JP5221828B2 - 回転成形法のための安定剤組み合わせ - Google Patents
回転成形法のための安定剤組み合わせ Download PDFInfo
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- JP5221828B2 JP5221828B2 JP2000053525A JP2000053525A JP5221828B2 JP 5221828 B2 JP5221828 B2 JP 5221828B2 JP 2000053525 A JP2000053525 A JP 2000053525A JP 2000053525 A JP2000053525 A JP 2000053525A JP 5221828 B2 JP5221828 B2 JP 5221828B2
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- butyl
- carbon atoms
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- bis
- Prior art date
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- 238000001175 rotational moulding Methods 0.000 title description 22
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 82
- 239000000203 mixture Substances 0.000 claims description 79
- 125000000217 alkyl group Chemical group 0.000 claims description 57
- 150000001412 amines Chemical class 0.000 claims description 54
- 150000001875 compounds Chemical class 0.000 claims description 38
- 239000000126 substance Substances 0.000 claims description 25
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 238000004519 manufacturing process Methods 0.000 claims description 11
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 10
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
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- 239000003054 catalyst Substances 0.000 description 9
- 125000005843 halogen group Chemical group 0.000 description 9
- 125000003710 aryl alkyl group Chemical group 0.000 description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 8
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- FQZYTYWMLGAPFJ-OQKDUQJOSA-N tamoxifen citrate Chemical compound [H+].[H+].[H+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.C=1C=CC=CC=1C(/CC)=C(C=1C=CC(OCCN(C)C)=CC=1)/C1=CC=CC=C1 FQZYTYWMLGAPFJ-OQKDUQJOSA-N 0.000 description 8
- 150000003512 tertiary amines Chemical class 0.000 description 8
- 125000002947 alkylene group Chemical group 0.000 description 7
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- 125000004430 oxygen atom Chemical group O* 0.000 description 7
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- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 6
- 229910052717 sulfur Inorganic materials 0.000 description 6
- 125000004434 sulfur atom Chemical group 0.000 description 6
- 239000003760 tallow Substances 0.000 description 6
- 239000007983 Tris buffer Substances 0.000 description 5
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- 125000002877 alkyl aryl group Chemical group 0.000 description 5
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 description 5
- 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 5
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- 230000003647 oxidation Effects 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
- 125000003884 phenylalkyl group Chemical group 0.000 description 5
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 5
- 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 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 5
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 4
- ZQMPWXFHAUDENN-UHFFFAOYSA-N 1,2-bis[(2-methylphenyl)amino]ethane Natural products CC1=CC=CC=C1NCCNC1=CC=CC=C1C ZQMPWXFHAUDENN-UHFFFAOYSA-N 0.000 description 4
- ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 4
- 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 4
- JLZIIHMTTRXXIN-UHFFFAOYSA-N 2-(2-hydroxy-4-methoxybenzoyl)benzoic acid Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1C(O)=O JLZIIHMTTRXXIN-UHFFFAOYSA-N 0.000 description 4
