FI118737B - Polyolefiinien stabilointi pitkäkestoisessa kontaktissa uuttavien väliaineiden kanssa - Google Patents
Polyolefiinien stabilointi pitkäkestoisessa kontaktissa uuttavien väliaineiden kanssa Download PDFInfo
- Publication number
- FI118737B FI118737B FI963613A FI963613A FI118737B FI 118737 B FI118737 B FI 118737B FI 963613 A FI963613 A FI 963613A FI 963613 A FI963613 A FI 963613A FI 118737 B FI118737 B FI 118737B
- Authority
- FI
- Finland
- Prior art keywords
- alkyl
- hydrogen
- tert
- component
- butyl
- Prior art date
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- 229920000098 polyolefin Polymers 0.000 title description 64
- 230000007774 longterm Effects 0.000 title description 8
- 230000006641 stabilisation Effects 0.000 title description 4
- 238000011105 stabilization Methods 0.000 title description 4
- -1 polyethylene Polymers 0.000 claims description 197
- 150000001875 compounds Chemical class 0.000 claims description 92
- 229910052739 hydrogen Inorganic materials 0.000 claims description 90
- 239000001257 hydrogen Substances 0.000 claims description 88
- 239000000203 mixture Substances 0.000 claims description 66
- 125000000217 alkyl group Chemical group 0.000 claims description 58
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 49
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 47
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 39
- 238000000605 extraction Methods 0.000 claims description 35
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 32
- 150000001412 amines Chemical class 0.000 claims description 31
- JKIJEFPNVSHHEI-UHFFFAOYSA-N Phenol, 2,4-bis(1,1-dimethylethyl)-, phosphite (3:1) Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OP(OC=1C(=CC(=CC=1)C(C)(C)C)C(C)(C)C)OC1=CC=C(C(C)(C)C)C=C1C(C)(C)C JKIJEFPNVSHHEI-UHFFFAOYSA-N 0.000 claims description 28
- 125000002947 alkylene group Chemical group 0.000 claims description 27
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 21
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 20
- 239000004698 Polyethylene Substances 0.000 claims description 18
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 18
- 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 18
- 229920000573 polyethylene Polymers 0.000 claims description 18
- 230000002035 prolonged effect Effects 0.000 claims description 18
- 239000007859 condensation product Substances 0.000 claims description 16
- 239000004743 Polypropylene Substances 0.000 claims description 11
- 229920001155 polypropylene Polymers 0.000 claims description 11
- 230000000087 stabilizing effect Effects 0.000 claims description 11
- 229920001577 copolymer Polymers 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
- 239000001301 oxygen Substances 0.000 claims description 9
- 239000007788 liquid Substances 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- RXFCIXRFAJRBSG-UHFFFAOYSA-N 3,2,3-tetramine Chemical compound NCCCNCCNCCCN RXFCIXRFAJRBSG-UHFFFAOYSA-N 0.000 claims description 7
- 125000004122 cyclic group Chemical group 0.000 claims description 6
- 150000001993 dienes Chemical class 0.000 claims description 6
- 230000005923 long-lasting effect Effects 0.000 claims description 6
- 150000005673 monoalkenes Chemical class 0.000 claims description 6
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 5
