AU725829B2 - Tris-aryl s-triazines substituted with biphenylyl groups - Google Patents
Tris-aryl s-triazines substituted with biphenylyl groups Download PDFInfo
- Publication number
- AU725829B2 AU725829B2 AU35175/97A AU3517597A AU725829B2 AU 725829 B2 AU725829 B2 AU 725829B2 AU 35175/97 A AU35175/97 A AU 35175/97A AU 3517597 A AU3517597 A AU 3517597A AU 725829 B2 AU725829 B2 AU 725829B2
- Authority
- AU
- Australia
- Prior art keywords
- carbon atoms
- alkyl
- bis
- substituted
- tris
- 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.)
- Ceased
Links
- -1 biphenylyl groups Chemical group 0.000 title claims description 105
- 125000004432 carbon atom Chemical group C* 0.000 claims description 85
- 239000000203 mixture Substances 0.000 claims description 77
- 125000000217 alkyl group Chemical group 0.000 claims description 61
- 150000001875 compounds Chemical class 0.000 claims description 40
- 238000000034 method Methods 0.000 claims description 28
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 claims description 27
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 25
- 239000006096 absorbing agent Substances 0.000 claims description 23
- 229920000642 polymer Polymers 0.000 claims description 22
- 229910052736 halogen Inorganic materials 0.000 claims description 21
- 150000002367 halogens Chemical class 0.000 claims description 21
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 19
- 150000001412 amines Chemical class 0.000 claims description 19
- 125000003545 alkoxy group Chemical group 0.000 claims description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 18
- 125000002947 alkylene group Chemical group 0.000 claims description 17
- 230000008569 process Effects 0.000 claims description 17
- 230000000087 stabilizing effect Effects 0.000 claims description 15
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000011368 organic material Substances 0.000 claims description 14
- 229920000877 Melamine resin Polymers 0.000 claims description 13
- 239000000463 material Substances 0.000 claims description 12
- 239000003381 stabilizer Substances 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 229920000178 Acrylic resin Polymers 0.000 claims description 9
- 150000002431 hydrogen Chemical class 0.000 claims description 9
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 9
- 238000006068 polycondensation reaction Methods 0.000 claims description 9
- 239000007787 solid Substances 0.000 claims description 9
- 239000004925 Acrylic resin Substances 0.000 claims description 8
- 239000004611 light stabiliser Substances 0.000 claims description 8
- 239000004593 Epoxy Substances 0.000 claims description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 239000011230 binding agent Substances 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- 230000005855 radiation Effects 0.000 claims description 7
- YZXTWMQYSSMUFH-UHFFFAOYSA-N 4-[6-(1-amino-2,2,6,6-tetramethylpiperidin-4-yl)hexyl]-2,2,6,6-tetramethylpiperidin-1-amine Chemical compound C1C(C)(C)N(N)C(C)(C)CC1CCCCCCC1CC(C)(C)N(N)C(C)(C)C1 YZXTWMQYSSMUFH-UHFFFAOYSA-N 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
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 6
- 125000004956 cyclohexylene group Chemical group 0.000 claims description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 6
- 229920001187 thermosetting polymer Polymers 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 239000004640 Melamine resin Substances 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- GGAUUQHSCNMCAU-UHFFFAOYSA-N butane-1,2,3,4-tetracarboxylic acid Chemical compound OC(=O)CC(C(O)=O)C(C(O)=O)CC(O)=O GGAUUQHSCNMCAU-UHFFFAOYSA-N 0.000 claims description 5
- 230000015556 catabolic process Effects 0.000 claims description 5
- 238000006731 degradation reaction Methods 0.000 claims description 5
- 229910052751 metal Inorganic materials 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 5
