AU718067B2 - Mixtures containing at least three different block oligomers containing 2,2,6,6-tetramethyl-4-piperidyl groups as stabilizers for organic materials - Google Patents

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Publication number

AU718067B2

AU718067B2 AU74142/96A AU7414296A AU718067B2 AU 718067 B2 AU718067 B2 AU 718067B2 AU 74142/96 A AU74142/96 A AU 74142/96A AU 7414296 A AU7414296 A AU 7414296A AU 718067 B2 AU718067 B2 AU 718067B2

Authority

AU

Australia

Prior art keywords

formula

alkyl

substituted

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

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• 239000011368 organic material Substances 0.000 title claims abstract description 21
• 239000000203 mixture Substances 0.000 title claims description 188
• -1 2,2,6,6-tetramethyl-4-piperidyl groups Chemical group 0.000 title claims description 139
• 239000003381 stabilizer Substances 0.000 title abstract description 24
• 150000001875 compounds Chemical class 0.000 claims abstract description 168
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 50
• 239000001257 hydrogen Substances 0.000 claims abstract description 47
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 29
• 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
• 230000000306 recurrent effect Effects 0.000 claims abstract description 4
• 125000000217 alkyl group Chemical group 0.000 claims description 54
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 39
• 150000002431 hydrogen Chemical class 0.000 claims description 34
• 229910052757 nitrogen Inorganic materials 0.000 claims description 32
• 125000002947 alkylene group Chemical group 0.000 claims description 26
• 239000004743 Polypropylene Substances 0.000 claims description 25
• 238000006243 chemical reaction Methods 0.000 claims description 24
• 238000000034 method Methods 0.000 claims description 23
• 229920001155 polypropylene Polymers 0.000 claims description 21
• 238000002360 preparation method Methods 0.000 claims description 20
• 125000003545 alkoxy group Chemical group 0.000 claims description 19
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 14
• 125000003342 alkenyl group Chemical group 0.000 claims description 13
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 13
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 12
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
• 150000007529 inorganic bases Chemical class 0.000 claims description 9
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 8
• 239000004698 Polyethylene Substances 0.000 claims description 8
• 125000002993 cycloalkylene group Chemical group 0.000 claims description 8
• 239000003960 organic solvent Substances 0.000 claims description 8
• 229920000573 polyethylene Polymers 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 7
• 125000002252 acyl 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
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 5
• 230000015556 catabolic process Effects 0.000 claims description 5
• 238000006731 degradation reaction Methods 0.000 claims description 5
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
• 125000004450 alkenylene group Chemical group 0.000 claims description 4
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
• 125000004956 cyclohexylene group Chemical group 0.000 claims description 3
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
• 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 3
• 230000000087 stabilizing effect Effects 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
• 239000000126 substance Substances 0.000 claims description 2
• 125000003031 C5-C7 cycloalkylene group Chemical group 0.000 claims 2
• JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 claims 2
• GJVFBWCTGUSGDD-UHFFFAOYSA-L pentamethonium bromide Chemical compound [Br-].[Br-].C[N+](C)(C)CCCCC[N+](C)(C)C GJVFBWCTGUSGDD-UHFFFAOYSA-L 0.000 claims 1
• 239000004611 light stabiliser Substances 0.000 abstract description 4
• 239000012760 heat stabilizer Substances 0.000 abstract description 2
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 72
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• 239000008096 xylene Substances 0.000 description 33
• 239000011572 manganese Substances 0.000 description 28
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 28
• 229920000642 polymer Polymers 0.000 description 24
• 238000004458 analytical method Methods 0.000 description 21
• 150000003254 radicals Chemical class 0.000 description 21
• 238000005227 gel permeation chromatography Methods 0.000 description 18
• 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
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
• 229910000027 potassium carbonate Inorganic materials 0.000 description 14
• 238000010992 reflux Methods 0.000 description 14
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• 239000007864 aqueous solution Substances 0.000 description 10
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• 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
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 8
• 238000002844 melting Methods 0.000 description 8
• 230000008018 melting Effects 0.000 description 8
• GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 8
• 239000000843 powder Substances 0.000 description 8
• 150000001252 acrylic acid derivatives Chemical class 0.000 description 7
• 150000001412 amines Chemical class 0.000 description 7
• 239000000460 chlorine Substances 0.000 description 7
• 150000001993 dienes Chemical class 0.000 description 7
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• 239000004700 high-density polyethylene Substances 0.000 description 7
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• 229920006324 polyoxymethylene Polymers 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
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• 239000000654 additive Substances 0.000 description 6
• 239000003054 catalyst Substances 0.000 description 6
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• 229920001903 high density polyethylene Polymers 0.000 description 6
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• WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 5
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• 239000008116 calcium stearate Substances 0.000 description 5
• 125000004432 carbon atom Chemical group C* 0.000 description 5
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• 239000008187 granular material Substances 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
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• 235000011152 sodium sulphate Nutrition 0.000 description 5
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