DE60112892T2 - Ausblühungsfreie uv absorber benzotriazole und damit stabilisierte zusammensetzungen - Google Patents

Info

Publication number

DE60112892T2

DE60112892T2 DE60112892T DE60112892T DE60112892T2 DE 60112892 T2 DE60112892 T2 DE 60112892T2 DE 60112892 T DE60112892 T DE 60112892T DE 60112892 T DE60112892 T DE 60112892T DE 60112892 T2 DE60112892 T2 DE 60112892T2

Authority

DE

Germany

Prior art keywords

carbon atoms

alkyl

tert

butyl

straight

Prior art date

2000-02-01

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 - Lifetime

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• 239000006096 absorbing agent Substances 0.000 title claims abstract description 65
• QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 title claims abstract description 19
• 239000012964 benzotriazole Substances 0.000 title claims abstract description 19
• 239000000203 mixture Substances 0.000 title claims description 83
• 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 170
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 97
• 229920000098 polyolefin Polymers 0.000 claims abstract description 14
• 230000006641 stabilisation Effects 0.000 claims abstract description 4
• 238000011105 stabilization Methods 0.000 claims abstract description 4
• -1 benzylidene, p -Xylylene Chemical group 0.000 claims description 185
• PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 83
• 229920001577 copolymer Polymers 0.000 claims description 71
• 150000001875 compounds Chemical class 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 44
• 150000001412 amines Chemical class 0.000 claims description 37
• VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 34
• 125000003342 alkenyl group Chemical group 0.000 claims description 34
• 229920000573 polyethylene Polymers 0.000 claims description 33
• 229920000642 polymer Polymers 0.000 claims description 32
• 125000003884 phenylalkyl group Chemical group 0.000 claims description 30
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 29
• 229920002647 polyamide Polymers 0.000 claims description 28
• 239000001257 hydrogen Substances 0.000 claims description 25
• 229910052739 hydrogen Inorganic materials 0.000 claims description 25
• VOXZDWNPVJITMN-ZBRFXRBCSA-N 17β-estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 VOXZDWNPVJITMN-ZBRFXRBCSA-N 0.000 claims description 24
• 239000004698 Polyethylene Substances 0.000 claims description 23
• 239000004952 Polyamide Substances 0.000 claims description 22
• 150000002431 hydrogen Chemical class 0.000 claims description 22
• 229920006324 polyoxymethylene Polymers 0.000 claims description 18
• 239000005977 Ethylene Substances 0.000 claims description 17
• 125000003118 aryl group Chemical group 0.000 claims description 17
• 239000004743 Polypropylene Substances 0.000 claims description 16
• 238000002844 melting Methods 0.000 claims description 15
• 230000008018 melting Effects 0.000 claims description 15
• 229920000915 polyvinyl chloride Polymers 0.000 claims description 15
• 239000004417 polycarbonate Substances 0.000 claims description 14
• 239000004800 polyvinyl chloride Substances 0.000 claims description 14
• 229920000122 acrylonitrile butadiene styrene Polymers 0.000 claims description 13
• 229920001155 polypropylene Polymers 0.000 claims description 13
• 229920000728 polyester Polymers 0.000 claims description 12
• 239000004814 polyurethane Substances 0.000 claims description 11
• 239000000155 melt Substances 0.000 claims description 10
• 230000000087 stabilizing effect Effects 0.000 claims description 9
• 125000002947 alkylene group Chemical group 0.000 claims description 8
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
• 229920000515 polycarbonate Polymers 0.000 claims description 8
• 229920000139 polyethylene terephthalate Polymers 0.000 claims description 8
• 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 8
• 229910052736 halogen Inorganic materials 0.000 claims description 7
• 150000002367 halogens Chemical class 0.000 claims description 7
• 239000011368 organic material Substances 0.000 claims description 7
• 238000004806 packaging method and process Methods 0.000 claims description 7
• 229920000058 polyacrylate Polymers 0.000 claims description 7
• 239000005020 polyethylene terephthalate Substances 0.000 claims description 7
• 229920002635 polyurethane Polymers 0.000 claims description 7
• KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 claims description 7
• 150000001565 benzotriazoles Chemical class 0.000 claims description 6
• 239000000460 chlorine Substances 0.000 claims description 6
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
• 238000000354 decomposition reaction Methods 0.000 claims description 6
• 235000013305 food Nutrition 0.000 claims description 6
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 6
• 230000001590 oxidative effect Effects 0.000 claims description 6
• 229930040373 Paraformaldehyde Natural products 0.000 claims description 5
• 229920000554 ionomer Polymers 0.000 claims description 5
• 229920002037 poly(vinyl butyral) polymer Polymers 0.000 claims description 5
• 229920005644 polyethylene terephthalate glycol copolymer Polymers 0.000 claims description 5
• 150000003839 salts Chemical class 0.000 claims description 5