- 239000000758 substrate Substances 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
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 4
- FNAZRRHPUDJQCJ-UHFFFAOYSA-N henicosane Chemical compound CCCCCCCCCCCCCCCCCCCCC FNAZRRHPUDJQCJ-UHFFFAOYSA-N 0.000 claims description 4
- 229940116351 sebacate Drugs 0.000 claims description 4
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 claims description 4
- XITRBUPOXXBIJN-UHFFFAOYSA-N bis(2,2,6,6-tetramethylpiperidin-4-yl) decanedioate Chemical compound C1C(C)(C)NC(C)(C)CC1OC(=O)CCCCCCCCC(=O)OC1CC(C)(C)NC(C)(C)C1 XITRBUPOXXBIJN-UHFFFAOYSA-N 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 3
- 230000002939 deleterious effect Effects 0.000 claims description 3
- 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 claims description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
- 229920006254 polymer film Polymers 0.000 claims description 3
- 229920002803 thermoplastic polyurethane Polymers 0.000 claims description 3
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 claims description 2
- ZMWRRFHBXARRRT-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4,6-bis(2-methylbutan-2-yl)phenol Chemical compound CCC(C)(C)C1=CC(C(C)(C)CC)=CC(N2N=C3C=CC=CC3=N2)=C1O ZMWRRFHBXARRRT-UHFFFAOYSA-N 0.000 claims description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 125000004442 acylamino group Chemical group 0.000 claims description 2
- 125000004423 acyloxy group Chemical group 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000001769 aryl amino group Chemical group 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 125000001589 carboacyl group Chemical group 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 239000001023 inorganic pigment Substances 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 239000012860 organic pigment Substances 0.000 claims description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 2
- 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 claims description 2
- OUBISKKOUYNDML-UHFFFAOYSA-N (2,2,6,6-tetramethylpiperidin-4-yl) 2-[bis[2-oxo-2-(2,2,6,6-tetramethylpiperidin-4-yl)oxyethyl]amino]acetate Chemical compound C1C(C)(C)NC(C)(C)CC1OC(=O)CN(CC(=O)OC1CC(C)(C)NC(C)(C)C1)CC(=O)OC1CC(C)(C)NC(C)(C)C1 OUBISKKOUYNDML-UHFFFAOYSA-N 0.000 claims 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- ZPNJBTBYIHBSIG-UHFFFAOYSA-N phenyl-(2,2,6,6-tetramethylpiperidin-4-yl)methanone Chemical compound C1C(C)(C)NC(C)(C)CC1C(=O)C1=CC=CC=C1 ZPNJBTBYIHBSIG-UHFFFAOYSA-N 0.000 claims 1
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 1
- 125000003003 spiro group Chemical group 0.000 claims 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 35
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinyl group Chemical group C1(O)=CC(O)=CC=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 33
- 238000006467 substitution reaction Methods 0.000 description 25
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 239000002253 acid Substances 0.000 description 15
- 229920001577 copolymer Polymers 0.000 description 15
- 238000000576 coating method Methods 0.000 description 14
- 150000003918 triazines Chemical class 0.000 description 13
- 229920005989 resin Polymers 0.000 description 12
- 239000011347 resin Substances 0.000 description 12
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 11
- 239000002585 base Substances 0.000 description 11
- 239000000835 fiber Substances 0.000 description 10
- 239000004743 Polypropylene Substances 0.000 description 9
- 239000011248 coating agent Substances 0.000 description 9
- 150000002148 esters Chemical class 0.000 description 9
- 239000000049 pigment Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 150000005207 1,3-dihydroxybenzenes Chemical group 0.000 description 8
- 239000004922 lacquer Substances 0.000 description 8
