JPH05194785A - 有機スルフィド系酸化防止剤で安定化された無毒性ポリマー組成物 - Google Patents
有機スルフィド系酸化防止剤で安定化された無毒性ポリマー組成物Info
- Publication number
- JPH05194785A JPH05194785A JP4214804A JP21480492A JPH05194785A JP H05194785 A JPH05194785 A JP H05194785A JP 4214804 A JP4214804 A JP 4214804A JP 21480492 A JP21480492 A JP 21480492A JP H05194785 A JPH05194785 A JP H05194785A
- Authority
- JP
- Japan
- Prior art keywords
- carbon atoms
- group
- polymer composition
- alkyl group
- food
- 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.)
- Withdrawn
Links
- 239000003963 antioxidant agent Substances 0.000 title claims abstract description 83
- 239000000203 mixture Substances 0.000 title claims abstract description 77
- 230000003078 antioxidant effect Effects 0.000 title claims abstract description 45
- 231100000252 nontoxic Toxicity 0.000 title claims abstract description 37
- 230000003000 nontoxic effect Effects 0.000 title claims abstract description 37
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 title claims description 75
- 229920000642 polymer Polymers 0.000 title claims description 59
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 50
- 229920005989 resin Polymers 0.000 claims abstract description 23
- 239000011347 resin Substances 0.000 claims abstract description 23
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 16
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 12
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- 239000004416 thermosoftening plastic Substances 0.000 claims abstract description 7
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 6
- 125000002619 bicyclic group Chemical group 0.000 claims abstract description 6
- 125000002950 monocyclic group Chemical group 0.000 claims abstract description 6
- 125000001424 substituent group Chemical group 0.000 claims abstract description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 98
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- 239000000126 substance Substances 0.000 claims description 46
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- 239000004743 Polypropylene Substances 0.000 claims description 27
- 239000002904 solvent Substances 0.000 claims description 25
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- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 20
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- 229920003002 synthetic resin Polymers 0.000 claims description 18
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- 125000005842 heteroatom Chemical group 0.000 claims description 15
- 229920001903 high density polyethylene Polymers 0.000 claims description 15
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- 229920002223 polystyrene Polymers 0.000 claims description 15
- 239000000243 solution Substances 0.000 claims description 12
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- 229920000098 polyolefin Polymers 0.000 claims description 8
- 229920005672 polyolefin resin Polymers 0.000 claims description 8
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 7
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- 238000004806 packaging method and process Methods 0.000 claims description 6
- 125000002723 alicyclic group Chemical group 0.000 claims description 5
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- JIIHLVXSBCEXML-UHFFFAOYSA-N 1-octadecylsulfanyl-3-(2-octadecylsulfanylethyl)cyclohexane Chemical group CCCCCCCCCCCCCCCCCCSCCC1CCCC(SCCCCCCCCCCCCCCCCCC)C1 JIIHLVXSBCEXML-UHFFFAOYSA-N 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 239000012965 benzophenone Substances 0.000 claims description 4
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- 229920000092 linear low density polyethylene Polymers 0.000 claims description 4
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- 150000002989 phenols Chemical class 0.000 claims description 4
- 229920000515 polycarbonate Polymers 0.000 claims description 4
- 239000004417 polycarbonate Substances 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 229920002678 cellulose Polymers 0.000 claims description 3
- 229920000728 polyester Polymers 0.000 claims description 3
- 238000003860 storage Methods 0.000 claims description 3
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- 239000012760 heat stabilizer Substances 0.000 claims 6
- 239000004611 light stabiliser Substances 0.000 claims 6