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
• 239000004716 Ethylene/acrylic acid copolymer Substances 0.000 claims description 4
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
• 125000001118 alkylidene group Chemical group 0.000 claims description 4
• LCIYFINKFGDAHD-UHFFFAOYSA-N azepane;3-nitrobenzoic acid Chemical compound C1CCCNCC1.OC(=O)C1=CC=CC([N+]([O-])=O)=C1 LCIYFINKFGDAHD-UHFFFAOYSA-N 0.000 claims description 4
• 229910052801 chlorine Inorganic materials 0.000 claims description 4
• 239000011737 fluorine Substances 0.000 claims description 4
• 229910052731 fluorine Inorganic materials 0.000 claims description 4
• 238000004519 manufacturing process Methods 0.000 claims description 4
• 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 4
• 229920001707 polybutylene terephthalate Polymers 0.000 claims description 4
• JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical class C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 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 3
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
• 239000004677 Nylon Substances 0.000 claims description 3
• 229930182556 Polyacetal Natural products 0.000 claims description 3
• 150000001558 benzoic acid derivatives Chemical class 0.000 claims description 3
• 150000002690 malonic acid derivatives Chemical class 0.000 claims description 3
• 229920001778 nylon Polymers 0.000 claims description 3
• 229920006280 packaging film Polymers 0.000 claims description 3
• 239000012785 packaging film Substances 0.000 claims description 3
• 150000003873 salicylate salts Chemical class 0.000 claims description 3
• 150000003440 styrenes Chemical class 0.000 claims description 3
• ZYZYQCACSQDPSB-UHFFFAOYSA-N 12,15-dioxatricyclo[8.6.0.02,7]hexadeca-1(10),2,4,6,8-pentaene-11,16-dione Chemical compound O=C1OCCOC(=O)C2=C1C=CC1=CC=CC=C21 ZYZYQCACSQDPSB-UHFFFAOYSA-N 0.000 claims description 2
• XPHBRTNHVJSEQD-UHFFFAOYSA-N anidoxime Chemical compound C=1C=CC=CC=1C(CCN(CC)CC)=NOC(=O)NC1=CC=C(OC)C=C1 XPHBRTNHVJSEQD-UHFFFAOYSA-N 0.000 claims description 2
• 235000013361 beverage Nutrition 0.000 claims description 2
• 238000010276 construction Methods 0.000 claims description 2
• 125000002993 cycloalkylene group Chemical group 0.000 claims description 2
• 125000004956 cyclohexylene group Chemical group 0.000 claims description 2
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
• 229920001059 synthetic polymer Polymers 0.000 claims description 2
• 150000002148 esters Chemical class 0.000 abstract description 23
• 238000002845 discoloration Methods 0.000 abstract description 3
• 125000001183 hydrocarbyl group Chemical group 0.000 abstract description 2
• 125000004430 oxygen atom Chemical group O* 0.000 abstract description 2
• 125000003368 amide group Chemical group 0.000 abstract 2
• 230000015556 catabolic process Effects 0.000 abstract 1
• 238000006731 degradation reaction Methods 0.000 abstract 1
• 239000001993 wax Substances 0.000 description 62
• 229920001684 low density polyethylene Polymers 0.000 description 33
• 239000004702 low-density polyethylene Substances 0.000 description 33
• 239000010408 film Substances 0.000 description 28
• 239000003381 stabilizer Substances 0.000 description 28
• NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 25
• 230000008859 change Effects 0.000 description 21
• 229920002857 polybutadiene Polymers 0.000 description 17
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 16
• 238000012360 testing method Methods 0.000 description 16
• 239000000047 product Substances 0.000 description 15
• 229910052757 nitrogen Inorganic materials 0.000 description 14
• 238000000034 method Methods 0.000 description 13
• 239000003921 oil Substances 0.000 description 13
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
• 239000000463 material Substances 0.000 description 12
• 235000019198 oils Nutrition 0.000 description 12
• 229920005989 resin Polymers 0.000 description 12
• 239000011347 resin Substances 0.000 description 12
• 239000000654 additive Substances 0.000 description 10
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 10
• 239000007787 solid Substances 0.000 description 10
• KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 9
• 239000004721 Polyphenylene oxide Substances 0.000 description 9
• 238000005562 fading Methods 0.000 description 9
• 229920001903 high density polyethylene Polymers 0.000 description 9
• 239000004700 high-density polyethylene Substances 0.000 description 9
• 239000002530 phenolic antioxidant Substances 0.000 description 9
• QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 9
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 9
• 238000005160 1H NMR spectroscopy Methods 0.000 description 8
• 239000005062 Polybutadiene Substances 0.000 description 8
• 238000004458 analytical method Methods 0.000 description 8
• 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 description 8
• 229910052751 metal Inorganic materials 0.000 description 8
• 239000002184 metal Substances 0.000 description 8
• 238000006068 polycondensation reaction Methods 0.000 description 8
• 229920006380 polyphenylene oxide Polymers 0.000 description 8
• 239000000523 sample Substances 0.000 description 8
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 7