- 239000011575 calcium Substances 0.000 claims description 5
- 150000001768 cations Chemical class 0.000 claims description 5
- 239000011147 inorganic material Substances 0.000 claims description 5
- 229910052751 metal Inorganic materials 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 5
- 125000001624 naphthyl group Chemical group 0.000 claims description 5
- 239000011368 organic material Substances 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- 239000003963 antioxidant agent Substances 0.000 claims description 3
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 2
- 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 claims description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 2
- 229910052791 calcium Inorganic materials 0.000 claims description 2
- BLBLVDQTHWVGRA-UHFFFAOYSA-N n-butyl-3-[4-[4-(butylamino)-1,2,2,6,6-pentamethylpiperidin-3-yl]-6-chloro-1,3,5-triazin-2-yl]-1,2,2,6,6-pentamethylpiperidin-4-amine Chemical compound CCCCNC1CC(C)(C)N(C)C(C)(C)C1C1=NC(Cl)=NC(C2C(N(C)C(C)(C)CC2NCCCC)(C)C)=N1 BLBLVDQTHWVGRA-UHFFFAOYSA-N 0.000 claims description 2
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 9
- 240000005265 Lupinus mutabilis Species 0.000 claims 1
- 235000008755 Lupinus mutabilis Nutrition 0.000 claims 1
- 235000019095 Sechium edule Nutrition 0.000 claims 1
- 230000003078 antioxidant effect Effects 0.000 claims 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 description 44
- 239000003381 stabilizer Substances 0.000 description 31
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 30
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000002253 acid Substances 0.000 description 14
- 125000001931 aliphatic group Chemical group 0.000 description 14
- XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 description 13
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 13
- 125000004432 carbon atom Chemical group C* 0.000 description 12
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 12
- 125000001424 substituent group Chemical group 0.000 description 12
- 239000000654 additive Substances 0.000 description 11
- 150000002148 esters Chemical class 0.000 description 10
- 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 9
- 125000003118 aryl group Chemical group 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- 239000012964 benzotriazole Substances 0.000 description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 8
- 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 7
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 7
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 7
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 7
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-Tetramethylpiperidine Substances CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 6
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- BGYHLZZASRKEJE-UHFFFAOYSA-N [3-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxy]-2,2-bis[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxymethyl]propyl] 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)OCC(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 BGYHLZZASRKEJE-UHFFFAOYSA-N 0.000 description 6
- KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 238000003809 water extraction Methods 0.000 description 6
