JP4798815B2 - 立体障害性アミンエーテルの製造 - Google Patents
立体障害性アミンエーテルの製造 Download PDFInfo
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- JP4798815B2 JP4798815B2 JP04790499A JP4790499A JP4798815B2 JP 4798815 B2 JP4798815 B2 JP 4798815B2 JP 04790499 A JP04790499 A JP 04790499A JP 4790499 A JP4790499 A JP 4790499A JP 4798815 B2 JP4798815 B2 JP 4798815B2
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- carbon atoms
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- butyl
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- 238000004519 manufacturing process Methods 0.000 title claims description 8
- -1 amine ethers Chemical class 0.000 title description 185
- 125000004432 carbon atom Chemical group C* 0.000 claims description 380
- 150000001875 compounds Chemical class 0.000 claims description 125
- 125000000217 alkyl group Chemical group 0.000 claims description 122
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 76
- 229920000642 polymer Polymers 0.000 claims description 42
- 125000002947 alkylene group Chemical group 0.000 claims description 40
- 238000000034 method Methods 0.000 claims description 35
- 125000005843 halogen group Chemical group 0.000 claims description 32
- 230000001590 oxidative effect Effects 0.000 claims description 5
- 230000002140 halogenating effect Effects 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 92
- 229910052799 carbon Inorganic materials 0.000 description 53
- 239000000243 solution Substances 0.000 description 52
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 51
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 49
- 125000003118 aryl group Chemical group 0.000 description 49
- 125000000753 cycloalkyl group Chemical group 0.000 description 45
- 239000000047 product Substances 0.000 description 42
- 229920001577 copolymer Polymers 0.000 description 38
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 37
- 238000003756 stirring Methods 0.000 description 33
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 31
- 125000001931 aliphatic group Chemical group 0.000 description 30
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 28
- 239000003054 catalyst Substances 0.000 description 28
- 238000000576 coating method Methods 0.000 description 28
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 125000003342 alkenyl group Chemical group 0.000 description 27
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 27
- 229910052757 nitrogen Inorganic materials 0.000 description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
- 150000001721 carbon Chemical group 0.000 description 26
- 239000003381 stabilizer Substances 0.000 description 24
- 125000003545 alkoxy group Chemical group 0.000 description 23
- 125000002723 alicyclic group Chemical group 0.000 description 22
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- 229910052751 metal Inorganic materials 0.000 description 21
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- 239000002253 acid Substances 0.000 description 20
- 150000001412 amines Chemical class 0.000 description 20
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 20
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- 229910000027 potassium carbonate Inorganic materials 0.000 description 16
- 239000004743 Polypropylene Substances 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 15
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- 150000002148 esters Chemical group 0.000 description 15
- 239000001257 hydrogen Substances 0.000 description 15
- 229910052739 hydrogen Inorganic materials 0.000 description 15
- 229920001684 low density polyethylene Polymers 0.000 description 15
- 229920001155 polypropylene Polymers 0.000 description 15
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 14
- 125000002252 acyl group Chemical group 0.000 description 14
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 14
- 239000002904 solvent Substances 0.000 description 14
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 13
- 239000005977 Ethylene Substances 0.000 description 13
- 229910052698 phosphorus Inorganic materials 0.000 description 13
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 13
- 239000000843 powder Substances 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 12
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 12
