JP6478997B2 - 2−(2−ヒドロキシフェニル)ベンゾトリアゾール化合物のコーティングにおける紫外線吸収剤としての使用 - Google Patents
2−(2−ヒドロキシフェニル)ベンゾトリアゾール化合物のコーティングにおける紫外線吸収剤としての使用 Download PDFInfo
- Publication number
- JP6478997B2 JP6478997B2 JP2016527408A JP2016527408A JP6478997B2 JP 6478997 B2 JP6478997 B2 JP 6478997B2 JP 2016527408 A JP2016527408 A JP 2016527408A JP 2016527408 A JP2016527408 A JP 2016527408A JP 6478997 B2 JP6478997 B2 JP 6478997B2
- Authority
- JP
- Japan
- Prior art keywords
- bis
- alkyl
- tetramethyl
- tert
- piperidyl
- 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.)
- Expired - Fee Related
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- 239000006096 absorbing agent Substances 0.000 title claims description 15
- 238000000576 coating method Methods 0.000 title description 27
- 239000011248 coating agent Substances 0.000 title description 20
- FJGQBLRYBUAASW-UHFFFAOYSA-N 2-(benzotriazol-2-yl)phenol Chemical class OC1=CC=CC=C1N1N=C2C=CC=CC2=N1 FJGQBLRYBUAASW-UHFFFAOYSA-N 0.000 title description 7
- -1 2- (2-hydroxyphenyl) benzotriazole compound Chemical class 0.000 claims description 84
- 125000000217 alkyl group Chemical group 0.000 claims description 71
- 150000001875 compounds Chemical class 0.000 claims description 63
- 239000000203 mixture Substances 0.000 claims description 53
- 229910052739 hydrogen Inorganic materials 0.000 claims description 30
- 229910052799 carbon Inorganic materials 0.000 claims description 25
- 229910052757 nitrogen Inorganic materials 0.000 claims description 24
- 239000003973 paint Substances 0.000 claims description 24
- 239000008199 coating composition Substances 0.000 claims description 22
- 125000002947 alkylene group Chemical group 0.000 claims description 19
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
- 229910052736 halogen Inorganic materials 0.000 claims description 16
- 150000002367 halogens Chemical class 0.000 claims description 16
- 239000004611 light stabiliser Substances 0.000 claims description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- 125000004450 alkenylene group Chemical group 0.000 claims description 13
- 125000003342 alkenyl group Chemical group 0.000 claims description 11
- 150000001412 amines Chemical class 0.000 claims description 11
- 125000001931 aliphatic group Chemical group 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 239000000047 product Substances 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- 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 claims description 6
- 239000011368 organic material Substances 0.000 claims description 6
- RXFCIXRFAJRBSG-UHFFFAOYSA-N 3,2,3-tetramine Chemical compound NCCCNCCNCCCN RXFCIXRFAJRBSG-UHFFFAOYSA-N 0.000 claims description 5
- 125000004122 cyclic group Chemical group 0.000 claims description 5
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 claims description 5
- 239000004922 lacquer Substances 0.000 claims description 5
- UKJARPDLRWBRAX-UHFFFAOYSA-N n,n'-bis(2,2,6,6-tetramethylpiperidin-4-yl)hexane-1,6-diamine Chemical compound C1C(C)(C)NC(C)(C)CC1NCCCCCCNC1CC(C)(C)NC(C)(C)C1 UKJARPDLRWBRAX-UHFFFAOYSA-N 0.000 claims description 5
- HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 claims description 4
- BWJKLDGAAPQXGO-UHFFFAOYSA-N 2,2,6,6-tetramethyl-4-octadecoxypiperidine Chemical compound CCCCCCCCCCCCCCCCCCOC1CC(C)(C)NC(C)(C)C1 BWJKLDGAAPQXGO-UHFFFAOYSA-N 0.000 claims description 4
- FBIXXCXCZOZFCO-UHFFFAOYSA-N 3-dodecyl-1-(2,2,6,6-tetramethylpiperidin-4-yl)pyrrolidine-2,5-dione Chemical compound O=C1C(CCCCCCCCCCCC)CC(=O)N1C1CC(C)(C)NC(C)(C)C1 FBIXXCXCZOZFCO-UHFFFAOYSA-N 0.000 claims description 4
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 claims description 4