- 150000008366 benzophenones Chemical class 0.000 claims 3
- 125000003354 benzotriazolyl group Chemical class N1N=NC2=C1C=CC=C2* 0.000 claims 3
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 claims 3
- 230000000153 supplemental effect Effects 0.000 claims 3
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 claims 2
- LVTJFTXABPFKCG-UHFFFAOYSA-N octadecylsulfanylcyclohexane Chemical compound CCCCCCCCCCCCCCCCCCSC1CCCCC1 LVTJFTXABPFKCG-UHFFFAOYSA-N 0.000 claims 2
- 229920006132 styrene block copolymer Polymers 0.000 claims 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims 1
- 239000004698 Polyethylene Substances 0.000 claims 1
- 230000015556 catabolic process Effects 0.000 claims 1
- 239000011248 coating agent Substances 0.000 claims 1
- 238000006731 degradation reaction Methods 0.000 claims 1
- LSUIEOBBDXBMCZ-NDENLUEZSA-N methyl 2-[(z)-(9-hydroxy-10-methoxy-2,2,4-trimethyl-1h-chromeno[3,4-f]quinolin-5-ylidene)methyl]thiophene-3-carboxylate Chemical compound C1=CSC(\C=C/2C3=C4C(C)=CC(C)(C)NC4=CC=C3C3=C(OC)C(O)=CC=C3O\2)=C1C(=O)OC LSUIEOBBDXBMCZ-NDENLUEZSA-N 0.000 claims 1
- 229920000573 polyethylene Polymers 0.000 claims 1
- 238000002156 mixing Methods 0.000 abstract description 6
- 231100000053 low toxicity Toxicity 0.000 abstract description 3
- 238000000605 extraction Methods 0.000 description 24
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 15
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 15
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 241001465754 Metazoa Species 0.000 description 14
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 13
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 10
- 239000000463 material Substances 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 230000002378 acidificating effect Effects 0.000 description 9
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- 231100000403 acute toxicity Toxicity 0.000 description 9
- 239000000654 additive Substances 0.000 description 9
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- 238000013508 migration Methods 0.000 description 8
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- CCCMONHAUSKTEQ-UHFFFAOYSA-N octadec-1-ene Chemical compound CCCCCCCCCCCCCCCCC=C CCCMONHAUSKTEQ-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 8
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical group OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 7
- 239000008188 pellet Substances 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- 238000009826 distribution Methods 0.000 description 6
- 229920005669 high impact polystyrene Polymers 0.000 description 6
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- 150000003568 thioethers Chemical class 0.000 description 6
- 230000001988 toxicity Effects 0.000 description 6
- 231100000419 toxicity Toxicity 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000002656 Distearyl thiodipropionate Substances 0.000 description 5
- 230000000996 additive effect Effects 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- PWWSSIYVTQUJQQ-UHFFFAOYSA-N distearyl thiodipropionate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCCCCCCCC PWWSSIYVTQUJQQ-UHFFFAOYSA-N 0.000 description 5
- 235000019305 distearyl thiodipropionate Nutrition 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 150000002978 peroxides Chemical class 0.000 description 5
- 231100000331 toxic Toxicity 0.000 description 5
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 4
- GHKOFFNLGXMVNJ-UHFFFAOYSA-N Didodecyl thiobispropanoate Chemical compound CCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCC GHKOFFNLGXMVNJ-UHFFFAOYSA-N 0.000 description 4
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 4
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- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 4
- 239000008116 calcium stearate Substances 0.000 description 4
- 235000013539 calcium stearate Nutrition 0.000 description 4
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- 239000005720 sucrose Substances 0.000 description 4
- 229940084778 1,4-sorbitan Drugs 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 239000003508 Dilauryl thiodipropionate Substances 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
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- ORTRWBYBJVGVQC-UHFFFAOYSA-N hexadecane-1-thiol Chemical compound CCCCCCCCCCCCCCCCS ORTRWBYBJVGVQC-UHFFFAOYSA-N 0.000 description 3
