CA2262435C - Preparation of sterically hindered amine ethers - Google Patents
Preparation of sterically hindered amine ethers Download PDFInfo
- Publication number
- CA2262435C CA2262435C CA002262435A CA2262435A CA2262435C CA 2262435 C CA2262435 C CA 2262435C CA 002262435 A CA002262435 A CA 002262435A CA 2262435 A CA2262435 A CA 2262435A CA 2262435 C CA2262435 C CA 2262435C
- Authority
- CA
- Canada
- Prior art keywords
- formula
- tert
- butyl
- compound
- bis
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- -1 amine ethers Chemical class 0.000 title claims abstract description 166
- 238000002360 preparation method Methods 0.000 title claims abstract description 20
- 150000001875 compounds Chemical class 0.000 claims abstract description 140
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 90
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 40
- 150000002367 halogens Chemical class 0.000 claims abstract description 40
- 238000000034 method Methods 0.000 claims abstract description 39
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 36
- 150000001721 carbon Chemical group 0.000 claims abstract description 31
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 30
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 29
- 239000001301 oxygen Substances 0.000 claims abstract description 29
- 230000008569 process Effects 0.000 claims abstract description 28
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 27
- 125000006575 electron-withdrawing group Chemical group 0.000 claims abstract description 16
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 14
- 239000000126 substance Substances 0.000 claims abstract description 14
- 125000005647 linker group Chemical group 0.000 claims abstract description 12
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 12
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 5
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims abstract description 4
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims abstract 4
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 85
- 229910052739 hydrogen Inorganic materials 0.000 claims description 78
- 239000001257 hydrogen Substances 0.000 claims description 63
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 37
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 35
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 20
- 229910052698 phosphorus Inorganic materials 0.000 claims description 16
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 15
- 239000011574 phosphorus Substances 0.000 claims description 15
- 125000005842 heteroatom Chemical group 0.000 claims description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
- 239000002904 solvent Substances 0.000 claims description 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 11
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- 239000011593 sulfur Substances 0.000 claims description 9
- 238000005984 hydrogenation reaction Methods 0.000 claims description 8
- 229920002554 vinyl polymer Polymers 0.000 claims description 8
- 230000001590 oxidative effect Effects 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 238000007254 oxidation reaction Methods 0.000 claims description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 6
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 5
- 230000026030 halogenation Effects 0.000 claims description 5
- 238000005658 halogenation reaction Methods 0.000 claims description 5
- 229930195733 hydrocarbon Natural products 0.000 claims description 5
- 150000002430 hydrocarbons Chemical class 0.000 claims description 5
- 239000007800 oxidant agent Substances 0.000 claims description 5
- 229910052710 silicon Inorganic materials 0.000 claims description 5
- 239000010703 silicon Substances 0.000 claims description 5
- 230000003647 oxidation Effects 0.000 claims description 4
- 150000002978 peroxides Chemical class 0.000 claims description 4
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- XTEGARKTQYYJKE-UHFFFAOYSA-M Chlorate Chemical class [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 claims description 2
- 150000002823 nitrates Chemical class 0.000 claims description 2