- FDAKZQLBIFPGSV-UHFFFAOYSA-N n-butyl-2,2,6,6-tetramethylpiperidin-4-amine Chemical compound CCCCNC1CC(C)(C)NC(C)(C)C1 FDAKZQLBIFPGSV-UHFFFAOYSA-N 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- JJYUJOJVFRXHAE-UHFFFAOYSA-N (3,5,5-trimethyl-6-oxomorpholin-3-yl)methyl 2-ethylhexanoate Chemical compound CCCCC(CC)C(=O)OCC1(C)COC(=O)C(C)(C)N1 JJYUJOJVFRXHAE-UHFFFAOYSA-N 0.000 claims description 3
- VXTRPEFUPWORNH-UHFFFAOYSA-N 1-(1-acetyl-2,2,6,6-tetramethylpiperidin-4-yl)-3-dodecylpyrrolidine-2,5-dione Chemical compound O=C1C(CCCCCCCCCCCC)CC(=O)N1C1CC(C)(C)N(C(C)=O)C(C)(C)C1 VXTRPEFUPWORNH-UHFFFAOYSA-N 0.000 claims description 3
- SAEZGDDJKSBNPT-UHFFFAOYSA-N 3-dodecyl-1-(1,2,2,6,6-pentamethylpiperidin-4-yl)pyrrolidine-2,5-dione Chemical compound O=C1C(CCCCCCCCCCCC)CC(=O)N1C1CC(C)(C)N(C)C(C)(C)C1 SAEZGDDJKSBNPT-UHFFFAOYSA-N 0.000 claims description 3
- 229920000089 Cyclic olefin copolymer Polymers 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 238000009833 condensation Methods 0.000 claims description 3
- 230000005494 condensation Effects 0.000 claims description 3
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 claims description 3
- 150000005690 diesters Chemical class 0.000 claims description 3
- UONLDZHKYCFZRW-UHFFFAOYSA-N n-[6-[formyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]hexyl]-n-(2,2,6,6-tetramethylpiperidin-4-yl)formamide Chemical compound C1C(C)(C)NC(C)(C)CC1N(C=O)CCCCCCN(C=O)C1CC(C)(C)NC(C)(C)C1 UONLDZHKYCFZRW-UHFFFAOYSA-N 0.000 claims description 3
- OUBISKKOUYNDML-UHFFFAOYSA-N (2,2,6,6-tetramethylpiperidin-4-yl) 2-[bis[2-oxo-2-(2,2,6,6-tetramethylpiperidin-4-yl)oxyethyl]amino]acetate Chemical compound C1C(C)(C)NC(C)(C)CC1OC(=O)CN(CC(=O)OC1CC(C)(C)NC(C)(C)C1)CC(=O)OC1CC(C)(C)NC(C)(C)C1 OUBISKKOUYNDML-UHFFFAOYSA-N 0.000 claims description 2
- CGXOAAMIQPDTPE-UHFFFAOYSA-N 1,2,2,6,6-pentamethylpiperidin-4-amine Chemical compound CN1C(C)(C)CC(N)CC1(C)C CGXOAAMIQPDTPE-UHFFFAOYSA-N 0.000 claims description 2
- NWHNXXMYEICZAT-UHFFFAOYSA-N 1,2,2,6,6-pentamethylpiperidin-4-ol Chemical compound CN1C(C)(C)CC(O)CC1(C)C NWHNXXMYEICZAT-UHFFFAOYSA-N 0.000 claims description 2
- ONABRCKXKDSXCA-UHFFFAOYSA-N 2-[3-amino-2,6-bis[butyl-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)amino]-2h-1,3,5-triazin-4-yl]ethanol Chemical compound N1=C(N(CCCC)C2CC(C)(C)N(OC3CCCCC3)C(C)(C)C2)N=C(CCO)N(N)C1N(CCCC)C(CC1(C)C)CC(C)(C)N1OC1CCCCC1 ONABRCKXKDSXCA-UHFFFAOYSA-N 0.000 claims description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 2
- GUCMKIKYKIHUTM-UHFFFAOYSA-N 3,3,5,5-tetramethyl-1-[2-(3,3,5,5-tetramethyl-2-oxopiperazin-1-yl)ethyl]piperazin-2-one Chemical compound O=C1C(C)(C)NC(C)(C)CN1CCN1C(=O)C(C)(C)NC(C)(C)C1 GUCMKIKYKIHUTM-UHFFFAOYSA-N 0.000 claims description 2
- NPYDPROENPLGBR-UHFFFAOYSA-N 4,6-dichloro-n-cyclohexyl-1,3,5-triazin-2-amine Chemical compound ClC1=NC(Cl)=NC(NC2CCCCC2)=N1 NPYDPROENPLGBR-UHFFFAOYSA-N 0.000 claims description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 2
- KGUHWHHMNQPSRV-UHFFFAOYSA-N [1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethylpiperidin-4-yl] octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC1CC(C)(C)N(OCC(C)(C)O)C(C)(C)C1 KGUHWHHMNQPSRV-UHFFFAOYSA-N 0.000 claims description 2
- 125000002723 alicyclic group Chemical group 0.000 claims description 2
- CMXLJKWFEJEFJE-UHFFFAOYSA-N bis(1,2,2,6,6-pentamethylpiperidin-4-yl) 2-[(4-methoxyphenyl)methylidene]propanedioate Chemical compound C1=CC(OC)=CC=C1C=C(C(=O)OC1CC(C)(C)N(C)C(C)(C)C1)C(=O)OC1CC(C)(C)N(C)C(C)(C)C1 CMXLJKWFEJEFJE-UHFFFAOYSA-N 0.000 claims description 2
- RSOILICUEWXSLA-UHFFFAOYSA-N bis(1,2,2,6,6-pentamethylpiperidin-4-yl) decanedioate Chemical compound C1C(C)(C)N(C)C(C)(C)CC1OC(=O)CCCCCCCCC(=O)OC1CC(C)(C)N(C)C(C)(C)C1 RSOILICUEWXSLA-UHFFFAOYSA-N 0.000 claims description 2
