BRPI0713466A2 - Absorvedores de uv benzotriazol deslocados por cumprimento de onda longo e seu uso - Google Patents

Info

Publication number

BRPI0713466A2

BRPI0713466A2 BRPI0713466-5A BRPI0713466A BRPI0713466A2 BR PI0713466 A2 BRPI0713466 A2 BR PI0713466A2 BR PI0713466 A BRPI0713466 A BR PI0713466A BR PI0713466 A2 BRPI0713466 A2 BR PI0713466A2

Authority

BR

Brazil

Prior art keywords

formula

straight

branched chain

carbon atoms

phenyl

Prior art date

2006-06-27

Links

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• 239000006096 absorbing agent Substances 0.000 title claims abstract description 38
• QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 title abstract description 16
• 239000012964 benzotriazole Substances 0.000 title abstract description 15
• 150000001875 compounds Chemical class 0.000 claims abstract description 71
• 239000000203 mixture Substances 0.000 claims abstract description 63
• 238000002360 preparation method Methods 0.000 claims abstract description 33
• 238000000034 method Methods 0.000 claims abstract description 27
• 230000008569 process Effects 0.000 claims abstract description 16
• 239000011368 organic material Substances 0.000 claims abstract description 15
• -1 C5-C12 cycloalkyl Chemical group 0.000 claims description 138
• 125000004432 carbon atom Chemical group C* 0.000 claims description 97
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 83
• 125000000217 alkyl group Chemical group 0.000 claims description 82
• 239000001257 hydrogen Substances 0.000 claims description 60
• 229910052739 hydrogen Inorganic materials 0.000 claims description 60
• 125000003884 phenylalkyl group Chemical group 0.000 claims description 47
• 125000003342 alkenyl group Chemical group 0.000 claims description 43
• 150000002431 hydrogen Chemical class 0.000 claims description 42
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 34
• 238000006243 chemical reaction Methods 0.000 claims description 33
• 238000000576 coating method Methods 0.000 claims description 33
• 125000001624 naphthyl group Chemical group 0.000 claims description 33
• 239000000463 material Substances 0.000 claims description 32
• 229910052717 sulfur Inorganic materials 0.000 claims description 31
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 29
• 229910052760 oxygen Inorganic materials 0.000 claims description 28
• 229920000642 polymer Polymers 0.000 claims description 28
• 239000002904 solvent Substances 0.000 claims description 26
• 239000011248 coating agent Substances 0.000 claims description 24
• 101100240527 Caenorhabditis elegans nhr-22 gene Proteins 0.000 claims description 22
• 150000001412 amines Chemical class 0.000 claims description 20
• 125000002947 alkylene group Chemical group 0.000 claims description 18
• 229910052757 nitrogen Inorganic materials 0.000 claims description 18
• VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 17
• 239000005977 Ethylene Substances 0.000 claims description 17
• 229910052799 carbon Inorganic materials 0.000 claims description 17
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
• 229910052751 metal Inorganic materials 0.000 claims description 15
• 239000002184 metal Substances 0.000 claims description 15
• 239000003054 catalyst Substances 0.000 claims description 14
• 229910052736 halogen Inorganic materials 0.000 claims description 14
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 12
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 11
• 125000001424 substituent group Chemical group 0.000 claims description 11
• 125000004429 atom Chemical group 0.000 claims description 10
• 239000003381 stabilizer Substances 0.000 claims description 10
• 239000000758 substrate Substances 0.000 claims description 10
• 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
• 125000006686 (C1-C24) alkyl group Chemical group 0.000 claims description 7
• 125000002993 cycloalkylene group Chemical group 0.000 claims description 7
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
• 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 6
• 125000001931 aliphatic group Chemical group 0.000 claims description 6
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
• 238000004519 manufacturing process Methods 0.000 claims description 6
• JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical class C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 claims description 5
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
• 150000001558 benzoic acid derivatives Chemical class 0.000 claims description 5
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
• HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical class OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 claims description 4
• 125000006702 (C1-C18) alkyl group Chemical group 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
• 230000015556 catabolic process Effects 0.000 claims description 4
• 125000004956 cyclohexylene group Chemical group 0.000 claims description 4
• 238000006731 degradation reaction Methods 0.000 claims description 4
• 239000003999 initiator Substances 0.000 claims description 4
• 229920001169 thermoplastic Polymers 0.000 claims description 4
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
