JP4975646B2 - 長波シフトしたベンゾトリアゾールｕｖ吸収剤及びそれらの使用 - Google Patents

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Publication number

JP4975646B2

JP4975646B2 JP2007553581A JP2007553581A JP4975646B2 JP 4975646 B2 JP4975646 B2 JP 4975646B2 JP 2007553581 A JP2007553581 A JP 2007553581A JP 2007553581 A JP2007553581 A JP 2007553581A JP 4975646 B2 JP4975646 B2 JP 4975646B2

Authority

JP

Japan

Prior art keywords

alkyl

carbon atoms

branched

linear

phenyl

Prior art date

2005-02-02

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.)

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• 239000006096 absorbing agent Substances 0.000 title claims abstract description 43
• 239000012964 benzotriazole Substances 0.000 title abstract description 15
• QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 title abstract description 13
• 239000000203 mixture Substances 0.000 claims abstract description 44
• 150000001875 compounds Chemical class 0.000 claims abstract description 43
• 239000011368 organic material Substances 0.000 claims abstract description 13
• -1 benzylidene, p-xylylene Chemical group 0.000 claims description 116
• 125000000217 alkyl group Chemical group 0.000 claims description 83
• 125000004432 carbon atom Chemical group C* 0.000 claims description 77
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 59
• 239000001257 hydrogen Substances 0.000 claims description 44
• 229910052739 hydrogen Inorganic materials 0.000 claims description 44
• 150000002431 hydrogen Chemical class 0.000 claims description 40
• 125000003342 alkenyl group Chemical group 0.000 claims description 30
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 29
• 238000000576 coating method Methods 0.000 claims description 25
• 125000002947 alkylene group Chemical group 0.000 claims description 21
• 150000001412 amines Chemical class 0.000 claims description 21
• 125000003884 phenylalkyl group Chemical group 0.000 claims description 21
• 239000011248 coating agent 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
• 229910052757 nitrogen Inorganic materials 0.000 claims description 16
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 15
• 125000001624 naphthyl group Chemical group 0.000 claims description 14
• 229910052736 halogen Inorganic materials 0.000 claims description 13
• 239000003381 stabilizer Substances 0.000 claims description 12
• 229910052794 bromium Inorganic materials 0.000 claims description 10
• 229910052801 chlorine Inorganic materials 0.000 claims description 10
• 150000002367 halogens Chemical class 0.000 claims description 10
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 9
• 125000002993 cycloalkylene group Chemical group 0.000 claims description 9
• 125000004429 atom Chemical group 0.000 claims description 8
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 7
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
• 229910052760 oxygen Inorganic materials 0.000 claims description 7
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 6
• 150000001565 benzotriazoles Chemical class 0.000 claims description 6
• 230000015556 catabolic process Effects 0.000 claims description 6
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
• 125000001424 substituent group Chemical group 0.000 claims description 6
• 238000006731 degradation reaction Methods 0.000 claims description 5
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
• 125000004956 cyclohexylene group Chemical group 0.000 claims description 4
• 229910052710 silicon Inorganic materials 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
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 3
• 125000001118 alkylidene group Chemical group 0.000 claims description 3
• 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 3
• 229910052731 fluorine Inorganic materials 0.000 claims description 3
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
• 125000000466 oxiranyl group Chemical group 0.000 claims description 3
• IJVRPNIWWODHHA-UHFFFAOYSA-N 2-cyanoprop-2-enoic acid Chemical class OC(=O)C(=C)C#N IJVRPNIWWODHHA-UHFFFAOYSA-N 0.000 claims description 2
• 150000001558 benzoic acid derivatives Chemical class 0.000 claims description 2
• 125000005569 butenylene group Chemical group 0.000 claims description 2
• 125000005622 butynylene group Chemical group 0.000 claims description 2
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
• 229910021645 metal ion Inorganic materials 0.000 claims description 2
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
• 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
• 238000000034 method Methods 0.000 abstract description 17
• 238000002360 preparation method Methods 0.000 abstract description 9
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• 238000000862 absorption spectrum Methods 0.000 abstract description 4
• 239000013036 UV Light Stabilizer Substances 0.000 abstract description 2
• 238000002835 absorbance Methods 0.000 abstract 1
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 51
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• 229920001577 copolymer Polymers 0.000 description 44
• 239000000463 material Substances 0.000 description 29
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
• 229920000642 polymer Polymers 0.000 description 24
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 19
• 239000010410 layer Substances 0.000 description 18
• GJVFBWCTGUSGDD-UHFFFAOYSA-L pentamethonium bromide Chemical compound [Br-].[Br-].C[N+](C)(C)CCCCC[N+](C)(C)C GJVFBWCTGUSGDD-UHFFFAOYSA-L 0.000 description 17
• 229920005989 resin Polymers 0.000 description 17
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• LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 15
• 239000007787 solid Substances 0.000 description 15
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• 238000005160 1H NMR spectroscopy Methods 0.000 description 12
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 12
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
• 239000003054 catalyst Substances 0.000 description 12
• MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 12
• 238000002844 melting Methods 0.000 description 12
• 230000008018 melting Effects 0.000 description 12
• 229910052751 metal Inorganic materials 0.000 description 12
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• 239000004952 Polyamide Substances 0.000 description 11
• 239000000460 chlorine Substances 0.000 description 11
• 239000000975 dye Substances 0.000 description 11
• 229920002647 polyamide Polymers 0.000 description 11
• 238000004070 electrodeposition Methods 0.000 description 10
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
• 239000005062 Polybutadiene Substances 0.000 description 9
• 239000004743 Polypropylene Substances 0.000 description 9
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• 150000001252 acrylic acid derivatives Chemical class 0.000 description 9
• 229920001684 low density polyethylene Polymers 0.000 description 9
• 239000004702 low-density polyethylene Substances 0.000 description 9
• JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 9
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
• 229920002857 polybutadiene Polymers 0.000 description 9
• 229920002554 vinyl polymer Polymers 0.000 description 9
• LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 8
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 8
• NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 8
• KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 8
• 238000006243 chemical reaction Methods 0.000 description 8
• ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 8
• GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 8
• 239000000123 paper Substances 0.000 description 8
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• 239000000243 solution Substances 0.000 description 8
• 229920000178 Acrylic resin Polymers 0.000 description 7
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
• 238000010521 absorption reaction Methods 0.000 description 7
• 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 7
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• 125000003118 aryl group Chemical group 0.000 description 7
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• 239000002904 solvent Substances 0.000 description 7
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• DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 6
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• 239000000725 suspension Substances 0.000 description 6
• SITYOOWCYAYOKL-UHFFFAOYSA-N 2-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-5-(3-dodecoxy-2-hydroxypropoxy)phenol Chemical compound OC1=CC(OCC(O)COCCCCCCCCCCCC)=CC=C1C1=NC(C=2C(=CC(C)=CC=2)C)=NC(C=2C(=CC(C)=CC=2)C)=N1 SITYOOWCYAYOKL-UHFFFAOYSA-N 0.000 description 5
• NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 5
• SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 5
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• LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 5
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