CA2443064C - Transition-metal-catalyzed process for the preparation of sterically hindered n-substituted alkoxyamines - Google Patents

Info

Publication number

CA2443064C

CA2443064C CA2443064A CA2443064A CA2443064C CA 2443064 C CA2443064 C CA 2443064C CA 2443064 A CA2443064 A CA 2443064A CA 2443064 A CA2443064 A CA 2443064A CA 2443064 C CA2443064 C CA 2443064C

Authority

CA

Canada

Prior art keywords

carbon atoms

tert

butyl

bis

hydroxy

Prior art date

2001-04-02

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 - Fee Related

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• 125000005262 alkoxyamine group Chemical class 0.000 title abstract description 3
• 238000000034 method Methods 0.000 title description 18
• 230000008569 process Effects 0.000 title description 6
• 238000002360 preparation method Methods 0.000 title description 3
• 150000001875 compounds Chemical class 0.000 claims abstract description 55
• 125000004432 carbon atom Chemical group C* 0.000 claims description 48
• 239000000203 mixture Substances 0.000 claims description 41
• 125000000217 alkyl group Chemical group 0.000 claims description 14
• 239000001257 hydrogen Substances 0.000 claims description 9
• 229910052739 hydrogen Inorganic materials 0.000 claims description 9
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
• 239000006096 absorbing agent Substances 0.000 claims description 8
• 125000003118 aryl group Chemical group 0.000 claims description 8
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
• 239000011368 organic material Substances 0.000 claims description 6
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
• 229910052736 halogen Inorganic materials 0.000 claims description 5
• 150000002367 halogens Chemical class 0.000 claims description 5
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
• CDNJZOYFSALNDL-UHFFFAOYSA-N 2,2,6,6-tetramethyl-1-[(3-phenyl-2h-1-benzofuran-3-yl)methoxy]piperidine Chemical compound CC1(C)CCCC(C)(C)N1OCC1(C=2C=CC=CC=2)C2=CC=CC=C2OC1 CDNJZOYFSALNDL-UHFFFAOYSA-N 0.000 claims description 4
• 125000003545 alkoxy group Chemical group 0.000 claims description 4
• 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 4
• 125000004414 alkyl thio group Chemical group 0.000 claims description 4
• 125000004104 aryloxy group Chemical group 0.000 claims description 4
• 125000004043 oxo group Chemical group O=* 0.000 claims description 3
• RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 3
• 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 3
• 125000003282 alkyl amino group Chemical group 0.000 claims description 2
• 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 2
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
• 230000015556 catabolic process Effects 0.000 claims description 2
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
• 238000006731 degradation reaction Methods 0.000 claims description 2
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
• 125000002950 monocyclic group Chemical group 0.000 claims description 2
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
• 239000001301 oxygen Substances 0.000 claims description 2
• 229910052760 oxygen Inorganic materials 0.000 claims description 2
• 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 2
• 125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 claims description 2
• 125000003367 polycyclic group Chemical group 0.000 claims description 2
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
• 125000001424 substituent group Chemical group 0.000 claims description 2
• 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 2
• 229920001059 synthetic polymer Polymers 0.000 claims description 2
• 239000012954 diazonium Substances 0.000 abstract description 9
• 150000001989 diazonium salts Chemical group 0.000 abstract description 9
• YLFIGGHWWPSIEG-UHFFFAOYSA-N aminoxyl Chemical compound [O]N YLFIGGHWWPSIEG-UHFFFAOYSA-N 0.000 abstract description 4
• 238000000354 decomposition reaction Methods 0.000 abstract description 4
• 239000004611 light stabiliser Substances 0.000 abstract description 4
• 239000000758 substrate Substances 0.000 abstract description 4
• 239000003017 thermal stabilizer Substances 0.000 abstract 1
• -1 alkyl radical Chemical class 0.000 description 62
• PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 48
• 229920001577 copolymer Polymers 0.000 description 36
• 239000000463 material Substances 0.000 description 29
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 28
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 28
• 239000001993 wax Substances 0.000 description 24
• 229920000642 polymer Polymers 0.000 description 22
• 239000003381 stabilizer Substances 0.000 description 19
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 17
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
• 239000000975 dye Substances 0.000 description 15
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 14
