JP2008528657A - 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
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 Download PDFInfo
- Publication number
- JP2008528657A JP2008528657A JP2007553581A JP2007553581A JP2008528657A JP 2008528657 A JP2008528657 A JP 2008528657A JP 2007553581 A JP2007553581 A JP 2007553581A JP 2007553581 A JP2007553581 A JP 2007553581A JP 2008528657 A JP2008528657 A JP 2008528657A
- Authority
- JP
- Japan
- Prior art keywords
- carbon atoms
- alkyl
- branched
- linear
- phenyl
- 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.)
- Granted
Links
- 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 68
- 238000000034 method Methods 0.000 claims abstract description 20
- 239000011368 organic material Substances 0.000 claims abstract description 17
- -1 benzylidene, p-xylylene Chemical group 0.000 claims description 118
- 125000000217 alkyl group Chemical group 0.000 claims description 102
- 125000004432 carbon atom Chemical group C* 0.000 claims description 99
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 78
- 239000001257 hydrogen Substances 0.000 claims description 54
- 229910052739 hydrogen Inorganic materials 0.000 claims description 54
- 150000002431 hydrogen Chemical class 0.000 claims description 50
- 150000001875 compounds Chemical class 0.000 claims description 46
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 40
- 125000003342 alkenyl group Chemical group 0.000 claims description 39
- 239000000463 material Substances 0.000 claims description 30
- 238000000576 coating method Methods 0.000 claims description 29
- 125000002947 alkylene group Chemical group 0.000 claims description 27
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 26
- 229920000642 polymer Polymers 0.000 claims description 25
- 239000011248 coating agent Substances 0.000 claims description 22
- 150000001412 amines Chemical class 0.000 claims description 21
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 18
- 239000005977 Ethylene Substances 0.000 claims description 18
- 125000001624 naphthyl group Chemical group 0.000 claims 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 claims description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 17
- 229910052757 nitrogen Inorganic materials 0.000 claims description 17
- 229910052736 halogen Inorganic materials 0.000 claims description 15
- 239000003054 catalyst Substances 0.000 claims description 13
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 12
- 229910052794 bromium Inorganic materials 0.000 claims description 12
- 229910052801 chlorine Inorganic materials 0.000 claims description 12
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 12
- 239000003381 stabilizer Substances 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 11
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 10
- 125000004429 atom Chemical group 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 8
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 239000000758 substrate Substances 0.000 claims description 7
- 150000001565 benzotriazoles Chemical class 0.000 claims description 6
- 230000015556 catabolic process Effects 0.000 claims description 6
- 238000006731 degradation reaction Methods 0.000 claims description 5
- 229910052710 silicon Inorganic materials 0.000 claims description 5
- 125000001424 substituent group Chemical group 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
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
- 125000001118 alkylidene group Chemical group 0.000 claims description 4
- 125000004956 cyclohexylene group Chemical group 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 125000000466 oxiranyl group Chemical group 0.000 claims description 4
- 229920001169 thermoplastic 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
- 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
- 230000005670 electromagnetic radiation Effects 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 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
- 229920001059 synthetic polymer Polymers 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 abstract description 9
- 238000010521 absorption reaction Methods 0.000 abstract description 8
- 238000000862 absorption spectrum Methods 0.000 abstract description 4
- 239000013036 UV Light Stabilizer Substances 0.000 abstract description 2
- 230000000087 stabilizing effect Effects 0.000 abstract description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 51
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical class C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 49
- 229920001577 copolymer Polymers 0.000 description 44
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 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
- 229920005989 resin Polymers 0.000 description 17
- 239000011347 resin Substances 0.000 description 17
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 15
- 239000010410 layer Substances 0.000 description 15
- 239000007787 solid Substances 0.000 description 15
- 229920000877 Melamine resin Polymers 0.000 description 14
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 13
- 150000002148 esters Chemical class 0.000 description 13
- 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
- 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
- 239000002184 metal Substances 0.000 description 12
- 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
- 0 CC1(C)CC(C)(CN)CC(*)C1 Chemical compound CC1(C)CC(C)(CN)CC(*)C1 0.000 description 9
- 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
- 239000002253 acid Substances 0.000 description 9
- 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
- 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
- 239000004417 polycarbonate Substances 0.000 description 8
- 229920000728 polyester Polymers 0.000 description 8
- 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
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 7
- 229920000180 alkyd Polymers 0.000 description 7
- 125000003118 aryl group Chemical group 0.000 description 7
- 150000001993 dienes Chemical class 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- 239000004700 high-density polyethylene Substances 0.000 description 7
- 239000000178 monomer Substances 0.000 description 7
- 229920006324 polyoxymethylene Polymers 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 7
- 239000004925 Acrylic resin Substances 0.000 description 6
- 229920000089 Cyclic olefin copolymer Polymers 0.000 description 6