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- PZRWFKGUFWPFID-UHFFFAOYSA-N 3,9-dioctadecoxy-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane Chemical compound C1OP(OCCCCCCCCCCCCCCCCCC)OCC21COP(OCCCCCCCCCCCCCCCCCC)OC2 PZRWFKGUFWPFID-UHFFFAOYSA-N 0.000 description 1
- UGWNXYHJYAYQIQ-UHFFFAOYSA-N 3-(2-sulfanylethyl)cyclohexane-1-thiol Chemical compound SCCC1CCCC(S)C1 UGWNXYHJYAYQIQ-UHFFFAOYSA-N 0.000 description 1
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- TXMMDZHPODEQPW-UHFFFAOYSA-N 4-(2-sulfanylethyl)cyclohexane-1-thiol Chemical compound SCCC1CCC(S)CC1 TXMMDZHPODEQPW-UHFFFAOYSA-N 0.000 description 1
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- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
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- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
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- 241000277331 Salmonidae Species 0.000 description 1
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- PQYJRMFWJJONBO-UHFFFAOYSA-N Tris(2,3-dibromopropyl) phosphate Chemical compound BrCC(Br)COP(=O)(OCC(Br)CBr)OCC(Br)CBr PQYJRMFWJJONBO-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
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- 150000008065 acid anhydrides Chemical class 0.000 description 1
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- 150000001447 alkali salts Chemical class 0.000 description 1
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- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
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- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
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- 150000005690 diesters Chemical class 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- ZJIPHXXDPROMEF-UHFFFAOYSA-N dihydroxyphosphanyl dihydrogen phosphite Chemical compound OP(O)OP(O)O ZJIPHXXDPROMEF-UHFFFAOYSA-N 0.000 description 1
- VTIIJXUACCWYHX-UHFFFAOYSA-L disodium;carboxylatooxy carbonate Chemical compound [Na+].[Na+].[O-]C(=O)OOC([O-])=O VTIIJXUACCWYHX-UHFFFAOYSA-L 0.000 description 1
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 1
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- 238000000921 elemental analysis Methods 0.000 description 1
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- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
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- 150000005309 metal halides Chemical class 0.000 description 1
- 150000004972 metal peroxides Chemical class 0.000 description 1
- 230000003278 mimic effect Effects 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- QJAOYSPHSNGHNC-UHFFFAOYSA-N octadecane-1-thiol Chemical compound CCCCCCCCCCCCCCCCCCS QJAOYSPHSNGHNC-UHFFFAOYSA-N 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229920006280 packaging film Polymers 0.000 description 1
- 239000012785 packaging film Substances 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000002530 phenolic antioxidant Substances 0.000 description 1
- 238000005375 photometry Methods 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000090 poly(aryl ether) Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
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- 150000003902 salicylic acid esters Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000035943 smell Effects 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229960001922 sodium perborate Drugs 0.000 description 1
- 229940045872 sodium percarbonate Drugs 0.000 description 1
- PFUVRDFDKPNGAV-UHFFFAOYSA-N sodium peroxide Chemical compound [Na+].[Na+].[O-][O-] PFUVRDFDKPNGAV-UHFFFAOYSA-N 0.000 description 1
- YKLJGMBLPUQQOI-UHFFFAOYSA-M sodium;oxidooxy(oxo)borane Chemical compound [Na+].[O-]OB=O YKLJGMBLPUQQOI-UHFFFAOYSA-M 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000002798 spectrophotometry method Methods 0.000 description 1
- 235000015096 spirit Nutrition 0.000 description 1
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- 239000012258 stirred mixture Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000012956 testing procedure Methods 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