- VDVUCLWJZJHFAV-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidin-4-ol Chemical compound CC1(C)CC(O)CC(C)(C)N1 VDVUCLWJZJHFAV-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 5
- 239000007983 Tris buffer Substances 0.000 description 5
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 5
- 230000032683 aging Effects 0.000 description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 125000001589 carboacyl group Chemical group 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 5
- 239000000945 filler Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 230000003647 oxidation Effects 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 description 4
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 4
- ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 4
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 4
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 4
- VSAWBBYYMBQKIK-UHFFFAOYSA-N 4-[[3,5-bis[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]-2,4,6-trimethylphenyl]methyl]-2,6-ditert-butylphenol Chemical compound CC1=C(CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)C(C)=C(CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)C(C)=C1CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 VSAWBBYYMBQKIK-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
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- FMRHJJZUHUTGKE-UHFFFAOYSA-N Ethylhexyl salicylate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1O FMRHJJZUHUTGKE-UHFFFAOYSA-N 0.000 description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 4
- 239000001273 butane Substances 0.000 description 4
- GGAUUQHSCNMCAU-UHFFFAOYSA-N butane-1,2,3,4-tetracarboxylic acid Chemical compound OC(=O)CC(C(O)=O)C(C(O)=O)CC(O)=O GGAUUQHSCNMCAU-UHFFFAOYSA-N 0.000 description 4
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 4
- 229920001179 medium density polyethylene Polymers 0.000 description 4
- 239000004701 medium-density polyethylene Substances 0.000 description 4
- UKJARPDLRWBRAX-UHFFFAOYSA-N n,n'-bis(2,2,6,6-tetramethylpiperidin-4-yl)hexane-1,6-diamine Chemical compound C1C(C)(C)NC(C)(C)CC1NCCCCCCNC1CC(C)(C)NC(C)(C)C1 UKJARPDLRWBRAX-UHFFFAOYSA-N 0.000 description 4
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 4
- 239000002530 phenolic antioxidant Substances 0.000 description 4
- 229920000728 polyester Polymers 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000012744 reinforcing agent Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 150000005846 sugar alcohols Polymers 0.000 description 4
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 4
- WGVKWNUPNGFDFJ-DQCZWYHMSA-N β-tocopherol Chemical compound OC1=CC(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C WGVKWNUPNGFDFJ-DQCZWYHMSA-N 0.000 description 4
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 3
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 3
- 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
- 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 3
- 125000004825 2,2-dimethylpropylene group Chemical group [H]C([H])([H])C(C([H])([H])[H])(C([H])([H])[*:1])C([H])([H])[*:2] 0.000 description 3
- MWOBEKURRKUZSG-UHFFFAOYSA-N 2,4-bis(2,4-dimethylphenyl)-1,3,5-triazine Chemical compound CC1=CC(C)=CC=C1C1=NC=NC(C=2C(=CC(C)=CC=2)C)=N1 MWOBEKURRKUZSG-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- ZPIRWAHWDCHWLM-UHFFFAOYSA-N 2-dodecylsulfanylethanol Chemical compound CCCCCCCCCCCCSCCO ZPIRWAHWDCHWLM-UHFFFAOYSA-N 0.000 description 3
