SE522839C2 - Trisresorcinyltriaziner - Google Patents

Info

Publication number

SE522839C2

SE522839C2 SE9901628A SE9901628A SE522839C2 SE 522839 C2 SE522839 C2 SE 522839C2 SE 9901628 A SE9901628 A SE 9901628A SE 9901628 A SE9901628 A SE 9901628A SE 522839 C2 SE522839 C2 SE 522839C2

Authority

SE

Sweden

Prior art keywords

alkyl

substituted

phenyl

cycloalkyl

alkenyl

Prior art date

1998-05-07

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• 150000001875 compounds Chemical class 0.000 claims abstract description 92
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 60
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 58
• 239000003381 stabilizer Substances 0.000 claims abstract description 37
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims abstract description 32
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 18
• 239000001301 oxygen Substances 0.000 claims abstract description 18
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 10
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 7
• 239000011368 organic material Substances 0.000 claims abstract description 7
• 101150020251 NR13 gene Proteins 0.000 claims abstract 3
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract 2
• -1 phenyloxy Chemical group 0.000 claims description 148
• 125000000217 alkyl group Chemical group 0.000 claims description 94
• 239000000203 mixture Substances 0.000 claims description 91
• 229910052757 nitrogen Inorganic materials 0.000 claims description 68
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 50
• 229920000642 polymer Polymers 0.000 claims description 41
• 125000003342 alkenyl group Chemical group 0.000 claims description 37
• 238000000576 coating method Methods 0.000 claims description 34
• 239000011230 binding agent Substances 0.000 claims description 31
• 239000000463 material Substances 0.000 claims description 31
• 125000005037 alkyl phenyl group Chemical group 0.000 claims description 24
• 229910052799 carbon Inorganic materials 0.000 claims description 21
• 239000011248 coating agent Substances 0.000 claims description 19
• 239000002023 wood Substances 0.000 claims description 19
• 125000003884 phenylalkyl group Chemical group 0.000 claims description 18
• 238000000034 method Methods 0.000 claims description 16
• 229910052736 halogen Inorganic materials 0.000 claims description 14
• 150000001412 amines Chemical class 0.000 claims description 13
• 125000004432 carbon atom Chemical group C* 0.000 claims description 13
• 229910003849 O-Si Inorganic materials 0.000 claims description 11
• 229910003872 O—Si Inorganic materials 0.000 claims description 11
• 150000001602 bicycloalkyls Chemical group 0.000 claims description 11
• 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 11
• 125000005842 heteroatom Chemical group 0.000 claims description 11
• 150000002367 halogens Chemical class 0.000 claims description 10
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 9
• 125000003545 alkoxy group Chemical group 0.000 claims description 9
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
• 229910052739 hydrogen Inorganic materials 0.000 claims description 9
• 238000005470 impregnation Methods 0.000 claims description 9
• 239000004611 light stabiliser Substances 0.000 claims description 9
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 8
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
• 229920001169 thermoplastic Polymers 0.000 claims description 8
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 7
• 125000005843 halogen group Chemical group 0.000 claims description 7
• 229920005613 synthetic organic polymer Polymers 0.000 claims description 7
• 125000003302 alkenyloxy group Chemical group 0.000 claims description 6
• 239000001257 hydrogen Substances 0.000 claims description 6
• 238000002156 mixing Methods 0.000 claims description 6
• HWRLEEPNFJNTOP-UHFFFAOYSA-N 2-(1,3,5-triazin-2-yl)phenol Chemical class OC1=CC=CC=C1C1=NC=NC=N1 HWRLEEPNFJNTOP-UHFFFAOYSA-N 0.000 claims description 5
• 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 5
• MPDRQNFMNLORAE-UHFFFAOYSA-N ethyl 2-[4-[4,6-bis[4-(1-ethoxy-2-methyl-1-oxopropan-2-yl)oxy-2-hydroxyphenyl]-1,3,5-triazin-2-yl]-3-hydroxyphenoxy]-2-methylpropanoate Chemical compound OC1=CC(OC(C)(C)C(=O)OCC)=CC=C1C1=NC(C=2C(=CC(OC(C)(C)C(=O)OCC)=CC=2)O)=NC(C=2C(=CC(OC(C)(C)C(=O)OCC)=CC=2)O)=N1 MPDRQNFMNLORAE-UHFFFAOYSA-N 0.000 claims description 5
• 230000000087 stabilizing effect Effects 0.000 claims description 5
• 229910052717 sulfur Inorganic materials 0.000 claims description 5
• 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 4
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 4
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
