NL1014139C2 - Benzotriazool-UV-absorptiemiddelen met een verbeterde duurzaamheid. - Google Patents

Info

Publication number

NL1014139C2

NL1014139C2 NL1014139A NL1014139A NL1014139C2 NL 1014139 C2 NL1014139 C2 NL 1014139C2 NL 1014139 A NL1014139 A NL 1014139A NL 1014139 A NL1014139 A NL 1014139A NL 1014139 C2 NL1014139 C2 NL 1014139C2

Authority

NL

Netherlands

Prior art keywords

carbon atoms

alkyl

phenyl

tert

straight

Prior art date

1999-01-21

Links

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• 239000006096 absorbing agent Substances 0.000 title claims description 28
• 239000012964 benzotriazole Substances 0.000 title description 41
• QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 title description 33
• -1 butylene, butynylene Chemical group 0.000 claims description 197
• 150000001875 compounds Chemical class 0.000 claims description 153
• 125000004432 carbon atom Chemical group C* 0.000 claims description 133
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 92
• 125000000217 alkyl group Chemical group 0.000 claims description 91
• 239000000203 mixture Substances 0.000 claims description 74
• 239000001257 hydrogen Substances 0.000 claims description 72
• 229910052739 hydrogen Inorganic materials 0.000 claims description 72
• PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 52
• 150000002431 hydrogen Chemical class 0.000 claims description 43
• 150000001565 benzotriazoles Chemical class 0.000 claims description 38
• 125000003884 phenylalkyl group Chemical group 0.000 claims description 36
• 125000003342 alkenyl group Chemical group 0.000 claims description 34
• 229920001577 copolymer Polymers 0.000 claims description 34
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 28
• 229920000642 polymer Polymers 0.000 claims description 27
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 24
• 125000002947 alkylene group Chemical group 0.000 claims description 24
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 22
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 21
• 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 20
• 239000004417 polycarbonate Substances 0.000 claims description 19
• VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 18
• 239000005977 Ethylene Substances 0.000 claims description 18
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 18
• 150000001412 amines Chemical class 0.000 claims description 17
• 229920000515 polycarbonate Polymers 0.000 claims description 17
• 238000000576 coating method Methods 0.000 claims description 16
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
• 125000001424 substituent group Chemical group 0.000 claims description 15
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 15
• 229910052731 fluorine Inorganic materials 0.000 claims description 14
• 239000011737 fluorine Substances 0.000 claims description 13
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 13
• 229920006324 polyoxymethylene Polymers 0.000 claims description 13
• 239000004952 Polyamide Substances 0.000 claims description 12
• 229920002647 polyamide Polymers 0.000 claims description 12
• 229920000915 polyvinyl chloride Polymers 0.000 claims description 12
• 239000004800 polyvinyl chloride Substances 0.000 claims description 12
• 125000003118 aryl group Chemical group 0.000 claims description 11
• 125000004956 cyclohexylene group Chemical group 0.000 claims description 11
• 150000003254 radicals Chemical class 0.000 claims description 11
• CUVYXWPVMUJMAU-UHFFFAOYSA-N 2,4-bis(2-methylbutan-2-yl)-6-[5-(trifluoromethyl)benzotriazol-2-yl]phenol Chemical compound CCC(C)(C)C1=CC(C(C)(C)CC)=CC(N2N=C3C=C(C=CC3=N2)C(F)(F)F)=C1O CUVYXWPVMUJMAU-UHFFFAOYSA-N 0.000 claims description 10
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
• 239000011368 organic material Substances 0.000 claims description 10