- 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 3
- WPMYUUITDBHVQZ-UHFFFAOYSA-N 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoic acid Chemical class CC(C)(C)C1=CC(CCC(O)=O)=CC(C(C)(C)C)=C1O WPMYUUITDBHVQZ-UHFFFAOYSA-N 0.000 description 3
- CKPKHTKLLYPGFM-UHFFFAOYSA-N 6,6-dimethylheptane-1,1-diol Chemical compound CC(CCCCC(O)O)(C)C CKPKHTKLLYPGFM-UHFFFAOYSA-N 0.000 description 3
- OWXXKGVQBCBSFJ-UHFFFAOYSA-N 6-n-[3-[[4,6-bis[butyl-(1,2,2,6,6-pentamethylpiperidin-4-yl)amino]-1,3,5-triazin-2-yl]-[2-[[4,6-bis[butyl-(1,2,2,6,6-pentamethylpiperidin-4-yl)amino]-1,3,5-triazin-2-yl]-[3-[[4,6-bis[butyl-(1,2,2,6,6-pentamethylpiperidin-4-yl)amino]-1,3,5-triazin-2-yl]ami Chemical compound N=1C(NCCCN(CCN(CCCNC=2N=C(N=C(N=2)N(CCCC)C2CC(C)(C)N(C)C(C)(C)C2)N(CCCC)C2CC(C)(C)N(C)C(C)(C)C2)C=2N=C(N=C(N=2)N(CCCC)C2CC(C)(C)N(C)C(C)(C)C2)N(CCCC)C2CC(C)(C)N(C)C(C)(C)C2)C=2N=C(N=C(N=2)N(CCCC)C2CC(C)(C)N(C)C(C)(C)C2)N(CCCC)C2CC(C)(C)N(C)C(C)(C)C2)=NC(N(CCCC)C2CC(C)(C)N(C)C(C)(C)C2)=NC=1N(CCCC)C1CC(C)(C)N(C)C(C)(C)C1 OWXXKGVQBCBSFJ-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 description 3
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 3
- XQVWYOYUZDUNRW-UHFFFAOYSA-N N-Phenyl-1-naphthylamine Chemical compound C=1C=CC2=CC=CC=C2C=1NC1=CC=CC=C1 XQVWYOYUZDUNRW-UHFFFAOYSA-N 0.000 description 3
- 239000004952 Polyamide Substances 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical group NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 3
- 125000003342 alkenyl group Chemical group 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 1
- IVIIAEVMQHEPAY-UHFFFAOYSA-N tridodecyl phosphite Chemical compound CCCCCCCCCCCCOP(OCCCCCCCCCCCC)OCCCCCCCCCCCC IVIIAEVMQHEPAY-UHFFFAOYSA-N 0.000 description 1
- CNUJLMSKURPSHE-UHFFFAOYSA-N trioctadecyl phosphite Chemical compound CCCCCCCCCCCCCCCCCCOP(OCCCCCCCCCCCCCCCCCC)OCCCCCCCCCCCCCCCCCC CNUJLMSKURPSHE-UHFFFAOYSA-N 0.000 description 1
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 1
- WGKLOLBTFWFKOD-UHFFFAOYSA-N tris(2-nonylphenyl) phosphite Chemical compound CCCCCCCCCC1=CC=CC=C1OP(OC=1C(=CC=CC=1)CCCCCCCCC)OC1=CC=CC=C1CCCCCCCCC WGKLOLBTFWFKOD-UHFFFAOYSA-N 0.000 description 1
- 125000002948 undecyl 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])[H] 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 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
- 150000003712 vitamin E derivatives Chemical class 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 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
- 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
- C08K5/3412—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
- C08K5/04—Oxygen-containing compounds
- C08K5/13—Phenols; Phenolates
-
- 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
- C08K5/3442—Heterocyclic compounds having nitrogen in the ring having two nitrogen atoms in the ring
- C08K5/3462—Six-membered rings
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)
- Hydrogenated Pyridines (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Paper (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH261695 | 1995-09-15 | ||
| CH261695 | 1995-09-15 | ||