- 229920001155 polypropylene Polymers 0.000 description 8
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 8
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 7
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 7
- 150000001993 dienes Chemical class 0.000 description 7
- 229920000728 polyester Polymers 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 7
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 6
- 239000005977 Ethylene Substances 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- 239000007983 Tris buffer Substances 0.000 description 6
- 150000001336 alkenes Chemical class 0.000 description 6
- 229920000180 alkyd Polymers 0.000 description 6
- 230000003197 catalytic effect Effects 0.000 description 6
- 239000000539 dimer Substances 0.000 description 6
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
- 229920002554 vinyl polymer Polymers 0.000 description 6
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 5
- 230000032798 delamination Effects 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 239000002530 phenolic antioxidant Substances 0.000 description 5
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 5
- 229920002857 polybutadiene Polymers 0.000 description 5
- 229920000647 polyepoxide Polymers 0.000 description 5
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 4
- NJCDRURWJZAMBM-UHFFFAOYSA-N 6-phenyl-1h-1,3,5-triazin-2-one Chemical compound OC1=NC=NC(C=2C=CC=CC=2)=N1 NJCDRURWJZAMBM-UHFFFAOYSA-N 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- 229920002292 Nylon 6 Polymers 0.000 description 4
- 239000004952 Polyamide Substances 0.000 description 4
- 239000005062 Polybutadiene Substances 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
- 239000003431 cross linking reagent Substances 0.000 description 4
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 4
- 150000002815 nickel Chemical class 0.000 description 4
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 4
- 229920002647 polyamide Polymers 0.000 description 4
- 239000004417 polycarbonate Substances 0.000 description 4
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- 229920001225 polyester resin Polymers 0.000 description 4
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- 229920000570 polyether Polymers 0.000 description 4
- 239000004800 polyvinyl chloride Substances 0.000 description 4
- 229920000915 polyvinyl chloride Polymers 0.000 description 4
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 4
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 4
- 229920001897 terpolymer Polymers 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- HPFWYRKGZUGGPB-UHFFFAOYSA-N 4,6-dichloro-n-(2,4,4-trimethylpentan-2-yl)-1,3,5-triazin-2-amine Chemical compound CC(C)(C)CC(C)(C)NC1=NC(Cl)=NC(Cl)=N1 HPFWYRKGZUGGPB-UHFFFAOYSA-N 0.000 description 3
- FROCQMFXPIROOK-UHFFFAOYSA-N 4-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]benzene-1,3-diol Chemical group CC1=CC(C)=CC=C1C1=NC(C=2C(=CC(C)=CC=2)C)=NC(C=2C(=CC(O)=CC=2)O)=N1 FROCQMFXPIROOK-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 239000004721 Polyphenylene oxide Substances 0.000 description 3
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 3
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 3
- 238000007792 addition Methods 0.000 description 3
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical class OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 3
- 125000005250 alkyl acrylate group Chemical group 0.000 description 3
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 3
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- 238000004587 chromatography analysis Methods 0.000 description 3
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- 150000001991 dicarboxylic acids Chemical class 0.000 description 3
- 150000004702 methyl esters Chemical class 0.000 description 3