- KXPXKNBDCUOENF-UHFFFAOYSA-N 2-(Octylthio)ethanol Chemical compound CCCCCCCCSCCO KXPXKNBDCUOENF-UHFFFAOYSA-N 0.000 description 4
- ZPIRWAHWDCHWLM-UHFFFAOYSA-N 2-dodecylsulfanylethanol Chemical compound CCCCCCCCCCCCSCCO ZPIRWAHWDCHWLM-UHFFFAOYSA-N 0.000 description 4
- CKPKHTKLLYPGFM-UHFFFAOYSA-N 6,6-dimethylheptane-1,1-diol Chemical compound CC(CCCCC(O)O)(C)C CKPKHTKLLYPGFM-UHFFFAOYSA-N 0.000 description 4
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
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- 150000001298 alcohols Chemical class 0.000 description 4
- ZEFSGHVBJCEKAZ-UHFFFAOYSA-N bis(2,4-ditert-butyl-6-methylphenyl) ethyl phosphite Chemical compound CC=1C=C(C(C)(C)C)C=C(C(C)(C)C)C=1OP(OCC)OC1=C(C)C=C(C(C)(C)C)C=C1C(C)(C)C ZEFSGHVBJCEKAZ-UHFFFAOYSA-N 0.000 description 4
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- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
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- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 4
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- 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 3
- AIBRSVLEQRWAEG-UHFFFAOYSA-N 3,9-bis(2,4-ditert-butylphenoxy)-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OP1OCC2(COP(OC=3C(=CC(=CC=3)C(C)(C)C)C(C)(C)C)OC2)CO1 AIBRSVLEQRWAEG-UHFFFAOYSA-N 0.000 description 3
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- 125000004429 atom Chemical group 0.000 description 3
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- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 3
- 125000002960 margaryl 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])[H] 0.000 description 3
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- 150000002903 organophosphorus compounds Chemical class 0.000 description 3
- 125000000913 palmityl 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])[H] 0.000 description 3
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- 125000002889 tridecyl 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])[H] 0.000 description 3
- HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 description 2
- 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 2
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- SLUKQUGVTITNSY-UHFFFAOYSA-N 2,6-di-tert-butyl-4-methoxyphenol Chemical compound COC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SLUKQUGVTITNSY-UHFFFAOYSA-N 0.000 description 2
- YTHQTKBAVNQRFN-UHFFFAOYSA-N 2-cyano-3-(4-methoxyphenyl)but-2-enoic acid Chemical compound COC1=CC=C(C(C)=C(C#N)C(O)=O)C=C1 YTHQTKBAVNQRFN-UHFFFAOYSA-N 0.000 description 2
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000003229 2-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
- 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 2
- QSZMLDPPGQRTQY-UHFFFAOYSA-N 3-[(3,5-ditert-butyl-4-hydroxyphenyl)methoxy]-3-oxopropanoic acid Chemical compound CC(C)(C)C1=CC(COC(=O)CC(O)=O)=CC(C(C)(C)C)=C1O QSZMLDPPGQRTQY-UHFFFAOYSA-N 0.000 description 2
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- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 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 2
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- 125000006547 cyclononyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- YQLZOAVZWJBZSY-UHFFFAOYSA-N decane-1,10-diamine Chemical compound NCCCCCCCCCCN YQLZOAVZWJBZSY-UHFFFAOYSA-N 0.000 description 1
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- 238000006731 degradation reaction Methods 0.000 description 1