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 12
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 12
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 12
- 239000004952 Polyamide Substances 0.000 description 12
- 125000003277 amino group Chemical group 0.000 description 12
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 12
- 125000005842 heteroatom Chemical group 0.000 description 12
- 150000002430 hydrocarbons Chemical group 0.000 description 12
- 239000000463 material Substances 0.000 description 12
- 125000003884 phenylalkyl group Chemical group 0.000 description 12
- 239000011574 phosphorus Chemical group 0.000 description 12
- 229920002647 polyamide Polymers 0.000 description 12
- 239000004417 polycarbonate Substances 0.000 description 12
- 229920000515 polycarbonate Polymers 0.000 description 12
- 239000008096 xylene Substances 0.000 description 12
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 11
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 11
- 125000002993 cycloalkylene group Chemical group 0.000 description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 11
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- 229920000728 polyester Polymers 0.000 description 11
- 239000004814 polyurethane Substances 0.000 description 11
- 230000008569 process Effects 0.000 description 11
- 229910052938 sodium sulfate Inorganic materials 0.000 description 11
- 235000011152 sodium sulphate Nutrition 0.000 description 11
- 229920000877 Melamine resin Polymers 0.000 description 10
- 239000000654 additive Substances 0.000 description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 10
- 125000004122 cyclic group Chemical group 0.000 description 10
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 10
- 239000011572 manganese Substances 0.000 description 10
- 125000004433 nitrogen atom Chemical group N* 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 9
- 239000004594 Masterbatch (MB) Substances 0.000 description 9
- 239000004721 Polyphenylene oxide Substances 0.000 description 9
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 9
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 9
- 238000001914 filtration Methods 0.000 description 9
- 125000001188 haloalkyl group Chemical group 0.000 description 9
- 238000005984 hydrogenation reaction Methods 0.000 description 9
- 239000010410 layer Substances 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 9
- 125000004430 oxygen atom Chemical group O* 0.000 description 9
- 229920002857 polybutadiene Polymers 0.000 description 9
- 229920002635 polyurethane Polymers 0.000 description 9
- 239000000758 substrate Substances 0.000 description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 8
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical group OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 8
- 239000005062 Polybutadiene Substances 0.000 description 8
- 239000004698 Polyethylene Substances 0.000 description 8
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 8
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 8
- 125000000732 arylene group Chemical group 0.000 description 8
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 8
- KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
- 239000000178 monomer Substances 0.000 description 8
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 8
- 239000011368 organic material Substances 0.000 description 8
- 229920000620 organic polymer Polymers 0.000 description 8
- 229920000647 polyepoxide Polymers 0.000 description 8
- 229920000573 polyethylene Polymers 0.000 description 8
- 238000006116 polymerization reaction Methods 0.000 description 8
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 8
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 8
- 238000011105 stabilization Methods 0.000 description 8
- 229910001220 stainless steel Inorganic materials 0.000 description 8
- 239000010935 stainless steel Substances 0.000 description 8
- 229920001169 thermoplastic Polymers 0.000 description 8
- 229920002554 vinyl polymer Polymers 0.000 description 8
- 239000004925 Acrylic resin Substances 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 7
- 150000007513 acids Chemical class 0.000 description 7
- 150000001993 dienes Chemical class 0.000 description 7
- 238000005227 gel permeation chromatography Methods 0.000 description 7