- SQDFHQJTAWCFIB-UHFFFAOYSA-N n-methylidenehydroxylamine Chemical compound ON=C SQDFHQJTAWCFIB-UHFFFAOYSA-N 0.000 description 3
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- 239000012299 nitrogen atmosphere Substances 0.000 description 3
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- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 3
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- 238000002360 preparation method Methods 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- 230000006641 stabilisation Effects 0.000 description 3
- 238000011105 stabilization Methods 0.000 description 3
- 150000005846 sugar alcohols Polymers 0.000 description 3
- 230000002195 synergetic effect Effects 0.000 description 3
- YHMYGUUIMTVXNW-UHFFFAOYSA-N 1,3-dihydrobenzimidazole-2-thione Chemical compound C1=CC=C2NC(S)=NC2=C1 YHMYGUUIMTVXNW-UHFFFAOYSA-N 0.000 description 2
- DXCHWXWXYPEZKM-UHFFFAOYSA-N 2,4-ditert-butyl-6-[1-(3,5-ditert-butyl-2-hydroxyphenyl)ethyl]phenol Chemical compound C=1C(C(C)(C)C)=CC(C(C)(C)C)=C(O)C=1C(C)C1=CC(C(C)(C)C)=CC(C(C)(C)C)=C1O DXCHWXWXYPEZKM-UHFFFAOYSA-N 0.000 description 2
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 2
- ZSSVCEUEVMALRD-UHFFFAOYSA-N 2-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-5-(octyloxy)phenol Chemical compound OC1=CC(OCCCCCCCC)=CC=C1C1=NC(C=2C(=CC(C)=CC=2)C)=NC(C=2C(=CC(C)=CC=2)C)=N1 ZSSVCEUEVMALRD-UHFFFAOYSA-N 0.000 description 2
- ZCILGMFPJBRCNO-UHFFFAOYSA-N 4-phenyl-2H-benzotriazol-5-ol Chemical compound OC1=CC=C2NN=NC2=C1C1=CC=CC=C1 ZCILGMFPJBRCNO-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 229920002943 EPDM rubber Polymers 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- 238000003547 Friedel-Crafts alkylation reaction Methods 0.000 description 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 2
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- SLYJXPKHTZCZOG-UHFFFAOYSA-N n-tetradecyltetradecan-1-imine oxide Chemical compound CCCCCCCCCCCCCC[N+]([O-])=CCCCCCCCCCCCCC SLYJXPKHTZCZOG-UHFFFAOYSA-N 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920005615 natural polymer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- 239000002667 nucleating agent Substances 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- JVIACMXZJQZCGM-UHFFFAOYSA-N octyl 2-[(3,5-ditert-butyl-4-hydroxyphenyl)methylsulfanyl]acetate Chemical compound CCCCCCCCOC(=O)CSCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 JVIACMXZJQZCGM-UHFFFAOYSA-N 0.000 description 1
- WSLDIBCXIOECNX-UHFFFAOYSA-N octylhydrazine Chemical compound CCCCCCCCNN WSLDIBCXIOECNX-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229960000969 phenyl salicylate Drugs 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 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
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920001084 poly(chloroprene) Polymers 0.000 description 1
- 229920001643 poly(ether ketone) Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920002312 polyamide-imide Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920001748 polybutylene Polymers 0.000 description 1
- 229920001707 polybutylene terephthalate Polymers 0.000 description 1
- 229920006289 polycarbonate film Polymers 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 238000012667 polymer degradation Methods 0.000 description 1
- 239000002897 polymer film coating Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920000069 polyphenylene sulfide Polymers 0.000 description 1
- 229920005606 polypropylene copolymer Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920002620 polyvinyl fluoride Polymers 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000011241 protective layer Substances 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
- 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
- WBHHMMIMDMUBKC-QJWNTBNXSA-M ricinoleate Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCCC([O-])=O WBHHMMIMDMUBKC-QJWNTBNXSA-M 0.000 description 1
