SK283984B6 - Zmes blokových oligomérov obsahujúca 2,2,6,6-tetrametyl-4- piperidylové skupiny, spôsob jej prípravy, kompozícia stabilizovaná touto zmesou a spôsob stabilizácie organického materiálu použitím tejto zmesi - Google Patents

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Publication number

SK283984B6

SK283984B6 SK1543-96A SK154396A SK283984B6 SK 283984 B6 SK283984 B6 SK 283984B6 SK 154396 A SK154396 A SK 154396A SK 283984 B6 SK283984 B6 SK 283984B6

Authority

SK

Slovakia

Prior art keywords

group

formula

carbon atoms

alkyl

substituted

Prior art date

1995-12-04

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• 239000003381 stabilizer Substances 0.000 title claims abstract description 22
• 239000011368 organic material Substances 0.000 title claims abstract description 18
• -1 2,2,6,6-tetramethyl-4-piperidyl groups Chemical group 0.000 title claims description 179
• 150000001875 compounds Chemical class 0.000 claims abstract description 178
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 25
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 19
• 239000001257 hydrogen Substances 0.000 claims abstract description 17
• 230000003647 oxidation Effects 0.000 claims abstract description 9
• 238000007254 oxidation reaction Methods 0.000 claims abstract description 9
• 229920001059 synthetic polymer Polymers 0.000 claims abstract description 8
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 7
• 239000000203 mixture Substances 0.000 claims description 189
• 125000004432 carbon atom Chemical group C* 0.000 claims description 119
• 125000000217 alkyl group Chemical group 0.000 claims description 87
• 125000002947 alkylene group Chemical group 0.000 claims description 49
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 38
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 35
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 27
• 238000000034 method Methods 0.000 claims description 27
• 239000004743 Polypropylene Substances 0.000 claims description 25
• 238000006243 chemical reaction Methods 0.000 claims description 25
• 229920000642 polymer Polymers 0.000 claims description 25
• 238000002360 preparation method Methods 0.000 claims description 24
• 125000003545 alkoxy group Chemical group 0.000 claims description 21
• 229920001155 polypropylene Polymers 0.000 claims description 21
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 19
• 125000003342 alkenyl group Chemical group 0.000 claims description 18
• 125000003884 phenylalkyl group Chemical group 0.000 claims description 17
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 16
• 229910052799 carbon Inorganic materials 0.000 claims description 14
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 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
• 125000002993 cycloalkylene group Chemical group 0.000 claims description 11
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 9
• 125000002252 acyl group Chemical group 0.000 claims description 9
• 150000007529 inorganic bases Chemical class 0.000 claims description 9
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 8
• 239000004698 Polyethylene Substances 0.000 claims description 8
• 125000004663 dialkyl amino 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
• 239000000843 powder Substances 0.000 claims description 8
• 230000015556 catabolic process Effects 0.000 claims description 6
• 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 6
• 238000006731 degradation reaction Methods 0.000 claims description 6
• 239000000155 melt Substances 0.000 claims description 6
• 125000003031 C5-C7 cycloalkylene group Chemical group 0.000 claims description 5
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 5
• CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 claims description 5
• 235000013539 calcium stearate Nutrition 0.000 claims description 5
• 239000008116 calcium stearate Substances 0.000 claims description 5
• 239000008187 granular material Substances 0.000 claims description 5
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
• 125000000229 (C1-C4)alkoxy 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
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
• 125000004956 cyclohexylene group Chemical group 0.000 claims description 4
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 4
• 239000001301 oxygen Substances 0.000 claims description 4
• 229910052760 oxygen Inorganic materials 0.000 claims description 4
• 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims description 3
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
• JKIJEFPNVSHHEI-UHFFFAOYSA-N Phenol, 2,4-bis(1,1-dimethylethyl)-, phosphite (3:1) Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OP(OC=1C(=CC(=CC=1)C(C)(C)C)C(C)(C)C)OC1=CC=C(C(C)(C)C)C=C1C(C)(C)C JKIJEFPNVSHHEI-UHFFFAOYSA-N 0.000 claims description 3
• 125000004450 alkenylene group Chemical group 0.000 claims description 3
• 125000000304 alkynyl group Chemical group 0.000 claims description 3
• 230000000087 stabilizing effect Effects 0.000 claims description 3
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 2
• 125000004915 dibutylamino group Chemical group C(CCC)N(CCCC)* 0.000 claims description 2
• 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
• 125000004429 atom Chemical group 0.000 claims 5
• GJVFBWCTGUSGDD-UHFFFAOYSA-L pentamethonium bromide Chemical compound [Br-].[Br-].C[N+](C)(C)CCCCC[N+](C)(C)C GJVFBWCTGUSGDD-UHFFFAOYSA-L 0.000 claims 4
• WPMYUUITDBHVQZ-UHFFFAOYSA-M 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=CC(CCC([O-])=O)=CC(C(C)(C)C)=C1O WPMYUUITDBHVQZ-UHFFFAOYSA-M 0.000 claims 1
• 230000032683 aging Effects 0.000 claims 1
• 230000003078 antioxidant effect Effects 0.000 claims 1
• 125000004122 cyclic group Chemical group 0.000 claims 1
• 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 1
• SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 1
• 238000004383 yellowing Methods 0.000 claims 1