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 7
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- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 7
- 229920006324 polyoxymethylene Polymers 0.000 description 7
- 230000006641 stabilisation Effects 0.000 description 7
- 229910052717 sulfur Inorganic materials 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 239000004593 Epoxy Substances 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 6
- 125000004450 alkenylene group Chemical group 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 229910052794 bromium Inorganic materials 0.000 description 6
- 239000007859 condensation product Substances 0.000 description 6
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 6
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- AFCCDDWKHLHPDF-UHFFFAOYSA-M metam-sodium Chemical compound [Na+].CNC([S-])=S AFCCDDWKHLHPDF-UHFFFAOYSA-M 0.000 description 6
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 6
- 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 6
- FTWUXYZHDFCGSV-UHFFFAOYSA-N n,n'-diphenyloxamide Chemical compound C=1C=CC=CC=1NC(=O)C(=O)NC1=CC=CC=C1 FTWUXYZHDFCGSV-UHFFFAOYSA-N 0.000 description 6
- 238000007254 oxidation reaction Methods 0.000 description 6
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- HWRLEEPNFJNTOP-UHFFFAOYSA-N 2-(1,3,5-triazin-2-yl)phenol Chemical compound OC1=CC=CC=C1C1=NC=NC=N1 HWRLEEPNFJNTOP-UHFFFAOYSA-N 0.000 description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 5
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- 150000008064 anhydrides Chemical class 0.000 description 5
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 5
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- 125000006575 electron-withdrawing group Chemical group 0.000 description 5
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 5
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 5
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- RXFCIXRFAJRBSG-UHFFFAOYSA-N 3,2,3-tetramine Chemical compound NCCCNCCNCCCN RXFCIXRFAJRBSG-UHFFFAOYSA-N 0.000 description 4
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- CKPKHTKLLYPGFM-UHFFFAOYSA-N 6,6-dimethylheptane-1,1-diol Chemical compound CC(CCCCC(O)O)(C)C CKPKHTKLLYPGFM-UHFFFAOYSA-N 0.000 description 4
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- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 4
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- 125000003710 aryl alkyl group Chemical group 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
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- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000004132 cross linking Methods 0.000 description 4
- 125000004093 cyano group Chemical group *C#N 0.000 description 4
- 125000001142 dicarboxylic acid group Chemical group 0.000 description 4
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 239000003822 epoxy resin Substances 0.000 description 4
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- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 4
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- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 229940116351 sebacate Drugs 0.000 description 1
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 239000002002 slurry Substances 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
- JMHCCAYJTTWMCX-QWPJCUCISA-M sodium;(2s)-2-amino-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]propanoate;pentahydrate Chemical compound O.O.O.O.O.[Na+].IC1=CC(C[C@H](N)C([O-])=O)=CC(I)=C1OC1=CC(I)=C(O)C(I)=C1 JMHCCAYJTTWMCX-QWPJCUCISA-M 0.000 description 1
- 238000000935 solvent evaporation Methods 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229920000638 styrene acrylonitrile Polymers 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 125000002730 succinyl group Chemical group C(CCC(=O)*)(=O)* 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- MHSKRLJMQQNJNC-UHFFFAOYSA-N terephthalamide Chemical compound NC(=O)C1=CC=C(C(N)=O)C=C1 MHSKRLJMQQNJNC-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 150000000000 tetracarboxylic acids Chemical class 0.000 description 1
- NZNAAUDJKMURFU-UHFFFAOYSA-N tetrakis(2,2,6,6-tetramethylpiperidin-4-yl) butane-1,2,3,4-tetracarboxylate Chemical compound C1C(C)(C)NC(C)(C)CC1OC(=O)CC(C(=O)OC1CC(C)(C)NC(C)(C)C1)C(C(=O)OC1CC(C)(C)NC(C)(C)C1)CC(=O)OC1CC(C)(C)NC(C)(C)C1 NZNAAUDJKMURFU-UHFFFAOYSA-N 0.000 description 1