- 229920003264 Maprenal® Polymers 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 125000001931 aliphatic group Chemical group 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 239000008199 coating composition Substances 0.000 description 6
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 6
- 229920001903 high density polyethylene Polymers 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 229920000573 polyethylene Polymers 0.000 description 6
- 239000004800 polyvinyl chloride Substances 0.000 description 6
- 229920000915 polyvinyl chloride Polymers 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 150000005846 sugar alcohols Polymers 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
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 5
- 239000004698 Polyethylene Substances 0.000 description 5
- 239000004721 Polyphenylene oxide Substances 0.000 description 5
- 239000007983 Tris buffer Substances 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 150000001340 alkali metals Chemical class 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 235000013877 carbamide Nutrition 0.000 description 5
- 238000004587 chromatography analysis Methods 0.000 description 5
- 229920001971 elastomer Polymers 0.000 description 5
- 239000003822 epoxy resin Substances 0.000 description 5
- 150000002170 ethers Chemical class 0.000 description 5
- 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
- 229920001519 homopolymer Polymers 0.000 description 5
- 238000007641 inkjet printing Methods 0.000 description 5
- 239000012948 isocyanate Substances 0.000 description 5
- 150000002513 isocyanates Chemical class 0.000 description 5
- 229940059574 pentaerithrityl Drugs 0.000 description 5
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 5
- 229920000647 polyepoxide Polymers 0.000 description 5
- 229920001225 polyester resin Polymers 0.000 description 5
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- 229920006380 polyphenylene oxide Polymers 0.000 description 5
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- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- KAKZBPTYRLMSJV-UHFFFAOYSA-N vinyl-ethylene Natural products C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 5
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 4
- BPXVHIRIPLPOPT-UHFFFAOYSA-N 1,3,5-tris(2-hydroxyethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound OCCN1C(=O)N(CCO)C(=O)N(CCO)C1=O BPXVHIRIPLPOPT-UHFFFAOYSA-N 0.000 description 4
- ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 4
- ONTODYXHFBKCDK-UHFFFAOYSA-N 2-(2,4-dimethylphenyl)-1,3,5-triazine Chemical compound CC1=CC(C)=CC=C1C1=NC=NC=N1 ONTODYXHFBKCDK-UHFFFAOYSA-N 0.000 description 4
- 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 description 4
- ZPIRWAHWDCHWLM-UHFFFAOYSA-N 2-dodecylsulfanylethanol Chemical compound CCCCCCCCCCCCSCCO ZPIRWAHWDCHWLM-UHFFFAOYSA-N 0.000 description 4
- CKPKHTKLLYPGFM-UHFFFAOYSA-N 6,6-dimethylheptane-1,1-diol Chemical compound CC(CCCCC(O)O)(C)C CKPKHTKLLYPGFM-UHFFFAOYSA-N 0.000 description 4
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000004593 Epoxy Substances 0.000 description 4
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 4
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 4
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- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 4
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- 238000009472 formulation Methods 0.000 description 4
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- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 4
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- FPQJEXTVQZHURJ-UHFFFAOYSA-N n,n'-bis(2-hydroxyethyl)oxamide Chemical compound OCCNC(=O)C(=O)NCCO FPQJEXTVQZHURJ-UHFFFAOYSA-N 0.000 description 4
- FTWUXYZHDFCGSV-UHFFFAOYSA-N n,n'-diphenyloxamide Chemical class C=1C=CC=CC=1NC(=O)C(=O)NC1=CC=CC=C1 FTWUXYZHDFCGSV-UHFFFAOYSA-N 0.000 description 4
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 4
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 4
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 4
- 229920001707 polybutylene terephthalate Polymers 0.000 description 4
- 239000004814 polyurethane Substances 0.000 description 4
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- 238000000746 purification Methods 0.000 description 4
- 230000005855 radiation Effects 0.000 description 4
- 239000000600 sorbitol Substances 0.000 description 4
- 239000012258 stirred mixture Substances 0.000 description 4
- 229920001897 terpolymer Polymers 0.000 description 4
- 229920001187 thermosetting polymer Polymers 0.000 description 4
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 4
- 238000000411 transmission spectrum Methods 0.000 description 4
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 4
- RXFCIXRFAJRBSG-UHFFFAOYSA-N 3,2,3-tetramine Chemical compound NCCCNCCNCCCN RXFCIXRFAJRBSG-UHFFFAOYSA-N 0.000 description 3
- 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 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 3
- 229920002943 EPDM rubber Polymers 0.000 description 3
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- 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 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 1
- XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical class OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 description 1
- 150000003012 phosphoric acid amides Chemical class 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 239000012994 photoredox catalyst Substances 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
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920001627 poly(4-methyl styrene) Polymers 0.000 description 1
- 229920001084 poly(chloroprene) Polymers 0.000 description 1
- 229920003055 poly(ester-imide) Polymers 0.000 description 1
- 229920001643 poly(ether ketone) Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 229920003251 poly(α-methylstyrene) Polymers 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920002312 polyamide-imide Polymers 0.000 description 1
- 229920002480 polybenzimidazole Polymers 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920001601 polyetherimide Polymers 0.000 description 1
- 229940068886 polyethylene glycol 300 Drugs 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 229920001470 polyketone Polymers 0.000 description 1
- 229920002959 polymer blend Polymers 0.000 description 1
- 229920000307 polymer substrate Polymers 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920000069 polyphenylene sulfide 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