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- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- AUPYNGCJRYOPQY-UHFFFAOYSA-N tris(2,5-ditert-butylphenyl) phosphite Chemical compound CC(C)(C)C1=CC=C(C(C)(C)C)C(OP(OC=2C(=CC=C(C=2)C(C)(C)C)C(C)(C)C)OC=2C(=CC=C(C=2)C(C)(C)C)C(C)(C)C)=C1 AUPYNGCJRYOPQY-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- 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
- C08K5/04—Oxygen-containing compounds
- C08K5/14—Peroxides
-
- 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
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/37—Thiols
- C08K5/372—Sulfides, e.g. R-(S)x-R'
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US735140 | 1991-07-24 | ||
| US07/735,140 US5284886A (en) | 1989-10-31 | 1991-07-24 | Non-toxic polymeric compositions stabilized with organosulfide antioxidants |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH05194785A true JPH05194785A (ja) | 1993-08-03 |
Family
ID=24954540
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4214804A Withdrawn JPH05194785A (ja) | 1991-07-24 | 1992-07-21 | 有機スルフィド系酸化防止剤で安定化された無毒性ポリマー組成物 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US5284886A (enExample) |
| EP (1) | EP0525664A1 (enExample) |
| JP (1) | JPH05194785A (enExample) |
| BR (1) | BR9202838A (enExample) |
| CA (1) | CA2074292A1 (enExample) |
| TW (1) | TW221451B (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5284886A (en) * | 1989-10-31 | 1994-02-08 | Elf Atochem North America, Inc. | Non-toxic polymeric compositions stabilized with organosulfide antioxidants |
| US6812314B2 (en) | 2001-10-17 | 2004-11-02 | University Of Florida | Thermally responsive polymer materials and uses thereof |
| US8147769B1 (en) | 2007-05-16 | 2012-04-03 | Abbott Cardiovascular Systems Inc. | Stent and delivery system with reduced chemical degradation |
| FR2917381B1 (fr) * | 2007-06-15 | 2009-10-16 | Ceva Sante Animale Sa | Conditionnement plastique multicouche pour la conservation d'une composition pharmaceutique |
| US20090319031A1 (en) * | 2008-06-19 | 2009-12-24 | Yunbing Wang | Bioabsorbable Polymeric Stent With Improved Structural And Molecular Weight Integrity |
| US9539587B1 (en) * | 2016-04-05 | 2017-01-10 | Chevron Phillips Chemical Company Lp | Mercaptanized dicyclopentadiene compositions and use thereof as a mining chemical collector |
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| US2868765A (en) * | 1955-07-06 | 1959-01-13 | Ethyl Corp | Polyvinyl chloride with alkali metal phosphate and organotin salt |
| US2995539A (en) * | 1956-03-01 | 1961-08-08 | Du Pont | Ethylene polymer composition containing alkanol sulfide polymer |
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| US2972597A (en) * | 1958-11-13 | 1961-02-21 | Eastman Kodak Co | Stabilized poly-alpha-olefin compositions |
| US3010937A (en) * | 1958-12-19 | 1961-11-28 | Bayer Ag | Process for stabilizing polymers of monoolefins |
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| NL255155A (enExample) * | 1959-08-28 | |||
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| NL252487A (enExample) * | 1960-06-10 | |||
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| GB1002431A (en) * | 1961-05-30 | 1965-08-25 | Ici Ltd | Solid olefine polymer compositions |
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| DE1545155A1 (de) * | 1964-01-31 | 1970-01-22 | Glanzstoff Ag | Verfahren zur Verbesserung der Stabilitaet von Polyolefinen |
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| CH476775A (de) * | 1966-02-08 | 1969-08-15 | Geigy Ag J R | Verfahren zum Schützen von oxydationsempfindlichem organischem Material |
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| US5096947A (en) * | 1989-10-31 | 1992-03-17 | Atochem North America, Inc. | Organic peroxide and organic sulfide antioxidant composition |
-
1991
- 1991-07-24 US US07/735,140 patent/US5284886A/en not_active Expired - Lifetime
-
1992
- 1992-07-03 TW TW081105282A patent/TW221451B/zh active
- 1992-07-21 CA CA002074292A patent/CA2074292A1/en not_active Abandoned
- 1992-07-21 JP JP4214804A patent/JPH05194785A/ja not_active Withdrawn
- 1992-07-23 BR BR929202838A patent/BR9202838A/pt not_active Application Discontinuation
- 1992-07-24 EP EP92112679A patent/EP0525664A1/en not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| US5284886A (en) | 1994-02-08 |
| EP0525664A1 (en) | 1993-02-03 |
| BR9202838A (pt) | 1993-03-23 |
| TW221451B (enExample) | 1994-03-01 |
| CA2074292A1 (en) | 1993-01-25 |
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