• 239000004611 light stabiliser Substances 0.000 abstract description 4
• 239000004608 Heat Stabiliser Substances 0.000 abstract 1
• 230000000306 recurrent effect Effects 0.000 abstract 1
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 72
• PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 46
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 46
• 229920001577 copolymer Polymers 0.000 description 40
• 239000000243 solution Substances 0.000 description 38
• 229910052757 nitrogen Inorganic materials 0.000 description 36
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 35
• CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 33
• 239000008096 xylene Substances 0.000 description 33
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 28
• 238000005227 gel permeation chromatography Methods 0.000 description 21
• 150000003254 radicals Chemical class 0.000 description 20
• 238000004458 analytical method Methods 0.000 description 18
• 239000000047 product Substances 0.000 description 15
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
• VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 14
• 239000005977 Ethylene Substances 0.000 description 14
• 229910000027 potassium carbonate Inorganic materials 0.000 description 14
• 239000007787 solid Substances 0.000 description 14
• 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 13
• 238000010992 reflux Methods 0.000 description 13
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
• 238000002844 melting Methods 0.000 description 12
• 230000008018 melting Effects 0.000 description 12
• NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 11
• 150000001412 amines Chemical class 0.000 description 11
• 238000001816 cooling Methods 0.000 description 11
• 239000004800 polyvinyl chloride Substances 0.000 description 11
• 229920000915 polyvinyl chloride Polymers 0.000 description 11
• FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 description 10
• 239000004952 Polyamide Substances 0.000 description 10
• 239000005062 Polybutadiene Substances 0.000 description 10
• 239000007864 aqueous solution Substances 0.000 description 10
• 238000004587 chromatography analysis Methods 0.000 description 10
• 238000001035 drying Methods 0.000 description 10
• 229920001684 low density polyethylene Polymers 0.000 description 10
• 239000004702 low-density polyethylene Substances 0.000 description 10
• GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 10
• 229920002647 polyamide Polymers 0.000 description 10
• 229920002857 polybutadiene Polymers 0.000 description 10
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
• 239000007983 Tris buffer Substances 0.000 description 9
• MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 9
• 239000000835 fiber Substances 0.000 description 9
• KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 8
• 238000009826 distribution Methods 0.000 description 8
• 150000002148 esters Chemical class 0.000 description 8
• 229920001903 high density polyethylene Polymers 0.000 description 8
• 239000004700 high-density polyethylene Substances 0.000 description 8
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• 229910052751 metal Inorganic materials 0.000 description 8
• 239000002184 metal Substances 0.000 description 8
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• 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 7
• 239000007859 condensation product Substances 0.000 description 7
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• 229910052938 sodium sulfate Inorganic materials 0.000 description 7
• 235000011152 sodium sulphate Nutrition 0.000 description 7
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
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• GHKOFFNLGXMVNJ-UHFFFAOYSA-N Didodecyl thiobispropanoate Chemical compound CCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCC GHKOFFNLGXMVNJ-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
• 150000001252 acrylic acid derivatives Chemical class 0.000 description 6
• 239000000654 additive Substances 0.000 description 6
• 239000000460 chlorine Substances 0.000 description 6
• QPJDMGCKMHUXFD-UHFFFAOYSA-N cyanogen chloride Chemical compound ClC#N QPJDMGCKMHUXFD-UHFFFAOYSA-N 0.000 description 6
• 150000001993 dienes Chemical class 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
• 239000000049 pigment Substances 0.000 description 6
• 238000006116 polymerization reaction Methods 0.000 description 6
• CKPKHTKLLYPGFM-UHFFFAOYSA-N 6,6-dimethylheptane-1,1-diol Chemical compound CC(CCCCC(O)O)(C)C CKPKHTKLLYPGFM-UHFFFAOYSA-N 0.000 description 5
• WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 5
• 239000003054 catalyst Substances 0.000 description 5
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• QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 5
• 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 5
• 150000005846 sugar alcohols Polymers 0.000 description 5
• 229920002554 vinyl polymer Polymers 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
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• 229910052801 chlorine Inorganic materials 0.000 description 4
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• 238000001914 filtration Methods 0.000 description 4
• NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 4
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• 150000002431 hydrogen Chemical class 0.000 description 4
• 239000000178 monomer Substances 0.000 description 4
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• 150000002815 nickel Chemical class 0.000 description 4
• WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 4
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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 4
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• 150000003839 salts Chemical class 0.000 description 3
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• GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 2
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