| US08/709,975 US6541547B1 (en) | 1995-09-15 | 1996-09-09 | Process for stabilization of polyolefins in permanent contact with extracting media |
| US70997596 | 1996-09-09 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI963613A0 FI963613A0 (fi) | 1996-09-13 |
| FI963613L FI963613L (fi) | 1997-03-16 |
| FI118737B true FI118737B (fi) | 2008-02-29 |
Family
ID=25690954
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI963613A FI118737B (fi) | 1995-09-15 | 1996-09-13 | Polyolefiinien stabilointi pitkäkestoisessa kontaktissa uuttavien väliaineiden kanssa |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US6541547B1 (enExample) |
| JP (1) | JPH09111056A (enExample) |
| AT (1) | AT406583B (enExample) |
| BE (1) | BE1010623A5 (enExample) |
| BR (1) | BR9603752A (enExample) |
| CA (1) | CA2185488C (enExample) |
| DE (1) | DE19637181B4 (enExample) |
| ES (1) | ES2137823B1 (enExample) |
| FI (1) | FI118737B (enExample) |
| FR (1) | FR2738834B1 (enExample) |
| GB (1) | GB2305180B (enExample) |
| IT (1) | IT1284515B1 (enExample) |
| NL (1) | NL1004035C2 (enExample) |
| NO (1) | NO323258B1 (enExample) |
| SE (1) | SE509371C2 (enExample) |
| TW (1) | TW438850B (enExample) |
Families Citing this family (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2311528A (en) * | 1996-03-29 | 1997-10-01 | Ciba Geigy Ag | Stabiliser mixtures for polyamides, polyesters and polyketones |
| US6521681B1 (en) * | 1996-07-05 | 2003-02-18 | Ciba Specialty Chemicals Corporation | Phenol-free stabilization of polyolefin fibres |
| TW464670B (en) | 1996-08-07 | 2001-11-21 | Ciba Sc Holding Ag | Stabilizer mixtures containing a hindered amine |
| DE19756276A1 (de) * | 1997-12-18 | 1999-06-24 | Basf Ag | Verwendung von durch sterisch gehinderte Amine oder deren N-Hydroxy- oder N-Oxylderivate stabilisierten Ethylenhomo- und -copolymeren zur Herstellung von Kunststoffkörpern und Bauteilen für die Lagerung und den Transport von Pflanzenölestern |
| KR20010050085A (ko) * | 1999-08-18 | 2001-06-15 | 잔디해머,한스루돌프하우스 | 신규한 입체 장애 아민 |
| GB0004437D0 (en) * | 2000-02-25 | 2000-04-12 | Clariant Int Ltd | Synergistic combinations of phenolic antioxidants |
| GB0004436D0 (en) | 2000-02-25 | 2000-04-12 | Clariant Int Ltd | Synergistic stabilizer compositions for thermoplastic polymers in prolonged contact with water |
| GB0019465D0 (en) * | 2000-08-09 | 2000-09-27 | Clariant Int Ltd | Synergistic stabilizer for color stable pigmented thermoplastic polyners in prolonged contact with water |
| GB0104371D0 (en) | 2001-02-22 | 2001-04-11 | Clariant Int Ltd | Color improving stabilizing compositions comprising leucine |
| ES2276075T3 (es) | 2002-01-31 | 2007-06-16 | Ciba Specialty Chemicals Holding Inc. | Estabilizacion de poliolefina en contacto permanente con agua clorada. |
| WO2004092263A1 (ja) * | 2003-04-16 | 2004-10-28 | Idemitsu Kosan Co., Ltd. | ポリオレフィン系樹脂組成物及びそれを用いた樹脂成形体の組み合わせ |
| US6824936B1 (en) * | 2003-08-05 | 2004-11-30 | Eastman Kodak Company | Hindered amine light stabilizer for improved yellow dark stability |
| US20060264540A1 (en) * | 2005-05-19 | 2006-11-23 | Gelbin Michael E | Stabilizer blend for improved chlorine resistance |
| US20080221242A1 (en) * | 2005-05-19 | 2008-09-11 | Gelbin Michael E | Stabilizer blend for improved chlorine resistance |
| DE602006018745D1 (de) | 2006-10-02 | 2011-01-20 | Borealis Tech Oy | Polyolefinzusammensetzung mit verbesserter Resistenz gegenüber CIO2-enthaltenden wasser |