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- MQOCIYICOGDBSG-UHFFFAOYSA-M potassium;hexadecanoate Chemical compound [K+].CCCCCCCCCCCCCCCC([O-])=O MQOCIYICOGDBSG-UHFFFAOYSA-M 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical class C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- IJRHDFLHUATAOS-DPMBMXLASA-M sodium ricinoleate Chemical compound [Na+].CCCCCC[C@@H](O)C\C=C/CCCCCCCC([O-])=O IJRHDFLHUATAOS-DPMBMXLASA-M 0.000 description 1
- 229940074404 sodium succinate Drugs 0.000 description 1
- ZDQYSKICYIVCPN-UHFFFAOYSA-L sodium succinate (anhydrous) Chemical compound [Na+].[Na+].[O-]C(=O)CCC([O-])=O ZDQYSKICYIVCPN-UHFFFAOYSA-L 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 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
- 239000010959 steel Substances 0.000 description 1
- 229920000638 styrene acrylonitrile Polymers 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 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
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 150000005621 tetraalkylammonium salts Chemical class 0.000 description 1
- 125000005497 tetraalkylphosphonium group Chemical group 0.000 description 1
- OLBWDGJTEXRJLY-UHFFFAOYSA-N tetradecyl 3-(2,2,4,4-tetramethyl-21-oxo-7-oxa-3,20-diazadispiro[5.1.11^{8}.2^{6}]henicosan-20-yl)propanoate Chemical compound O1C2(CCCCCCCCCCC2)N(CCC(=O)OCCCCCCCCCCCCCC)C(=O)C21CC(C)(C)NC(C)(C)C2 OLBWDGJTEXRJLY-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 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 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
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- YONPGGFAJWQGJC-UHFFFAOYSA-K titanium(iii) chloride Chemical compound Cl[Ti](Cl)Cl YONPGGFAJWQGJC-UHFFFAOYSA-K 0.000 description 1
- 229960000984 tocofersolan Drugs 0.000 description 1
- AOBORMOPSGHCAX-DGHZZKTQSA-N tocofersolan Chemical compound OCCOC(=O)CCC(=O)OC1=C(C)C(C)=C2O[C@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C AOBORMOPSGHCAX-DGHZZKTQSA-N 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- 235000019149 tocopherols Nutrition 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- INNSFNJTGFCSRN-UHFFFAOYSA-N tridecyl 2-[(3,5-ditert-butyl-4-hydroxyphenyl)methylsulfanyl]acetate Chemical compound CCCCCCCCCCCCCOC(=O)CSCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 INNSFNJTGFCSRN-UHFFFAOYSA-N 0.000 description 1
- IVIIAEVMQHEPAY-UHFFFAOYSA-N tridodecyl phosphite Chemical compound CCCCCCCCCCCCOP(OCCCCCCCCCCCC)OCCCCCCCCCCCC IVIIAEVMQHEPAY-UHFFFAOYSA-N 0.000 description 1
- CNUJLMSKURPSHE-UHFFFAOYSA-N trioctadecyl phosphite Chemical compound CCCCCCCCCCCCCCCCCCOP(OCCCCCCCCCCCCCCCCCC)OCCCCCCCCCCCCCCCCCC CNUJLMSKURPSHE-UHFFFAOYSA-N 0.000 description 1
- 229920001862 ultra low molecular weight polyethylene Polymers 0.000 description 1
- KJIOQYGWTQBHNH-UHFFFAOYSA-N undecanol Chemical compound CCCCCCCCCCCO KJIOQYGWTQBHNH-UHFFFAOYSA-N 0.000 description 1
- 229920001866 very low density polyethylene Polymers 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 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
- 239000004711 α-olefin Substances 0.000 description 1
- 239000002076 α-tocopherol Substances 0.000 description 1
- 235000004835 α-tocopherol Nutrition 0.000 description 1
- 235000007680 β-tocopherol Nutrition 0.000 description 1
- 239000011590 β-tocopherol Substances 0.000 description 1
- QUEDXNHFTDJVIY-UHFFFAOYSA-N γ-tocopherol Chemical class OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-UHFFFAOYSA-N 0.000 description 1
- QUEDXNHFTDJVIY-DQCZWYHMSA-N γ-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-DQCZWYHMSA-N 0.000 description 1
- GZIFEOYASATJEH-VHFRWLAGSA-N δ-tocopherol Chemical compound OC1=CC(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1 GZIFEOYASATJEH-VHFRWLAGSA-N 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
- C08K5/3472—Five-membered rings
- C08K5/3475—Five-membered rings condensed with carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Abstract
Description
R1は、水素、炭素原子1〜24個の直鎖若しくは分岐鎖アルキル、炭素原子2〜18個の直鎖若しくは分岐鎖アルケニル、炭素原子5〜12個のシクロアルキル、炭素原子7〜15個のフェニルアルキル、フェニル、又は炭素原子1〜4個のアルキルの1〜4つによりフェニル環で置換されている前記フェニル若しくは前記フェニルアルキルであるか;或いは
R1は、下記式:
ここでLは、炭素原子1〜12個のアルキレン、炭素原子2〜12個のアルキリデン、ベンジリデン、p−キシリレン又は炭素原子5〜7個のシクロアルキレンであり;
R2は、炭素原子1〜24個の直鎖若しくは分岐鎖アルキル、炭素原子2〜18個の直鎖若しくは分岐鎖アルケニル、炭素原子5〜12個のシクロアルキル、炭素原子7〜15個のフェニルアルキル、フェニル、又は炭素原子1〜4個のアルキルの1〜3つによりフェニル環で置換されている前記フェニル若しくは前記フェニルアルキルであるか;或いは、
−OH、−OCO−R11、−OR14、−NCO若しくは−NH2基又はこれらの混合物の1つ以上で置換されている前記アルキルか、又は−O−、−NH−若しくは−NR14−基又はこれらの混合物の1つ以上で中断され、かつ非置換であるか、又は−OH、−OR14若しくは−NH2基又はこれらの混合物の1つ以上で置換されていることができる前記アルキル若しくは前記アルケニルであり;ここで、
R11は、水素、直鎖若しくは分岐鎖C1〜C18アルキル、C5〜C12シクロアルキル、直鎖若しくは分岐鎖C3〜C18アルケニル、フェニル、ナフチル又はC7〜C15フェニルアルキルであり;そして
R14は、水素、炭素原子1〜24個の直鎖若しくは分岐鎖アルキルであるか;或いは:
R2は、−OR14、基−C(O)−O−R14、−C(O)−NHR14又は−C(O)−NR14R′14であり、ここでR′14は、R14と同じ意味を有するか;或いは
R2は、−SR13、−NHR13又は−N(R13)2であるか;或いは
R2は、−(CH2)m−CO−X1−(Z)p−Y−R15であり、ここで、
X1は、−O−又は−N(R16)−であり、
Yは、−O−若しくは−N(R17)−又は直接結合であり、
Zは、C2〜C12アルキレン、1〜3個の窒素原子、酸素原子若しくはその混合物で中断されているC4〜C12アルキレンであるか、又はそれぞれヒドロキシル基で追加的に置換されていてもよいC3〜C12アルキレン、ブテニレン、ブチニレン、シクロヘキシレン若しくはフェニレンであるか、或いは、
下記式:
ここで*は、結合を示すか、又は
Yが直接結合である場合、Zは、追加的に直接結合であることもでき、
mは、0、1又は2であり、
pは、1であるか、又はX及びYが、それぞれ−N(R16)−及び−N(R17)−である場合、0でもあり、
R15は、水素、C1〜C12アルキルか、又は下記式:
R18は、水素又はメチルであり、そしてR19は、水素、メチル又は−CO−X1−R20であり、ここで、
R20は、水素、C1〜C12アルキル又は下記式:
R5、R6、R7及びR8は、独立して、水素、ハロゲン、CN、NO2又はNH2であり;
R13は、炭素原子1〜20個のアルキル、炭素原子2〜20個のヒドロキシアルキル、炭素原子3〜18個のアルケニル、炭素原子5〜12個のシクロアルキル、炭素原子7〜15個のフェニルアルキル、両方とも炭素原子1〜4個のアルキルの1又は2つで置換されていてもよいフェニル又はナフチルであり;
R16及びR17は、互いに独立して、水素、C1〜C12アルキル、1〜3個の酸素原子で中断されているC3〜C12アルキルであるか、又はシクロヘキシル若しくはC7〜C15フェニルアルキルであり、Zがエチレンである場合、R16は、また、R17と一緒になってエチレンを形成し;
Xは、O又はNE1であり、ここで、
E1は、水素、直鎖若しくは分岐鎖C1〜C24アルキル、直鎖若しくは分岐鎖C2〜C18アルケニル、C2〜C6アルキニル、C5〜C12シクロアルキル、フェニル、ナフチル又はC7〜C15フェニルアルキルであるか、又は前記直鎖若しくは分岐鎖C1〜C24アルキル、直鎖若しくは分岐鎖C2〜C24アルケニル、C5〜C12シクロアルキル、C2〜C6アルキニルは、−F、−OH、−OR22、−NH2、−NHR22、−N(R22)2、−NHCOR23、−NR22COR23、−OCOR24、−COR25、−SO2R26、−PO(R27)n(R28)2−n、−Si(R29)n(R30)3−n、−Si(R22)3、−N+(R22)3A−、−S+(R22)2A−、オキシラニル基又はこれらの混合物の1つ以上で置換されていることができ、前記直鎖若しくは分岐鎖C1〜C24アルキル、直鎖若しくは分岐鎖の非置換若しくは置換C2〜C24アルケニル、C5〜C12シクロアルキル又はC2〜C6アルキニルは、また、−O−、−S−、−NH−若しくは−NR22−基又はこれらの組み合わせの1つ以上で中断されていることができ;
前記フェニル、ナフチル又はC7〜C15フェニルアルキルは、また、−ハロゲン、−CN、−CF3、−NO2、−NHR22、−N(R22)2、−SO2R26、−PO(R27)n(R28)2−n、−OH、−OR22、−COR25、−R25の1つ以上で置換されていることができ、ここで、
nは、0、1又は2であり;
R22は、直鎖若しくは分岐鎖C1〜18アルキル、直鎖若しくは分岐鎖C2〜C18アルケニル、C5〜C10シクロアルキル、フェニル又はナフチル、C7〜C15フェニルアルキルであるか、或いはN又はSi原子に結合している場合、2つのR22は、それらが結合している原子と一緒になって、ピロリジン、ピペリジン又はモルホリン環を形成することができ;
R23は、水素、OR22、NHR22、N(R22)2であるか、又はR22と同じ意味を有し、
R24は、OR22、NHR22、N(R22)2であるか、又はR22と同じ意味を有し、
R25は、水素、OH、OR22、NHR22若しくはN(R22)2、O−グリシジルであるか、又はR22と同じ意味を有し、