- 229940066675 ricinoleate Drugs 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
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000009987 spinning Methods 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
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- MHSKRLJMQQNJNC-UHFFFAOYSA-N terephthalamide Chemical compound NC(=O)C1=CC=C(C(N)=O)C=C1 MHSKRLJMQQNJNC-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
- 239000004753 textile Substances 0.000 description 1
- 239000004634 thermosetting polymer Substances 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 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
- 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
- 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
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- UIYCHXAGWOYNNA-UHFFFAOYSA-N vinyl sulfide Chemical group C=CSC=C UIYCHXAGWOYNNA-UHFFFAOYSA-N 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
Classifications
-
- 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
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31678—Of metal
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31678—Of metal
- Y10T428/31692—Next to addition polymer from unsaturated monomers
- Y10T428/31699—Ester, halide or nitrile of addition polymer
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)
- Adhesives Or Adhesive Processes (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/703751 | 1996-08-27 | ||
| US08/703,751 US5726309A (en) | 1996-08-27 | 1996-08-27 | Tris-aryls-triazines substituted with biphenylyl groups |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU3517597A AU3517597A (en) | 1998-03-05 |
| AU725829B2 true AU725829B2 (en) | 2000-10-19 |
Family
ID=24826635
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU35175/97A Ceased AU725829B2 (en) | 1996-08-27 | 1997-08-20 | Tris-aryl s-triazines substituted with biphenylyl groups |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US5726309A (enExample) |
| EP (1) | EP0826675A1 (enExample) |
| JP (1) | JPH1087637A (enExample) |
| KR (1) | KR100474240B1 (enExample) |
| AU (1) | AU725829B2 (enExample) |
| BR (1) | BR9704503A (enExample) |
| CA (1) | CA2213958A1 (enExample) |
| MX (1) | MX9706168A (enExample) |
| TW (1) | TW470761B (enExample) |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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. |
| US6239276B1 (en) | 1998-06-22 | 2001-05-29 | Cytec Technology Corporation | Non-yellowing para-tertiary-alkyl phenyl substituted triazine and pyrimidine ultraviolet light absorbers |
| US6297377B1 (en) | 1998-06-22 | 2001-10-02 | Cytec Technology Corporation | Benzocycle-substituted triazine and pyrimidine ultraviolet light absorbers |
| TWI259182B (en) | 1998-11-17 | 2006-08-01 | Cytec Tech Corp | Process for preparing triazines using a combination of Lewis acids with reaction promoters |
| US6191199B1 (en) | 1999-05-03 | 2001-02-20 | Ciba Speciatly Chemicals Corporation | Stabilized adhesive compositions containing highly soluble, high extinction photostable hydroxyphenyl-s-triazine UV absorbers and laminated articles derived therefrom |
| AU780351B2 (en) * | 2000-02-01 | 2005-03-17 | Ciba Specialty Chemicals Holding Inc. | Method of content protection with durable UV absorbers |
| GB2361005B (en) | 2000-04-04 | 2002-08-14 | Ciba Sc Holding Ag | Synergistic mixtures of uv-absorbers in polyolefins |
| US6867250B1 (en) | 2000-10-30 | 2005-03-15 | Cytec Technology Corp. | Non-yellowing ortho-dialkyl aryl substituted triazine ultraviolet light absorbers |
| US6492521B2 (en) | 2000-11-03 | 2002-12-10 | Cytec Technology Corp. | Hindered amine light stabilizers based on multi-functional carbonyl compounds and methods of making same |
| US6545156B1 (en) | 2000-11-03 | 2003-04-08 | Cytec Technology Corp. | Oligomeric hindered amine light stabilizers based on multi-functional carbonyl compounds and methods of making same |