| DE602006013992D1 (de) | 2006-10-04 | 2010-06-10 | Borealis Tech Oy | Migrationsarme Polyolefinzusammensetzung |
| CN101522813B (zh) | 2006-10-17 | 2013-01-30 | 三井化学株式会社 | 树脂组合物以及由该组合物得到的成型体 |
| ES2356137T3 (es) * | 2007-07-13 | 2011-04-05 | Borealis Technology Oy | Composición de poliolefina de baja migración que comprende un estabilizante de tipo vitamina e. |
| EP2199330A1 (en) | 2008-12-22 | 2010-06-23 | Borealis AG | Polyolefin composition for water pipes with good resistance to chlorine dioxide and low migration |
| ES2689146T3 (es) * | 2009-05-29 | 2018-11-08 | Uponor Innovation Ab | Métodos y composiciones para producir tuberías que tienen resistencia oxidativa mejorada |
| JP5695081B2 (ja) * | 2009-12-22 | 2015-04-01 | バーゼル・ポリオレフィン・イタリア・ソチエタ・ア・レスポンサビリタ・リミタータ | 膜用ポリオレフィン組成物 |
| US20110162867A1 (en) * | 2010-01-07 | 2011-07-07 | Hanwha Chemical Corporation | Telephone cable insulation composition, and telephone cable using thereof |
| EP3786216A1 (en) | 2010-12-13 | 2021-03-03 | 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 |
| EP2511332B1 (en) | 2011-04-15 | 2014-09-17 | Borealis AG | Polyolefin pipe with improved migration behaviour |
| EP2551294B1 (en) | 2011-07-25 | 2018-11-07 | Borealis AG | Use of a polyolefin composition for pipes and fittings with increased resistance to chlorine dioxide |
| BRPI1102315A8 (pt) * | 2011-08-04 | 2017-10-10 | Neo Plastic Embalagens Plasticas Ltda | Geomembrana produzida com misturas de polietileno de alta densidade, polietileno linear de baixa densidade e polietileno de baixa densidade |
| US20140127438A1 (en) * | 2012-11-08 | 2014-05-08 | Robert L. Sherman, Jr. | Stabilized high-density polyethylene composition with improved resistance to deterioration and stabilizer system |
| CN106458883A (zh) | 2014-06-11 | 2017-02-22 | 弗纳技术股份有限公司 | 耐氯聚乙烯化合物和由其制造的制品 |
| JP2016173328A (ja) * | 2015-03-17 | 2016-09-29 | 日本ポリプロ株式会社 | ポリオレフィン中に含まれる添加剤の定量分析方法 |
| JP6859660B2 (ja) * | 2016-10-28 | 2021-04-14 | Toto株式会社 | 樹脂材料および成形体 |
| SG11202105659PA (en) * | 2018-12-04 | 2021-06-29 | Basf Se | Polyethylene or polypropylene articles |
| US11661531B2 (en) | 2019-01-31 | 2023-05-30 | Synthomer Adhesives Technology LLC | Hygiene adhesives comprising low volatile tackifier compositions |
| CN113906097B (zh) * | 2019-05-27 | 2023-07-18 | 三井化学株式会社 | 环状烯烃系树脂组合物、成型体及光学部件 |
| WO2021148352A1 (en) * | 2020-01-21 | 2021-07-29 | Sabic Global Technologies B.V. | Pipe for transport of water containing chlorinated disinfectant |
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|---|---|---|---|---|
| US3558554A (en) * | 1966-06-09 | 1971-01-26 | Yoshitomi Pharmaceutical | Oxidatively stable polyolefin composition |
| US3901955A (en) * | 1968-08-28 | 1975-08-26 | Sandoz Ltd | Reaction products of phenols with phosphorous trichlorides |
| GB1372528A (en) * | 1970-10-22 | 1974-10-30 | Sandoz Ltd | Benzene phosphonous acid compounds their production and use as stabilizers for organic materials |
| US4263230A (en) * | 1979-10-11 | 1981-04-21 | Stauffer Chemical Company | Bisphosphonites |
| US4318845A (en) * | 1980-11-24 | 1982-03-09 | Ciba-Geigy Corporation | Alkanolamine esters of 1,1'-biphenyl-2,2'-diyl-and alkylidene-1,1'-biphenyl-2,2'-diyl-cyclic phosphites |