- 229920002725 thermoplastic elastomer Polymers 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000004149 thio group Chemical group *S* 0.000 description 1
- 125000000101 thioether group Chemical group 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 235000010215 titanium dioxide Nutrition 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
- 239000011732 tocopherol Substances 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 150000003628 tricarboxylic acids 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
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 229920001866 very low density polyethylene Polymers 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 150000003751 zinc Chemical class 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-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
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/56—Nitrogen atoms
- C07D211/58—Nitrogen atoms attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/92—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with a hetero atom directly attached to the ring nitrogen atom
- C07D211/94—Oxygen atom, e.g. piperidine N-oxide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/40—Nitrogen atoms
- C07D251/54—Three nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- 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
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0066—Flame-proofing or flame-retarding additives
-
- 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
- C08K5/16—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
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
- C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
- C09K15/30—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing heterocyclic ring with at least one nitrogen atom as ring member
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Hydrogenated Pyridines (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT98MI000366A ITMI980366A1 (it) | 1998-02-25 | 1998-02-25 | Preparazione di eteri amminici stericamente impediti |
| ITMI98A000366 | 1998-02-25 | ||
| US10471898A | 1998-06-25 | 1998-06-25 | |
| US09/104718 | 1998-06-25 | ||
| US98A000366 | 1998-06-25 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010182352A Division JP2011006443A (ja) | 1998-02-25 | 2010-08-17 | 立体障害性アミンエーテルの製造 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JPH11315067A JPH11315067A (ja) | 1999-11-16 |
| JPH11315067A5 JPH11315067A5 (enrdf_load_stackoverflow) | 2006-03-30 |
| JP4798815B2 true JP4798815B2 (ja) | 2011-10-19 |
Family
ID=26331570
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
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| JP04790499A Expired - Lifetime JP4798815B2 (ja) | 1998-02-25 | 1999-02-25 | 立体障害性アミンエーテルの製造 |
| JP2010182352A Pending JP2011006443A (ja) | 1998-02-25 | 2010-08-17 | 立体障害性アミンエーテルの製造 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010182352A Pending JP2011006443A (ja) | 1998-02-25 | 2010-08-17 | 立体障害性アミンエーテルの製造 |
Country Status (17)
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH693416A5 (de) | 1998-03-09 | 2003-07-31 | Ciba Sc Holding Ag | 1-Alkoxypolyalkylpiperidinderivate und ihre Verwendung als Polymerisationsregler. |
| JP2004083913A (ja) * | 2000-04-06 | 2004-03-18 | Mitsubishi Rayon Co Ltd | 難燃性ポリプロピレンフィルム |
| JP3540759B2 (ja) * | 2000-04-06 | 2004-07-07 | 三菱レイヨン株式会社 | 難燃性ポリプロピレン繊維及びその製造方法 |
| TW572896B (en) * | 2000-05-26 | 2004-01-21 | Ciba Sc Holding Ag | Process for the synthesis of amine ethers from secondary amino oxides |
| EP1038912A3 (en) * | 2000-06-22 | 2000-12-27 | Ciba SC Holding AG | High molecular weight hindered hydrocarbyloxyamine stabilizers |
| TWI273115B (en) * | 2000-12-12 | 2007-02-11 | Ciba Sc Holding Ag | Improved weatherability of flame retardant polyolefin |
| TW200407307A (en) * | 2001-11-26 | 2004-05-16 | Ciba Sc Holding Ag | Process for the synthesis of amine ethers from secondary amino oxides |
| US7230042B2 (en) * | 2002-04-17 | 2007-06-12 | Ciba Specialty Chemicals Corp. | Flame retardant polymer compositions containing hydroxylamine esters |
| JP4167522B2 (ja) * | 2002-05-31 | 2008-10-15 | サンテーラ株式会社 | オレフィン系樹脂組成物およびそれからなる積層フィルム |