| US6727300B2 (en) | 2000-11-03 | 2004-04-27 | Cytec Technology Corp. | Polymeric articles containing hindered amine light stabilizers based on multi-functional carbonyl compounds |
| US6414155B1 (en) | 2000-11-03 | 2002-07-02 | Cytec Technology Corp. | Oligomeric hindered amine light stabilizers based on multi-functional carbonyl compounds and methods of making same |
| DE60219447T2 (de) * | 2001-03-22 | 2007-12-13 | Ciba Speciality Chemicals Holding Inc. | Verwendung von aromatischen verbindungen als mittel zur kontrolle der phase sowie zur reduzierung der teilchengrösse von chinacridonpigmenten |
| US6855269B2 (en) * | 2001-11-09 | 2005-02-15 | Cytec Technology Corp. | Phenyl ether-substituted hydroxyphenyl triazine ultraviolet light absorbers |
| ATE539058T1 (de) | 2003-02-26 | 2012-01-15 | Basf Se | Wasserverträgliche sterisch gehinderte hydroxysubstitutierte alkoxyamine |
| US7595011B2 (en) | 2004-07-12 | 2009-09-29 | Ciba Specialty Chemicals Corporation | Stabilized electrochromic media |
| DE102005041952A1 (de) * | 2005-09-03 | 2007-03-08 | Bayer Materialscience Ag | Zusammensetzungen enthaltend Polycarbonat und neuartige UV-Absorber |
| US20070238814A1 (en) * | 2006-04-10 | 2007-10-11 | Basf Corporation | Method of making coating compositions |
| US8399536B2 (en) | 2007-06-29 | 2013-03-19 | Basell Poliolefine Italia, s.r.l. | Irradiated polyolefin composition comprising a non-phenolic stabilizer |
| DK2331625T3 (da) | 2008-09-05 | 2012-04-02 | Thor Gmbh | Flammebeskyttelsespræparat indeholdende et phosphonsyrederivat |
| BRPI0923420A2 (pt) | 2008-12-22 | 2018-10-16 | Basf Se | uso, ou método de uso, ou processo de uso de um agente de redução de fricção em combinação com um polímero enxertado , em adição a uma amida de acido graxo. |
| ES2463674T3 (es) | 2009-01-19 | 2014-05-28 | Basf Se | Pigmentos negros orgánicos y su preparación |
| CN102471090B (zh) | 2009-07-07 | 2015-11-25 | 巴斯夫欧洲公司 | 钾铯钨青铜颗粒 |
| JP5898201B2 (ja) | 2010-09-14 | 2016-04-06 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | 特定のビス（ビフェニル）トリアジン誘導体及びその混合物の紫外線吸収剤としての使用 |
| EP2912017A4 (en) | 2012-10-23 | 2016-07-20 | Basf Se | ETHYLENICALLY UNSATURATED OLIGOMERS WITH POLYMER STABILIZATION GROUPS |
| EP3049464B1 (en) | 2013-09-27 | 2020-04-01 | Basf Se | Polyolefin compositions for building materials |
| US10294423B2 (en) | 2013-11-22 | 2019-05-21 | Polnox Corporation | Macromolecular antioxidants based on dual type moiety per molecule: structures, methods of making and using the same |
| TWI685524B (zh) | 2013-12-17 | 2020-02-21 | 美商畢克美國股份有限公司 | 預先脫層之層狀材料 |
| EP3564299B1 (en) | 2015-07-20 | 2023-09-06 | Basf Se | Flame retardant polyolefin articles |
| EP3841166B2 (en) | 2018-08-22 | 2025-05-07 | Basf Se | Stabilized rotomolded polyolefin |
| WO2020190833A1 (en) | 2019-03-18 | 2020-09-24 | Basf Se | Uv curable compositions for dirt pick-up resistance |
| US20220282064A1 (en) | 2019-07-30 | 2022-09-08 | Basf Se | Stabilizer composition |
Family Cites Families (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE614726A (enExample) * | 1961-03-06 | |||
| US3118887A (en) * | 1961-03-06 | 1964-01-21 | American Cyanamid Co | O-hydroxy substituted tris aryl-s-triazines |
| NL299881A (enExample) * | 1962-10-30 | |||
| CH480090A (de) * | 1962-10-30 | 1969-10-31 | Ciba Geigy | Verwendung von neuen Hydroxyphenyl-1,3,5-triazinen als Ultraviolettschutzmittel ausserhalb der Textilindustrie |
| NL130993C (enExample) * | 1963-02-07 | |||
| FR1494413A (fr) * | 1965-09-24 | 1967-09-08 | Ciba Geigy | Nouveaux dérivés hydroxyphényl-1,3,5-triazines contenant des groupes sulfoniques, procédé pour les préparer et leur emploi |
| CH478589A (de) * | 1965-09-24 | 1969-09-30 | Ciba Geigy | Verwendung von Aryl-1,3,5-triazinen als Stabilisierungsmittel gegen Ultraviolettstrahlung und Hitzeeinwirkung ausserhalb der Textilindustrie |