• 150000001252 acrylic acid derivatives Chemical class 0.000 description 7
• WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 7
• 150000001993 dienes Chemical class 0.000 description 7
• 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 7
• FXNDIJDIPNCZQJ-UHFFFAOYSA-N 2,4,4-trimethylpent-1-ene Chemical compound CC(=C)CC(C)(C)C FXNDIJDIPNCZQJ-UHFFFAOYSA-N 0.000 description 6
• WPMYUUITDBHVQZ-UHFFFAOYSA-N 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoic acid Chemical compound CC(C)(C)C1=CC(CCC(O)=O)=CC(C(C)(C)C)=C1O WPMYUUITDBHVQZ-UHFFFAOYSA-N 0.000 description 6
• NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 6
• NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 6
• 229920002943 EPDM rubber Polymers 0.000 description 6
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
• 229920000877 Melamine resin Polymers 0.000 description 6
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
• 125000005907 alkyl ester 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
• 229920001971 elastomer Polymers 0.000 description 6
• 239000005038 ethylene vinyl acetate Substances 0.000 description 6
• 239000003205 fragrance Substances 0.000 description 6
• 230000009021 linear effect Effects 0.000 description 6
• 229920000092 linear low density polyethylene Polymers 0.000 description 6
• 239000004707 linear low-density polyethylene Substances 0.000 description 6
• GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 6
• 229920002554 vinyl polymer Polymers 0.000 description 6
• HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 description 5
• IYAZLDLPUNDVAG-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4-(2,4,4-trimethylpentan-2-yl)phenol Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 IYAZLDLPUNDVAG-UHFFFAOYSA-N 0.000 description 5
• FJGQBLRYBUAASW-UHFFFAOYSA-N 2-(benzotriazol-2-yl)phenol Chemical compound OC1=CC=CC=C1N1N=C2C=CC=CC2=N1 FJGQBLRYBUAASW-UHFFFAOYSA-N 0.000 description 5
• NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 5
• 229920002396 Polyurea Polymers 0.000 description 5
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
• 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 description 5
• 239000003963 antioxidant agent Substances 0.000 description 5
• 235000006708 antioxidants Nutrition 0.000 description 5
• 235000010354 butylated hydroxytoluene Nutrition 0.000 description 5
• 239000003054 catalyst Substances 0.000 description 5
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• 238000013508 migration Methods 0.000 description 5
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• AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 5
• 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 5
• 239000000126 substance Substances 0.000 description 5
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 5
• VNQNXQYZMPJLQX-UHFFFAOYSA-N 1,3,5-tris[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]-1,3,5-triazinane-2,4,6-trione Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CN2C(N(CC=3C=C(C(O)=C(C=3)C(C)(C)C)C(C)(C)C)C(=O)N(CC=3C=C(C(O)=C(C=3)C(C)(C)C)C(C)(C)C)C2=O)=O)=C1 VNQNXQYZMPJLQX-UHFFFAOYSA-N 0.000 description 4
• YHMYGUUIMTVXNW-UHFFFAOYSA-N 1,3-dihydrobenzimidazole-2-thione Chemical compound C1=CC=C2NC(S)=NC2=C1 YHMYGUUIMTVXNW-UHFFFAOYSA-N 0.000 description 4
• 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 description 4
• HCILJBJJZALOAL-UHFFFAOYSA-N 3-(3,5-ditert-butyl-4-hydroxyphenyl)-n'-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyl]propanehydrazide Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)NNC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 HCILJBJJZALOAL-UHFFFAOYSA-N 0.000 description 4
• FLZYQMOKBVFXJS-UHFFFAOYSA-N 3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propanoic acid Chemical compound CC1=CC(CCC(O)=O)=CC(C(C)(C)C)=C1O FLZYQMOKBVFXJS-UHFFFAOYSA-N 0.000 description 4
• ACZGCWSMSTYWDQ-UHFFFAOYSA-N 3h-1-benzofuran-2-one Chemical compound C1=CC=C2OC(=O)CC2=C1 ACZGCWSMSTYWDQ-UHFFFAOYSA-N 0.000 description 4
• HPFWYRKGZUGGPB-UHFFFAOYSA-N 4,6-dichloro-n-(2,4,4-trimethylpentan-2-yl)-1,3,5-triazin-2-amine Chemical compound CC(C)(C)CC(C)(C)NC1=NC(Cl)=NC(Cl)=N1 HPFWYRKGZUGGPB-UHFFFAOYSA-N 0.000 description 4
• YZXTWMQYSSMUFH-UHFFFAOYSA-N 4-[6-(1-amino-2,2,6,6-tetramethylpiperidin-4-yl)hexyl]-2,2,6,6-tetramethylpiperidin-1-amine Chemical compound C1C(C)(C)N(N)C(C)(C)CC1CCCCCCC1CC(C)(C)N(N)C(C)(C)C1 YZXTWMQYSSMUFH-UHFFFAOYSA-N 0.000 description 4
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• 125000003438 dodecyl group Chemical group [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])* 0.000 description 4
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• SQDFHQJTAWCFIB-UHFFFAOYSA-N n-methylidenehydroxylamine Chemical compound ON=C SQDFHQJTAWCFIB-UHFFFAOYSA-N 0.000 description 4
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• 238000002360 preparation method Methods 0.000 description 4
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• 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 4
• 229920001897 terpolymer Polymers 0.000 description 4
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• GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 3
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