RU2414471C2 - Бензотриазоловые поглотители уф-лучей со смещенным в длинноволновую область спектром поглощения и их применение - Google Patents

Info

Publication number

RU2414471C2

RU2414471C2 RU2007132974/04A RU2007132974A RU2414471C2 RU 2414471 C2 RU2414471 C2 RU 2414471C2 RU 2007132974/04 A RU2007132974/04 A RU 2007132974/04A RU 2007132974 A RU2007132974 A RU 2007132974A RU 2414471 C2 RU2414471 C2 RU 2414471C2

Authority

RU

Russia

Prior art keywords

carbon atoms

phenyl

phenylalkyl

butyl

branched

Prior art date

2005-02-02

Links

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• 239000006096 absorbing agent Substances 0.000 title claims abstract description 48
• QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 title abstract description 13
• 239000012964 benzotriazole Substances 0.000 title abstract description 13
• 238000000862 absorption spectrum Methods 0.000 title abstract description 11
• 238000000576 coating method Methods 0.000 claims abstract description 69
• 239000011248 coating agent Substances 0.000 claims abstract description 57
• 150000001875 compounds Chemical class 0.000 claims abstract description 56
• 239000000203 mixture Substances 0.000 claims abstract description 47
• 239000003381 stabilizer Substances 0.000 claims abstract description 13
• -1 oxanilides Chemical class 0.000 claims description 103
• 125000004432 carbon atom Chemical group C* 0.000 claims description 67
• 125000000217 alkyl group Chemical group 0.000 claims description 62
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 56
• 239000000463 material Substances 0.000 claims description 38
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 33
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 26
• 125000003884 phenylalkyl group Chemical group 0.000 claims description 26
• 125000003342 alkenyl group Chemical group 0.000 claims description 24
• 150000001412 amines Chemical class 0.000 claims description 24
• 125000002947 alkylene group Chemical group 0.000 claims description 19
• 239000011368 organic material Substances 0.000 claims description 13
• 229910052794 bromium Inorganic materials 0.000 claims description 10
• 229910052801 chlorine Inorganic materials 0.000 claims description 10
• 125000001624 naphthyl group Chemical group 0.000 claims description 10
• 150000001565 benzotriazoles Chemical class 0.000 claims description 9
• 125000005843 halogen group Chemical group 0.000 claims description 7
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
• 239000000758 substrate Substances 0.000 claims description 5
• 230000006378 damage Effects 0.000 claims description 4
• 150000003918 triazines Chemical class 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
• 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
• 125000003031 C5-C7 cycloalkylene group Chemical group 0.000 claims description 2
• 230000009471 action Effects 0.000 claims description 2
• 150000001558 benzoic acid derivatives Chemical class 0.000 claims description 2
• 230000015556 catabolic process Effects 0.000 claims description 2
• 238000006731 degradation reaction Methods 0.000 claims description 2
• 229910052738 indium Inorganic materials 0.000 claims description 2
• 229910052799 carbon Inorganic materials 0.000 claims 1
• 230000005855 radiation Effects 0.000 abstract description 9
• 239000000126 substance Substances 0.000 abstract description 8
• 150000003254 radicals Chemical class 0.000 abstract description 7
• 230000003287 optical effect Effects 0.000 abstract description 4
• 230000000694 effects Effects 0.000 abstract 1
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 54
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• 229920000642 polymer Polymers 0.000 description 27
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 25
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• GJVFBWCTGUSGDD-UHFFFAOYSA-L pentamethonium bromide Chemical compound [Br-].[Br-].C[N+](C)(C)CCCCC[N+](C)(C)C GJVFBWCTGUSGDD-UHFFFAOYSA-L 0.000 description 17
• LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 15
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• 238000005160 1H NMR spectroscopy Methods 0.000 description 12
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• 229920000877 Melamine resin Polymers 0.000 description 12
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
• 239000000460 chlorine Substances 0.000 description 12
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• 238000000034 method Methods 0.000 description 12
• 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 11
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 11
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• NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 8
• VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 8
• 239000005977 Ethylene Substances 0.000 description 8
• LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 8
• 239000005062 Polybutadiene Substances 0.000 description 8
• 239000004743 Polypropylene Substances 0.000 description 8
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
• 125000003118 aryl group Chemical group 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
• 238000004519 manufacturing process Methods 0.000 description 8
• GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 8
• 239000004417 polycarbonate Substances 0.000 description 8
• 229920000728 polyester Polymers 0.000 description 8
• NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 7
• 239000002253 acid Substances 0.000 description 7
• 229920000180 alkyd Polymers 0.000 description 7
• 239000000178 monomer Substances 0.000 description 7
• 229920006324 polyoxymethylene Polymers 0.000 description 7
• 239000000243 solution Substances 0.000 description 7
• 239000002904 solvent Substances 0.000 description 7
• FANCTJAFZSYTIS-IQUVVAJASA-N (1r,3s,5z)-5-[(2e)-2-[(1r,3as,7ar)-7a-methyl-1-[(2r)-4-(phenylsulfonimidoyl)butan-2-yl]-2,3,3a,5,6,7-hexahydro-1h-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol Chemical compound C([C@@H](C)[C@@H]1[C@]2(CCCC(/[C@@H]2CC1)=C\C=C\1C([C@@H](O)C[C@H](O)C/1)=C)C)CS(=N)(=O)C1=CC=CC=C1 FANCTJAFZSYTIS-IQUVVAJASA-N 0.000 description 6
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 6
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
• 229920003264 Maprenal® Polymers 0.000 description 6
• 239000004721 Polyphenylene oxide Substances 0.000 description 6
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 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
• 229910052783 alkali metal Inorganic materials 0.000 description 6
• 229910052784 alkaline earth metal Inorganic materials 0.000 description 6
• 239000008199 coating composition Substances 0.000 description 6
• 125000002993 cycloalkylene group Chemical group 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
• 239000003921 oil Substances 0.000 description 6
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• 150000003839 salts Chemical class 0.000 description 6
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• SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 5
• 150000007513 acids Chemical class 0.000 description 5
• 150000001298 alcohols Chemical class 0.000 description 5
• 150000001340 alkali metals Chemical class 0.000 description 5
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• 238000004458 analytical method Methods 0.000 description 5
• 125000004429 atom Chemical group 0.000 description 5
• FLPKSBDJMLUTEX-UHFFFAOYSA-N bis(1,2,2,6,6-pentamethylpiperidin-4-yl) 2-butyl-2-[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]propanedioate Chemical compound C1C(C)(C)N(C)C(C)(C)CC1OC(=O)C(C(=O)OC1CC(C)(C)N(C)C(C)(C)C1)(CCCC)CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 FLPKSBDJMLUTEX-UHFFFAOYSA-N 0.000 description 5
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
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• 239000003431 cross linking reagent Substances 0.000 description 5
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• 150000001993 dienes Chemical class 0.000 description 5
• 229920001971 elastomer Polymers 0.000 description 5
• 125000003700 epoxy group Chemical group 0.000 description 5
• 150000002170 ethers Chemical class 0.000 description 5
• 229920001903 high density polyethylene Polymers 0.000 description 5
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• 229920001519 homopolymer Polymers 0.000 description 5
• 239000012948 isocyanate Substances 0.000 description 5
• 150000002513 isocyanates Chemical class 0.000 description 5
• 229920001684 low density polyethylene Polymers 0.000 description 5
• 239000004702 low-density polyethylene Substances 0.000 description 5
• 229920000647 polyepoxide Polymers 0.000 description 5
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• 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
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• 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
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• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
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• WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 4
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