| EP0165608B1 (de) * | 1984-06-22 | 1991-01-02 | Ilford Ag | Hydroxyphenyltriazine, Verfahren zu ihrer Herstellung und ihre Verwendung als UV-Absorber |
| US4619956A (en) * | 1985-05-03 | 1986-10-28 | American Cyanamid Co. | Stabilization of high solids coatings with synergistic combinations |
| US4831068A (en) * | 1987-02-27 | 1989-05-16 | Ciba-Geigy Corporation | Process for improving the photochemical stability of dyeings on polyester fibre materials |
| US4950304A (en) * | 1987-10-02 | 1990-08-21 | Ciba-Geigy Corporation | Process for quenching or suppressing the fluorescence of substrates treated with fluorescent whitening agents |
| US4826978A (en) * | 1987-12-29 | 1989-05-02 | Milliken Research Corporation | Reactive, non-yellowing triazine compounds useful as UV screening agents for polymers |
| US4962142A (en) * | 1987-12-29 | 1990-10-09 | Milliken Research Corporation | Reactive, non-yellowing triazine compounds useful as UV screening agents for polymers |
| DE59008517D1 (de) * | 1989-08-25 | 1995-03-30 | Ciba Geigy Ag | Lichtstabilisierte Tinten. |
| ATE151097T1 (de) * | 1989-12-05 | 1997-04-15 | Ciba Geigy | Stabilisiertes organisches material |
| EP0442847B2 (de) * | 1990-02-16 | 2000-08-23 | Ciba SC Holding AG | Gegen Schädigung durch Licht, Wärme und Sauerstoff stabilisierte Ueberzugsmittel |
| EP0444323B1 (en) * | 1990-02-28 | 1997-03-19 | Cytec Technology Corp. | Stabilization of high solids coating with liquid compositions of triazine UV absorbers |
| ES2081458T3 (es) * | 1990-03-30 | 1996-03-16 | Ciba Geigy Ag | Composicion de pintura. |
| ES2074688T5 (es) * | 1990-07-23 | 1998-11-01 | Ciba Geigy Ag | Dispersion acuosa de absorbentes de uv poco solubles. |
| ES2099721T3 (es) * | 1990-10-29 | 1997-06-01 | Cytec Tech Corp | Composiciones sinergicas absorbentes de radiacion ultravioleta que contienen hidroxi aril triazinas y tetraalquil piperidinas. |
| TW222292B (enExample) * | 1991-02-21 | 1994-04-11 | Ciba Geigy Ag | |
| KR100187320B1 (ko) * | 1991-02-21 | 1999-04-01 | 월터 클리웨인 | 광, 산소 및 열에 대해 안정화된 도료 |
| US5354794A (en) * | 1993-02-03 | 1994-10-11 | Ciba-Geigy Corporation | Electro coat/base coat/clear coat finishes stabilized with S-triazine UV absorbers |
| US5556973A (en) * | 1994-07-27 | 1996-09-17 | Ciba-Geigy Corporation | Red-shifted tris-aryl-s-triazines and compositions stabilized therewith |
| EP1213283B1 (en) * | 1995-03-15 | 2009-04-29 | Ciba Holding Inc. | Biphenyl-substituted triazines as light stabilisers |
| US5726309A (en) * | 1996-08-27 | 1998-03-10 | Ciba Specialty Chemicals Corporation | Tris-aryls-triazines substituted with biphenylyl groups |
-
1996
- 1996-08-27 US US08/703,751 patent/US5726309A/en not_active Expired - Fee Related
-
1997
- 1997-08-13 MX MX9706168A patent/MX9706168A/es unknown
- 1997-08-19 EP EP97810583A patent/EP0826675A1/en not_active Withdrawn
- 1997-08-20 AU AU35175/97A patent/AU725829B2/en not_active Ceased
- 1997-08-25 TW TW086112171A patent/TW470761B/zh not_active IP Right Cessation
- 1997-08-25 KR KR1019970040583A patent/KR100474240B1/ko not_active Expired - Fee Related
- 1997-08-25 CA CA002213958A patent/CA2213958A1/en not_active Abandoned
- 1997-08-26 JP JP9244677A patent/JPH1087637A/ja not_active Withdrawn
- 1997-08-26 BR BR9704503A patent/BR9704503A/pt active Search and Examination
- 1997-09-08 US US08/925,016 patent/US5849821A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| KR100474240B1 (ko) | 2005-06-20 |
| JPH1087637A (ja) | 1998-04-07 |
| KR19980018969A (ko) | 1998-06-05 |
| BR9704503A (pt) | 1998-11-17 |
| CA2213958A1 (en) | 1998-02-27 |
| US5849821A (en) | 1998-12-15 |
| EP0826675A1 (en) | 1998-03-04 |
| TW470761B (en) | 2002-01-01 |
| AU3517597A (en) | 1998-03-05 |
| MX9706168A (es) | 1998-02-28 |
| US5726309A (en) | 1998-03-10 |
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