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- FVCOIAYSJZGECG-UHFFFAOYSA-N diethylhydroxylamine Chemical compound CCN(O)CC FVCOIAYSJZGECG-UHFFFAOYSA-N 0.000 description 1
- ZJIPHXXDPROMEF-UHFFFAOYSA-N dihydroxyphosphanyl dihydrogen phosphite Chemical compound OP(O)OP(O)O ZJIPHXXDPROMEF-UHFFFAOYSA-N 0.000 description 1
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- 235000019305 distearyl thiodipropionate Nutrition 0.000 description 1
- MCPKSFINULVDNX-UHFFFAOYSA-N drometrizole Chemical compound CC1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 MCPKSFINULVDNX-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
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- 238000005265 energy consumption Methods 0.000 description 1
- IAJNXBNRYMEYAZ-UHFFFAOYSA-N ethyl 2-cyano-3,3-diphenylprop-2-enoate Chemical compound C=1C=CC=CC=1C(=C(C#N)C(=O)OCC)C1=CC=CC=C1 IAJNXBNRYMEYAZ-UHFFFAOYSA-N 0.000 description 1
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- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
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- 239000004615 ingredient Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
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- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- OBQVOBQZMOXRAL-UHFFFAOYSA-L magnesium;docosanoate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCCCCCC([O-])=O OBQVOBQZMOXRAL-UHFFFAOYSA-L 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 150000002690 malonic acid derivatives Chemical class 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
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- UJRDRFZCRQNLJM-UHFFFAOYSA-N methyl 3-[3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyphenyl]propanoate Chemical compound CC(C)(C)C1=CC(CCC(=O)OC)=CC(N2N=C3C=CC=CC3=N2)=C1O UJRDRFZCRQNLJM-UHFFFAOYSA-N 0.000 description 1
- VRBLLGLKTUGCSG-UHFFFAOYSA-N methyl 3-[3-tert-butyl-5-(5-chlorobenzotriazol-2-yl)-4-hydroxyphenyl]propanoate Chemical compound CC(C)(C)C1=CC(CCC(=O)OC)=CC(N2N=C3C=C(Cl)C=CC3=N2)=C1O VRBLLGLKTUGCSG-UHFFFAOYSA-N 0.000 description 1
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 1
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- DDLNUIWJEDITCB-UHFFFAOYSA-N n,n-di(tetradecyl)hydroxylamine Chemical compound CCCCCCCCCCCCCCN(O)CCCCCCCCCCCCCC DDLNUIWJEDITCB-UHFFFAOYSA-N 0.000 description 1
- FZWOVYKSFQAUGD-UHFFFAOYSA-N n,n-didodecyldodecan-1-amine oxide Chemical compound CCCCCCCCCCCC[N+]([O-])(CCCCCCCCCCCC)CCCCCCCCCCCC FZWOVYKSFQAUGD-UHFFFAOYSA-N 0.000 description 1
- IDIFYCUWDANIJH-UHFFFAOYSA-N n,n-dihexadecylhexadecan-1-amine oxide Chemical compound CCCCCCCCCCCCCCCC[N+]([O-])(CCCCCCCCCCCCCCCC)CCCCCCCCCCCCCCCC IDIFYCUWDANIJH-UHFFFAOYSA-N 0.000 description 1
- OTXXCIYKATWWQI-UHFFFAOYSA-N n,n-dihexadecylhydroxylamine Chemical compound CCCCCCCCCCCCCCCCN(O)CCCCCCCCCCCCCCCC OTXXCIYKATWWQI-UHFFFAOYSA-N 0.000 description 1
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- SAVBPLYIBMOJIH-UHFFFAOYSA-N n-(4-methylpentyl)-n-phenylaniline Chemical compound C=1C=CC=CC=1N(CCCC(C)C)C1=CC=CC=C1 SAVBPLYIBMOJIH-UHFFFAOYSA-N 0.000 description 1
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- UBINNYMQZVKNFF-UHFFFAOYSA-N n-benzyl-1-phenylmethanimine oxide Chemical compound C=1C=CC=CC=1C=[N+]([O-])CC1=CC=CC=C1 UBINNYMQZVKNFF-UHFFFAOYSA-N 0.000 description 1
- BYYFPVDBAHOLDX-UHFFFAOYSA-N n-dodecyl-n-phenylaniline Chemical class C=1C=CC=CC=1N(CCCCCCCCCCCC)C1=CC=CC=C1 BYYFPVDBAHOLDX-UHFFFAOYSA-N 0.000 description 1