- NLMFVJSIGDIJBB-UHFFFAOYSA-N bis(2,2,6,6-tetramethyl-1-octoxypiperidin-3-yl) decanedioate Chemical compound CC1(C)N(OCCCCCCCC)C(C)(C)CCC1OC(=O)CCCCCCCCC(=O)OC1C(C)(C)N(OCCCCCCCC)C(C)(C)CC1 NLMFVJSIGDIJBB-UHFFFAOYSA-N 0.000 claims description 2
- OSIVCXJNIBEGCL-UHFFFAOYSA-N bis(2,2,6,6-tetramethyl-1-octoxypiperidin-4-yl) decanedioate Chemical compound C1C(C)(C)N(OCCCCCCCC)C(C)(C)CC1OC(=O)CCCCCCCCC(=O)OC1CC(C)(C)N(OCCCCCCCC)C(C)(C)C1 OSIVCXJNIBEGCL-UHFFFAOYSA-N 0.000 claims description 2
- GOJOVSYIGHASEI-UHFFFAOYSA-N bis(2,2,6,6-tetramethylpiperidin-4-yl) butanedioate Chemical compound C1C(C)(C)NC(C)(C)CC1OC(=O)CCC(=O)OC1CC(C)(C)NC(C)(C)C1 GOJOVSYIGHASEI-UHFFFAOYSA-N 0.000 claims description 2
- XITRBUPOXXBIJN-UHFFFAOYSA-N bis(2,2,6,6-tetramethylpiperidin-4-yl) decanedioate Chemical compound C1C(C)(C)NC(C)(C)CC1OC(=O)CCCCCCCCC(=O)OC1CC(C)(C)NC(C)(C)C1 XITRBUPOXXBIJN-UHFFFAOYSA-N 0.000 claims description 2
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims description 2
- 125000006309 butyl amino group Chemical group 0.000 claims description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 claims description 2
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims description 2
- DARUEKWVLGHJJT-UHFFFAOYSA-N n-butyl-1-[4-[4-(butylamino)-2,2,6,6-tetramethylpiperidin-1-yl]-6-chloro-1,3,5-triazin-2-yl]-2,2,6,6-tetramethylpiperidin-4-amine Chemical compound CC1(C)CC(NCCCC)CC(C)(C)N1C1=NC(Cl)=NC(N2C(CC(CC2(C)C)NCCCC)(C)C)=N1 DARUEKWVLGHJJT-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- 229920000642 polymer Polymers 0.000 claims description 2
- 230000005855 radiation Effects 0.000 claims description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 claims description 2
- 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 claims description 2
- 239000004711 α-olefin Substances 0.000 claims description 2
- WTVNFKVGGUWHQC-UHFFFAOYSA-N decane-2,4-dione Chemical compound CCCCCCC(=O)CC(C)=O WTVNFKVGGUWHQC-UHFFFAOYSA-N 0.000 claims 2
- YAXWOADCWUUUNX-UHFFFAOYSA-N 1,2,2,3-tetramethylpiperidine Chemical class CC1CCCN(C)C1(C)C YAXWOADCWUUUNX-UHFFFAOYSA-N 0.000 claims 1
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 claims 1
- KKOFPMFUCMGHDX-UHFFFAOYSA-N 1-[[3,5-bis[cyclohexyl-(3,3,4,5,5-pentamethyl-2-oxopiperazin-1-yl)amino]-1,3,5-triazinan-1-yl]-cyclohexylamino]-3,3,4,5,5-pentamethylpiperazin-2-one Chemical compound O=C1C(C)(C)N(C)C(C)(C)CN1N(N1CN(CN(C1)N(C1CCCCC1)N1C(C(C)(C)N(C)C(C)(C)C1)=O)N(C1CCCCC1)N1C(C(C)(C)N(C)C(C)(C)C1)=O)C1CCCCC1 KKOFPMFUCMGHDX-UHFFFAOYSA-N 0.000 claims 1
- MESWESDXDWUFHK-UHFFFAOYSA-N 1-[[3,5-bis[cyclohexyl-(3,3,5,5-tetramethyl-2-oxopiperazin-1-yl)amino]-1,3,5-triazinan-1-yl]-cyclohexylamino]-3,3,5,5-tetramethylpiperazin-2-one Chemical compound O=C1C(C)(C)NC(C)(C)CN1N(N1CN(CN(C1)N(C1CCCCC1)N1C(C(C)(C)NC(C)(C)C1)=O)N(C1CCCCC1)N1C(C(C)(C)NC(C)(C)C1)=O)C1CCCCC1 MESWESDXDWUFHK-UHFFFAOYSA-N 0.000 claims 1
- IXAKLSFFPBJWBS-UHFFFAOYSA-N 2-cycloundecyl-7,7,9,9-tetramethyl-1-oxa-3,8-diazaspiro[4.5]decan-4-one Chemical compound C1C(C)(C)NC(C)(C)CC21C(=O)NC(C1CCCCCCCCCC1)O2 IXAKLSFFPBJWBS-UHFFFAOYSA-N 0.000 claims 1
- ZCILGMFPJBRCNO-UHFFFAOYSA-N 4-phenyl-2H-benzotriazol-5-ol Chemical compound OC1=CC=C2NN=NC2=C1C1=CC=CC=C1 ZCILGMFPJBRCNO-UHFFFAOYSA-N 0.000 claims 1
- VMRIVYANZGSGRV-UHFFFAOYSA-N 4-phenyl-2h-triazin-5-one Chemical compound OC1=CN=NN=C1C1=CC=CC=C1 VMRIVYANZGSGRV-UHFFFAOYSA-N 0.000 claims 1
- LWMPFIOTEAXAGV-UHFFFAOYSA-N piperidin-1-amine Chemical compound NN1CCCCC1 LWMPFIOTEAXAGV-UHFFFAOYSA-N 0.000 claims 1
- 229920005989 resin Polymers 0.000 description 19
- 239000011347 resin Substances 0.000 description 19
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 17
- 229920000223 polyglycerol Polymers 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 12