R26は、OH、OR22、NHR22又はN(R22)2であり、
R27は、NH2、NHR22又はN(R22)2であり、
R28は、OH又はOR22であり、
R29は、Cl又はOR22であり、
R30は、直鎖又は分岐鎖C1〜C18アルキルであるか;或いは
E1は、下記式:
ここで、R1〜R8は、上記で定義されたとおりの意味を有し、そして
Qは、直鎖若しくは分岐鎖C2〜C12アルキレン、−O−、NH若しくはNR14原子の1個以上で中断されているC2〜C12アルキレン、C5〜C10シクロアルキレン、パラ−フェニレン、又は下記式:
ここで*は、結合を示す〕
で示される化合物である。
ここで*は、結合を示す。
R1が、水素、炭素原子1〜24個の直鎖若しくは分岐鎖アルキル、炭素原子2〜18個の直鎖若しくは分岐鎖アルケニル、炭素原子5〜12個のシクロアルキル、炭素原子7〜15個のフェニルアルキル、フェニル、又は炭素原子1〜4個のアルキルの1〜4つによりフェニル環で置換されている前記フェニル若しくは前記フェニルアルキルであるか;或いは
R1が、下記式:
ここでLが、炭素原子1〜12個のアルキレン、炭素原子2〜12個のアルキリデン、ベンジリデン、p−キシリレン又は炭素原子5〜7個のシクロアルキレンであり;
R2が、炭素原子1〜24個の直鎖若しくは分岐鎖アルキル、炭素原子2〜18個の直鎖若しくは分岐鎖アルケニル、炭素原子5〜12個のシクロアルキル、炭素原子7〜15個のフェニルアルキル、フェニル、又は炭素原子1〜4個のアルキルの1〜3つによりフェニル環で置換されている前記フェニル若しくは前記フェニルアルキルであるか;或いは、
R2が、−(CH2)m−CO−X1−(Z)p−Y−R15であり、ここで、
X1が、−O−であり、
Yが、−O−又は直接結合であり、
Zが、C2〜C12アルキレン、1〜3個の窒素原子、酸素原子若しくはその混合物で中断されているC4〜C12アルキレンであるか、又はYが直接結合である場合、Zが、追加的に直接結合であることもでき;
mが、2であり、
pが、1であり、
R15が、水素、C1〜C12アルキル又は下記式:
R5、R6、R7及びR8が、独立して、水素、Cl又はBrであり;
Xが、O又はNE1であり、ここで、
E1が、水素、直鎖若しくは分岐鎖C1〜C24アルキル、直鎖若しくは分岐鎖C2〜C18アルケニル、C2〜C6アルキニル、C5〜C12シクロアルキル、フェニル、ナフチル又はC7〜C15フェニルアルキルであるか、又は前記直鎖若しくは分岐鎖C1〜C24アルキル、直鎖若しくは分岐鎖C2〜C24アルケニル、C5〜C12シクロアルキル、C2〜C6アルキニルが、−F、−OH、−OR22、−NH2、−NHR22、−N(R22)2、−NHCOR23、−NR22COR23、−OCOR24、−COR25、−SO2R26、−PO(R27)n(R28)2−n、−Si(R29)n(R30)3−n、−Si(R22)3、−N+(R22)3A−、−S+(R22)2A−、オキシラニル基又はこれらの混合物の1つ以上で置換されていることができ、前記直鎖若しくは分岐鎖C1〜C24アルキル、直鎖若しくは分岐鎖の非置換若しくは置換C2〜C24アルケニル、C5〜C12シクロアルキル又はC2〜C6アルキニルが、また、−O−、−S−、−NH−若しくは−NR22−基又はこれらの組み合わせの1つ以上で中断されていることができ;
前記フェニル、ナフチル又はC7〜C15フェニルアルキルが、また、−ハロゲン、−CN、−CF3、−NO2、−NHR22、−N(R22)2、−SO2R26、−PO(R27)n(R28)2−n、−OH、−OR22、−COR25、−R25の1つ以上で置換されていることができ、ここで、
nが、0、1又は2であり;
R22が、直鎖若しくは分岐鎖C1〜18アルキル、直鎖若しくは分岐鎖C2〜C18アルケニル、C5〜C10シクロアルキル、フェニル又はナフチル、C7〜C15フェニルアルキルであるか、或いはN又はSi原子に結合している場合、2つのR22が、それらが結合している原子と一緒になって、ピロリジン、ピペリジン又はモルホリン環を形成することができ;
R23が、水素、OR22、NHR22、N(R22)2であるか、又はR22と同じ意味を有し、
R24が、OR22、NHR22、N(R22)2であるか、又はR22と同じ意味を有し、
R25が、水素、OH、OR22、NHR22若しくはN(R22)2、O−グリシジルであるか、又はR22と同じ意味を有し、
R26が、OH、OR22、NHR22又はN(R22)2であり、
R27が、NH2、NHR22又はN(R22)2であり、
R28が、OH又はOR22であり、
R29が、Cl又はOR22であり、
R30が、直鎖又は分岐鎖C1〜C18アルキルであるか;或いは
E1が、下記式:
ここで、R1〜R8が、上記で定義されたとおりの意味を有し、そして
Qが、直鎖若しくは分岐鎖C2〜12アルキレン、C5〜C10シクロアルキレン若しくはパラ−フェニレン又は下記式:
式(I)又は(II)の化合物である。
R1は、水素、炭素原子1〜24個の直鎖若しくは分岐鎖アルキル、炭素原子2〜18個の直鎖若しくは分岐鎖アルケニル、炭素原子5〜12個のシクロアルキル、炭素原子7〜15個のフェニルアルキル、フェニル、又は炭素原子1〜4個のアルキルの1〜4つによりフェニル環で置換されている前記フェニル若しくは前記フェニルアルキルであり;
R2は、炭素原子1〜24個の直鎖若しくは分岐鎖アルキル、炭素原子2〜18個の直鎖若しくは分岐鎖アルケニル、炭素原子5〜12個のシクロアルキル、炭素原子7〜15個のフェニルアルキル、フェニル、又は炭素原子1〜4個のアルキルの1〜3つによりフェニル環で置換されている前記フェニル若しくは前記フェニルアルキルであるか;或いは、
R2は、−(CH2)2−CO−O−(Z)−O−R15であり、ここで、
Zは、C2〜C12アルキレン、1〜3個の酸素原子で中断されているC4〜C12アルキレンであり;
R15は、水素、C1〜C12アルキル又は下記式:
R5、R6、R7及びR8は、独立して、水素、Cl又はBrであり;
Xは、O又はNE1であり、ここで、
E1は、水素、直鎖若しくは分岐鎖C1〜24アルキル、C5〜C12シクロアルキル、フェニル、又はC7〜C15フェニルアルキルであるか;又は前記直鎖若しくは分岐鎖C1〜24アルキル又はC5〜C12シクロアルキルは、−F、−OH、−OR22、−NH2、−NHR22、−N(R22)2の1つ以上で置換されていることができ;
前記フェニル又はC7〜C15フェニルアルキルは、また、ハロゲン、−CN、−CF3、−OH、−OR22、−COR22、−R22の1つ以上で置換されていることができ;ここで、
R22は、直鎖若しくは分岐鎖C1〜18アルキル、直鎖若しくは分岐鎖C2〜18アルケニル、C5〜C10シクロアルキル、C6〜C16フェニル若しくはナフチル、C7〜C15フェニルアルキルであるか;或いは
E1は、下記式:
ここで、R1〜R8は、上記で定義されたとおりの意味を有し、そして
Qは、C2〜C12アルキレンC5〜C7シクロアルキレン、パラ−フェニレン又は下記式:
R1が、水素、炭素原子1〜12個の直鎖若しくは分岐鎖アルキル、又は炭素原子7〜15個のフェニルアルキルであり;
R2が、炭素原子1〜12個の直鎖若しくは分岐鎖アルキル、若しくは炭素原子7〜15個のフェニルアルキル、フェニル、又は炭素原子1〜4個のアルキルの1〜3つによりフェニル環で置換されている前記フェニル若しくは前記フェニルアルキルであり;
R5及びR6が、水素であるか、又は両方のうちの一方がCl若しくはBrであり;
R7及びR8が、独立して、水素、Cl又はBrであり;
Xが、O又はNE1であり、ここで、
E1が、水素、非置換又は1〜4つのOHで置換されている直鎖若しくは分岐鎖C1〜6アルキル、非置換又はF、CF3、CN若しくはClで置換されているフェニル、又はC7〜C9フェニルアルキルである
式(I)又は(II)の化合物である。
式(X):
Mは、n価金属イオン、下記:
R101、R102、R103及びR104は、互いに独立して、水素又はC1〜C18アルキルであり、
R105は、C1〜C18アルキルであり;そして
rは、1、2又は3である)で示されるアジド化合物と反応させることを含む
方法である。
好ましいものは、式III、IV又はVの化合物の量と式Xのアジド化合物の量のモル比が、1:1〜1:3、特に1:1〜1:2、例えば1:1〜1:1.3である、式I又はIIの化合物の調製方法である。アジドと反応することもできる官能側基が存在する場合、式IXの過剰量のアジド化合物が対応して増加される。
(a)光誘発性分解に付される有機材料、及び
(b)上記で記載された式I又はIIの化合物
を含む、光誘発性分解に対して安定化された組成物である。
水溶性成分、例えば結合剤を水に溶解し、一緒に撹拌する。固体成分、例えば、充填剤及び既に記載されている他の添加剤を、この水性媒体に分散する。分散を、例えば超音波装置、タービン撹拌器、ホモジナイザー、コロイドミル、ビーズミル、サンドミル、高速撹拌器などの装置によって都合よく実施する。式I又はIIの化合物は、被覆組成物に容易に混和することができる。
式I又はIIの化合物は、また、光重合、光可塑化若しくはマイクロカプセルの破裂の原理に基づく記録材料に用いられるか、又は感熱及び感光ジアゾニウム塩の場合は、酸化剤を有するロイコ染料若しくはルイス酸を有する染料ラクトンが使用される。
a)ラジカル重合(通常、高圧及び高温下)。
b)通常、周期表のIVb、Vb、VIb又はVIII族の1つ又は1つ以上の金属を含有する触媒を使用する触媒重合。これらの金属は、通常、1つ又は1つ以上のリガンド、典型的には、π−若しくはσ−配位のいずれかであってよい酸化物、ハロゲン化物、アルコラート、エステル、エーテル、アミン、アルキル、アルケニル及び/又はアリールを有する。これらの金属錯体は、遊離形態であっても、基材に、典型的には活性化塩化マグネシウム、塩化チタン(III)、アルミナ又は酸化ケイ素に固定されていてもよい。これらの触媒は、重合媒質に可溶性又は不溶性であることができる。触媒はそれ自体重合に使用できるか、又は更に活性化剤を使用してもよく、典型的には金属アルキル、金属水素化物、金属アルキルハロゲン化物、金属アルキル酸化物又は金属アルキルオキサンであり、前記金属は周期表のIa、IIa及び/又はIIIa族の元素である。活性化剤を、更にエステル、エーテル、アミン又はシリルエーテル基により都合よく変性してもよい。これらの触媒系は、通常、Phillips、Standard Oil Indiana、Ziegler (-Natta)、TNZ (DuPont)、メタロセン又はシングルサイト触媒(SSC)と呼ばれる。
1.1 アルキル化モノフェノール、例えば2,6−ジ−tert−ブチル−4−メチルフェノール、2−ブチル−4,6−ジメチルフェノール、2,6−ジ−tert−ブチル−4−エチルフェノール、2,6−ジ−tert−ブチル−4−n−ブチルフェノール、2,6−ジ−tert−ブチル−4−イソブチルフェノール、2,6−ジシクロペンチル−4−メチルフェノール、2−(α−メチルシクロヘキシル)−4,6−ジメチルフェノール、2,6−ジオクタデシル−4−メチルフェノール、2,4,6−トリシクロヘキシルフェノール、2,6−ジ−tert−ブチル−4−メトキシメチルフェノール、側鎖において直鎖状又は分岐鎖状であるノニルフェノール、例えば2,6−ジ−ノニル−4−メチルフェノール、2,4−ジメチル−6−(1’−メチルウンデカ−1’−イル)フェノール、2,4−ジメチル−6−(1’−メチルヘプタデカ−1’−イル)フェノール、2,4−ジメチル−6−(1’−メチルトリデカ−1’−イル)フェノール及びその混合物。
2.1. 2−(2’−ヒドロキシフェニル)−ベンゾトリアゾール、例えば2−(2’−ヒドロキシ−5’−メチルフェニル)−ベンゾトリアゾール、2−(3’,5’−ジ−tert−ブチル−2’−ヒドロキシフェニル)−ベンゾトリアゾール、2−(5’−tert−ブチル−2’−ヒドロキシフェニル)−ベンゾトリアゾール、2−(2’−ヒドロキシ−5’−(1,1,3,3−テトラメチルブチル)フェニル)−ベンゾトリアゾール、2−(3’,5’−ジ−tert−ブチル−2’−ヒドロキシフェニル)−5−クロロ−ベンゾトリアゾール、2−(3’−tert−ブチル−2’−ヒドロキシ−5’−メチルフェニル)−5−クロロ−ベンゾトリアゾール、2−(3’−sec−ブチル−5’−tert−ブチル−2’−ヒドロキシフェニル)−ベンゾトリアゾール、2−(2’−ヒドロキシ−4’−オクチルオキシフェニル)−ベンゾトリアゾール、2−(3’,5’−ジ−tert−アミル−2’−ヒドロキシフェニル)−ベンゾトリアゾール、2−(3’,5’−ビス(α,α―ジメチルベンジル)−2’−ヒドロキシフェニル)−ベンゾトリアゾール、2−(3’−tert−ブチル−2’−ヒドロキシ−5’−(2−オクチルオキシカルボニルエチル)フェニル)−5−クロロ−ベンゾトリアゾール、2−(3’−tert−ブチル−5’−[2−(2−エチルヘキシルオキシ)−カルボニルエチル]−2’−ヒドロキシフェニル)−5−クロロ−ベンゾトリアゾール、2−(3’−tert−ブチル−2’−ヒドロキシ−5’−(2−メトキシカルボニルエチル)フェニル)−5−クロロ−ベンゾトリアゾール、2−(3’−tert−ブチル−2’−ヒドロキシ−5’−(2−メトキシカルボニルエチル)フェニル)−ベンゾトリアゾール、2−(3’−tert−ブチル−2’−ヒドロキシ−5’−(2−オクチルオキシカルボニルエチル)フェニル)−ベンゾトリアゾール、2−(3’−tert−ブチル−5’−[2−(2−エチルヘキシルオキシ)カルボニルエチル]−2’−ヒドロキシフェニル)−ベンゾトリアゾール、2−(3’−ドデシル−2’−ヒドロキシ−5’−メチルフェニル)−ベンゾトリアゾール、2−(3’−tert−ブチル−2’−ヒドロキシ−5’−(2−イソオクチルオキシカルボニルエチル)フェニルベンゾトリアゾール、2,2’−メチレン−ビス[4−(1,1,3,3−テトラメチルブチル)−6−ベンゾトリアゾール−2−イルフェノール];2−[3’−tert−ブチル−5’−(2−メトキシカルボニルエチル)−2’−ヒドロキシフェニル]−ベンゾトリアゾールとポリエチレングリコール300とのエステル交換生成物;
トリス(2,4−ジ−tert−ブチルフェニル)ホスファイト(Irgafos(登録商標)168, Ciba Specialty Chemicals Inc.)、トリス(ノニルフェニル)ホスファイト、
実施例A1.ヒドロキシフェニルベンゾトリアゾール1bの調製
融点:178〜179℃。
1H-NMR (300MHz, CD2CI2), δ (ppm): 13.14 (s, 1H), 8.34 (s, 1H), 8.18 (s, 1H), 7.92 (d-like, 1 H), 7.76 (d-like, 1 H), 7.28 - 7.24 (m, 4H), 7.20 - 7.15 (m, 1H), 3.20 (s, 3H), 1.87 (s, 2H), 1.82 (s, 6H), 1.51 (s, 6H), 0.86 (s, 9H).