- LRUUZFQPCUFYPV-UHFFFAOYSA-N n-dodecyldodecan-1-imine oxide Chemical compound CCCCCCCCCCCC[N+]([O-])=CCCCCCCCCCCC LRUUZFQPCUFYPV-UHFFFAOYSA-N 0.000 description 1
- GBMIPYGHTZRCRH-UHFFFAOYSA-N n-ethylethanimine oxide Chemical compound CC[N+]([O-])=CC GBMIPYGHTZRCRH-UHFFFAOYSA-N 0.000 description 1
- JQARHBQLKPQLRB-UHFFFAOYSA-N n-heptadecyl-n-hexadecylhydroxylamine Chemical compound CCCCCCCCCCCCCCCCCN(O)CCCCCCCCCCCCCCCC JQARHBQLKPQLRB-UHFFFAOYSA-N 0.000 description 1
- ZRPOKHXBOZQSOX-UHFFFAOYSA-N n-heptadecyl-n-octadecylhydroxylamine Chemical compound CCCCCCCCCCCCCCCCCCN(O)CCCCCCCCCCCCCCCCC ZRPOKHXBOZQSOX-UHFFFAOYSA-N 0.000 description 1
- WGCBLWIBXXQTAW-UHFFFAOYSA-N n-hexadecyl-n-octadecylhydroxylamine Chemical compound CCCCCCCCCCCCCCCCCCN(O)CCCCCCCCCCCCCCCC WGCBLWIBXXQTAW-UHFFFAOYSA-N 0.000 description 1
- IUMKEVRMAYGUGZ-UHFFFAOYSA-N n-hexadecyl-n-tetradecylhydroxylamine Chemical compound CCCCCCCCCCCCCCCCN(O)CCCCCCCCCCCCCC IUMKEVRMAYGUGZ-UHFFFAOYSA-N 0.000 description 1
- GCDJFNYVSDFWDB-UHFFFAOYSA-N n-hexadecylhexadecan-1-imine oxide Chemical compound CCCCCCCCCCCCCCCC[N+]([O-])=CCCCCCCCCCCCCCCC GCDJFNYVSDFWDB-UHFFFAOYSA-N 0.000 description 1
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- MCMMSXFAWOGWQE-UHFFFAOYSA-N n-octadecylhexadecan-1-imine oxide Chemical compound CCCCCCCCCCCCCCCCCC[N+]([O-])=CCCCCCCCCCCCCCCC MCMMSXFAWOGWQE-UHFFFAOYSA-N 0.000 description 1
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- XQAABEDPVQWFPN-UHFFFAOYSA-N octyl 3-[3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyphenyl]propanoate Chemical compound CC(C)(C)C1=CC(CCC(=O)OCCCCCCCC)=CC(N2N=C3C=CC=CC3=N2)=C1O XQAABEDPVQWFPN-UHFFFAOYSA-N 0.000 description 1
- DMFXLIFZVRXRRR-UHFFFAOYSA-N octyl 3-[3-tert-butyl-5-(5-chlorobenzotriazol-2-yl)-4-hydroxyphenyl]propanoate Chemical compound CC(C)(C)C1=CC(CCC(=O)OCCCCCCCC)=CC(N2N=C3C=C(Cl)C=CC3=N2)=C1O DMFXLIFZVRXRRR-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
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- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 229960000969 phenyl salicylate Drugs 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 239000011990 phillips catalyst Substances 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004597 plastic additive Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 229920005672 polyolefin resin Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- MQOCIYICOGDBSG-UHFFFAOYSA-M potassium;hexadecanoate Chemical compound [K+].CCCCCCCCCCCCCCCC([O-])=O MQOCIYICOGDBSG-UHFFFAOYSA-M 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
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- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 238000010106 rotational casting Methods 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical class OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 1
- 229940116351 sebacate Drugs 0.000 description 1
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- 150000004760 silicates Chemical class 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- IJRHDFLHUATAOS-DPMBMXLASA-M sodium ricinoleate Chemical compound [Na+].CCCCCC[C@@H](O)C\C=C/CCCCCCCC([O-])=O IJRHDFLHUATAOS-DPMBMXLASA-M 0.000 description 1
- 229940074404 sodium succinate Drugs 0.000 description 1
- ZDQYSKICYIVCPN-UHFFFAOYSA-L sodium succinate (anhydrous) Chemical compound [Na+].[Na+].[O-]C(=O)CCC([O-])=O ZDQYSKICYIVCPN-UHFFFAOYSA-L 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- YONPGGFAJWQGJC-UHFFFAOYSA-K titanium(iii) chloride Chemical compound Cl[Ti](Cl)Cl YONPGGFAJWQGJC-UHFFFAOYSA-K 0.000 description 1