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- 239000007787 solid Substances 0.000 description 11
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- 239000011230 binding agent Substances 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 9
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 9
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 9
- 239000012948 isocyanate Substances 0.000 description 9
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- 239000003381 stabilizer Substances 0.000 description 8
- QFZGGTOFNBHBBS-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-6-(chloromethyl)-4-methylphenol Chemical compound CC1=CC(CCl)=C(O)C(N2N=C3C=CC=CC3=N2)=C1 QFZGGTOFNBHBBS-UHFFFAOYSA-N 0.000 description 7
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- 125000003545 alkoxy group Chemical group 0.000 description 7
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- 239000000654 additive Substances 0.000 description 6
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- 230000014509 gene expression Effects 0.000 description 5
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 5
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- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 5
- 229920000570 polyether Polymers 0.000 description 5
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- ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 4
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Classifications
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/60—Additives non-macromolecular
- C09D7/63—Additives non-macromolecular organic
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/48—Stabilisers against degradation by oxygen, light or heat
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/16—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
- C07D249/18—Benzotriazoles
- C07D249/20—Benzotriazoles with aryl radicals directly attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/62—Polymers of compounds having carbon-to-carbon double bonds
- C08G18/6216—Polymers of alpha-beta ethylenically unsaturated carboxylic acids or of derivatives thereof
- C08G18/622—Polymers of esters of alpha-beta ethylenically unsaturated carboxylic acids
- C08G18/6225—Polymers of esters of acrylic or methacrylic acid
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/78—Nitrogen
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- C08G18/7818—Nitrogen containing -N-C=0 groups containing ureum or ureum derivative groups
- C08G18/7831—Nitrogen containing -N-C=0 groups containing ureum or ureum derivative groups containing biuret groups
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- 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
- C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
- C08K5/3432—Six-membered rings
- C08K5/3435—Piperidines
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- 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
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- C08K5/3475—Five-membered rings condensed with carbocyclic rings
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- C—CHEMISTRY; METALLURGY
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Description
のベンゾトリアゾール系化合物を開示している。化合物は、ジベンゾイルメタン誘導体のための光安定剤及び可溶化剤として有用であり、化粧品サンケア組成物に使用されている。
の紫外線吸収剤を開示している。しかしながら、式(4)は、酸素原子とR6との間のカルボニル基が欠落しているという点で不適切である。これは、式(1)の化合物(R6がHである式(4)に対応する)及び酸を適切な溶媒中に溶解し、その後、必要であれば、酸触媒、例えば、硫酸又はメタンスルホン酸の存在下で、これを従来の方法によって室温〜還流温度で処理することを含む製造方法から明らかである。かかる酸の例は、酢酸、プロピオン酸、ブタン酸、アクリル酸等である。R6が上記で定義された通りである式(4)のエーテル化合物は、この方法によって製造することができない。これは、さらに、式(4)の化合物を指す表1によって確認されている。しかしながら、表1に示す化合物は、エーテル化合物ではなく、エステル化合物である。
R(QUV)n (I)
で示され、その式(I)において、
Rが、1価〜15価の脂肪族基、脂環式基又は芳香族基であり;
UVが以下の式(II):
R1、R2、及びR3は、同一又は異なってもよく、H、C1〜C20アルキル、C1〜C5アルコキシ、C1〜C5アルコキシカルボニル、C3〜C7シクロアルキル、フェニル、ナフチル又はフェニル−C1〜C5アルキルであり;