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- 239000003381 stabilizer Substances 0.000 abstract description 24
- 239000011368 organic material Substances 0.000 abstract description 9
- 230000015556 catabolic process Effects 0.000 abstract description 6
- 238000006731 degradation reaction Methods 0.000 abstract description 6
- 239000003063 flame retardant Substances 0.000 abstract description 6
- 238000004383 yellowing Methods 0.000 abstract description 4
- 238000007796 conventional method Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 92
- 239000000243 solution Substances 0.000 description 55
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 49
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 48
- 150000003254 radicals Chemical class 0.000 description 43
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 40
- 239000000047 product Substances 0.000 description 40
- 229920001577 copolymer Polymers 0.000 description 38
- 229920000642 polymer Polymers 0.000 description 34
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
- 238000003756 stirring Methods 0.000 description 31
- 125000001931 aliphatic group Chemical group 0.000 description 29
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 238000000576 coating method Methods 0.000 description 27
- 239000003054 catalyst Substances 0.000 description 26
- 150000002431 hydrogen Chemical class 0.000 description 24
- 229920005989 resin Polymers 0.000 description 24
- 239000011347 resin Substances 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
- 125000003118 aryl group Chemical group 0.000 description 22
- 239000003973 paint Substances 0.000 description 22
- 229910052751 metal Inorganic materials 0.000 description 21
- 239000002184 metal Substances 0.000 description 21
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 20
- 239000008199 coating composition Substances 0.000 description 20
- 229910000027 potassium carbonate Inorganic materials 0.000 description 20
- 229920001684 low density polyethylene Polymers 0.000 description 19
- 239000004702 low-density polyethylene Substances 0.000 description 19
- 239000002253 acid Substances 0.000 description 18
- 150000001412 amines Chemical class 0.000 description 18
- 239000011230 binding agent Substances 0.000 description 18
- 235000011181 potassium carbonates Nutrition 0.000 description 18
- 239000007787 solid Substances 0.000 description 18
- 239000012044 organic layer Substances 0.000 description 17
- WMNPPTFIWBUUQT-NAWIUCTOSA-N G12 Chemical compound C1=NC(C(NC(N)=N2)=O)=C2N1[C@@H]([C@@H]1O)O[C@H](COP(O)(=O)O[C@H]2[C@H]([C@@H](O[C@@H]2COP(O)(=O)O[C@H]2[C@H]([C@@H](O[C@@H]2COP(O)(=O)O[C@H]2[C@H]([C@@H](O[C@@H]2COP(O)(=O)O[C@H]2[C@H]([C@@H](O[C@@H]2COP(O)(=O)O[C@H]2[C@H]([C@@H](O[C@@H]2COP(O)(=O)O[C@H]2[C@H]([C@@H](O[C@@H]2COP(O)(=O)O[C@H]2[C@H]([C@@H](O[C@@H]2COP(O)(=O)O[C@H]2[C@H]([C@@H](O[C@@H]2COP(O)(=O)O[C@H]2[C@H]([C@@H](O[C@@H]2COP(O)(=O)O[C@H]2[C@H]([C@@H](O[C@@H]2CO)N2C3=C(C(NC(N)=N3)=O)N=C2)O)N2C3=C(C(NC(N)=N3)=O)N=C2)O)N2C3=C(C(NC(N)=N3)=O)N=C2)O)N2C3=C(C(NC(N)=N3)=O)N=C2)O)N2C3=C(C(NC(N)=N3)=O)N=C2)O)N2C3=C(C(NC(N)=N3)=O)N=C2)O)N2C3=C(C(NC(N)=N3)=O)N=C2)O)N2C3=C(C(NC(N)=N3)=O)N=C2)O)N2C3=C(C(NC(N)=N3)=O)N=C2)O)N2C3=C(C(NC(N)=N3)=O)N=C2)O)[C@H]1OP(O)(=O)OC[C@H]([C@@H](O)[C@H]1O)O[C@H]1N1C(N=C(NC2=O)N)=C2N=C1 WMNPPTFIWBUUQT-NAWIUCTOSA-N 0.000 description 16
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 15
- 150000002148 esters Chemical class 0.000 description 15
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 14
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 14
- 239000004743 Polypropylene Substances 0.000 description 14
- 229920001155 polypropylene Polymers 0.000 description 14
- 125000000217 alkyl group Chemical group 0.000 description 13
- 239000000463 material Substances 0.000 description 13
- 235000014786 phosphorus Nutrition 0.000 description 13
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 13
- 239000000843 powder Substances 0.000 description 13
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-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
- 239000004952 Polyamide Substances 0.000 description 12
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 12