融点:198〜199℃。
1H-NMR (300MHz, CD2CI2), δ (ppm): 10.97 (s, 1H), 8.40 - 8.39 (m, 3H), 7.76 (d-like, 1H), 7.31 - 7.24 (m, 4H), 7.20 - 7.15 (m, 1H), 3.25 (s, 3H), 1.91 (s, 2H), 1.83 (s, 6H), 1.54 (s, 6H), 0.86 (s, 9H).
収量:3.18g(95%)。
融点:216℃〜218℃。
1H-NMR (300MHz, DMSO-d6), δ (ppm): 7.92 (s, 1H), 6.46 (s, broad, 2H), 2.96 (s, 3H).
収量16.6g(62%)
融点:180℃(分解)
1H-NMR (300MHz, CDCI3), δ (ppm): 11.70 (s, 1H), 8.14 (s, 1H), 7.78 (d-like, 1H), 7.70 (d-like, 1H), 7.30 - 7.28 (m, 4H), 7.21 - 7.17 (m, 1H), 3.16 (s, 3H), 1.82 (s, 6H), 1.81 (s, 2H), 1.46 (s, 6H), 0.83 (s, 9H).
収量1.05g(17.4%)
融点:221℃〜225℃(分解)。
1H-NMR (300MHz, CDCI3), δ (ppm): 10.89 (s, 1H), 8.41 (s, 1H) 8.39 (d-like, 1H), 7.74 (d-like, 1 H), 7.29 - 7.26 (m, 4H), 7.22 - 7.17 (m, 1H), 3.26 (s, 3H), 1.87 (s, 2H), 1.84 (s, 6H), 1.53 (s, 6H), 0.84 (s, 9H).
融点:150〜175℃(分解)
HPLC - UV / APCI - MS negative : 529.3 (M); C31H35N3O5の計算値: 529.3
1H-NMR (300MHz, DMSO-d6), δ (ppm): 10.38 (s, 1H), 8.57 (br s, 2H), 7.98 (d, J = 1.9Hz, 1H), 7.64 (d, J = 1.9Hz, 1H), 7.26 - 7.18 (m, 4H), 7.14 - 7.08 (m, 1H), 1.80 (s, 2H), 1.75 (s, 6H), 1.43 (s, 6H), 0.78 (s, 9H).
融点:220〜221℃。
分析 C37H38N4O3の計算値(586.74): C, 75.74; H, 6.53; N, 9.55. 実測値: C, 75.52; H, 6.53; N, 9.28.
1H-NMR (400MHz, DMSO-d6), δ (ppm): 10.26 (br s, 1H), 8.68 (s, 2H), 7.96 (d, J = 1.8Hz, 1H), 7.69 (d, J = 1.8Hz, 1H), 7.56 - 7.45 (m, 5H), 7.26 - 7.20 (m, 4H), 7.14 - 7.10 (m, 1H), 1.82 (s, 2H), 1.76 (s, 6H), 1.45 (s, 6H), 0.79 (s, 9H).
融点:252〜253℃。
分析 C38H37N5O3の計算値(611.75): C, 74.61 ; H, 6.10; N, 11.45. 実測値: C, 74.04; H, 5.83; N, 11.37.
1H-NMR (400MHz, DMSO-d6), δ (ppm): 10.24 (br s, 1H), 8.72 (s, 2H), 8.05 (d, J = 8.5Hz, 2H), 7.95 (d, J = 1.8Hz, 1H), 7.76 (d, J = 8.5Hz, 2H), 7.69 (d, J = 1.8Hz, 1H), 7.26 - 7.18 (m, 4H), 7.16 - 7.10 (m, 1H), 1.82 (s, 2H), 1.76 (s, 6H), 1.44 (s, 6H), 0.79 (s, 9H).
融点:179〜180℃。
分析 C37H37CIN4O3の計算値(621.19): C, 71.54; H, 6.00; Cl, 5.71 ; N, 9.02. 実測値: C, 71.04; H, 5.90; Cl, 5.93; N, 8.89.
1H-NMR (300MHz, DMSO-d6), δ (ppm): 10.22 (s, 1H), 8.76 (s, 2H), 7.95 (d, J = 2.1 Hz, 1H), 7.75 - 7.67 (m, 3H), 7.62 - 7.53 (m, 2H), 7.27 - 7.19 (m, 4H), 7.15 - 7.09 (m, 1H), 1.82 (s, 2H), 1.76 (s, 6H), 1.45 (s, 6H), 0.79 (s, 9H).
融点:210〜211℃。
分析 C43H50N4O3の計算値(670.90): C, 76.98; H, 7.51; N, 8.35. 実測値: C, 76.70; H, 7.47; N, 8.29.
1H-NMR (300MHz, CD2CI2), δ (ppm): 11.03 (s, 1H), 8.53 (s, 2H), 8.45 (d, J = 2.4Hz, 1H), 7.79 (d, J = 2.4Hz, 1H), 7.58 - 7.53 (m, 1H), 7.39 - 7.36 (m, 2H), 7.33 - 7.26 (m, 4H), 7.22 - 7.16 (m, 1H), 2.78 (septet, J = 6.8Hz, 2H), 1.93 (s, 2H), 1.85 (s, 6H), 1.56 (s, 6H), 1.19 (d, J = 6.8Hz, 12H), 0.88 (s, 9H).
融点:161〜162℃。
分析 C33H38N4O4の計算値(554.70): C, 71.46; H, 6.90; N, 10.10. 実測値: C, 71.07; H, 6.92; N, 10.03.
1H-NMR (300MHz, DMSO-d6), δ (ppm): 10.23 (s, 1H), 8.57 (s, 2H), 7.94 (d, J = 2.2Hz, 1H), 7.67 (d, J = 2.2Hz, 1H), 7.26 - 7.18 (m, 4H), 7.14 - 7.08 (m, 1H), 4.88 (t, J = 5.9Hz, 1H), 3.72 - 3.59 (m, 4H), 1.81 (s, 2H), 1.75 (s, 6H), 1.44 (s, 6H), 0.78 (s, 9H).
融点:145〜160℃(分解)
HPLC - UV / APCI - MS negative): 511.2 (M); C31H33N3O4の計算値: 511.2
1H-NMR (300MHz, CD2CI2), δ (ppm): 10.89 (s, 1H), 8.63 (s, 2H), 8.44 (d, J = 2.3Hz, 1H), 7.81 (d, J = 2.3Hz, 1H), 7.31 - 7.24 (m, 4H), 7.22 - 7.15 (m, 1H), 1.91 (s, 2H), 1.84 (s, 6H), 1.55 (s, 6H), 0.86 (s, 9H).