R4、R5、R6及びR7は、同一又は異なってもよく、H、C1〜C5アルキル、C1〜C5アルコキシ、又はハロゲンであり;
R10はH又はC1〜C20アルキルである)
の基であり;
QがOであり;
nが1、2、3、4、5、6、7、8、9、10、11、12、13、14又は15である、2−(2−ヒドロキシフェニル)ベンゾトリアゾール化合物の、コーティングにおける紫外線吸収剤としての使用に関する本発明によって解決される。
実施態様によれば、R1がC1〜C8アルキル、特にメチルであり、且つR2及びR3がHである、式(I)の化合物が使用される。
C1〜C20アルキル、好ましくはC1〜C18アルキル、特にC4〜C12アルキル;(Rは異なるアルキル基の混合物、例えば、C5〜C8アルキル基の混合物であってよい。かかるアルキル基の混合物を有する式(I)の化合物は液体であることの利点を有する);
C2〜C20アルケニル、好ましくはC2〜C6アルケニル;
C1〜C20アルキルカルボニル、好ましくはC1〜C18アルキルカルボニル;
C2〜C20アルケニルカルボニル、好ましくはC2〜C6アルケニルカルボニル;
C1〜C5アルキル、ハロゲン、ヒドロキシ及びC1〜C5アルコキシから独立して選択される1つ、2つ又は3つの置換基で置換され得るC3〜C7シクロアルキル(好ましくはシクロペンチル又はシクロヘキシル);及び
−(AO)x−R22(式中、Aは−C2H4−、−C3H6−又は−C4H8−、好ましくは−C2H4−又は−C3H6−であり、R22はH、C1〜C20アルキル又は−CO−R24であり、ここで、R24はC1〜C20アルキルであり、且つR22は好ましくはH又はC1〜C18アルキルであり且つxは1〜20、好ましくは1〜12、特に1〜8である)
から選択される、化合物が使用される。
C1〜C20アルキル、好ましくはC1〜C18アルキル、特にC4〜C12アルキル;(Rは異なるアルキル基の混合物、例えば、C5〜C8アルキル基の混合物であってよい。かかるアルキル基の混合物を有する式(I)の化合物は液体であることの利点を有する);
C2〜C20アルケニル、好ましくはC2〜C6アルケニル;
C1〜C20アルキルカルボニル、好ましくはC1〜C18アルキルカルボニル;
C2〜C20アルケニルカルボニル、好ましくはC2〜C6アルケニルカルボニル;
C1〜C5アルキル、ハロゲン、ヒドロキシ及びC1〜C5アルコキシから独立して選択される1つ、2つ又は3つの置換基で置換され得るC3〜C7シクロアルキル(好ましくはシクロペンチル又はシクロヘキシル);及び
−(AO)x−R22(式中、Aは−C2H4−、−C3H6−又は−C4H8−、好ましくは−C2H4−又は−C3H6−であり、R22はH、C1〜C20アルキル又は−CO−R24であり、その際、R24はC1〜C20アルキルであり、R22は好ましくはH又はC1〜C18アルキルであり、且つxは1〜20、好ましくは1〜12、特に1〜8である)
から選択される化合物が使用され、
その際、以下の通り、式(I)で示され、その式中、UVが式(II)の基であり且つR2及びR4、R5、R6、R7及びR10がHであり且つ
a)R1がCH3であり、R3がHであり且つRが−COCH3であり;
b)R1がt−C4H9であり、R3がHであり且つRが−COC(CH3)=CH2であり;
c)R1がCH3であり、R3がCH3であり且つRが−COCH3である
化合物が除外される。
C1〜C20アルキル、好ましくはC1〜C18アルキル、特にC4〜C12アルキル;(Rは異なるアルキル基の混合物、例えば、C5〜C8アルキル基の混合物であってよい。かかるアルキル基の混合物を有する式(I)の化合物は液体であることの利点を有する);
C2〜C20アルケニル、好ましくはC2〜C6アルケニル;
C1〜C5アルキル、ハロゲン、ヒドロキシ及びC1〜C5アルコキシから独立して選択される1つ、2つ又は3つの置換基で置換され得るC3〜C7シクロアルキル(好ましくはシクロペンチル又はシクロヘキシル);及び
−(AO)x−R22(式中、Aは−C2H4−、−C3H6−又は−C4H8−、好ましくは−C2H4−又は−C3H6−であり、R22はH、C1〜C20アルキル、又は−CO−R24であり、その際、R24はC1〜C20アルキルであり、R22は好ましくはH又はC1〜C18アルキルであり且つxは1〜20、好ましくは1〜12、特に1〜8である)
から選択される化合物が使用される。
Rが−(AO)x−A−(式中、AがC2H4、C3H6又はC4H8、好ましくはC2H4又はC3H6であり、且つxが1〜20、好ましくは1〜12、特に1〜8である)であり;且つQがOである、化合物が使用される。
Rが−(AO)x−A−(式中、Aは−C2H4−、−C3H6−又は−C4H8−、好ましくは−C2H4−又は−C3H6−であり、且つxは1〜20、好ましくは1〜12、特に1〜8である)であり;且つQがOである化合物が使用され、
その際、以下の通り、式(I)で示され、その式中、UVが式(II)の基であり且つR2及びR4、R5、R6、R7及びR10がHであり且つ
a)R1がOCH3であり、R3がHであり且つRが−COCH2CH2CO−であり;
b)R1がCH3であり、R3がHであり且つRが−CO(CH2)4CO−であり;
c)R1がCH3であり、R3がHであり且つRが−CO(CH2)8CO−である
化合物が除外される。
RがC1〜C20アルキレン、好ましくはC1〜C12アルキレン、特にC1〜C8アルキレン、C2〜C20アルケニレン、好ましくはC2〜C8アルケニレン、C3〜C7シクロアルキレン、好ましくはシクロペンチル又はシクロヘキシルであるか又は
Rが−(AO)x−A−(式中、Aが−C2H4−、−C3H6−又は−C4H8−、好ましくは−C2H4−又は−C3H6−であり、且つxが1〜20、好ましくは1〜12、特に1〜8である)であり;
且つQがOである、化合物が使用される。
n’が3、4、5、6、7、8、9、10、11、12、13、14又は15であり;
R25がH、R23、COR23又はUVであり且つ
R26がH、R23、COR23又はUVであり;
R23がC1〜C22アルキル又はC2〜C22アルケニルであり且つ
UVが上記で定義される通りである)
の形の式(I)の化合物が使用される。好ましくは、n’は5、6、7、8、9、10、11、12、13、14又は15である。実施態様によれば、少なくとも2つの基R25はUVである。
の化合物と、を反応させることによって得られる。好ましくは、前記化合物は2−(2H−ベンゾトリアゾール−2−イル)−6−(クロロメチル)−4−メチルフェノールである。
本発明は、また、式(I):
R(QUV)n (I)
で示され、その式中、
nが1であり且つRが−(AO)x−R22であり、ここでAは−C2H4−、−C3H6−又は−C4H8−であり、R22はH、C1〜C20アルキル、又は−CO−R24であり、ここでR24はC1〜C20アルキルであり、且つxが1〜20であるか;又は
nが2であり且つRがC1〜C20アルキレン、C1〜C20アルケニレン、−CO−C1〜C12−CO−、C3〜C7シクロアルキレン、又は−(AO)x−A−であり、ここでAは−C2H4−、−C3H6−又は−C4H8−であり、且つxが1〜20であるか;又は
nが3、4、5、6、7、8、9、10、11、12、13、14又は15、特に5、6、7、8、9、10、11、12、13、14、又は15又は5、6、7、8、9、又は10であり、且つRが3価又は15価のC3〜C40アルキル基、特に5価〜15価又は10価のC5〜C40アルキル基であり、ここでアルキル基は酸素ヘテロ原子によって中断されてよく;且つQがOであり;
UVが以下の式(II):
R4、R5、R6及びR7は、同一又は異なってもよく、H、C1〜C5アルキル、C1〜C5アルコキシ、又はハロゲンであり;
R10はH又はC1〜C20アルキルである)
の基であり;
QがOである、化合物に関する。
且つQはOである。
n’は3、4、5、6、7、8、9、10、11、12、13、14又は15であり;
R25はH、R23、−COR23又はUVであり且つ
R26はH、−COR23又はUVであり;
R23はC1〜C22アルキル又はC2〜C22アルケニルであり且つ
UVは上記で定義された通りである)
の形である。好ましくは、n’は5、6、7、8、9、10、11、12、13、14又は15である。更なる実施態様によれば、少なくとも2つの基R25はUVである。
1.必要な場合、硬化触媒を添加した、冷架橋性又は熱架橋性アルキド、アクリレート、ポリエステル、エポキシ又はメラミン樹脂又はかかる樹脂の混合物に基づく塗料;