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 12
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 12
- 239000008096 xylene Substances 0.000 description 12
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 11
- 239000003795 chemical substances by application Substances 0.000 description 11
- 125000000753 cycloalkyl group Chemical group 0.000 description 11
- 239000011572 manganese Substances 0.000 description 11
- 229920002647 polyamide Polymers 0.000 description 11
- 229910052938 sodium sulfate Inorganic materials 0.000 description 11
- 235000011152 sodium sulphate Nutrition 0.000 description 11
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 10
- 239000005977 Ethylene Substances 0.000 description 10
- 229920000877 Melamine resin Polymers 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
- 239000011248 coating agent Substances 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
- 229940093470 ethylene Drugs 0.000 description 10
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 10
- 230000000087 stabilizing effect Effects 0.000 description 10
- 239000004594 Masterbatch (MB) Substances 0.000 description 9
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 9
- 239000004698 Polyethylene Substances 0.000 description 9
- 239000000654 additive Substances 0.000 description 9
- 238000001914 filtration Methods 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
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- 125000001424 substituent group Chemical group 0.000 description 9
- 239000000758 substrate Substances 0.000 description 9
- 239000005062 Polybutadiene Substances 0.000 description 8
- 239000004721 Polyphenylene oxide Substances 0.000 description 8
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 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
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 8
- 238000001723 curing Methods 0.000 description 8
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 8
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- 229920000515 polycarbonate Polymers 0.000 description 8
- 239000004417 polycarbonate Substances 0.000 description 8
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- 229910001220 stainless steel Inorganic materials 0.000 description 8
- 239000010935 stainless steel Substances 0.000 description 8
- 229920001169 thermoplastic Polymers 0.000 description 8
- 150000008064 anhydrides Chemical class 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 7
- 150000001993 dienes Chemical class 0.000 description 7
- 238000005227 gel permeation chromatography Methods 0.000 description 7
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- 229920006324 polyoxymethylene Polymers 0.000 description 7
- 229920002635 polyurethane Polymers 0.000 description 7
- OLRJXMHANKMLTD-UHFFFAOYSA-N silyl Chemical compound [SiH3] OLRJXMHANKMLTD-UHFFFAOYSA-N 0.000 description 7
- 230000006641 stabilisation Effects 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-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
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-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
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 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
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 6
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 6
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- 229910052748 manganese Inorganic materials 0.000 description 6
- AFCCDDWKHLHPDF-UHFFFAOYSA-M metam-sodium Chemical compound [Na+].CNC([S-])=S AFCCDDWKHLHPDF-UHFFFAOYSA-M 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
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- HWRLEEPNFJNTOP-UHFFFAOYSA-N 2-(1,3,5-triazin-2-yl)phenol Chemical class 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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- 150000003839 salts Chemical class 0.000 description 5
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 238000011105 stabilization Methods 0.000 description 5
- 150000005846 sugar alcohols Polymers 0.000 description 5