| US8105504B2 (en) * | 2004-08-31 | 2012-01-31 | Basf Se | Stabilization of organic materials |
| EP2993168B1 (en) * | 2004-11-02 | 2017-05-17 | Basf Se | Process for the synthesis of n-alkoxyamines |
| WO2008061923A1 (en) * | 2006-11-23 | 2008-05-29 | Ciba Holding Inc. | Process for the preparation of tertiary n-allyl sterically hindered amines |
| US9150701B2 (en) * | 2007-12-21 | 2015-10-06 | Basf Se | Nano structured UV absorbers |
| KR20120043090A (ko) * | 2009-08-18 | 2012-05-03 | 바스프 에스이 | 안정화된 중합체 봉지재를 가진 광전 모듈 |
| ES2655321T3 (es) * | 2009-09-10 | 2018-02-19 | Basf Se | Estabilizador de aminas estéricamente impedidas |
| CN103153985A (zh) | 2010-10-20 | 2013-06-12 | 巴斯夫欧洲公司 | 多功能位阻胺光稳定剂 |
| EP2514800B2 (de) | 2011-04-21 | 2018-03-07 | Merck Patent GmbH | Verbindungen und flüssigkristallines Medium |
| US11001698B2 (en) | 2016-10-14 | 2021-05-11 | Basf Se | Stabilizer composition |
| AU2018246964B2 (en) * | 2017-03-28 | 2023-08-17 | Basf Se | Light stabilizer mixture |
| CN109503554B (zh) * | 2018-12-13 | 2020-10-30 | 天津利安隆新材料股份有限公司 | 一种聚合型受阻胺类光稳定剂ha-88的制备方法 |
| KR102848554B1 (ko) * | 2019-03-08 | 2025-08-22 | 바스프 에스이 | 입체 장애 아민 안정화제 혼합물 |
| CN112126060B (zh) * | 2019-06-25 | 2022-05-31 | 北京天罡助剂有限责任公司 | 一种聚合型高分子空间位阻胺及其制备方法 |
| CN113354813B (zh) * | 2021-06-02 | 2023-07-04 | 宿迁联盛科技股份有限公司 | 一种低碱性受阻胺光稳定剂nor 371的制备方法 |
| JP2025511683A (ja) | 2022-04-04 | 2025-04-16 | ジェネアスケム・アーゲー | 立体障害ニトロキシルエーテルを調製するためのプロセス |
| WO2025067782A1 (en) | 2023-09-27 | 2025-04-03 | Geneuschem Ag | Preparation of n-alkoxyamine hals from corresponding hydroxylamines |
Family Cites Families (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1215462B (it) * | 1987-05-07 | 1990-02-14 | Ciba Geigy Spa | Composti piperidinici utilizzabili come stabilizzanti alla luce, al calore e all'ossidazione per polimeri sintetici. |
| US4824884A (en) * | 1987-08-12 | 1989-04-25 | Pennwalt Corporation | Cyclic anhydride derivatives of hydrazide functionalized hindered amine light stabilizers |
| US5204473A (en) * | 1987-09-21 | 1993-04-20 | Ciba-Geigy Corporation | O-substituted N-hydroxy hindered amine stabilizers |
| ES2065924T5 (es) * | 1987-09-21 | 2002-12-16 | Ciba Sc Holding Ag | Estabilizadores a base de amidas bloqueadas n-substituidas. |
| US5124378A (en) * | 1987-09-21 | 1992-06-23 | Ciba-Geigy Corporation | Stabilization of ambient cured coatings |
| US4921962A (en) * | 1988-10-19 | 1990-05-01 | Ciba-Geigy Corporation | Process for preparing N-hydrocarbyloxy derivatives of sterically hindered amines |
| US5004770A (en) * | 1988-10-19 | 1991-04-02 | Ciba-Geigy Corporation | Polymeric substrates stabilized with N-substituted hindered amines |
| US5096950A (en) * | 1988-10-19 | 1992-03-17 | Ciba-Geigy Corporation | Polyolefin compositions stabilized with NOR-substituted hindered amines |
| US4978699A (en) * | 1988-10-24 | 1990-12-18 | Atochem North America, Inc. | Light stabilizing flame retardants |
| JPH03504984A (ja) * | 1989-02-13 | 1991-10-31 | アトケム ノース アメリカ，インコーポレイテッド | 反応性ヒンダードアミンによる光安定剤 |
| DE69012615T2 (de) * | 1989-03-21 | 1995-01-26 | Ciba Geigy Ag | Äthylenisch ungesättigte Verbindungen, die 1-Hydrocarbyloxy-2,2,6,6-tetramethylpiperidine-Teile enthalten, und Polymere, Copolymere und stabilisierte Zusammensetzungen. |
| EP0389429B1 (en) * | 1989-03-21 | 1994-09-21 | Ciba-Geigy Ag | Azo compounds containing hindered amine moieties with low basicity |
| EP0389428A3 (en) * | 1989-03-21 | 1991-10-09 | Ciba-Geigy Ag | N,n-bis(l-hydroxycarbyloxy-2,2,6,6-tetramethyl-piperidin-4-yl) amino triazines and stabilized compositions |
| ES2086394T3 (es) * | 1989-03-21 | 1996-07-01 | Ciba Geigy Ag | Compuestos aminicos impedidos de 1-hidrocarbiloxilo no migrantes como estabilizadores de polimeros. |
| IT1246170B (it) * | 1990-07-24 | 1994-11-16 | Ciba Geigy Spa | Composizione stabilizzante per polipropilene comprendente composti triazinici contenenti gruppi piperidinici e composti metallici |
| US5180830A (en) * | 1991-04-24 | 1993-01-19 | Himont Incorporated | Process for preparing hindered amine light stabilizers |
| US5216156A (en) * | 1992-05-05 | 1993-06-01 | Ciba-Geigy Corporation | Non-migrating 1-hydrocarbyloxy-2,2,6,6-tetramethylpiperidine 1,3,5-triazine derivatives |
| IT1263993B (it) * | 1993-04-05 | 1996-09-06 | Ciba Geigy Spa | Composti piperidin-triazinici atti all'impiego come stabilizzanti per materiali organici |