• VNHBJPHMBDPOJS-UHFFFAOYSA-N 2,4-ditert-butyl-6-[5-(trifluoromethyl)benzotriazol-2-yl]phenol Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC(N2N=C3C=C(C=CC3=N2)C(F)(F)F)=C1O VNHBJPHMBDPOJS-UHFFFAOYSA-N 0.000 claims description 9
• 229920000122 acrylonitrile butadiene styrene Polymers 0.000 claims description 9
• 239000011248 coating agent Substances 0.000 claims description 9
• 229920000728 polyester Polymers 0.000 claims description 9
• 230000000087 stabilizing effect Effects 0.000 claims description 9
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 8
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 8
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 8
• 230000015556 catabolic process Effects 0.000 claims description 8
• 238000006731 degradation reaction Methods 0.000 claims description 8
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 7
• 239000004814 polyurethane Substances 0.000 claims description 7
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 6
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
• 230000001590 oxidative effect Effects 0.000 claims description 6
• 229920000098 polyolefin Polymers 0.000 claims description 6
• WMBMNOPFBSLJLS-UHFFFAOYSA-N 4-(3-hydroxypropyl)-2-[5-(trifluoromethyl)benzotriazol-2-yl]phenol Chemical compound OCCCC1=CC=C(O)C(N2N=C3C=C(C=CC3=N2)C(F)(F)F)=C1 WMBMNOPFBSLJLS-UHFFFAOYSA-N 0.000 claims description 5
• 229930182556 Polyacetal Natural products 0.000 claims description 5
• 125000001118 alkylidene group Chemical group 0.000 claims description 5
• 125000003438 dodecyl group Chemical group [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])* 0.000 claims description 5
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 5
• 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 5
• 229920002635 polyurethane Polymers 0.000 claims description 5
• VLZRPBFWPDEATD-UHFFFAOYSA-N 3-[4-hydroxy-3-[5-(trifluoromethyl)benzotriazol-2-yl]phenyl]propyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCC1=CC=C(O)C(N2N=C3C=C(C=CC3=N2)C(F)(F)F)=C1 VLZRPBFWPDEATD-UHFFFAOYSA-N 0.000 claims description 4
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 4
• 239000000460 chlorine Substances 0.000 claims description 4
• 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 4
• 229920001971 elastomer Polymers 0.000 claims description 4
• 229920000554 ionomer Polymers 0.000 claims description 4
• 229920000058 polyacrylate Polymers 0.000 claims description 4
• HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical class OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 claims description 3
• JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical class C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 claims description 3
• YCWJIUAUMAHNDB-UHFFFAOYSA-N 2-[5-(trifluoromethyl)benzotriazol-2-yl]-4,6-bis(2,4,4-trimethylpentan-2-yl)phenol Chemical compound CC(C)(C)CC(C)(C)C1=CC(C(C)(C)CC(C)(C)C)=CC(N2N=C3C=C(C=CC3=N2)C(F)(F)F)=C1O YCWJIUAUMAHNDB-UHFFFAOYSA-N 0.000 claims description 3
• UKLWBVVORWJQLP-UHFFFAOYSA-N 2-[[2-hydroxy-3-[5-(1,1,2,2,2-pentafluoroethyl)benzotriazol-2-yl]-5-(2,4,4-trimethylpentan-2-yl)phenyl]methyl]-6-[5-(1,1,2,2,2-pentafluoroethyl)benzotriazol-2-yl]-4-(2,4,4-trimethylpentan-2-yl)phenol Chemical compound C(C1=C(C(=CC(=C1)C(C)(C)CC(C)(C)C)N1N=C2C(=N1)C=CC(=C2)C(C(F)(F)F)(F)F)O)C2=C(C(=CC(=C2)C(C)(C)CC(C)(C)C)N2N=C1C(=N2)C=CC(=C1)C(C(F)(F)F)(F)F)O UKLWBVVORWJQLP-UHFFFAOYSA-N 0.000 claims description 3
• MMPCZTQLVSESIT-UHFFFAOYSA-N 3-[3-tert-butyl-4-hydroxy-5-[5-(trifluoromethyl)benzotriazol-2-yl]phenyl]propanoic acid Chemical compound CC(C)(C)C1=CC(CCC(O)=O)=CC(N2N=C3C=C(C=CC3=N2)C(F)(F)F)=C1O MMPCZTQLVSESIT-UHFFFAOYSA-N 0.000 claims description 3
• QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims description 3
• YBGAHDSWZZNBNR-UHFFFAOYSA-N 4-(2-hydroxyethyl)-2-[5-(trifluoromethyl)benzotriazol-2-yl]phenol Chemical compound OCCC1=CC=C(O)C(N2N=C3C=C(C=CC3=N2)C(F)(F)F)=C1 YBGAHDSWZZNBNR-UHFFFAOYSA-N 0.000 claims description 3