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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 4
- ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-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
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- 238000005406 washing Methods 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- BOXSVZNGTQTENJ-UHFFFAOYSA-L zinc dibutyldithiocarbamate Chemical compound [Zn+2].CCCCN(C([S-])=S)CCCC.CCCCN(C([S-])=S)CCCC BOXSVZNGTQTENJ-UHFFFAOYSA-L 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
- 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 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
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)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA2643170A CA2643170C (en) | 1998-02-25 | 1999-02-23 | Sterically hindered amine ethers as stabilizers against light, oxygen and/or heat |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ITMI98A000366 | 1998-02-25 | ||
| IT98MI000366A ITMI980366A1 (it) | 1998-02-25 | 1998-02-25 | Preparazione di eteri amminici stericamente impediti |
| US10471898A | 1998-06-25 | 1998-06-25 | |
| US09/104,718 | 1998-06-25 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2643170A Division CA2643170C (en) | 1998-02-25 | 1999-02-23 | Sterically hindered amine ethers as stabilizers against light, oxygen and/or heat |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2262435A1 CA2262435A1 (en) | 1999-08-25 |
| CA2262435C true CA2262435C (en) | 2009-12-22 |
Family
ID=26331570
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002262435A Expired - Lifetime CA2262435C (en) | 1998-02-25 | 1999-02-23 | Preparation of sterically hindered amine ethers |
| CA2643170A Expired - Lifetime CA2643170C (en) | 1998-02-25 | 1999-02-23 | Sterically hindered amine ethers as stabilizers against light, oxygen and/or heat |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2643170A Expired - Lifetime CA2643170C (en) | 1998-02-25 | 1999-02-23 | Sterically hindered amine ethers as stabilizers against light, oxygen and/or heat |
Country Status (17)
| Country | Link |
|---|---|
| JP (2) | JP4798815B2 (cs) |
| KR (1) | KR100561146B1 (cs) |
| CN (2) | CN1202085C (cs) |
| AR (1) | AR015238A1 (cs) |
| BE (1) | BE1014990A5 (cs) |
| BR (1) | BR9900807B1 (cs) |
| CA (2) | CA2262435C (cs) |
| CZ (1) | CZ302752B6 (cs) |
| DE (2) | DE19964603B4 (cs) |
| ES (1) | ES2159462B1 (cs) |
| FR (1) | FR2777004B1 (cs) |
| GB (1) | GB2334717B (cs) |
| ID (1) | ID23225A (cs) |
| MY (1) | MY123467A (cs) |
| NL (1) | NL1011394C2 (cs) |
| RU (1) | RU2224758C2 (cs) |
| SG (1) | SG74700A1 (cs) |
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 |
| JP4324940B2 (ja) * | 2002-04-17 | 2009-09-02 | チバ ホールディング インコーポレーテッド | ヒドロキシルアミンエステル含有難燃性ポリマー組成物 |
| 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 |
| CA2576816C (en) * | 2004-08-31 | 2012-10-16 | Ciba Specialty Chemicals Holding Inc. | Stabilization of organic materials |
| PL1807395T3 (pl) * | 2004-11-02 | 2016-06-30 | Basf Se | Sposób syntezy n-alkoksyamin |
| US8217170B2 (en) * | 2006-11-23 | 2012-07-10 | Basf Se | 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 |
| US20120145241A1 (en) * | 2009-08-18 | 2012-06-14 | Basf Se | Photovoltaic module with stabilized polymeric encapsulant |
| EP2475655B1 (en) * | 2009-09-10 | 2017-10-11 | Basf Se | Sterically hindered amine stabilizer |
| CN105693698B (zh) * | 2010-10-20 | 2019-11-22 | 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 |
| WO2018069530A1 (en) * | 2016-10-14 | 2018-04-19 | Basf Se | Stabilizer composition |
| EP3601428A1 (en) * | 2017-03-28 | 2020-02-05 | 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 |
| JP7515497B2 (ja) * | 2019-03-08 | 2024-07-12 | ビーエーエスエフ ソシエタス・ヨーロピア | 立体障害アミン安定剤混合物 |
| 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 |
| US20250223403A1 (en) | 2022-04-04 | 2025-07-10 | Geneuschem Ag | Process for the preparation of sterically hindered nitroxyl ethers |
| 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 |
| US5124378A (en) * | 1987-09-21 | 1992-06-23 | Ciba-Geigy Corporation | Stabilization of ambient cured coatings |