• KPBUNDYOCHPZNJ-UHFFFAOYSA-N 1-(2,3-dihydro-1-benzofuran-3-ylmethoxy)-2,2,6,6-tetramethylpiperidine Chemical compound CC1(C)CCCC(C)(C)N1OCC1C2=CC=CC=C2OC1 KPBUNDYOCHPZNJ-UHFFFAOYSA-N 0.000 description 13
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• 150000002148 esters Chemical class 0.000 description 13
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• NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 12
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• 239000005977 Ethylene Substances 0.000 description 12
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 12
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• NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 12
• 239000003054 catalyst Substances 0.000 description 12
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• 229940093470 ethylene Drugs 0.000 description 12
• 229920002647 polyamide Polymers 0.000 description 12
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 12
• 229910052751 metal Inorganic materials 0.000 description 11
• 239000002184 metal Substances 0.000 description 11
• XQAABEDPVQWFPN-UHFFFAOYSA-N octyl 3-[3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyphenyl]propanoate Chemical compound CC(C)(C)C1=CC(CCC(=O)OCCCCCCCC)=CC(N2N=C3C=CC=CC3=N2)=C1O XQAABEDPVQWFPN-UHFFFAOYSA-N 0.000 description 11
• 239000000654 additive Substances 0.000 description 10
• 150000001412 amines Chemical class 0.000 description 10
• MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Substances ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 9
• 229920001684 low density polyethylene Polymers 0.000 description 9
• 239000004702 low-density polyethylene Substances 0.000 description 9
• 229920002857 polybutadiene Polymers 0.000 description 9
• 229920006324 polyoxymethylene Polymers 0.000 description 9
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 8
• 239000005062 Polybutadiene Substances 0.000 description 8
• 239000002253 acid Substances 0.000 description 8
• 150000001252 acrylic acid derivatives Chemical class 0.000 description 8
• KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 8
• GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 8
• 229920001155 polypropylene Polymers 0.000 description 8
• 229920000178 Acrylic resin Polymers 0.000 description 7
• 150000001993 dienes Chemical class 0.000 description 7
• 239000000839 emulsion Substances 0.000 description 7
• 239000004922 lacquer Substances 0.000 description 7
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
• 229920000728 polyester Polymers 0.000 description 7
• 229920000915 polyvinyl chloride Polymers 0.000 description 7
• 239000004800 polyvinyl chloride Substances 0.000 description 7
• IOGXOCVLYRDXLW-UHFFFAOYSA-N tert-butyl nitrite Chemical compound CC(C)(C)ON=O IOGXOCVLYRDXLW-UHFFFAOYSA-N 0.000 description 7
• 239000012414 tert-butyl nitrite Substances 0.000 description 7
• 229910052723 transition metal Inorganic materials 0.000 description 7
• 150000003624 transition metals Chemical class 0.000 description 7
• 239000004925 Acrylic resin Substances 0.000 description 6
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
• 239000004698 Polyethylene Substances 0.000 description 6
• 239000004721 Polyphenylene oxide Substances 0.000 description 6
• 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 6
• 229920000180 alkyd Polymers 0.000 description 6
• UHOVQNZJYSORNB-MZWXYZOWSA-N benzene-d6 Chemical compound [2H]C1=C([2H])C([2H])=C([2H])C([2H])=C1[2H] UHOVQNZJYSORNB-MZWXYZOWSA-N 0.000 description 6
• 239000008199 coating composition 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
• 229920001971 elastomer Polymers 0.000 description 6
• 229920000573 polyethylene Polymers 0.000 description 6
• 238000012360 testing method Methods 0.000 description 6
• 229920002554 vinyl polymer Polymers 0.000 description 6
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• 239000004593 Epoxy Substances 0.000 description 5
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• QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 5
• 239000012964 benzotriazole Substances 0.000 description 5
• 238000006243 chemical reaction Methods 0.000 description 5
• PCZWNUHBFITYKI-PNHSAAKESA-N cobalt 2,4-ditert-butyl-6-[[(1S,2S)-2-[(3,5-ditert-butyl-2-hydroxyphenyl)methylideneamino]cyclohexyl]iminomethyl]phenol Chemical compound [Co].CC(C)(C)c1cc(C=N[C@H]2CCCC[C@@H]2N=Cc2cc(cc(c2O)C(C)(C)C)C(C)(C)C)c(O)c(c1)C(C)(C)C PCZWNUHBFITYKI-PNHSAAKESA-N 0.000 description 5
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• JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 5
• 239000000178 monomer Substances 0.000 description 5
• 229910052757 nitrogen Inorganic materials 0.000 description 5
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• WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 5
• AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 5
• 239000004417 polycarbonate Substances 0.000 description 5
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