DE69626095T2 - 2,2,6,6-Tetramethyl-4-piperidylgruppen enthaltende Blockoligomere als Stabilisatoren für organische Materialien - Google Patents

Info

Publication number

DE69626095T2

DE69626095T2 DE69626095T DE69626095T DE69626095T2 DE 69626095 T2 DE69626095 T2 DE 69626095T2 DE 69626095 T DE69626095 T DE 69626095T DE 69626095 T DE69626095 T DE 69626095T DE 69626095 T2 DE69626095 T2 DE 69626095T2

Authority

DE

Germany

Prior art keywords

formula

substituted

alkyl

unsubstituted

group

Prior art date

1995-12-04

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

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• 150000001875 compounds Chemical class 0.000 claims abstract description 162
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 49
• 239000001257 hydrogen Substances 0.000 claims abstract description 48
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 22
• 239000011368 organic material Substances 0.000 claims abstract description 18
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 13
• 230000003647 oxidation Effects 0.000 claims abstract description 8
• 238000007254 oxidation reaction Methods 0.000 claims abstract description 8
• 229920001059 synthetic polymer Polymers 0.000 claims abstract description 7
• 239000000203 mixture Substances 0.000 claims description 192
• -1 1,4-piperazinediyl Chemical group 0.000 claims description 136
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 57
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 37
• 150000002431 hydrogen Chemical group 0.000 claims description 34
• 239000004743 Polypropylene Substances 0.000 claims description 24
• 238000006243 chemical reaction Methods 0.000 claims description 24
• 229920001155 polypropylene Polymers 0.000 claims description 21
• 238000000034 method Methods 0.000 claims description 18
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 15
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 14
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 14
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 12
• 125000002947 alkylene group Chemical group 0.000 claims description 11
• 239000004698 Polyethylene Substances 0.000 claims description 9
• 150000007529 inorganic bases Chemical class 0.000 claims description 9
• 229920000573 polyethylene Polymers 0.000 claims description 9
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 8
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 8
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 8
• 239000003960 organic solvent Substances 0.000 claims description 8
• 125000003031 C5-C7 cycloalkylene group Chemical group 0.000 claims description 7
• 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 7
• FDAKZQLBIFPGSV-UHFFFAOYSA-N n-butyl-2,2,6,6-tetramethylpiperidin-4-amine Chemical group CCCCNC1CC(C)(C)NC(C)(C)C1 FDAKZQLBIFPGSV-UHFFFAOYSA-N 0.000 claims description 7
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 5
• 125000003342 alkenyl group Chemical group 0.000 claims description 5
• 230000015556 catabolic process Effects 0.000 claims description 5
• 238000006731 degradation reaction Methods 0.000 claims description 5
• 238000004519 manufacturing process Methods 0.000 claims description 5
• 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims description 4
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
• 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 3
• 125000000304 alkynyl group Chemical group 0.000 claims description 3
• 125000004956 cyclohexylene group Chemical group 0.000 claims description 3
• 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 2
• 230000000087 stabilizing effect Effects 0.000 claims description 2
• 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims 2
• JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 claims 2
• 125000003884 phenylalkyl group Chemical group 0.000 claims 2
• 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims 1
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
• 125000006528 (C2-C6) alkyl group Chemical group 0.000 claims 1
• 101100311330 Schizosaccharomyces pombe (strain 972 / ATCC 24843) uap56 gene Proteins 0.000 claims 1
• 125000002993 cycloalkylene group Chemical group 0.000 claims 1
• 101150018444 sub2 gene Proteins 0.000 claims 1
• 239000003381 stabilizer Substances 0.000 abstract description 21
• 239000004611 light stabiliser Substances 0.000 abstract description 4
• 239000012760 heat stabilizer Substances 0.000 abstract description 2
• 230000000306 recurrent effect Effects 0.000 abstract 1
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• 229920000642 polymer Polymers 0.000 description 25
• 238000004458 analytical method Methods 0.000 description 20
• 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 18
• 238000002360 preparation method Methods 0.000 description 18
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• 238000010992 reflux Methods 0.000 description 14
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• 230000008018 melting Effects 0.000 description 13
• 239000000047 product Substances 0.000 description 13
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• 150000002148 esters Chemical class 0.000 description 11
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• FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 description 10
• 239000007864 aqueous solution Substances 0.000 description 10
• MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 10
• MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 10
• 239000007787 solid Substances 0.000 description 10
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• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
• 229920001684 low density polyethylene Polymers 0.000 description 9
• 239000004702 low-density polyethylene Substances 0.000 description 9
• 239000000463 material Substances 0.000 description 9
• 229920002857 polybutadiene 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
• KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 8
• 238000001816 cooling Methods 0.000 description 8
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• 229910052751 metal Inorganic materials 0.000 description 8
• 239000002184 metal Substances 0.000 description 8
• GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 8
• 239000000843 powder Substances 0.000 description 8
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
• 150000001252 acrylic acid derivatives Chemical class 0.000 description 7
• 150000001412 amines Chemical class 0.000 description 7
• 150000001993 dienes Chemical class 0.000 description 7
• 229920001903 high density polyethylene Polymers 0.000 description 7
• 239000004700 high-density polyethylene Substances 0.000 description 7
• 239000012074 organic phase Substances 0.000 description 7
• 229920006324 polyoxymethylene Polymers 0.000 description 7
• 239000004800 polyvinyl chloride Substances 0.000 description 7
• 229920000915 polyvinyl chloride Polymers 0.000 description 7
• 229910052938 sodium sulfate Inorganic materials 0.000 description 7
• 235000011152 sodium sulphate Nutrition 0.000 description 7
• CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 6
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
• GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 6
• 239000000654 additive Substances 0.000 description 6
• 239000003054 catalyst 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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• 239000000049 pigment Substances 0.000 description 6
• 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 5
• WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 5
• CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 5
• 235000013539 calcium stearate Nutrition 0.000 description 5
• 239000008116 calcium stearate Substances 0.000 description 5
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• 238000005406 washing Methods 0.000 description 5
• DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 4
• ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 4
• YEWBOZCFGXOUQW-UHFFFAOYSA-N 2,6,7-trioxa-1-phosphabicyclo[2.2.2]octan-4-ylmethanol Chemical compound C1OP2OCC1(CO)CO2 YEWBOZCFGXOUQW-UHFFFAOYSA-N 0.000 description 4
• KXPXKNBDCUOENF-UHFFFAOYSA-N 2-(Octylthio)ethanol Chemical compound CCCCCCCCSCCO KXPXKNBDCUOENF-UHFFFAOYSA-N 0.000 description 4
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