- 229960000984 tocofersolan Drugs 0.000 description 1
- AOBORMOPSGHCAX-DGHZZKTQSA-N tocofersolan Chemical compound OCCOC(=O)CCC(=O)OC1=C(C)C(C)=C2O[C@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C AOBORMOPSGHCAX-DGHZZKTQSA-N 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- 235000019149 tocopherols Nutrition 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- IVIIAEVMQHEPAY-UHFFFAOYSA-N tridodecyl phosphite Chemical compound CCCCCCCCCCCCOP(OCCCCCCCCCCCC)OCCCCCCCCCCCC IVIIAEVMQHEPAY-UHFFFAOYSA-N 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- CNUJLMSKURPSHE-UHFFFAOYSA-N trioctadecyl phosphite Chemical compound CCCCCCCCCCCCCCCCCCOP(OCCCCCCCCCCCCCCCCCC)OCCCCCCCCCCCCCCCCCC CNUJLMSKURPSHE-UHFFFAOYSA-N 0.000 description 1
- 229920001862 ultra low molecular weight polyethylene Polymers 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 229920001866 very low density polyethylene Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- KAKZBPTYRLMSJV-UHFFFAOYSA-N vinyl-ethylene Natural products C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
- 239000002076 α-tocopherol Substances 0.000 description 1
- 235000004835 α-tocopherol Nutrition 0.000 description 1
- 239000011590 β-tocopherol Substances 0.000 description 1
- 235000007680 β-tocopherol Nutrition 0.000 description 1
- 239000002478 γ-tocopherol Substances 0.000 description 1
- QUEDXNHFTDJVIY-UHFFFAOYSA-N γ-tocopherol Chemical class OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-UHFFFAOYSA-N 0.000 description 1
- QUEDXNHFTDJVIY-DQCZWYHMSA-N γ-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-DQCZWYHMSA-N 0.000 description 1
- 239000002446 δ-tocopherol Substances 0.000 description 1
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
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
- C08K5/3477—Six-membered rings
- C08K5/3492—Triazines
- C08K5/34926—Triazines also containing heterocyclic groups other than triazine groups
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
- B29C41/00—Shaping by coating a mould, core or other substrate, i.e. by depositing material and stripping-off the shaped article; Apparatus therefor
- B29C41/02—Shaping by coating a mould, core or other substrate, i.e. by depositing material and stripping-off the shaped article; Apparatus therefor for making articles of definite length, i.e. discrete articles
- B29C41/04—Rotational or centrifugal casting, i.e. coating the inside of a mould by rotating the mould
- B29C41/06—Rotational or centrifugal casting, i.e. coating the inside of a mould by rotating the mould about two or more axes
-
- 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
- C08K5/16—Nitrogen-containing compounds
- C08K5/32—Compounds containing nitrogen bound to oxygen
-
- 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
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
- C08K5/3432—Six-membered rings
- C08K5/3435—Piperidines
-
- 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
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Moulding By Coating Moulds (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
- Paper (AREA)
- Vehicle Body Suspensions (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US25972499A | 1999-03-01 | 1999-03-01 | |
| US09/259724 | 1999-03-01 | ||
| US09/455,143 US6444733B1 (en) | 1999-03-01 | 1999-12-06 | Stabilizer combination for the rotomolding process |