| DE3852742T3 (de) * | 1987-09-21 | 2005-02-10 | Ciba Speciality Chemicals Holding Inc. | N-substituierte sterisch gehinderte Amin-Stabilisatoren. |
| US5204473A (en) * | 1987-09-21 | 1993-04-20 | Ciba-Geigy Corporation | O-substituted N-hydroxy hindered amine stabilizers |
| 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 |
| US4921962A (en) * | 1988-10-19 | 1990-05-01 | Ciba-Geigy Corporation | Process for preparing N-hydrocarbyloxy derivatives of sterically hindered amines |
| US4978699A (en) * | 1988-10-24 | 1990-12-18 | Atochem North America, Inc. | Light stabilizing flame retardants |
| WO1990009408A1 (en) * | 1989-02-13 | 1990-08-23 | Atochem North America, Inc. | Reactive hindered amine light stabilizers |
| EP0389429B1 (en) * | 1989-03-21 | 1994-09-21 | Ciba-Geigy Ag | Azo compounds containing hindered amine moieties with low basicity |
| DE69026747T2 (de) * | 1989-03-21 | 1996-11-14 | Ciba Geigy Ag | Nichtwandernde 1-Hydrocarbyloxy-gehinderte Amineverbindungen als Polymerstabilisatoren |
| 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 |
| 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. |
| 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 (cs) * | 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 |
| WO1997013752A1 (en) * | 1995-10-12 | 1997-04-17 | Ciba Specialty Chemicals Holding Inc. | 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 |
| EP0894786B1 (en) * | 1997-02-03 | 2006-05-24 | Fuji Photo Film Co., Ltd. | Silver halide color photographic material, phenidone compounds used therefor, and process for preparing the same |
| 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 FR FR9902218A patent/FR2777004B1/fr not_active Expired - Lifetime
- 1999-02-23 CA CA2643170A patent/CA2643170C/en not_active Expired - Lifetime
- 1999-02-23 AR ARP990100722A patent/AR015238A1/es active IP Right Grant
- 1999-02-24 RU RU99103614/04A patent/RU2224758C2/ru active
- 1999-02-24 DE DE19964603A patent/DE19964603B4/de not_active Expired - Lifetime
- 1999-02-24 DE DE19907945A patent/DE19907945B4/de not_active Expired - Lifetime
- 1999-02-24 KR KR1019990006156A patent/KR100561146B1/ko not_active Expired - Lifetime
- 1999-02-24 CN CNB991033833A patent/CN1202085C/zh not_active Expired - Lifetime
- 1999-02-24 CN CNB2004100473618A patent/CN100384826C/zh not_active Expired - Lifetime
- 1999-02-24 ID IDP990142D patent/ID23225A/id unknown
- 1999-02-24 ES ES009900376A patent/ES2159462B1/es not_active Expired - Lifetime
- 1999-02-25 BR BRPI9900807-6B1A patent/BR9900807B1/pt active IP Right Grant
- 1999-02-25 NL NL1011394A patent/NL1011394C2/nl not_active IP Right Cessation
- 1999-02-25 JP JP04790499A patent/JP4798815B2/ja not_active Expired - Lifetime
- 1999-02-25 BE BE9900127A patent/BE1014990A5/fr not_active IP Right Cessation
-
2010
- 2010-08-17 JP JP2010182352A patent/JP2011006443A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| ES2159462A1 (es) | 2001-10-01 |
| JP2011006443A (ja) | 2011-01-13 |
| CA2643170C (en) | 2013-04-16 |
| NL1011394A1 (nl) | 1999-08-26 |
| CN1202085C (zh) | 2005-05-18 |
| BR9900807B1 (pt) | 2013-06-11 |
| NL1011394C2 (nl) | 1999-10-26 |
| CA2643170A1 (en) | 1999-08-25 |
| DE19964603B4 (de) | 2013-02-28 |
| BE1014990A5 (fr) | 2004-08-03 |
| ID23225A (id) | 2000-03-30 |
| CN1235159A (zh) | 1999-11-17 |
| JPH11315067A (ja) | 1999-11-16 |
| CA2262435A1 (en) | 1999-08-25 |
| GB9903463D0 (en) | 1999-04-07 |
| DE19907945B4 (de) | 2013-06-06 |
| FR2777004B1 (fr) | 2005-12-30 |
| AR015238A1 (es) | 2001-04-18 |
| GB2334717B (en) | 2000-04-26 |
| KR19990072904A (ko) | 1999-09-27 |
| CN100384826C (zh) | 2008-04-30 |
| ES2159462B1 (es) | 2002-05-01 |
| RU2224758C2 (ru) | 2004-02-27 |
| MY123467A (en) | 2006-05-31 |
| BR9900807A (pt) | 2000-03-28 |
| CN1552758A (zh) | 2004-12-08 |
| JP4798815B2 (ja) | 2011-10-19 |
| SG74700A1 (en) | 2000-08-22 |
| GB2334717A (en) | 1999-09-01 |
| FR2777004A1 (fr) | 1999-10-08 |
| KR100561146B1 (ko) | 2006-03-15 |
| CZ302752B6 (cs) | 2011-10-19 |
| DE19907945A1 (de) | 1999-08-26 |
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| Date | Code | Title | Description |
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| EEER | Examination request | ||
| MKEX | Expiry |
Effective date: 20190225 |