2.ヒドロキシル含有アクリレート、ポリエステル又はポリエーテル樹脂及び脂肪族又は芳香族イソシアネート、イソシアヌレート又はポリイソシアネートに基づく2成分ポリウレタン塗料;
3.チオール含有アクリレート、ポリエステル又はポリエーテル樹脂及び脂肪族又は芳香族イソシアネート、イソシアヌレート又はポリイソシアネートに基づく2成分ポリウレタン塗料;
4.必要な場合、メラミン樹脂を添加した、焼成の間に脱ブロック化されたブロック化イソシアネート、イソシアヌレート又はポリイソシアネートに基づく1成分ポリウレタン塗料;
5.脂肪族又は芳香族ウレタン又はポリウレタン及びヒドロキシル含有アクリレート、ポリエステル又はポリエーテル樹脂に基づく1成分ポリウレタン塗料;
6.必要な場合、硬化触媒を用いる、脂肪族又は芳香族ウレタンアクリレート又はウレタン構造内に遊離アミノ基を有するポリウレタンアクリレート及びメラミン樹脂又はポリエーテル樹脂に基づく1成分ポリウレタン塗料;
7.(ポリ)ケチミン及び脂肪族又は芳香族イソシアネート、イソシアヌレート又はポリイソシアネートに基づく二成分塗料;
8.(ポリ)ケチミン及び不飽和アクリレート樹脂又はポリアセトアセテート樹脂又はメタクリルアミドグリコレートメチルエステルに基づく二成分塗料;
9.カルボキシル又はアミノ含有ポリアクリレート及びポリエポキシドに基づく2成分塗料;
10.無水物基を有するアクリレート樹脂及びポリヒドロキシ又はポリアミノ成分に基づく2成分塗料;
11.アクリレート含有無水物及びポリエポキシドに基づく2成分塗料;
12.(ポリ)オキサゾリン及び無水物基を有するアクリレート樹脂、又は不飽和アクリレート樹脂、又は脂肪族又は芳香族イソシアネート、イソシアヌレート又はポリイソシアネートに基づく2成分塗料;
13.不飽和ポリアクリレート及びポリマロネートに基づく2成分塗料;
14.エーテル化されたメラミン樹脂と組み合わせた熱可塑性アクリレート樹脂又は外部架橋(externally crosslinking)アクリレート樹脂に基づく熱可塑性ポリアクリレート塗料;
15.シロキサン変性又はフッ素変性アクリレート樹脂に基づく塗料系;
16.架橋剤としてメラミン樹脂(例えば、ヘキサメトキシメチルメラミン)を用いる(酸触媒された)マロネートブロック化イソシアネートに基づく、特にクリアコート用の塗料系;
17.必要な場合、他のオリゴマー又はモノマーと組み合わせた、オリゴマーウレタンアクリレート及び/又は他のアクリレートに基づくUV硬化系;
18.最初に熱により硬化され、その後、UV又は電子照射により硬化されるか、又はその逆により硬化され、その成分が、光開始剤の存在下でのUV光による又は電子ビームによる照射時に反応可能なエチレン性二重結合を含む、二重硬化系。
好ましいHALS化合物は、商品名Chimassorb(登録商標)、Tinuvin(登録商標)、Hostavin(登録商標)及びUvinul(登録商標)の下で入手可能な化合物である。例は、Chimassorb(登録商標)119FL、2020、又は940、Tinuvin(登録商標)111、292、123、144、152、492、494、622、765、770、783、791又はC353、Hostavin(登録商標)3050、3051、3052、3055、3058、PR31、及びUvinul(登録商標)4050H、4077H、又は5050Hである。
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−tert−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枝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)フェノール及びそれらの混合物。
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]−2H−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;[R−CH2CH2−COO−CH2CH2−]2−(R=3’−tert−ブチル−4’−ヒドロキシ−5’−2H−ベンゾトリアゾール−2−イルフェニル)、2−[2’−ヒドロキシ−3’−(α,α−ジメチルベンジル)−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−[2’−ヒドロキシ−3’−(1,1,3,3−テトラメチルブチル)−5’−(α,α−ジメチルベンジル)−フェニル]ベンゾトリアゾール、6−ブチル−2−[2−ヒドロキシ−3−(1−メチル−1−フェニルエチル)−5−(1,1,3,3−テトラメチルブチル)フェニル]−ピロロ[3,4−f]ベンゾトリアゾール−5,7(2H,6H)−ジオン。
実施例6:2成分ポリウレタンコーティングの安定化
本発明のUV吸収剤を以下の組成を有するクリアコート中で試験する:
b)芳香族炭化水素混合物、沸騰範囲182〜203℃(ソルベッソ150)又は
161〜178℃(ソルベッソ100);製造業者:ESSO
c)ジメチルポリシロキサンに基づくレベリング剤(ビックケミー社、ヴェーゼル、独国)
d)イソシアネート硬化剤(75質量%のメトキシプロピルアセテート/キシレン
1:1;バイエルマテリアルサイエンス社)
本発明のUV吸収剤を、以下の組成を有するクリアコート内で試験する:
2)アクリル樹脂(75%のソルベッソ1004)の溶液);サイテックインダストリーズ社
3)メラミン樹脂(55%のイソブタノールの溶液);イネオスメラミン社
4)芳香族炭化水素混合物、沸点範囲182〜203℃(ソルベッソ150)又は
161〜178℃(ソルベッソ100);エクソン社
5)脂肪族炭化水素混合物、沸点範囲145〜200℃、シェル社
6)ソルベッソ1504)中1%;ボルヒャース(Borchers)社
Claims (16)
- 以下の式(I):
R(QUV)n (I)
で示され、その式中、
Rが、1価〜15価の脂肪族基、脂環式基又は芳香族基であり;
UVが以下の式(II):
R1、R2及びR3は、同一又は異なってもよく、H、C1〜C20アルキル、C1〜C5アルコキシ、C1〜C5アルコキシカルボニル、C3〜C7シクロアルキル、フェニル、ナフチル又はフェニル−C1〜C5アルキルであり;
R4、R5、R6及びR7は、同一又は異なってもよく、H、C1〜C5アルキル、C1〜C5アルコキシ、又はハロゲンであり;
R10はH又はC1〜C20アルキルである)
の基であり;
QがOであり;
nが1であり且つRがC1〜C20アルキル;C2〜C20アルケニル;C1〜C5アルキル、ハロゲン、ヒドロキシ及びC1〜C5アルコキシから独立して選択される1つ、2つ又は3つの置換基で置換されていてもよいC3〜C7シクロアルキル;及び−(AO)x−R22(式中、Aは−C2H4−、−C3H6−又は−C4H8−であり、R22はH、C1〜C20アルキル、又は−CO−R24であり、ここでR24はC1〜C20アルキルであり、且つxは1〜20である)から選択されるか;又は
nが2であり且つRがC1〜C20アルキレン、C2〜C20アルケニレン、C3〜C7シクロアルキレン、又は−(AO)x−A−(式中、Aは−C2H4−、−C3H6−又は−C4H8であり且つxは1〜20である)であるか;又は
式(I)が以下の式(Ia):
その式中、
n’が3、4、5、6、7、8、9、10、11、12、13、14又は15であり;
R25がH、R23、COR23又はUVであり;且つ
R26がH、R23、COR23又はUVであり;且つ
R23がC1〜C22アルキル又はC2〜C22アルケニルである、
前記式(I)の2−(2−ヒドロキシフェニル)ベンゾトリアゾール化合物の、ラッカー、塗料及び放射線硬化性組成物から選択されるコーティング組成物におけるUV吸収剤としての使用。 - R1がC1〜C8アルキルであり且つR2及びR3がHである、請求項1に記載の使用。
- R4、R5、R6及びR7がH又はハロゲンである、請求項1又は2に記載の使用。
- R4、R5、R6及びR7がHであるか又はR4及びR7がHであり且つR5及びR6がハロゲンである、請求項3に記載の使用。
- nが1であり且つRがC1〜C20アルキルであるか;又はnが2であり且つRがC1〜C20アルキレン又は−(AO)x−A−である、請求項1から4までのいずれか1項に記載の使用。
- 式(Ia)においてR25がH又はUVであり、R26がH又はCOR23である、請求項1から4までのいずれか1項に記載の使用。
