | プリンタ装置 |
| DE69633927T2 (de) * | 1995-08-30 | 2005-11-24 | Cytec Technology Corp., Wilmington | Zusammensetzungen enthaltend 1,3,5-Triazincarbamate und Epoxyverbindungen |
| US5759689A (en) * | 1996-06-13 | 1998-06-02 | General Electric Company | Coextruded polycarbonate sheet with improved weathering |
| US5726309A (en) * | 1996-08-27 | 1998-03-10 | Ciba Specialty Chemicals Corporation | Tris-aryls-triazines substituted with biphenylyl groups |
| BE1012529A3 (fr) * | 1996-09-13 | 2000-12-05 | Ciba Sc Holding Ag | Melange de triaryltriazines et son utilisation pour la stabilisation de materiaux organiques. |
| DE19739781A1 (de) * | 1996-09-13 | 1998-03-19 | Ciba Geigy Ag | Hydroxyphenyltriazine |
| CA2267791A1 (en) * | 1996-10-08 | 1998-04-16 | Cytec Technology Corp. | Crosslinker compositions and low gloss epoxy coatings therefrom |
| KR100562926B1 (ko) * | 1996-11-20 | 2006-10-19 | 시바 스페셜티 케미칼스 홀딩 인크. | 히드록시페닐트리아진 |
| GB2319523B (en) | 1996-11-20 | 2000-11-08 | Ciba Sc Holding Ag | Hydroxyphenyltriazines |
| US6117997A (en) * | 1997-11-19 | 2000-09-12 | Ciba Specialty Chemicals Corporation | Hydroxyphenyltriazines |
| ZA9810604B (en) | 1997-11-21 | 1999-05-25 | Cytec Tech Corp | Novel trisaryl-1,3,5-triazine ultraviolet light absorbers |
| US5985251A (en) * | 1997-12-01 | 1999-11-16 | Roche Vitamins Inc. | Light screening compositions |
| US6018044A (en) * | 1998-01-02 | 2000-01-25 | Roche Vitamins Inc. | Light screening compositions |
| EP0941989B1 (en) * | 1998-03-02 | 2009-07-08 | Ciba Holding Inc. | Process for the preparation of 2,4-diaryl-6-o-hydroxyphenyl-1,3,5-triazine derivatives in the presence of a protic acid catalyst |
| JP2000026435A (ja) * | 1998-05-07 | 2000-01-25 | Ciba Specialty Chem Holding Inc | トリスレゾリシニルトリアジン |
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- 1995-06-02 US US08/463,573 patent/US5648488A/en not_active Expired - Lifetime
- 1995-07-18 DE DE69528331T patent/DE69528331T2/de not_active Expired - Fee Related
- 1995-07-18 AT AT95810471T patent/ATE224880T1/de not_active IP Right Cessation
- 1995-07-18 EP EP95810471A patent/EP0704437B1/en not_active Expired - Lifetime
- 1995-07-18 ES ES95810471T patent/ES2181760T3/es not_active Expired - Lifetime
- 1995-07-21 KR KR1019950021471A patent/KR100346064B1/ko not_active Expired - Fee Related
- 1995-07-25 CZ CZ951925A patent/CZ192595A3/cs unknown
- 1995-07-25 CA CA002154626A patent/CA2154626A1/en not_active Abandoned
- 1995-07-25 SK SK935-95A patent/SK283404B6/sk unknown
- 1995-07-26 BR BR9503460A patent/BR9503460A/pt not_active Application Discontinuation
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- 1995-09-01 TW TW084109140A patent/TW308602B/zh active
-
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Also Published As
| Publication number | Publication date |
|---|---|
| US5675004A (en) | 1997-10-07 |
| EP0704437A2 (en) | 1996-04-03 |
| US5637706A (en) | 1997-06-10 |
| SK93595A3 (en) | 1996-02-07 |
| DE69528331D1 (de) | 2002-10-31 |
| CZ192595A3 (en) | 1996-02-14 |
| ES2181760T3 (es) | 2003-03-01 |
| JP3965603B2 (ja) | 2007-08-29 |
| US5681955A (en) | 1997-10-28 |
| TW308602B (OSRAM) | 1997-06-21 |
| US5648488A (en) | 1997-07-15 |
| EP0704437A3 (en) | 1996-10-23 |
| BR9503460A (pt) | 1996-02-27 |
| ATE224880T1 (de) | 2002-10-15 |
| EP0704437B1 (en) | 2002-09-25 |
| KR100346064B1 (ko) | 2002-11-16 |
| US5556973A (en) | 1996-09-17 |
| SK283404B6 (sk) | 2003-07-01 |
| JPH0853427A (ja) | 1996-02-27 |
| US5543518A (en) | 1996-08-06 |
| CA2154626A1 (en) | 1996-01-28 |
| US5684070A (en) | 1997-11-04 |
| KR960004328A (ko) | 1996-02-23 |
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