BRPI0407482B1 - Composto polialquilpiperidina estabilizador de luz, sua composição e seus usos, métodos de estabilização de um material orgânico contra degradação induzida por ozona e/ou induzida por luz, dinâmica, térmica, oxidativa, e método de enxertamento do referido composto sobre um material orgânico - Google Patents

Info

Publication number

BRPI0407482B1

BRPI0407482B1 BRPI0407482-3A BRPI0407482A BRPI0407482B1 BR PI0407482 B1 BRPI0407482 B1 BR PI0407482B1 BR PI0407482 A BRPI0407482 A BR PI0407482A BR PI0407482 B1 BRPI0407482 B1 BR PI0407482B1

Authority

BR

Brazil

Prior art keywords

alkyl

alkylene

hydrogen

tert

compound

Prior art date

2003-02-14

Links

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• 150000001875 compounds Chemical class 0.000 title claims abstract description 113
• 239000011368 organic material Substances 0.000 title claims abstract description 37
• CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 title claims abstract description 17
• 230000015556 catabolic process Effects 0.000 title claims abstract description 8
• 238000006731 degradation reaction Methods 0.000 title claims abstract description 8
• 230000001590 oxidative effect Effects 0.000 title claims abstract description 8
• 239000000203 mixture Substances 0.000 title claims description 56
• 238000000034 method Methods 0.000 title claims description 17
• 230000000087 stabilizing effect Effects 0.000 title claims description 8
• 239000003381 stabilizer Substances 0.000 claims abstract description 10
• 229920001059 synthetic polymer Polymers 0.000 claims abstract description 4
• -1 cyclohexoxy, benzyl Chemical group 0.000 claims description 197
• PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 53
• 229920001577 copolymer Polymers 0.000 claims description 47
• 125000002947 alkylene group Chemical group 0.000 claims description 36
• 125000000217 alkyl group Chemical group 0.000 claims description 32
• 239000001257 hydrogen Substances 0.000 claims description 32
• 229910052739 hydrogen Inorganic materials 0.000 claims description 32
• 239000000654 additive Substances 0.000 claims description 27
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 25
• 229910052717 sulfur Inorganic materials 0.000 claims description 25
• 239000011593 sulfur Substances 0.000 claims description 25
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 24
• 239000001301 oxygen Substances 0.000 claims description 24
• 229910052760 oxygen Inorganic materials 0.000 claims description 24
• 150000002431 hydrogen Chemical class 0.000 claims description 22
• 239000005977 Ethylene Substances 0.000 claims description 17
• 229920001971 elastomer Polymers 0.000 claims description 17
• VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 16
• 239000003795 chemical substances by application Substances 0.000 claims description 15
• 229910052751 metal Inorganic materials 0.000 claims description 14
• 239000002184 metal Substances 0.000 claims description 14
• 239000003963 antioxidant agent Substances 0.000 claims description 13
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
• 125000003342 alkenyl group Chemical group 0.000 claims description 11
• 239000000806 elastomer Substances 0.000 claims description 11
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 9
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
• 239000003623 enhancer Substances 0.000 claims description 8
• 239000004611 light stabiliser Substances 0.000 claims description 8
• 238000012545 processing Methods 0.000 claims description 8
• 125000003545 alkoxy group Chemical group 0.000 claims description 7
• 238000010525 oxidative degradation reaction Methods 0.000 claims description 7
• AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 claims description 7
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 6
• 125000001589 carboacyl group Chemical group 0.000 claims description 6
• 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 6
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
• 229920000098 polyolefin Polymers 0.000 claims description 6
• 238000004073 vulcanization Methods 0.000 claims description 6
• 239000002270 dispersing agent Substances 0.000 claims description 5
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 5
• 239000002904 solvent Substances 0.000 claims description 5
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
• 239000000945 filler Substances 0.000 claims description 4
• 238000010348 incorporation Methods 0.000 claims description 4
• 239000002530 phenolic antioxidant Substances 0.000 claims description 4
• 239000002318 adhesion promoter Substances 0.000 claims description 3
• 239000000975 dye Substances 0.000 claims description 3
• 125000003884 phenylalkyl group Chemical group 0.000 claims description 3
• XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical class OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 claims description 3
• 239000000049 pigment Substances 0.000 claims description 3
• 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 2
• 238000010438 heat treatment Methods 0.000 claims description 2
• 239000004014 plasticizer Substances 0.000 claims description 2
• 239000013008 thixotropic agent Substances 0.000 claims description 2
• 239000012936 vulcanization activator Substances 0.000 claims description 2
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 3
• 125000000000 cycloalkoxy group Chemical group 0.000 claims 2
• 230000004927 fusion Effects 0.000 claims 2
• 229920000642 polymer Polymers 0.000 description 40
• 239000003921 oil Substances 0.000 description 34
• 229910052757 nitrogen Inorganic materials 0.000 description 33
• 235000019198 oils Nutrition 0.000 description 33
• 239000000314 lubricant Substances 0.000 description 25
• 239000002253 acid Substances 0.000 description 23
• 150000001412 amines Chemical class 0.000 description 23
• 239000012530 fluid Substances 0.000 description 22
• 150000002148 esters Chemical class 0.000 description 21
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 17
• NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 13
• 239000005062 Polybutadiene Substances 0.000 description 13
• 229920002857 polybutadiene Polymers 0.000 description 13
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
• MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 12
• 239000004952 Polyamide Substances 0.000 description 11
• 235000006708 antioxidants Nutrition 0.000 description 11
• 229920002647 polyamide Polymers 0.000 description 11
• 239000000446 fuel Substances 0.000 description 10
• 150000003254 radicals Chemical class 0.000 description 10
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
• 150000007513 acids Chemical class 0.000 description 9
• MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 8
• 239000004743 Polypropylene Substances 0.000 description 8
• 239000012964 benzotriazole Substances 0.000 description 8
• KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 8
• 239000007859 condensation product Substances 0.000 description 8
• 238000005555 metalworking 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
• 229920002554 vinyl polymer Polymers 0.000 description 8
• KAKZBPTYRLMSJV-UHFFFAOYSA-N vinyl-ethylene Natural products C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 8
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
• 239000004721 Polyphenylene oxide Substances 0.000 description 7
• 239000007983 Tris buffer Substances 0.000 description 7
• 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 7
• QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 7
• 125000004432 carbon atom Chemical group C* 0.000 description 7
• 239000003054 catalyst Substances 0.000 description 7
• 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 7
• 239000000178 monomer Substances 0.000 description 7
• 229920006324 polyoxymethylene Polymers 0.000 description 7
• 238000002360 preparation method Methods 0.000 description 7
• 150000003839 salts Chemical class 0.000 description 7
• 239000001993 wax Substances 0.000 description 7
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
• 239000004698 Polyethylene Substances 0.000 description 6
• 150000001252 acrylic acid derivatives Chemical class 0.000 description 6
• 125000001931 aliphatic group Chemical group 0.000 description 6
• 125000003118 aryl group Chemical group 0.000 description 6
• 150000001993 dienes Chemical class 0.000 description 6
• 229920001684 low density polyethylene Polymers 0.000 description 6
• 239000004702 low-density polyethylene Substances 0.000 description 6
• 239000002480 mineral oil Substances 0.000 description 6
• 150000002978 peroxides Chemical class 0.000 description 6
• 229920000570 polyether Polymers 0.000 description 6
• 229920000573 polyethylene Polymers 0.000 description 6
• 229920000915 polyvinyl chloride Polymers 0.000 description 6
• 239000004800 polyvinyl chloride Substances 0.000 description 6
• 239000005060 rubber Substances 0.000 description 6
• SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 description 6
• 150000005846 sugar alcohols Polymers 0.000 description 6
• 239000003760 tallow Substances 0.000 description 6
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 6
• CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 5
• 229910019142 PO4 Inorganic materials 0.000 description 5
• XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 5
• WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 5
• 150000001298 alcohols Chemical class 0.000 description 5
• 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 5
• HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 5
• 229910052736 halogen Inorganic materials 0.000 description 5