| TW270131B (enrdf_load_stackoverflow) * | 1993-07-13 | 1996-02-11 | Ciba Geigy | |
| IT1264946B1 (it) * | 1993-07-16 | 1996-10-17 | Ciba Geigy Spa | Derivati del 2,2,6,6-tetrametil-4-piperidinolo utili come stabilizzanti alla luce ed all'ossidazione per materiali organici. |
| US5393812A (en) * | 1993-08-31 | 1995-02-28 | Hercules Incorporated | Flame retardant, light stable composition |
| US5380828A (en) * | 1993-10-05 | 1995-01-10 | Ciba-Geigy Corporation | Azodicarboxylic acid derivatives containing hindered amine moieties as polymer stabilizers |
| AU7216796A (en) * | 1995-10-12 | 1997-04-30 | Ciba-Geigy Ag | Thermally stable hindered amines as stabilizers |
| US6046304A (en) * | 1995-12-04 | 2000-04-04 | Ciba Specialty Chemicals Corporation | Block oligomers containing 2,2,6,6-tetramethyl-4-piperidyl groups as stabilizers for organic materials |
| EP0782994B1 (en) * | 1995-12-04 | 2003-02-05 | Ciba SC Holding AG | Block oligomers containing 2,2,6,6-tetramethyl-4-piperidyl groups as stabilizers for organic materials |
| EP0792911A3 (en) * | 1996-02-27 | 1998-01-14 | Fmc Corporation | Flame resistant polyolefin compositions |
| JPH09292682A (ja) * | 1996-04-23 | 1997-11-11 | Fuji Photo Film Co Ltd | ハロゲン化銀カラー写真感光材料 |
| JP4010567B2 (ja) * | 1997-02-03 | 2007-11-21 | 富士フイルム株式会社 | ハロゲン化銀カラー写真感光材料とそれに用いるフェニドン化合物、及びその製造方法 |
| ITMI980366A1 (it) * | 1998-02-25 | 1999-08-25 | Ciba Spec Chem Spa | Preparazione di eteri amminici stericamente impediti |
-
1999
- 1999-02-06 SG SG1999000492A patent/SG74700A1/en unknown
- 1999-02-08 MY MYPI99000420A patent/MY123467A/en unknown
- 1999-02-17 GB GB9903463A patent/GB2334717B/en not_active Expired - Lifetime
- 1999-02-22 CZ CZ20080401A patent/CZ302752B6/cs not_active IP Right Cessation
- 1999-02-23 CA CA002262435A patent/CA2262435C/en not_active Expired - Lifetime
- 1999-02-23 AR ARP990100722A patent/AR015238A1/es active IP Right Grant
- 1999-02-23 FR FR9902218A patent/FR2777004B1/fr not_active Expired - Lifetime
- 1999-02-23 CA CA2643170A patent/CA2643170C/en not_active Expired - Lifetime
- 1999-02-24 ES ES009900376A patent/ES2159462B1/es not_active Expired - Lifetime
- 1999-02-24 ID IDP990142D patent/ID23225A/id unknown
- 1999-02-24 CN CNB991033833A patent/CN1202085C/zh not_active Expired - Lifetime
- 1999-02-24 CN CNB2004100473618A patent/CN100384826C/zh not_active Expired - Lifetime
- 1999-02-24 DE DE19964603A patent/DE19964603B4/de not_active Expired - Lifetime
- 1999-02-24 RU RU99103614/04A patent/RU2224758C2/ru active
- 1999-02-24 DE DE19907945A patent/DE19907945B4/de not_active Expired - Lifetime
- 1999-02-24 KR KR1019990006156A patent/KR100561146B1/ko not_active Expired - Lifetime
- 1999-02-25 BR BRPI9900807-6B1A patent/BR9900807B1/pt active IP Right Grant
- 1999-02-25 JP JP04790499A patent/JP4798815B2/ja not_active Expired - Lifetime
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- 1999-02-25 BE BE9900127A patent/BE1014990A5/fr not_active IP Right Cessation
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2010
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Also Published As
| Publication number | Publication date |
|---|---|
| GB2334717A (en) | 1999-09-01 |
| JPH11315067A (ja) | 1999-11-16 |
| GB2334717B (en) | 2000-04-26 |
| ES2159462B1 (es) | 2002-05-01 |
| KR19990072904A (ko) | 1999-09-27 |
| CN1235159A (zh) | 1999-11-17 |
| SG74700A1 (en) | 2000-08-22 |
| JP2011006443A (ja) | 2011-01-13 |
| FR2777004B1 (fr) | 2005-12-30 |
| CA2643170A1 (en) | 1999-08-25 |
| FR2777004A1 (fr) | 1999-10-08 |
| CN1552758A (zh) | 2004-12-08 |
| ES2159462A1 (es) | 2001-10-01 |
| CN1202085C (zh) | 2005-05-18 |
| NL1011394A1 (nl) | 1999-08-26 |
| AR015238A1 (es) | 2001-04-18 |
| CN100384826C (zh) | 2008-04-30 |
| BR9900807B1 (pt) | 2013-06-11 |
| DE19907945A1 (de) | 1999-08-26 |
| BR9900807A (pt) | 2000-03-28 |
| CA2262435A1 (en) | 1999-08-25 |
| MY123467A (en) | 2006-05-31 |
| GB9903463D0 (en) | 1999-04-07 |
| BE1014990A5 (fr) | 2004-08-03 |
| RU2224758C2 (ru) | 2004-02-27 |
| NL1011394C2 (nl) | 1999-10-26 |
| CZ302752B6 (cs) | 2011-10-19 |
| ID23225A (id) | 2000-03-30 |
| KR100561146B1 (ko) | 2006-03-15 |
| DE19907945B4 (de) | 2013-06-06 |
| CA2262435C (en) | 2009-12-22 |
| CA2643170C (en) | 2013-04-16 |
| DE19964603B4 (de) | 2013-02-28 |
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