• IJVRPNIWWODHHA-UHFFFAOYSA-N 2-cyanoprop-2-enoic acid Chemical class OC(=O)C(=C)C#N IJVRPNIWWODHHA-UHFFFAOYSA-N 0.000 claims description 3
• JYNZIOFUHBJABQ-UHFFFAOYSA-N allyl-{6-[3-(4-bromo-phenyl)-benzofuran-6-yloxy]-hexyl-}-methyl-amin Chemical group C=1OC2=CC(OCCCCCCN(C)CC=C)=CC=C2C=1C1=CC=C(Br)C=C1 JYNZIOFUHBJABQ-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
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
• 239000002987 primer (paints) Substances 0.000 claims description 3
• 229910052710 silicon Inorganic materials 0.000 claims description 3
• 229910006067 SO3−M Inorganic materials 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
• 150000001768 cations Chemical class 0.000 claims description 2
• 230000005670 electromagnetic radiation Effects 0.000 claims description 2
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
• 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
• 230000002829 reductive effect Effects 0.000 claims description 2
• 229920001059 synthetic polymer Polymers 0.000 claims description 2
• 125000003354 benzotriazolyl group Chemical class N1N=NC2=C1C=CC=C2* 0.000 claims 2
• 125000006730 (C2-C5) alkynyl group Chemical group 0.000 claims 1
• 229920001651 Cyanoacrylate Polymers 0.000 claims 1
• 125000005843 halogen group Chemical group 0.000 claims 1
• 238000000862 absorption spectrum Methods 0.000 abstract description 4
• 238000002835 absorbance Methods 0.000 abstract description 3
• 239000013036 UV Light Stabilizer Substances 0.000 abstract description 2
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 159
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 142
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 108
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 90
• 239000011541 reaction mixture Substances 0.000 description 57
• 239000000243 solution Substances 0.000 description 49
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 44
• PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 43
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 39
• 229920001577 copolymer Polymers 0.000 description 38
• 238000002844 melting Methods 0.000 description 38
• 230000008018 melting Effects 0.000 description 38
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 36
• PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 32
• 239000012258 stirred mixture Substances 0.000 description 32
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 30
• SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 30
• LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 26
• 239000000725 suspension Substances 0.000 description 26
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 23
• 239000012267 brine Substances 0.000 description 21
• 239000010410 layer Substances 0.000 description 21
• 239000000741 silica gel Substances 0.000 description 21
• 229910002027 silica gel Inorganic materials 0.000 description 21
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 21
• 239000012074 organic phase Substances 0.000 description 20
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
• 238000001816 cooling Methods 0.000 description 19
• 239000000543 intermediate Substances 0.000 description 18
• 238000003756 stirring Methods 0.000 description 18
• 239000008346 aqueous phase Substances 0.000 description 17
• 229920005989 resin Polymers 0.000 description 17
• 239000011347 resin Substances 0.000 description 17
• CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 16
• 230000002459 sustained effect Effects 0.000 description 16
• 239000008096 xylene Substances 0.000 description 16
• LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 15
• CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 description 14
• VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 14
• 239000011734 sodium Substances 0.000 description 14
• 229920000877 Melamine resin Polymers 0.000 description 13
• 235000010288 sodium nitrite Nutrition 0.000 description 13
• ONHZKWDILKBQLS-UHFFFAOYSA-N 2-(2-phenylpropan-2-yl)-4-(2,4,4-trimethylpentan-2-yl)phenol Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(O)C(C(C)(C)C=2C=CC=CC=2)=C1 ONHZKWDILKBQLS-UHFFFAOYSA-N 0.000 description 12
• NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 12
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 12
• MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 12
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 11
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• 239000000975 dye Substances 0.000 description 11
• 229920002647 polyamide Polymers 0.000 description 11
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• 239000004743 Polypropylene Substances 0.000 description 9
• 239000002253 acid Substances 0.000 description 9
• 150000001565 benzotriazoles Chemical class 0.000 description 9
• NKNDPYCGAZPOFS-UHFFFAOYSA-M copper(i) bromide Chemical compound Br[Cu] NKNDPYCGAZPOFS-UHFFFAOYSA-M 0.000 description 9
• JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 9
• 239000007787 solid Substances 0.000 description 9
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• KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 8
• 239000000178 monomer Substances 0.000 description 8
• GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 8
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