• 150000002367 halogens Chemical group 0.000 description 5
• 229920001903 high density polyethylene Polymers 0.000 description 5
• 239000004700 high-density polyethylene Substances 0.000 description 5
• UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 description 5
• WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 5
• 235000021317 phosphate Nutrition 0.000 description 5
• 229920000728 polyester Polymers 0.000 description 5
• 239000000047 product Substances 0.000 description 5
• 229920005989 resin Polymers 0.000 description 5
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• 230000006641 stabilisation Effects 0.000 description 5
• 238000011105 stabilization Methods 0.000 description 5
• 239000000126 substance Substances 0.000 description 5
• 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
• LRUDIIUSNGCQKF-UHFFFAOYSA-N 5-methyl-1H-benzotriazole Chemical compound C1=C(C)C=CC2=NNN=C21 LRUDIIUSNGCQKF-UHFFFAOYSA-N 0.000 description 4
• 229920000089 Cyclic olefin copolymer Polymers 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
• 229920000877 Melamine resin Polymers 0.000 description 4
• 235000019484 Rapeseed oil Nutrition 0.000 description 4
• ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 4
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
• DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 4
• RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
• XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 4
• 229920001519 homopolymer Polymers 0.000 description 4
• FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 4
• 239000000463 material Substances 0.000 description 4
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
• FTWUXYZHDFCGSV-UHFFFAOYSA-N n,n'-diphenyloxamide Chemical compound C=1C=CC=CC=1NC(=O)C(=O)NC1=CC=CC=C1 FTWUXYZHDFCGSV-UHFFFAOYSA-N 0.000 description 4
• SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 4
• 229920001707 polybutylene terephthalate Polymers 0.000 description 4
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• 239000004814 polyurethane Substances 0.000 description 4
• 239000011541 reaction mixture Substances 0.000 description 4
• 239000000243 solution Substances 0.000 description 4
• 239000000600 sorbitol Substances 0.000 description 4
• 150000003871 sulfonates Chemical class 0.000 description 4
• 229920001897 terpolymer Polymers 0.000 description 4
• YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 4
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• 239000008158 vegetable oil Substances 0.000 description 4
• DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 3
• FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 3
• ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 3
• RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-Tetramethylpiperidine Substances CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 3
• 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 3
• KXPXKNBDCUOENF-UHFFFAOYSA-N 2-(Octylthio)ethanol Chemical compound CCCCCCCCSCCO KXPXKNBDCUOENF-UHFFFAOYSA-N 0.000 description 3
• ZPIRWAHWDCHWLM-UHFFFAOYSA-N 2-dodecylsulfanylethanol Chemical compound CCCCCCCCCCCCSCCO ZPIRWAHWDCHWLM-UHFFFAOYSA-N 0.000 description 3
• GAODDBNJCKQQDY-UHFFFAOYSA-N 2-methyl-4,6-bis(octylsulfanylmethyl)phenol Chemical compound CCCCCCCCSCC1=CC(C)=C(O)C(CSCCCCCCCC)=C1 GAODDBNJCKQQDY-UHFFFAOYSA-N 0.000 description 3
• RXFCIXRFAJRBSG-UHFFFAOYSA-N 3,2,3-tetramine Chemical compound NCCCNCCNCCCN RXFCIXRFAJRBSG-UHFFFAOYSA-N 0.000 description 3
• RREANTFLPGEWEN-MBLPBCRHSA-N 7-[4-[[(3z)-3-[4-amino-5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidin-2-yl]imino-5-fluoro-2-oxoindol-1-yl]methyl]piperazin-1-yl]-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(\N=C/3C4=CC(F)=CC=C4N(CN4CCN(CC4)C=4C(=CC=5C(=O)C(C(O)=O)=CN(C=5C=4)C4CC4)F)C\3=O)=NC=2)N)=C1 RREANTFLPGEWEN-MBLPBCRHSA-N 0.000 description 3
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• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
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• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
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• JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 3
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• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 3
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• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
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• 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
• 235000012424 soybean oil Nutrition 0.000 description 3
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
• 229920001169 thermoplastic Polymers 0.000 description 3
• 235000015112 vegetable and seed oil Nutrition 0.000 description 3
• 239000011701 zinc Substances 0.000 description 3
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