CH693032A5 - Benzotriazol-UV-Absorptionsmittel mit erhöhter Haltbarkeit. - Google Patents

Info

Publication number

CH693032A5

CH693032A5 CH02549/97A CH254997A CH693032A5 CH 693032 A5 CH693032 A5 CH 693032A5 CH 02549/97 A CH02549/97 A CH 02549/97A CH 254997 A CH254997 A CH 254997A CH 693032 A5 CH693032 A5 CH 693032A5

Authority

CH

Switzerland

Prior art keywords

carbon atoms

alkyl

chain

tert

phenyl

Prior art date

1996-11-07

Links

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• QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 title claims description 29
• 239000012964 benzotriazole Substances 0.000 title claims description 29
• 230000002745 absorbent Effects 0.000 title 1
• 239000002250 absorbent Substances 0.000 title 1
• -1 acrylic polyol Chemical class 0.000 claims description 157
• 125000004432 carbon atom Chemical group C* 0.000 claims description 93
• 239000000203 mixture Substances 0.000 claims description 75
• 150000001875 compounds Chemical class 0.000 claims description 66
• 239000001257 hydrogen Substances 0.000 claims description 62
• 229910052739 hydrogen Inorganic materials 0.000 claims description 62
• 125000000217 alkyl group Chemical group 0.000 claims description 59
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 55
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 25
• 125000003884 phenylalkyl group Chemical group 0.000 claims description 21
• 239000007787 solid Substances 0.000 claims description 20
• 229920000877 Melamine resin Polymers 0.000 claims description 19
• NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 19
• 229920005989 resin Polymers 0.000 claims description 18
• 239000011347 resin Substances 0.000 claims description 18
• VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 16
• 239000005977 Ethylene Substances 0.000 claims description 16
• 150000003254 radicals Chemical class 0.000 claims description 16
• 125000002947 alkylene group Chemical group 0.000 claims description 15
• 238000000576 coating method Methods 0.000 claims description 15
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 14
• 125000003342 alkenyl group Chemical group 0.000 claims description 13
• 238000002835 absorbance Methods 0.000 claims description 11
• 125000003118 aryl group Chemical group 0.000 claims description 11
• 125000004956 cyclohexylene group Chemical group 0.000 claims description 11
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• 239000004593 Epoxy Substances 0.000 claims description 9
• 239000011248 coating agent Substances 0.000 claims description 9
• 239000004925 Acrylic resin Substances 0.000 claims description 8
• 239000000460 chlorine Substances 0.000 claims description 8
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
• 229910052736 halogen Inorganic materials 0.000 claims description 7
• 150000002367 halogens Chemical class 0.000 claims description 7
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
• JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 claims description 7
• 229920001187 thermosetting polymer Polymers 0.000 claims description 7
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
• 239000004640 Melamine resin Substances 0.000 claims description 6
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
• 229910052801 chlorine Inorganic materials 0.000 claims description 6
• 125000002993 cycloalkylene group Chemical group 0.000 claims description 6
• 239000011737 fluorine Substances 0.000 claims description 6
• 229910052731 fluorine Inorganic materials 0.000 claims description 6
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 5
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
• KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 4
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 4
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
• 125000004429 atom Chemical group 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
• 230000005855 radiation Effects 0.000 claims description 4
• 229920002803 thermoplastic polyurethane Polymers 0.000 claims description 4
• 229910052724 xenon Inorganic materials 0.000 claims description 4
• FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 claims description 4
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• 125000005569 butenylene group Chemical group 0.000 claims description 3
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• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 2
• 125000001118 alkylidene group Chemical group 0.000 claims description 2
• 125000005622 butynylene group Chemical group 0.000 claims description 2
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
• 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims description 2
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
• 150000002431 hydrogen Chemical class 0.000 claims 12
• KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims 1
• 125000000753 cycloalkyl group Chemical group 0.000 claims 1
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• 229920001577 copolymer Polymers 0.000 description 33
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
• 238000000034 method Methods 0.000 description 28
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
• 239000000243 solution Substances 0.000 description 26
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
• 238000002360 preparation method Methods 0.000 description 24
• 239000006096 absorbing agent Substances 0.000 description 21
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• 150000001565 benzotriazoles Chemical class 0.000 description 18
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• 239000012043 crude product Substances 0.000 description 17
• 229910052757 nitrogen Inorganic materials 0.000 description 17
• 239000008096 xylene Substances 0.000 description 17
• NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 description 16
• 125000004435 hydrogen atom Chemical class [H]* 0.000 description 14
• NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 13
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 13
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 13
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
• 239000000155 melt Substances 0.000 description 12
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
• 150000002148 esters Chemical class 0.000 description 11
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
• MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 10
• 239000004952 Polyamide Substances 0.000 description 10
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• 150000001412 amines Chemical class 0.000 description 10
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• RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 9
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• 239000000543 intermediate Substances 0.000 description 8
• 239000004922 lacquer Substances 0.000 description 8
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 7
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• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
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• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
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• ATXBGHLILIABGX-UHFFFAOYSA-N 2-nitro-4-(trifluoromethyl)aniline Chemical compound NC1=CC=C(C(F)(F)F)C=C1[N+]([O-])=O ATXBGHLILIABGX-UHFFFAOYSA-N 0.000 description 5
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• 229920006163 vinyl copolymer Polymers 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