使用した材料
アクリル/メラミンクリアコート配合:
a)Viacryl(登録商標)SC3031(キシレン/ブタノール中65%溶液、26:9wt./wt.) 27.51g
b)Viacryl(登録商標)SC3702(Solvesso 1003中75%) 23.34g
c)Maprenal(登録商標)MF 6504(イソブタノール中55%) 27.29g
d)酢酸ブチル/ブタノール(37:8wt./wt.) 4.33g
e)イソブタノール 4.87g
f)Solvesso(登録商標)1505 2.72g
g)Crystal oil 306 8.74g
h)Baysilone(登録商標)MA7(Solvesso(登録商標)150中1%) 1.20g
合計 100.00g
結合剤原材料:
1Viacryl(登録商標)SC 303:アクリル樹脂(Solutia、旧Vianova Resins)
2Viacryl(登録商標)SC 370:アクリル樹脂(Solutia、旧Vianova Resins)
3Solvesso(登録商標)100:芳香族炭化水素、沸点163〜180℃(Exxon Corp.)
4Maprenal(登録商標)MF 650:メラミン樹脂(Solutia、旧Vianova Resins)
5Solvesso(登録商標)150:芳香族炭化水素、沸点180〜203℃(Exxon Corp.)
6Crystal oil 30:脂肪族炭化水素、沸点145〜200℃(Shell Corp.)
7Baysilone(登録商標)MA:均展剤(Bayer AG)
UV吸収剤及び他の安定剤
Tinuvin 384(登録商標)、Ciba Specialty Chemicalsから市販されているUV吸収剤
Tinuvin 928(登録商標)、Ciba Specialty Chemicalsから市販されているUV吸収剤
Tinuvin 400(登録商標)、Ciba Specialty Chemicalsから市販されているUV吸収剤
Tinuvin 109(登録商標)、Ciba Specialty Chemicalsから市販されているUV吸収剤
オキサニリドは、Sanduvor 3206である。
実施例A1及びA3の化合物1b及び3d(I)〜(V)は、本発明のUV吸収剤である。
Tinuvin 152(登録商標)、Ciba Specialty Chemicalsからの立体障害アミン安定剤
UV吸収剤の耐光性を以下のように評価した。
本発明のUV吸収剤を、配合物の固形分(固形分:50.4%)に基づき3%の濃度で、(Viacryl(登録商標)SC 303/Viacryl(登録商標)SC 370/Maprenal(登録商標)MF 650に基づく)熱硬化アクリル/メラミンクリアコートに混和した。クリアコートをガラスプレートに噴霧し、硬化した後(130℃/30′)、クリアコートの乾燥膜厚20μmを得た。
第2の実施例では、2つのクリアコートを続けて互いに重ねて適用した。第1のクリアコート(クリアコートI)を安定化し、実施例B1でより詳細に記載したように適用した。続いて、(Viacryl(登録商標)SC 303/Viacryl(登録商標)SC 370/Maprenal(登録商標)MF 650に基づく)第2の熱硬化性アクリル/メラミンクリアコートを第1のクリアコートに噴霧し、硬化した後(130℃/30′)、第2のクリアコート(クリアコートII)の乾燥膜厚40μmを得た。第2のクリアコートを、3%のTinuvin 109/1.5%のTinuvin 400及び1%のTinuvin 152を共安定剤(HALS)とするUV吸収剤の組み合わせを使用して、安定化した。基準:非安定化第1クリアコート。実施例B1で記載したように、UV透過性スペクトルを、試験片を暴露する前に、UV/VISスペクトロメーター(Perkin Elmer, Lamda 40)を使用して記録した。続いて試験片を、SAE J 1960に従って、Xenon-WOMウエザロメーター(登録商標)(Atlas Corp.)で曝露した。暴露時間の関数として(396nmで決定した)透過値を、一定間隔の暴露の後で透過スペクトルを記録することによってモニタリングした試験結果を表2にまとめた。
熱硬化性アクリル/メラミンクリアコートを、実施例B1で記載したように調製した。塗料を、ACT Laboratories(ACT Laboratories, Inc., Southfield, Michigan 48 075, USA)から市販されている電着アルミニウムパネル(ED 6950A、10×30cm)に噴霧し、硬化の後(130℃/30分)、乾燥フィルム厚20μmを得た。続いてパネルを、SAE J 1960に従って、Xenon-WOMウエザロメーター(登録商標)(Atlas Corp.)で曝露した。クリアコートの下の電着塗膜のUV保護の程度は、電着塗膜の黄変(DIN6174によるb*値)を関数として、一定間隔の暴露でモニタリングした。結果を表3にまとめた。
a)適切なUV保護のない電着塗膜の著しい黄変/UV光線誘発崩壊
b)300〜385nmのUV光線を全て遮断する現存のUV吸収剤パッケージ(Tinuvin 109/Tinuvin 400)を有する電着塗膜の不十分な保護
c)可視波長領域への顕著な吸収を持つUV吸収剤を有する電着塗膜の優れた保護
を明確に示した。
実施例2でより詳細に記載されているように、2つのクリアコート層を、ACT Laboratories(ACT Laboratories, Inc., Southfield, Michigan 48 075, USA)から市販されている電着アルミニウムパネル(ED 6950A、10×30cm)の上に続けて適用した。基準:a)両方のクリアコートとも安定化されていない、b)第2のクリアコートがTinuvin 109/Tinuvin 400の基づく現存のUV吸収剤パッケージで安定化されている、すなわち300〜385nmのUV光線を全て遮断する。
HALS、すなわち配合物の固形分に基づいて1%のTINUVIN(登録商標)123を共安定剤として組み合わせてUV吸収剤を試験した以外は、実験パラメータは、実施例B1で概説したとおりであった。
更なる実施例では、2つのクリアコートを続けて互いに重ねて適用した。第1のクリアコート(クリアコートI)を、立体障害アミンと一緒に本発明のUV吸収剤で安定化し、実施例B1で記載したように適用した。続いて、(Viacryl(登録商標)SC 303/Viacryl(登録商標)SC 370/Maprenal(登録商標)MF 650に基づく)第2の熱硬化性アクリル/メラミンクリアコートを第1のクリアコートに噴霧し、硬化した後(130℃/30′)、第2のクリアコート(クリアコートII)の乾燥膜厚40μmを得た。第2のクリアコートを、3%のTinuvin 109(登録商標)/1.5%のTinuvin 400(登録商標)及び1%のTinuvin 152(登録商標)を共安定剤(HALS)とするUV吸収剤の組み合わせを使用して、安定化した。基準は非安定化の第1クリアコートであった。
a)Viacryl(登録商標)SC 3031 27.51g
(キシレン/ブタノール中65%溶液、26:9wt./wt.)
b)Viacryl(登録商標)SC 3702 23.34g
(Solvesso 1003中の75%)
c)Maprenal(登録商標)MF 6504 27.29g
(イソブタノール中55%)
d)酢酸ブチル/ブタノール(37:8wt./wt.) 4.33g
e)イソブタノール 4.87g
f)Solvesso(登録商標)1505 2.72g
g)Crystal oil 306 8.74g
h)Baysilone(登録商標)MA7(Solvesso(登録商標)150中1%) 1.20g
合計 100.00g
Claims (20)
- 式(I)又は(II):
〔式中、
R1は、水素、炭素原子1〜24個の直鎖若しくは分岐鎖アルキル、炭素原子2〜18個の直鎖若しくは分岐鎖アルケニル、炭素原子5〜12個のシクロアルキル、炭素原子7〜15個のフェニルアルキル、フェニル、又は炭素原子1〜4個のアルキルの1〜4つによりフェニル環で置換されている前記フェニル若しくは前記フェニルアルキルであるか;或いは
R1は、下記式:
の基又は下記式:
の基であり、
ここでLは、炭素原子1〜12個のアルキレン、炭素原子2〜12個のアルキリデン、ベンジリデン、p−キシリレン又は炭素原子5〜7個のシクロアルキレンであり;
R2は、炭素原子1〜24個の直鎖若しくは分岐鎖アルキル、炭素原子2〜18個の直鎖若しくは分岐鎖アルケニル、炭素原子5〜12個のシクロアルキル、炭素原子7〜15個のフェニルアルキル、フェニル、又は炭素原子1〜4個のアルキルの1〜3つによりフェニル環で置換されている前記フェニル若しくは前記フェニルアルキルであるか;或いは、
−OH、−OCO−R11、−OR14、−NCO若しくは−NH2基又はこれらの混合物の1つ以上で置換されている前記アルキルか、又は−O−、−NH−若しくは−NR14−基又はこれらの混合物の1つ以上で中断され、かつ非置換であるか、又は−OH、−OR14若しくは−NH2基又はこれらの混合物の1つ以上で置換されていることができる前記アルキル若しくは前記アルケニルであり;ここで、
R11は、水素、直鎖若しくは分岐鎖C1〜C18アルキル、C5〜C12シクロアルキル、直鎖若しくは分岐鎖C3〜C18アルケニル、フェニル、ナフチル又はC7〜C15フェニルアルキルであり;そして