| US09/455143 | 1999-12-06 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010203640A Division JP5554666B2 (ja) | 1999-03-01 | 2010-09-10 | 回転成形法のための安定剤組み合わせ |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2000248075A JP2000248075A (ja) | 2000-09-12 |
| JP2000248075A5 JP2000248075A5 (enExample) | 2007-04-05 |
| JP5221828B2 true JP5221828B2 (ja) | 2013-06-26 |
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| JP2000053525A Expired - Lifetime JP5221828B2 (ja) | 1999-03-01 | 2000-02-29 | 回転成形法のための安定剤組み合わせ |
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| CN (1) | CN1196740C (enExample) |
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| BE (1) | BE1013624A5 (enExample) |
| BR (1) | BR0000971B1 (enExample) |
| CA (1) | CA2299712C (enExample) |
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| IT (1) | IT1317865B1 (enExample) |
| NL (1) | NL1014465C2 (enExample) |
| TW (1) | TW500751B (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JP2002121333A (ja) * | 2000-10-13 | 2002-04-23 | Daiwabo Co Ltd | ポリオレフィン樹脂成形物及びそれからなるフィルム |
| JP2003292688A (ja) * | 2002-03-29 | 2003-10-15 | Daiwabo Co Ltd | 難燃性ポリオレフィン樹脂成形物およびこれを用いた積層体とエアフィルター |
| JP4437417B2 (ja) * | 2004-03-15 | 2010-03-24 | 株式会社Adeka | ポリプロピレンの安定化方法 |
| GB2413331B (en) * | 2004-03-19 | 2008-10-29 | Pvaxx Res & Dev Ltd | Load-carrying apparatus and methods of manufacture |
| CA2557933A1 (en) * | 2004-03-19 | 2005-09-29 | Pvaxx Research And Development Limited | Load-carrying apparatus and methods of manufacture |
| US7241437B2 (en) * | 2004-12-30 | 2007-07-10 | 3M Innovative Properties Company | Zirconia particles |
| US20060204745A1 (en) * | 2005-03-14 | 2006-09-14 | Jones Clint L | Light management films with zirconia particles |
| EP1869509A2 (en) * | 2005-03-11 | 2007-12-26 | 3M Innovative Properties Company | Light management films with zirconia particles |
| GB2425506B (en) | 2005-04-26 | 2010-11-10 | Pvaxx Res & Dev Ltd | Load carrying apparatus and method of manufacture |
| SA07280006B1 (ar) * | 2006-02-01 | 2011-05-14 | سيبا سبشيالتي كيميكالز هولدينج انك | استخدام امينات ثنائية معاقة فراغياً كإضافات معالجة في عمليات التشكيل الدوراني |
| US8880410B2 (en) * | 2008-07-11 | 2014-11-04 | Fraunhofer-Gesellschaft Zur Foerderung Der Angewandten Forschung E.V. | Apparatus and method for generating a bandwidth extended signal |
| US8067490B2 (en) * | 2008-09-24 | 2011-11-29 | Chemtura Corporation | Blended phosphite or phosphonite compositions having improved hydrolytic stability |
| JP2010159396A (ja) | 2008-12-12 | 2010-07-22 | Sumitomo Chemical Co Ltd | 回転成形体用ポリオレフィン組成物 |
| CA2651514C (en) * | 2009-01-29 | 2016-05-03 | Nova Chemicals Corporation | Stabilized rotomolded parts |
| SG165299A1 (en) * | 2009-04-06 | 2010-10-28 | Sumitomo Chemical Co | Amorphous compound and production method thereof |
| WO2010123810A2 (en) * | 2009-04-21 | 2010-10-28 | Basf Performance Products Llc | Rotomolding process for polyethylene articles |
| CA2821278C (en) * | 2010-12-13 | 2019-06-18 | Cytec Technology Corp. | Processing additives and uses of same in rotational molding |
| US11267951B2 (en) | 2010-12-13 | 2022-03-08 | Cytec Technology Corp. | Stabilizer compositions containing substituted chroman compounds and methods of use |
| US9046196B2 (en) | 2011-01-11 | 2015-06-02 | Fina Technology, Inc. | Polyethylene composition for large diameter pipe stability |
| EP2729523B1 (en) * | 2011-07-07 | 2015-09-16 | Dow Global Technologies LLC | Ethylene-based polymers compositions |