• 239000003963 antioxidant agent Substances 0.000 claims description 4
• 125000003118 aryl group Chemical group 0.000 claims description 4
• 230000009931 harmful effect Effects 0.000 claims description 4
• FJGQBLRYBUAASW-UHFFFAOYSA-N 2-(benzotriazol-2-yl)phenol Chemical class OC1=CC=CC=C1N1N=C2C=CC=CC2=N1 FJGQBLRYBUAASW-UHFFFAOYSA-N 0.000 claims description 3
• 239000000853 adhesive Substances 0.000 claims description 3
• 230000001070 adhesive effect Effects 0.000 claims description 3
• 125000000623 heterocyclic group Chemical group 0.000 claims description 3
• XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical class OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 claims description 3
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 2
• JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical class C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 claims description 2
• 125000005915 C6-C14 aryl group Chemical group 0.000 claims 4
• 125000005293 bicycloalkoxy group Chemical group 0.000 claims 2
• 125000001183 hydrocarbyl group Chemical group 0.000 claims 2
• 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims 1
• ACZGCWSMSTYWDQ-UHFFFAOYSA-N 3h-1-benzofuran-2-one Chemical class C1=CC=C2OC(=O)CC2=C1 ACZGCWSMSTYWDQ-UHFFFAOYSA-N 0.000 claims 1
• 101000941450 Lasioglossum laticeps Lasioglossin-1 Proteins 0.000 claims 1
• 235000015097 nutrients Nutrition 0.000 claims 1
• 239000011253 protective coating Substances 0.000 claims 1
• 125000000896 monocarboxylic acid group Chemical group 0.000 abstract description 6
• 101100240519 Caenorhabditis elegans nhr-13 gene Proteins 0.000 abstract 1
• 230000000254 damaging effect Effects 0.000 abstract 1
• PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 49
• 239000010410 layer Substances 0.000 description 35
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• 239000003973 paint Substances 0.000 description 26
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• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 21
• 239000008199 coating composition Substances 0.000 description 19
• 229910052751 metal Inorganic materials 0.000 description 19
• 239000002184 metal Substances 0.000 description 19
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
• 239000007983 Tris buffer Substances 0.000 description 16
• 239000003054 catalyst Substances 0.000 description 16
• 239000003795 chemical substances by application Substances 0.000 description 16
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 15
• KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 14
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
• 239000005977 Ethylene Substances 0.000 description 13
• MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 13
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 13
• NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 12
• VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 12
• 150000001252 acrylic acid derivatives Chemical class 0.000 description 12
• 150000002148 esters Chemical class 0.000 description 12
• 239000000758 substrate Substances 0.000 description 12
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• 239000004952 Polyamide Substances 0.000 description 11
• 238000006243 chemical reaction Methods 0.000 description 11
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• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
• 229960003742 phenol Drugs 0.000 description 10
• 239000004814 polyurethane Substances 0.000 description 10
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
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• 238000001723 curing Methods 0.000 description 9
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
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• 239000004721 Polyphenylene oxide Substances 0.000 description 8
• 229920000180 alkyd Polymers 0.000 description 8
• 239000012964 benzotriazole Substances 0.000 description 8
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• GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 8
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• QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 7
• 229940125904 compound 1 Drugs 0.000 description 7
• 238000001035 drying Methods 0.000 description 7
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• SGZWJGRZDJCDIM-UHFFFAOYSA-N 4-[4,6-bis(2,4-dihydroxyphenyl)-1,3,5-triazin-2-yl]benzene-1,3-diol Chemical compound OC1=CC(O)=CC=C1C1=NC(C=2C(=CC(O)=CC=2)O)=NC(C=2C(=CC(O)=CC=2)O)=N1 SGZWJGRZDJCDIM-UHFFFAOYSA-N 0.000 description 6
• 239000004925 Acrylic resin Substances 0.000 description 6
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• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
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