• GIXUOHIZMFNXGJ-UHFFFAOYSA-N 4-tert-butyl-2-[5-(1,1,2,2,2-pentafluoroethyl)benzotriazol-2-yl]phenol Chemical compound CC(C)(C)C1=CC(N2N=C3C=CC(=CC3=N2)C(F)(F)C(F)(F)F)=C(O)C=C1 GIXUOHIZMFNXGJ-UHFFFAOYSA-N 0.000 claims description 3
• CIYRKILUPYIMEP-UHFFFAOYSA-N C(C)(CC)N(C(=O)C=1C=C(C=CC=1F)C1NC(NC(=C1C(=O)NC=1C=C2C=NNC2=CC=1)C)=O)C Chemical compound C(C)(CC)N(C(=O)C=1C=C(C=CC=1F)C1NC(NC(=C1C(=O)NC=1C=C2C=NNC2=CC=1)C)=O)C CIYRKILUPYIMEP-UHFFFAOYSA-N 0.000 claims description 3
• SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims description 3
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 3
• 239000004677 Nylon Substances 0.000 claims description 3
• 229930040373 Paraformaldehyde Natural products 0.000 claims description 3
• 125000004450 alkenylene group Chemical group 0.000 claims description 3
• 125000000732 arylene group Chemical group 0.000 claims description 3
• 150000001558 benzoic acid derivatives Chemical class 0.000 claims description 3
• 125000005569 butenylene group Chemical group 0.000 claims description 3
• 229910052801 chlorine Inorganic materials 0.000 claims description 3
• 125000002993 cycloalkylene group Chemical group 0.000 claims description 3
• 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 claims description 3
• 229920001778 nylon Polymers 0.000 claims description 3
• 125000004193 piperazinyl group Chemical group 0.000 claims description 3
• 229920002037 poly(vinyl butyral) polymer Polymers 0.000 claims description 3
• 150000003839 salts Chemical class 0.000 claims description 3
• 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 2
• RDTOLUHUJLQOAV-UHFFFAOYSA-N 2-(5-fluorobenzotriazol-2-yl)-4,6-bis(2-phenylpropan-2-yl)phenol Chemical compound C=1C(N2N=C3C=C(F)C=CC3=N2)=C(O)C(C(C)(C)C=2C=CC=CC=2)=CC=1C(C)(C)C1=CC=CC=C1 RDTOLUHUJLQOAV-UHFFFAOYSA-N 0.000 claims description 2
• BLYCZGIZZQKNOA-UHFFFAOYSA-N 2-dodecyl-4-methyl-6-[5-(trifluoromethyl)benzotriazol-2-yl]phenol Chemical compound CCCCCCCCCCCCC1=CC(C)=CC(N2N=C3C=C(C=CC3=N2)C(F)(F)F)=C1O BLYCZGIZZQKNOA-UHFFFAOYSA-N 0.000 claims description 2
• YVVFERCUUGXZLE-UHFFFAOYSA-N 2-tert-butyl-4-(2-hydroxyethyl)-6-[5-(trifluoromethyl)benzotriazol-2-yl]phenol Chemical compound CC(C)(C)C1=CC(CCO)=CC(N2N=C3C=C(C=CC3=N2)C(F)(F)F)=C1O YVVFERCUUGXZLE-UHFFFAOYSA-N 0.000 claims description 2
• RLVCEWCIXYRSGI-UHFFFAOYSA-N 2-tert-butyl-4-(3-hydroxypropyl)-6-[5-(trifluoromethyl)benzotriazol-2-yl]phenol Chemical compound CC(C)(C)C1=CC(CCCO)=CC(N2N=C3C=C(C=CC3=N2)C(F)(F)F)=C1O RLVCEWCIXYRSGI-UHFFFAOYSA-N 0.000 claims description 2
• JMKCXYQPSPGNEB-UHFFFAOYSA-N 3-[4-hydroxy-3-[5-(trifluoromethyl)benzotriazol-2-yl]phenyl]propyl prop-2-enoate Chemical compound OC1=CC=C(CCCOC(=O)C=C)C=C1N1N=C2C=C(C(F)(F)F)C=CC2=N1 JMKCXYQPSPGNEB-UHFFFAOYSA-N 0.000 claims description 2
• VQBWHLAHWBTSPR-UHFFFAOYSA-N 3-[4-hydroxy-3-[5-(trifluoromethyl)benzotriazol-2-yl]phenyl]propyl propanoate Chemical compound CCC(=O)OCCCC1=CC(N2N=C3C=CC(=CC3=N2)C(F)(F)F)=C(O)C=C1 VQBWHLAHWBTSPR-UHFFFAOYSA-N 0.000 claims description 2
• FXUZBFKATOWFLD-UHFFFAOYSA-N 6-methylheptyl 3-[3-tert-butyl-4-hydroxy-5-[5-(trifluoromethyl)benzotriazol-2-yl]phenyl]propanoate Chemical compound CC(C)(C)C1=CC(CCC(=O)OCCCCCC(C)C)=CC(N2N=C3C=C(C=CC3=N2)C(F)(F)F)=C1O FXUZBFKATOWFLD-UHFFFAOYSA-N 0.000 claims description 2
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• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
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• IEWIVPAOIABCGF-UHFFFAOYSA-N n-[3-[4-hydroxy-3-[5-(trifluoromethyl)benzotriazol-2-yl]phenyl]propyl]prop-2-enamide Chemical compound OC1=CC=C(CCCNC(=O)C=C)C=C1N1N=C2C=C(C(F)(F)F)C=CC2=N1 IEWIVPAOIABCGF-UHFFFAOYSA-N 0.000 claims description 2
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• 125000006686 (C1-C24) alkyl group Chemical group 0.000 claims 3
• GLSKMRNRRMNAQS-UHFFFAOYSA-N 5-(trifluoromethyl)-2h-benzotriazole Chemical compound C1=C(C(F)(F)F)C=CC2=NNN=C21 GLSKMRNRRMNAQS-UHFFFAOYSA-N 0.000 claims 1
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