| ITMI20112343A1 (it) * | 2011-12-21 | 2013-06-22 | Ifs License B V | Composizione addittivante per polimeri termoplastici |
| EP2864310B1 (en) * | 2012-06-13 | 2022-10-26 | Cytec Technology Corp. | Stabilizer compositions containing substituted chroman compounds and methods of use |
| TWI637017B (zh) * | 2012-06-13 | 2018-10-01 | 美商氰特科技股份有限公司 | 含經取代之唍化合物的安定劑組合物及使用方法 |
| TWI637018B (zh) * | 2012-06-13 | 2018-10-01 | 氰特科技股份有限公司 | 產生模製物件之方法 |
| CN104231408A (zh) * | 2014-08-07 | 2014-12-24 | 浙江瑞堂塑料科技有限公司 | 一种高耐候滚塑聚乙烯材料及其制备方法 |
| WO2016081823A1 (en) | 2014-11-20 | 2016-05-26 | Cytec Industries Inc. | Stabilizer compositions and methods for using same for protecting organic materials from uv light and thermal degradation |
| WO2018094085A1 (en) | 2016-11-18 | 2018-05-24 | Equistar Chemicals, Lp | Polyolefin materials for rotational molding applications having improved impact properties and color stability |
| GB2567456B (en) | 2017-10-12 | 2021-08-11 | Si Group Switzerland Chaa Gmbh | Antidegradant blend |
| CA3089890A1 (en) | 2018-02-27 | 2019-09-06 | Basf Se | Flame retardant rotomolded polyolefin |
| EP3578599A1 (en) | 2018-06-08 | 2019-12-11 | Cytec Industries Inc. | Granular stabilizer compositions for use in polymer resins and methods of making same |
| GB201807302D0 (en) | 2018-05-03 | 2018-06-20 | Addivant Switzerland Gmbh | Antidegradant blend |
| EP3841166B2 (en) | 2018-08-22 | 2025-05-07 | Basf Se | Stabilized rotomolded polyolefin |
| CN109134928B (zh) * | 2018-10-31 | 2020-05-19 | 天集化工助剂(沧州)有限公司 | N-取代的三嗪受阻胺光稳定剂及其制备方法和应用 |
| JP7343150B2 (ja) * | 2019-07-24 | 2023-09-12 | スイコー株式会社 | 回転成形用成形材料及び成形体 |
| WO2024083872A1 (en) | 2022-10-18 | 2024-04-25 | Cytec Industries Inc. | Synergistic stabilizer compositions and methods for using same for protecting organic materials from uv light and thermal degradation |
| WO2025056330A1 (en) | 2023-09-13 | 2025-03-20 | Cytec Industries Inc. | Stabilized polymer compositions with improved color resistance |
| WO2025219501A1 (en) | 2024-04-17 | 2025-10-23 | Cytec Industries Inc. | Stabilizing compositions for polymeric materials |
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| JPS59150719A (ja) * | 1983-02-16 | 1984-08-29 | Sumitomo Chem Co Ltd | ポリプロピレンの粉末成形法 |
| US4703073A (en) | 1983-10-11 | 1987-10-27 | Ciba-Geigy Corporation | Alkylated N,N-dibenzylhydroxylamines and polyolefin compositions stabilized therewith |
| US4590231A (en) | 1983-10-11 | 1986-05-20 | Ciba-Geigy Corporation | Polyolefin compositions stabilized against degradation using hydroxylamine derivatives |
| CA1230271A (en) * | 1983-12-12 | 1987-12-15 | Ahmed A. Alim | Rotational molding grade lldpe resin |
| US4649221A (en) | 1984-07-23 | 1987-03-10 | Ciba-Geigy Corporation | Polyhydroxylamines |
| US4691015A (en) | 1984-07-23 | 1987-09-01 | Ciba-Geigy Corporation | Hydroxylamines derived from hindered amines |
| US4668721A (en) * | 1984-07-23 | 1987-05-26 | Ciba-Geigy Corporation | Polyolefin compositions stabilized against degradation using hydroxylamine derivatives |
| US4668727A (en) * | 1985-11-21 | 1987-05-26 | Ciba-Geigy Corporation | Ester substituted benzylhydroxylamines and stabilized polyolefin compositions |
| US5013510A (en) | 1986-12-29 | 1991-05-07 | Ciba-Geigy Corporation | Process for preparing long chain N,N-dialkylhydroxylamines by direct oxidation |
| US4782105A (en) | 1987-04-10 | 1988-11-01 | Ciba-Geigy Corporation | Long chain N,N,-dialkylhydroxylamines and stabilized compositions |
| US4876300A (en) * | 1987-12-30 | 1989-10-24 | Ciba-Geigy Corporation | Polyolefin compositions stabilized with long chain N,N-dialkylhydroxylamines |