- 式(I)の化合物をヒンダードアミン光安定剤(HALS)化合物と一緒に使用する、請求項1から6までのいずれか1項に記載の使用。
- ヒンダードアミン光安定剤(HALS)化合物が、ビス(2,2,6,6−テトラメチル−4−ピペリジル)セバケート、ビス(2,2,6,6−テトラメチル−4−ピペリジル)スクシネート、ビス(1,2,2,6,6−ペンタメチル−4−ピペリジル)セバケート、ビス(1−オクチルオキシ−2,2,6,6−テトラメチル−4−ピペリジル)セバケート、ビス(1,2,2,6,6−ペンタメチル−4−ピペリジル)n−ブチル−3,5−ジ−tert−ブチル−4−ヒドロキシベンジルマロネート、1−(2−ヒドロキシエチル)−2,2,6,6−テトラメチル−4−ヒドロキシピペリジンとコハク酸との縮合物、N,N’−ビス(2,2,6,6−テトラメチル−4−ピペリジル)ヘキサメチレンジアミンと4−tert−オクチルアミノ−2,6−ジクロロ−1,3,5−トリアジンとの直鎖状又は環状縮合物、トリス(2,2,6,6−テトラメチル−4−ピペリジル)ニトリロトリアセタート、テトラキス(2,2,6,6−テトラメチル−4−ピペリジル)−1,2,3,4−ブタンテトラカルボキシレート、1,1’−(1,2−エタンジイル)−ビス(3,3,5,5−テトラメチルピペラジノン)、4−ベンゾイル−2,2,6,6−テトラメチルピペリジン、4−ステアリルオキシ−2,2,6,6−テトラメチル−ピペリジン、ビス(1,2,2,6,6−ペンタメチルピペリジル)−2−n−ブチル−2−(2−ヒドロキシ−3,5−ジ−tert−ブチルベンジル)−マロネート、3−n−オクチル−7,7,9,9−テトラメチル−1,3,8−トリアザスピロ[4.5]デカン−2,4−ジオン、ビス(1−オクチル−オキシ−2,2,6,6−テトラメチルピペリジル)セバケート、ビス(1−オクチルオキシ−2,2,6,6−テトラメチルピペリジル)スクシネート、N,N’−ビス(2,2,6,6−テトラメチル−4−ピペリジル)ヘキサメチレン−ジアミンと4−モルホリノ−2,6−ジクロロ−1,3,5−トリアジンとの直鎖状又は環状縮合物、2−クロロ−4,6−ビス(4−n−ブチルアミノ−2,2,6,6−テトラメチルピペリジル)−1,3,5−トリアジンと1,2−ビス(3−アミノプロピルアミノ)−エタンとの縮合物、2−クロロ−4,6−ジ−(4−n−ブチルアミノ−1,2,2,6,6−ペンタメチルピペリジル)−1,3,5−トリアジンと1,2−ビス(3−アミノプロピルアミノ)エタンとの縮合物、8−アセチル−3−ドデシル−7,7,9,9−テトラメチル−1,3,8−トリアザスピロ[4.5]デカン−2,4−ジオン、3−ドデシル−1−(2,2,6,6−テトラメチル−4−ピペリジル)ピロリジン−2,5−ジオン、3−ドデシル−1−(1,2,2,6,6−ペンタメチル−4−ピペリジル)ピロリジン−2,5−ジオン、4−ヘキサデシルオキシ−及び4−ステアリルオキシ−2,2,6,6−テトラメチルピペリジンの混合物、N,N’−ビス(2,2,6,6−テトラメチル−4−ピペリジル)ヘキサメチレンジアミンと4−シクロヘキシルアミノ−2,6−ジクロロ−1,3,5−トリアジンとの縮合物、1,2−ビス(3−アミノプロピルアミノ)エタン及び2,4,6−トリクロロ−1,3,5−トリアジン並びに4−ブチルアミノ−2,2,6,6−テトラメチルピペリジンの縮合物(CAS登録番号[136504−96−6]);1,6−ヘキサンジアミン及び2,4,6−トリクロロ−1,3,5−トリアジン並びにN,N−ジブチルアミン及び4−ブチルアミノ−2,2,6,6−テトラメチルピペリジンの縮合物(CAS登録番号[192268−64−7]);N−(2,2,6,6−テトラメチル−4−ピペリジル)−n−ドデシルスクシンイミド、N−(1,2,2,6,6−ペンタメチル−4−ピペリジル)−n−ドデシルスクシンイミド、2−ウンデシル−7,7,9,9−テトラメチル−1−オキサ−3,8−ジアザ−4−オキソ−スピロ−[4,5]デカン、7,7,9,9−テトラメチル−2−シクロウンデシル−1−オキサ−3,8−ジアザ−4−オキソ−スピロ−[4,5]デカンとエピクロロヒドリンとの反応生成物、1,1−ビス(1,2,2,6,6−ペンタメチル−4−ピペリジルオキシカルボニル)−2−(4−メトキシフェニル)エテン、N,N’−ビス−ホルミル−N,N’−ビス(2,2,6,6−テトラメチル−4−ピペリジル)ヘキサメチレンジアミン、4−メトキシメチレンマロン酸と1,2,2,6,6−ペンタメチル−4−ヒドロキシピペリジンとのジエステル、ポリ[メチルプロピル−3−オキシ−4−(2,2,6,6−テトラメチル−4−ピペリジル)]シロキサン、マレイン酸無水物−α−オレフィンコポリマーと2,2,6,6−テトラメチル−4−アミノピペリジン又は1,2,2,6,6−ペンタメチル−4−アミノピペリジンとの反応生成物、2,4−ビス[N−(1−シクロヘキシルオキシ−2,2,6,6−テトラメチルピペリジン−4−イル)−N−ブチルアミノ]−6−(2−ヒドロキシエチル)アミノ−1,3,5−トリアジン、1−(2−ヒドロキシ−2−メチルプロポキシ)−4−オクタデカノイルオキシ−2,2,6,6−テトラメチルピペリジン、5−(2−エチルヘキサノイル)−オキシメチル−3,3,5−トリメチル−2−モルホリノン、Sanduvor(CAS登録番号106917−31−1)、5−(2−エチルヘキサノイル)オキシメチル−3,3,5−トリメチル−2−モルホリノン、2,4−ビス[(1−シクロヘキシルオキシ−2,2,6,6−ピペリジン−4−イル)ブチルアミノ]−6−クロロ−s−トリアジンとN,N’−ビス(3−アミノプロピル)エチレンジアミン)との反応生成物、1,3,5−トリス(N−シクロヘキシル−N−(2,2,6,6−テトラメチルピペラジン−3−オン−4−イル)アミノ)−s−トリアジン、1,3,5−トリス(N−シクロヘキシル−N−(1,2,2,6,6−ペンタメチルピペラジン−3−オン−4−イル)アミノ)−s−トリアジン、及び2,2,6,6−テトラメチル−1−[2−(3,5,5−トリメチル−ヘキサノイルオキシ)−エチル]−ピペリジン−4−イルエステルから選択される、請求項7に記載の使用。
- 以下の式(I’)
R(QUV)n (I’)
で示され、その式中、
nが1であり且つRが−(AO)x−R22(式中、Aは−C2H4−、−C3H6−又は−C4H8−であり、R22はH又はC1〜C20アルキル、又は−CO−R24であり、ここでR24はC1〜C20アルキルであり、且つxは1〜20である)であるか;又は
nが2であり且つRがC1〜C20アルキレン、C1〜C20アルケニレン、C3〜C7シクロアルキレン、又は−(AO)x−A−(式中、Aは−C2H4−、−C3H6−又は−C4H8−であり、且つxは1〜20である)であるか;又は
式(I’)が以下の式(Ia):
n’が3、4、5、6、7、8、9、10、11、12、13、14又は15であり;R25がH、R23、−COR23又はUVであり;R26がH、R23、−COR23又はUVであり;且つR23がC1〜C22アルキル又はC2〜C22アルケニルであり;
UVが以下の式(II):
R1、R2及びR3が、同一又は異なってもよく、H、C1〜C20アルキル、C1〜C5アルコキシ、C1〜C5アルコキシカルボニル、フェニル、ナフチル又はフェニル−C1〜C5アルキルであり;
R4、R5、R6及びR7が、同一又は異なってもよく、H、C1〜C5アルキル、C1〜C5アルコキシ、又はハロゲンであり;
R10がH又はC1〜C20アルキルであり;且つ
QがOである、化合物。 - nが2であり且つRが−(AO)x−A−である、請求項9に記載の化合物。
- R25がH又はUVであり且つR26がH又は−COR23である、式(Ia)の形の請求項9に記載の化合物。
- 請求項9から11までのいずれか1項に記載の化合物及び有機材料を含むコーティング組成物。
- 有機材料が、1種以上のポリマー、式(I’)のもの以外のヒドロキシ−フェニル−ベンゾトリアゾール又はヒドロキシフェニル−トリアジン又はヒドロキシ−ベンゾフェノン又はオキサニリドクラスの1種以上のUV吸収剤及びそれらの組み合わせから選択される、請求項12に記載の組成物。
- 特にテトラメチル−ピペリジン誘導体のクラスから選択されるヒンダードアミン光安定剤(HALS)化合物を更に含む、請求項12又は13に記載の組成物。
- 請求項12から14までのいずれか1項に記載の組成物で被覆された被覆物品。
- 請求項9から11までのいずれか1項に記載の化合物の光安定剤としての使用。