R14は、水素、炭素原子1〜24個の直鎖若しくは分岐鎖アルキルであるか;或いは:
R2は、−OR14、基−C(O)−O−R14、−C(O)−NHR14又は−C(O)−NR14R′14であり、ここでR′14は、R14と同じ意味を有するか;或いは
R2は、−SR13、−NHR13又は−N(R13)2であるか;或いは
R2は、−(CH2)m−CO−X1−(Z)p−Y−R15であり、ここで、
X1は、−O−又は−N(R16)−であり、
Yは、−O−若しくは−N(R17)−又は直接結合であり、
Zは、C2〜C12アルキレン、1〜3個の窒素原子、酸素原子若しくはその混合物で中断されているC4〜C12アルキレンであるか、又はそれぞれヒドロキシル基で追加的に置換されていてもよいC3〜C12アルキレン、ブテニレン、ブチニレン、シクロヘキシレン若しくはフェニレンであるか、或いは、
下記式:
の基であり、
ここで*は、結合を示すか、又は
Yが直接結合である場合、Zは、追加的に直接結合であることもでき、
mは、0、1又は2であり、
pは、1であるか、又はX及びYが、それぞれ−N(R16)−及び−N(R17)−である場合、0でもあり、
R15は、水素、C1〜C12アルキルか、又は下記式:
の基か、又は基−CO−C(R18)=C(H)R19か、又はYが−N(R17)−である場合、R17と一緒になって、基−CO−CH=CH−CO−を形成し、ここで、
R18は、水素又はメチルであり、そしてR19は、水素、メチル又は−CO−X1−R20であり、ここで、
R20は、水素、C1〜C12アルキル又は下記式:
の基であり;
R5、R6、R7及びR8は、独立して、水素、ハロゲン、CN、NO2又はNH2であり;
R13は、炭素原子1〜20個のアルキル、炭素原子2〜20個のヒドロキシアルキル、炭素原子3〜18個のアルケニル、炭素原子5〜12個のシクロアルキル、炭素原子7〜15個のフェニルアルキル、両方とも炭素原子1〜4個のアルキルの1又は2つで置換されていてもよいフェニル又はナフチルであり;
R16及びR17は、互いに独立して、水素、C1〜C12アルキル、1〜3個の酸素原子で中断されているC3〜C12アルキルであるか、又はシクロヘキシル若しくはC7〜C15フェニルアルキルであり、Zがエチレンである場合、R16は、また、R17と一緒になってエチレンを形成し;
Xは、O又はNE1であり、ここで、
E1は、水素、直鎖若しくは分岐鎖C1〜C24アルキル、直鎖若しくは分岐鎖C2〜C18アルケニル、C2〜C6アルキニル、C5〜C12シクロアルキル、フェニル、ナフチル又はC7〜C15フェニルアルキルであるか、又は前記直鎖若しくは分岐鎖C1〜C24アルキル、直鎖若しくは分岐鎖C2〜C24アルケニル、C5〜C12シクロアルキル、C2〜C6アルキニルは、−F、−OH、−OR22、−NH2、−NHR22、−N(R22)2、−NHCOR23、−NR22COR23、−OCOR24、−COR25、−SO2R26、−PO(R27)n(R28)2−n、−Si(R29)n(R30)3−n、−Si(R22)3、−N+(R22)3A−、−S+(R22)2A−、オキシラニル基又はこれらの混合物の1つ以上で置換されていることができ、前記直鎖若しくは分岐鎖C1〜C24アルキル、直鎖若しくは分岐鎖の非置換若しくは置換C2〜C24アルケニル、C5〜C12シクロアルキル又はC2〜C6アルキニルは、また、−O−、−S−、−NH−若しくは−NR22−基又はこれらの組み合わせの1つ以上で中断されていることができ;
前記フェニル、ナフチル又はC7〜C15フェニルアルキルは、また、−ハロゲン、−CN、−CF3、−NO2、−NHR22、−N(R22)2、−SO2R26、−PO(R27)n(R28)2−n、−OH、−OR22、−COR25、−R25の1つ以上で置換されていることができ、ここで、
nは、0、1又は2であり;
R22は、直鎖若しくは分岐鎖C1〜18アルキル、直鎖若しくは分岐鎖C2〜C18アルケニル、C5〜C10シクロアルキル、フェニル又はナフチル、C7〜C15フェニルアルキルであるか、或いはN又はSi原子に結合している場合、2つのR22は、それらが結合している原子と一緒になって、ピロリジン、ピペリジン又はモルホリン環を形成することができ;
R23は、水素、OR22、NHR22、N(R22)2であるか、又はR22と同じ意味を有し、
R24は、OR22、NHR22、N(R22)2であるか、又はR22と同じ意味を有し、
R25は、水素、OH、OR22、NHR22若しくはN(R22)2、O−グリシジルであるか、又はR22と同じ意味を有し、
R26は、OH、OR22、NHR22又はN(R22)2であり、
R27は、NH2、NHR22又はN(R22)2であり、
R28は、OH又はOR22であり、
R29は、Cl又はOR22であり、
R30は、直鎖又は分岐鎖C1〜C18アルキルであるか;或いは
E1は、下記式:
の基であり、
ここで、R1〜R8は、上記で定義されたとおりの意味を有し、そして
Qは、直鎖若しくは分岐鎖C2〜C12アルキレン、−O−、NH若しくはNR14原子の1個以上で中断されているC2〜C12アルキレン、C5〜C10シクロアルキレン、パラ−フェニレン、又は下記式:
の基であり、
ここで*は、結合を示す〕
で示される化合物。 - R1が、水素、炭素原子1〜24個の直鎖若しくは分岐鎖アルキル、炭素原子2〜18個の直鎖若しくは分岐鎖アルケニル、炭素原子5〜12個のシクロアルキル、炭素原子7〜15個のフェニルアルキル、フェニル、又は炭素原子1〜4個のアルキルの1〜4つによりフェニル環で置換されている前記フェニル若しくは前記フェニルアルキルであるか;或いは
R1が、下記式:
の基又は下記式:
の基であり、
ここでLが、炭素原子1〜12個のアルキレン、炭素原子2〜12個のアルキリデン、ベンジリデン、p−キシリレン又は炭素原子5〜7個のシクロアルキレンであり;
R2が、炭素原子1〜24個の直鎖若しくは分岐鎖アルキル、炭素原子2〜18個の直鎖若しくは分岐鎖アルケニル、炭素原子5〜12個のシクロアルキル、炭素原子7〜15個のフェニルアルキル、フェニル、又は炭素原子1〜4個のアルキルの1〜3つによりフェニル環で置換されている前記フェニル若しくは前記フェニルアルキルであるか;或いは、
R2が、−(CH2)m−CO−X1−(Z)p−Y−R15であり、ここで、
Yが、−O−又は直接結合であり、
Zが、C2〜C12アルキレン、1〜3個の窒素原子、酸素原子若しくはその混合物で中断されているC4〜C12アルキレンであるか、又はYが直接結合である場合、Zが、追加的に直接結合であることもでき;
mが、2であり、
pが、1であり、
R15が、水素、C1〜C12アルキル又は下記式:
の基であり、
R5、R6、R7及びR8が、独立して、水素、Cl又はBrであり;
Xが、O又はNE1であり、ここで、
E1が、水素、直鎖若しくは分岐鎖C1〜C24アルキル、直鎖若しくは分岐鎖C2〜C18アルケニル、C2〜C6アルキニル、C5〜C12シクロアルキル、フェニル、ナフチル又はC7〜C15フェニルアルキルであるか、又は前記直鎖若しくは分岐鎖C1〜C24アルキル、直鎖若しくは分岐鎖C2〜C24アルケニル、C5〜C12シクロアルキル、C2〜C6アルキニルが、−F、−OH、−OR22、−NH2、−NHR22、−N(R22)2、−NHCOR23、−NR22COR23、−OCOR24、−COR25、−SO2R26、−PO(R27)n(R28)2−n、−Si(R29)n(R30)3−n、−Si(R22)3、−N+(R22)3A−、−S+(R22)2A−、オキシラニル基又はこれらの混合物の1つ以上で置換されていることができ、前記直鎖若しくは分岐鎖C1〜C24アルキル、直鎖若しくは分岐鎖の非置換若しくは置換C2〜C24アルケニル、C5〜C12シクロアルキル又はC2〜C6アルキニルが、また、−O−、−S−、−NH−若しくは−NR22−基又はこれらの組み合わせの1つ以上で中断されていることができ;
前記フェニル、ナフチル又はC7〜C15フェニルアルキルが、また、−ハロゲン、−CN、−CF3、−NO2、−NHR22、−N(R22)2、−SO2R26、−PO(R27)n(R28)2−n、−OH、−OR22、−COR25、−R25の1つ以上で置換されていることができ、ここで、
nが、0、1又は2であり;
R22が、直鎖若しくは分岐鎖C1〜18アルキル、直鎖若しくは分岐鎖C2〜C18アルケニル、C5〜C10シクロアルキル、フェニル又はナフチル、C7〜C15フェニルアルキルであるか、或いはN又はSi原子に結合している場合、2つのR22が、それらが結合している原子と一緒になって、ピロリジン、ピペリジン又はモルホリン環を形成することができ;
R23が、水素、OR22、NHR22、N(R22)2であるか、又はR22と同じ意味を有し、
R24が、OR22、NHR22、N(R22)2であるか、又はR22と同じ意味を有し、
R25が、水素、OH、OR22、NHR22若しくはN(R22)2、O−グリシジルであるか、又はR22と同じ意味を有し、
R26が、OH、OR22、NHR22又はN(R22)2であり、
R27が、NH2、NHR22又はN(R22)2であり、
R28が、OH又はOR22であり、
R29が、Cl又はOR22であり、
R30が、直鎖又は分岐鎖C1〜C18アルキルであるか;或いは
E1が、下記式:
の基であり、
ここで、R1〜R8が、上記で定義されたとおりの意味を有し、そして