| US5149774A (en) | 1990-07-31 | 1992-09-22 | Ciba-Geigy Corporation | Method for recycling discolored polyolefins |
| JPH0621205B2 (ja) * | 1990-10-24 | 1994-03-23 | チッソ株式会社 | 結晶性ポリプロピレン組成物 |
| JP3131599B2 (ja) * | 1990-10-25 | 2001-02-05 | 三菱化学株式会社 | 積層体の製造方法 |
| US5260381A (en) * | 1991-10-08 | 1993-11-09 | Neeco, Inc. | Crosslinkable polyethylene-based composition for rotational molding |
| GB2275473B (en) * | 1993-02-26 | 1996-08-07 | Victaulic Plc | Rotational moulding of fibre-reinforced thermoplastics particles |
| US5596033A (en) | 1993-04-15 | 1997-01-21 | Ciba-Geigy Corporation | Gas fade resistant stabilizer system for polypropylene fiber |
| TW268052B (enExample) * | 1993-04-15 | 1996-01-11 | Ciba Geigy | |
| US5844029A (en) | 1995-09-25 | 1998-12-01 | General Electric Company | Polymer compositions containing hydrocarbon amine oxide and hydrocarbon amine oxide stabilizer compositions |
| DE59702969D1 (de) | 1996-10-30 | 2001-03-08 | Ciba Sc Holding Ag | Stabilisatorkombination für das Rotomolding-Verfahren |
| US5834541A (en) * | 1997-05-02 | 1998-11-10 | Montell North America Inc. | Olefin polymer composition having low smoke generation and fiber and film prepared therefrom |
-
2000
- 2000-02-22 NL NL1014465A patent/NL1014465C2/nl not_active IP Right Cessation
- 2000-02-24 GB GB0004230A patent/GB2347426B/en not_active Expired - Lifetime
- 2000-02-28 AU AU19522/00A patent/AU773507B2/en not_active Expired
- 2000-02-28 CA CA002299712A patent/CA2299712C/en not_active Expired - Lifetime
- 2000-02-28 DE DE10009416.3A patent/DE10009416B9/de not_active Expired - Lifetime
- 2000-02-29 TW TW089103466A patent/TW500751B/zh not_active IP Right Cessation
- 2000-02-29 ES ES200000477A patent/ES2170639B1/es not_active Expired - Fee Related
- 2000-02-29 FR FR0002509A patent/FR2791063B1/fr not_active Expired - Lifetime
- 2000-02-29 JP JP2000053525A patent/JP5221828B2/ja not_active Expired - Lifetime
- 2000-02-29 BR BRPI0000971-7A patent/BR0000971B1/pt not_active IP Right Cessation
- 2000-02-29 BE BE2000/0163A patent/BE1013624A5/fr not_active IP Right Cessation
- 2000-03-01 IT IT2000MI000398A patent/IT1317865B1/it active
- 2000-03-01 CN CN00103708.0A patent/CN1196740C/zh not_active Expired - Lifetime
-
2002
- 2002-01-08 US US10/041,151 patent/US20020156162A1/en not_active Abandoned
-
2004
- 2004-01-22 US US10/762,601 patent/US6902695B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| GB2347426A (en) | 2000-09-06 |
| DE10009416B9 (de) | 2015-01-22 |
| TW500751B (en) | 2002-09-01 |
| FR2791063A1 (fr) | 2000-09-22 |
| US6902695B2 (en) | 2005-06-07 |
| DE10009416B4 (de) | 2014-10-30 |
| US20040152807A1 (en) | 2004-08-05 |
| ES2170639A1 (es) | 2002-08-01 |
| AU1952200A (en) | 2000-09-07 |
| US20020156162A1 (en) | 2002-10-24 |
| BR0000971A (pt) | 2000-10-03 |
| CN1269378A (zh) | 2000-10-11 |
| CA2299712C (en) | 2008-07-29 |
| GB0004230D0 (en) | 2000-04-12 |
| IT1317865B1 (it) | 2003-07-15 |
| NL1014465A1 (nl) | 2000-09-04 |
| NL1014465C2 (nl) | 2002-01-29 |
| ES2170639B1 (es) | 2003-11-16 |
| GB2347426B (en) | 2001-10-10 |
| DE10009416A1 (de) | 2000-09-07 |
| CA2299712A1 (en) | 2000-09-01 |
| CN1196740C (zh) | 2005-04-13 |
| ITMI20000398A1 (it) | 2001-09-03 |
| ITMI20000398A0 (it) | 2000-03-01 |
| JP2000248075A (ja) | 2000-09-12 |
| AU773507B2 (en) | 2004-05-27 |
| BR0000971B1 (pt) | 2009-05-05 |
| BE1013624A5 (fr) | 2002-05-07 |
| FR2791063B1 (fr) | 2003-03-28 |
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