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CN105358528B (zh) | 2013-07-08 | 2021-07-20 | 巴斯夫欧洲公司 | 新型光稳定剂 |
US11773277B2 (en) * | 2018-04-04 | 2023-10-03 | Basf Se | Use of an ultraviolet radiation absorbing polymer composition (UVRAP) as an UV absorbing agent in a coating for non-living and non-keratinous materials |
CA3094725A1 (en) * | 2018-04-04 | 2019-10-10 | Basf Se | Use of an ultraviolet radiation absorbing composition as a light stabilizer for a shaped artificial polymer article |
KR101997791B1 (ko) * | 2018-10-09 | 2019-07-09 | 대한민국 | 암막 코팅 조성물 |
CN110437416B (zh) * | 2019-08-19 | 2021-08-10 | 美瑞新材料股份有限公司 | 一种梳形结构的氟硅化聚氨酯弹性体的制备方法 |
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DE3264154D1 (en) | 1981-01-23 | 1985-07-25 | Ciba Geigy Ag | 2-(2-hydroxyphenyl)-benzotriazoles, their use as ultraviolet stabilizers and their preparation |
US4926190A (en) | 1987-02-18 | 1990-05-15 | Ciba-Geigy Corporation | Ink jet recording process using certain benzotriazole derivatives as light stabilizers |
US5175312A (en) | 1989-08-31 | 1992-12-29 | Ciba-Geigy Corporation | 3-phenylbenzofuran-2-ones |
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TW206220B (ja) | 1991-07-01 | 1993-05-21 | Ciba Geigy Ag | |
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NL9300801A (nl) | 1992-05-22 | 1993-12-16 | Ciba Geigy | 3-(acyloxyfenyl)benzofuran-2-on als stabilisatoren. |
GB2267490B (en) | 1992-05-22 | 1995-08-09 | Ciba Geigy Ag | 3-(Carboxymethoxyphenyl)benzofuran-2-one stabilisers |
TW255902B (ja) | 1992-09-23 | 1995-09-01 | Ciba Geigy | |
MX9305489A (es) | 1992-09-23 | 1994-03-31 | Ciba Geigy Ag | 3-(dihidrobenzofuran-5-il)benzofuran-2-onas, estabilizadores. |
DE4338361A1 (de) | 1993-11-10 | 1995-05-11 | Inst Neue Mat Gemein Gmbh | Verfahren zur Herstellung von Zusammensetzungen auf der Basis von Epoxidgruppen-haltigen Silanen |
JPH07207192A (ja) * | 1994-01-18 | 1995-08-08 | Hitachi Maxell Ltd | 曇り止め剤 |
JPH08208628A (ja) * | 1995-01-31 | 1996-08-13 | Osaka Seika Kogyo Kk | ベンゾトリアゾ−ル化合物及びその製造方法 |
DE19724397A1 (de) | 1997-06-10 | 1999-01-14 | Bayer Ag | UV-Stabilisatoren für Siloxan-Systeme |
DE19724396A1 (de) | 1997-06-10 | 1998-12-24 | Bayer Ag | UV-Stabilisatoren für Siloxan-Systeme |
JP2000141875A (ja) * | 1998-11-10 | 2000-05-23 | Oji Paper Co Ltd | インクジェット記録用シート |
US6451887B1 (en) * | 2000-08-03 | 2002-09-17 | Ciba Specialty Chemicals Corporation | Benzotriazoles containing α-cumyl groups substituted by heteroatoms and compositions stabilized therewith |
TW593303B (en) | 2001-09-11 | 2004-06-21 | Ciba Sc Holding Ag | Stabilization of synthetic polymers |
WO2010060698A2 (de) * | 2008-11-03 | 2010-06-03 | Basf Se | Pigmentzusammensetzungen |
TWI453199B (zh) * | 2008-11-04 | 2014-09-21 | Alcon Inc | 用於眼用鏡片材料之紫外光/可見光吸收劑 |
US9034955B2 (en) | 2009-05-15 | 2015-05-19 | Basf Se | High molecular weight nonpolar benzotriazoles |
JP2011074070A (ja) * | 2009-09-07 | 2011-04-14 | Fujifilm Corp | 紫外線吸収性組成物 |
WO2011086127A1 (en) | 2010-01-15 | 2011-07-21 | Dsm Ip Assets B.V. | Process to make uv radiation absorbing 2 - phenyl - 1, 2, 3 - benzotriazoles |
WO2012163936A1 (en) | 2011-05-31 | 2012-12-06 | Dsm Ip Assets B.V. | Process for the synthesis of benzotriazoles useful as uv-filters |
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- 2014-10-23 WO PCT/EP2014/072700 patent/WO2015062946A1/en active Application Filing
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EP3068839A1 (en) | 2016-09-21 |
WO2015062946A1 (en) | 2015-05-07 |
CN105683313A (zh) | 2016-06-15 |
KR20160077074A (ko) | 2016-07-01 |
CN105683313B (zh) | 2019-09-17 |
JP2016538382A (ja) | 2016-12-08 |
US10119039B2 (en) | 2018-11-06 |
US20160215151A1 (en) | 2016-07-28 |
EP3068839B1 (en) | 2019-01-16 |
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