Qが、直鎖若しくは分岐鎖C2〜12アルキレン、C5〜C10シクロアルキレン若しくはパラ−フェニレン又は下記式:
の基である、
式(I)又は(II)で示される請求項1記載の化合物。 - R1が、水素、炭素原子1〜24個の直鎖若しくは分岐鎖アルキル、炭素原子2〜18個の直鎖若しくは分岐鎖アルケニル、炭素原子5〜12個のシクロアルキル、炭素原子7〜15個のフェニルアルキル、フェニル、又は炭素原子1〜4個のアルキルの1〜4つによりフェニル環で置換されている前記フェニル若しくは前記フェニルアルキルであり;
R2が、炭素原子1〜24個の直鎖若しくは分岐鎖アルキル、炭素原子2〜18個の直鎖若しくは分岐鎖アルケニル、炭素原子5〜12個のシクロアルキル、炭素原子7〜15個のフェニルアルキル、フェニル、又は炭素原子1〜4個のアルキルの1〜3つによりフェニル環で置換されている前記フェニル若しくは前記フェニルアルキルであるか;或いは、
R2が、−(CH2)2−CO−O−(Z)−O−R15であり、ここで、
Zが、C2〜C12アルキレン、1〜3個の酸素原子で中断されているC4〜C12アルキレンであり;
R15が、水素、C1〜C12アルキル又は下記式:
の基であり、
R5、R6、R7及びR8が、独立して、水素、Cl又はBrであり;
Xが、O又はNE1であり、ここで、
E1が、水素、直鎖若しくは分岐鎖C1〜24アルキル、C5〜C12シクロアルキル、フェニル、又はC7〜C15フェニルアルキルであるか;又は前記直鎖若しくは分岐鎖C1〜24アルキル又はC5〜C12シクロアルキルが、−F、−OH、−OR22、−NH2、−NHR22、−N(R22)2の1つ以上で置換されていることができ;
前記フェニル又はC7〜C15フェニルアルキルが、また、ハロゲン、−CN、−CF3、−OH、−OR22、−COR22、−R22の1つ以上で置換されていることができ;ここで、
R22が、直鎖若しくは分岐鎖C1〜18アルキル、直鎖若しくは分岐鎖C2〜18アルケニル、C5〜C10シクロアルキル、C6〜C16フェニル若しくはナフチル、C7〜C15フェニルアルキルであるか;或いは
E1が、下記式:
の基であり、
ここで、R1〜R8が、上記で定義されたとおりの意味を有し、そして
Qが、C2〜C12アルキレンC5〜C7シクロアルキレン、パラ−フェニレン又は下記式:
の基である
請求項2記載の化合物。 - R1が、水素、炭素原子1〜12個の直鎖若しくは分岐鎖アルキル、又は炭素原子7〜15個のフェニルアルキルであり;
R2が、炭素原子1〜12個の直鎖若しくは分岐鎖アルキル、炭素原子7〜15個のフェニルアルキル、フェニル、又は炭素原子1〜4個のアルキルの1〜3つによりフェニル環で置換されている前記フェニル若しくは前記フェニルアルキルであり;
R5及びR6が、水素であるか、両方のうちの一方がCl又はBrであり;
R7及びR8が、独立して、水素、Cl又はBrであり;
Xが、O又はNE1であり、ここで、
E1が、水素、非置換又は1〜4つのOHで置換されている直鎖若しくは分岐鎖C1〜6アルキル、非置換又はF、CF3、CN若しくはClで置換されているフェニル、又はC7〜C9フェニルアルキルである
請求項3記載の化合物。 - 式(I)で示される請求項1記載の化合物。
- 反応が溶媒中で実施される、請求項7記載の方法。
- 式III、IV又はVの化合物の量と式Xのアジド化合物の量とのモル比が、1:1〜1:3である、請求項7記載の方法。
- 反応が触媒の存在下で実施される、請求項7記載の方法。
- (a)光誘発性分解に付される有機材料、及び
(b)請求項1記載の式I又はIIの化合物
を含む、光誘発性分解に対して安定化された組成物。 - s−トリアジン、オキサニリド、ヒドロキシベンゾフェノン、ベンゾエート、α−シアノアクリレート、及び請求項1記載の式(I)又は(II)のものと異なるベンゾトリアゾールからなる群より選択される立体障害アミン安定剤及び/又はUV吸収剤を追加的に含有する、請求項11記載の組成物。
- 有機材料が記録材料である、請求項11記載の組成物。
- 有機材料が、天然、半合成、又は合成ポリマーである、請求項11記載の組成物。
- ポリマーが熱可塑性ポリマーである、請求項14記載の組成物。
- 有機材料が被覆である、請求項11記載の組成物。
- 被覆が自動車用被覆である、請求項16記載の組成物。
- 被覆が、380nmを越える波長の電磁放射線に感受性がある基材の一面にわたって適用される、請求項16記載の組成物。
- 式I又はIIの組成物が、有機材料の重量に基づいて0.1重量%〜30重量%の量で存在する、請求項11記載の組成物。
- 被覆における紫外線(UV)及び可視光線(VIS)吸収剤としての、式I又はIIの化合物の使用。
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- 2006-01-23 RU RU2007132974/04A patent/RU2414471C2/ru not_active IP Right Cessation
- 2006-01-26 MY MYPI20060366A patent/MY144674A/en unknown
- 2006-01-26 TW TW095103077A patent/TWI391393B/zh not_active IP Right Cessation
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Cited By (9)
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JP2009541416A (ja) * | 2006-06-27 | 2009-11-26 | チバ ホールディング インコーポレーテッド | 長波長シフトしたベンゾトリアゾール紫外線吸収剤およびその使用 |
JP2016514756A (ja) * | 2013-04-02 | 2016-05-23 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | 被覆されている炭素繊維強化プラスチック部品 |
JP2020513449A (ja) * | 2016-11-30 | 2020-05-14 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | 光硬化性ハードコート組成物、方法、およびその組成物由来の物品 |
JP7073369B2 (ja) | 2016-11-30 | 2022-05-23 | ビーエーエスエフ ソシエタス・ヨーロピア | 光硬化性ハードコート組成物、方法、およびその組成物由来の物品 |
WO2019066042A1 (ja) * | 2017-09-29 | 2019-04-04 | 積水化学工業株式会社 | ガラス構成体 |
JPWO2019066042A1 (ja) * | 2017-09-29 | 2019-11-14 | 積水化学工業株式会社 | ガラス構成体 |
US11048112B2 (en) | 2017-09-29 | 2021-06-29 | Sekisui Chemical Co., Ltd. | Glass structure |
JP2020035743A (ja) * | 2018-08-30 | 2020-03-05 | 三星エスディアイ株式会社Samsung SDI Co., Ltd. | 有機発光素子封止用組成物及びこれから製造された有機層を含む有機発光素子表示装置 |
JP7475119B2 (ja) | 2018-08-30 | 2024-04-26 | 三星エスディアイ株式会社 | 有機発光素子封止用組成物及びこれから製造された有機層を含む有機発光素子表示装置 |
Also Published As
Publication number | Publication date |
---|---|
US7695643B2 (en) | 2010-04-13 |
CN101111496B (zh) | 2010-12-29 |
KR20070104640A (ko) | 2007-10-26 |
WO2006082145A1 (en) | 2006-08-10 |
TWI391393B (zh) | 2013-04-01 |
KR101322194B1 (ko) | 2013-10-30 |
MY144674A (en) | 2011-10-31 |
ATE502942T1 (de) | 2011-04-15 |
BRPI0606893B1 (pt) | 2014-10-14 |
EP1844049A1 (en) | 2007-10-17 |
DE602006020839D1 (de) | 2011-05-05 |
US20080157025A1 (en) | 2008-07-03 |
CN101111496A (zh) | 2008-01-23 |
BRPI0606893A2 (pt) | 2009-07-21 |
EP1844049B1 (en) | 2011-03-23 |
RU2414471C2 (ru) | 2011-03-20 |
JP4975646B2 (ja) | 2012-07-11 |
TW200633988A (en) | 2006-10-01 |
RU2007132974A (ru) | 2009-03-10 |
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