| US4374219A (en) * | 1980-11-24 | 1983-02-15 | Ciba-Geigy Corporation | Alkanolamine ester of 1,1-biphenyl-2,2-diyl-and alkylidene-1,1-biphenyl-2,2-diyl-cyclic phosphites |
| JPS5832642A (ja) * | 1981-08-20 | 1983-02-25 | Adeka Argus Chem Co Ltd | 安定化された合成樹脂組成物 |
| US4474914A (en) * | 1981-08-31 | 1984-10-02 | Ciba-Geigy Corporation | Ortho-alkylated phenyl phosphonites and stabilized organic compositions |
| EP0124664B1 (en) | 1983-05-04 | 1987-12-09 | Mitsui Petrochemical Industries, Ltd. | Poly-1-butene resin composition and water pipe manufactured therefrom |
| US4532165A (en) * | 1983-05-09 | 1985-07-30 | Mitsui Petrochemical Industries Ltd. | Poly-1-butene resin composition |
| FR2557882B1 (fr) * | 1984-01-06 | 1986-05-02 | Solvay | Compositions stabilisees a base de polymeres d'alpha-olefines |
| EP0184191A3 (en) * | 1984-12-03 | 1987-08-19 | Phillips Petroleum Company | Stabilization of polyolefins |
| JPH0759652B2 (ja) * | 1985-08-07 | 1995-06-28 | 住友化学工業株式会社 | ポリオレフイン樹脂組成物 |
| US4863981A (en) * | 1986-06-30 | 1989-09-05 | Ciba-Geigy Corporation | Synergistic mixture of stabilizers |
| US4824885A (en) * | 1986-07-23 | 1989-04-25 | Enichem Sintesi S.P.A. | Process of (co) polymerization of alpha-olefins in the presence of antioxidants |
| DE3634531A1 (de) * | 1986-10-10 | 1988-04-14 | Basf Ag | Stabilisatorgemische fuer kunststoffe |
| US4985479A (en) * | 1986-11-27 | 1991-01-15 | Sumitomo Chemical Company, Ltd. | Stabilized polyolefin composition |
| JP2553537B2 (ja) * | 1987-01-23 | 1996-11-13 | 東燃化学 株式会社 | ポレプロピレン繊維防糸用組成物 |
| IT1202611B (it) * | 1987-03-03 | 1989-02-09 | Enichem Sintesi | Composizione solida stabilizzante per polimeri sintetici |
| GB2202853B (en) * | 1987-04-03 | 1990-10-24 | Ciba Geigy Ag | Light stabiliser combination |
| US4812500A (en) | 1987-09-30 | 1989-03-14 | Shell Oil Company | Polyolefin compositions for water pipes and for wire and cable coatings |
| US5162406A (en) * | 1987-12-17 | 1992-11-10 | The Dow Chemical Company | Polymer stabilizing compositions |
| DE3742933A1 (de) * | 1987-12-18 | 1989-06-29 | Hoechst Ag | Polyolefinformmasse fuer dauerkontakt mit extrahierenden medien |
| JP2529714B2 (ja) * | 1988-02-10 | 1996-09-04 | 旭電化工業株式会社 | 安定化された合成樹脂組成物 |
| IT1218004B (it) * | 1988-05-27 | 1990-03-30 | Enichem Sintesi | Stabilizzanti uv per poli eri organici |
| JP2653681B2 (ja) * | 1988-09-16 | 1997-09-17 | 旭電化工業株式会社 | 安定化された合成樹脂組成物 |
| JP2762101B2 (ja) * | 1989-03-07 | 1998-06-04 | 旭電化工業株式会社 | 安定化された合成樹脂組成物 |
| JP2763569B2 (ja) * | 1989-03-13 | 1998-06-11 | 旭電化工業株式会社 | 安定化された合成樹脂組成物 |
| IT1229141B (it) | 1989-04-06 | 1991-07-22 | Himont Inc | Poliolefine atte alla filatura e fibre termosaldabili da esse ottenute. |
| IT1231769B (it) | 1989-08-02 | 1991-12-21 | Himont Inc | Procedimento per la stabilizzazione di poliolefine e prodotti da esso ottenuti. |
| US5225526A (en) * | 1989-08-17 | 1993-07-06 | Asahi Kasei Kogyo Kabushiki Kaisha | Stabilized aromatic polycarbonate composition and process for producing same |
| IT1237129B (it) * | 1989-11-10 | 1993-05-18 | Valerio Borzatta | Composti piperidin-triazinici atti all'impiego come stabilizzanti per materiali organici. |
| TW209224B (enExample) * | 1991-05-27 | 1993-07-11 | Yoshitomi Pharmaceutical | |
| EP0553498A3 (en) * | 1991-12-31 | 1993-11-03 | Phillips Petroleum Co | Additive composition for improved stability of poly(4-methyl-1-pentene) |
| KR100394565B1 (ko) * | 1992-09-25 | 2003-11-20 | 시바 스페셜티 케미칼스 홀딩 인크. | 재생된플라스틱혼합물을안정화시키는방법및이를위한안정화제혼합물 |
| FR2705679B1 (fr) * | 1993-05-24 | 1998-07-10 | Sandoz Sa | Nouvelles compositions stabilisantes des matières polymères, à base de phosphonites ou phosphites et d'un stabilisant contre l'hydrolyse. |
| EP0635514B1 (en) * | 1993-07-22 | 1999-05-12 | General Electric Company | Neo-diol phosphites as polymer stabilizers |
| TW302377B (enExample) | 1993-12-24 | 1997-04-11 | Sumitomo Chemical Co | |
| FR2725451B1 (fr) | 1994-10-06 | 1998-04-17 | Sandoz Sa | Nouvelle composition stabilisante pour les matieres polymeres |
-
1996
- 1996-08-27 TW TW085110401A patent/TW438850B/zh not_active IP Right Cessation
- 1996-09-06 GB GB9618701A patent/GB2305180B/en not_active Expired - Lifetime
- 1996-09-09 US US08/709,975 patent/US6541547B1/en not_active Expired - Lifetime
- 1996-09-11 ES ES009601926A patent/ES2137823B1/es not_active Expired - Fee Related
- 1996-09-12 DE DE19637181A patent/DE19637181B4/de not_active Expired - Lifetime
- 1996-09-12 FR FR9611122A patent/FR2738834B1/fr not_active Expired - Lifetime
- 1996-09-12 IT IT96MI001874A patent/IT1284515B1/it active IP Right Grant
- 1996-09-12 SE SE9603317A patent/SE509371C2/sv not_active IP Right Cessation
- 1996-09-12 AT AT0161796A patent/AT406583B/de not_active IP Right Cessation
- 1996-09-13 NL NL1004035A patent/NL1004035C2/nl not_active IP Right Cessation
- 1996-09-13 NO NO19963830A patent/NO323258B1/no not_active IP Right Cessation
- 1996-09-13 BE BE9600771A patent/BE1010623A5/fr active
- 1996-09-13 CA CA002185488A patent/CA2185488C/en not_active Expired - Lifetime
- 1996-09-13 BR BR9603752A patent/BR9603752A/pt not_active IP Right Cessation
- 1996-09-13 FI FI963613A patent/FI118737B/fi not_active IP Right Cessation
- 1996-09-17 JP JP8266774A patent/JPH09111056A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| AT406583B (de) | 2000-06-26 |
| DE19637181A1 (de) | 1997-03-20 |
| JPH09111056A (ja) | 1997-04-28 |
| FI963613L (fi) | 1997-03-16 |
| GB2305180A (en) | 1997-04-02 |
| DE19637181B4 (de) | 2007-11-15 |
| FR2738834B1 (fr) | 1998-11-27 |
| ES2137823B1 (es) | 2000-08-16 |
| CA2185488A1 (en) | 1997-03-16 |
| ITMI961874A1 (it) | 1998-03-12 |
| ES2137823A1 (es) | 1999-12-16 |
| US6541547B1 (en) | 2003-04-01 |
| NL1004035C2 (nl) | 1998-03-17 |
| SE509371C2 (sv) | 1999-01-18 |
| BE1010623A5 (fr) | 1998-11-03 |
| BR9603752A (pt) | 1998-06-02 |
| ATA161796A (de) | 1999-11-15 |
| SE9603317L (sv) | 1997-03-16 |
| IT1284515B1 (it) | 1998-05-21 |
| NO323258B1 (no) | 2007-02-19 |
| FI963613A0 (fi) | 1996-09-13 |
| SE9603317D0 (sv) | 1996-09-12 |
| GB9618701D0 (en) | 1996-10-16 |
| GB2305180B (en) | 2000-04-12 |
| NO963830L (no) | 1997-03-17 |
| NL1004035A1 (nl) | 1997-03-20 |
| NO963830D0 (no) | 1996-09-13 |
| FR2738834A1 (fr) | 1997-03-21 |
| TW438850B (en) | 2001-06-07 |
| CA2185488C (en) | 2009-03-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| GB | Transfer or assigment of application |
Owner name: CIBA SPECIALTY CHEMICALS HOLDING INC. |
|
| HC | Name/ company changed in application |
Owner name: CIBA SPECIALTY CHEMICALS HOLDING INC. |
|
| FG | Patent granted |
Ref document number: 118737 Country of ref document: FI |
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| MA | Patent expired |