DE60002859T2 - Polysilanstabilisatoren mit sterisch gehinderten aminogruppen - Google Patents

Info

Publication number

DE60002859T2

DE60002859T2 DE60002859T DE60002859T DE60002859T2 DE 60002859 T2 DE60002859 T2 DE 60002859T2 DE 60002859 T DE60002859 T DE 60002859T DE 60002859 T DE60002859 T DE 60002859T DE 60002859 T2 DE60002859 T2 DE 60002859T2

Authority

DE

Germany

Prior art keywords

formula

alkyl

group

hydrogen

independently

Prior art date

1999-04-27

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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• -1 AMINO GROUPS Chemical group 0.000 title claims description 90
• 229920000548 poly(silane) polymer Polymers 0.000 title claims description 41
• 239000003381 stabilizer Substances 0.000 title description 18
• 150000001875 compounds Chemical class 0.000 claims abstract description 104
• 239000001257 hydrogen Substances 0.000 claims abstract description 53
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 53
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 36
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 34
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 27
• 239000011368 organic material Substances 0.000 claims abstract description 16
• 230000003647 oxidation Effects 0.000 claims abstract description 7
• 238000007254 oxidation reaction Methods 0.000 claims abstract description 7
• 230000000087 stabilizing effect Effects 0.000 claims abstract description 4
• 239000000203 mixture Substances 0.000 claims description 61
• 229920001577 copolymer Polymers 0.000 claims description 37
• 238000000034 method Methods 0.000 claims description 33
• 238000009826 distribution Methods 0.000 claims description 22
• 239000004743 Polypropylene Substances 0.000 claims description 20
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 19
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
• 229920001155 polypropylene Polymers 0.000 claims description 14
• 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 11
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
• 125000002947 alkylene group Chemical group 0.000 claims description 10
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
• 239000004698 Polyethylene Substances 0.000 claims description 7
• 125000000217 alkyl group Chemical group 0.000 claims description 7
• 229920000573 polyethylene Polymers 0.000 claims description 7
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 5
• 229920001059 synthetic polymer Polymers 0.000 claims description 5
• 125000004169 (C1-C6) 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
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 4
• 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims description 3
• 125000004429 atom Chemical group 0.000 claims description 3
• 150000002431 hydrogen Chemical group 0.000 claims 15
• 125000000753 cycloalkyl group Chemical group 0.000 claims 1
• 238000000354 decomposition reaction Methods 0.000 claims 1
• 230000006866 deterioration Effects 0.000 claims 1
• 230000015556 catabolic process Effects 0.000 abstract description 3
• 238000006731 degradation reaction Methods 0.000 abstract description 3
• BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 abstract 1
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 72
• 238000005227 gel permeation chromatography Methods 0.000 description 54
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• 238000002360 preparation method Methods 0.000 description 46
• 229910052757 nitrogen Inorganic materials 0.000 description 28
• 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 25
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 25
• 229920000642 polymer Polymers 0.000 description 24
• 239000011541 reaction mixture Substances 0.000 description 24
• 238000004458 analytical method Methods 0.000 description 23
• OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 21
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• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
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• LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 18
• 238000002844 melting Methods 0.000 description 16
• 230000008018 melting Effects 0.000 description 16
• 239000000243 solution Substances 0.000 description 15
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• 239000002904 solvent Substances 0.000 description 14
• NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 13
• 150000002148 esters Chemical class 0.000 description 13
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
• MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 12
• 239000000725 suspension Substances 0.000 description 12
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• 238000003756 stirring Methods 0.000 description 10
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• 238000006243 chemical reaction Methods 0.000 description 8
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• GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 8
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
• XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 7
• MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 7
• 150000001252 acrylic acid derivatives Chemical class 0.000 description 7
• QRUYYSPCOGSZGQ-UHFFFAOYSA-L cyclopentane;dichlorozirconium Chemical compound Cl[Zr]Cl.[CH]1[CH][CH][CH][CH]1.[CH]1[CH][CH][CH][CH]1 QRUYYSPCOGSZGQ-UHFFFAOYSA-L 0.000 description 7
• 229920001903 high density polyethylene Polymers 0.000 description 7
• 239000004700 high-density polyethylene Substances 0.000 description 7
• 239000000463 material Substances 0.000 description 7
• 229920006324 polyoxymethylene Polymers 0.000 description 7
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 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
• 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
• 239000000835 fiber Substances 0.000 description 6
• 238000004817 gas chromatography Methods 0.000 description 6
• 239000004800 polyvinyl chloride Substances 0.000 description 6
• 229920000915 polyvinyl chloride Polymers 0.000 description 6
• 239000012262 resinous product Substances 0.000 description 6
• WNVSWLWUPQMHQK-UHFFFAOYSA-N 1,2,2,6,6-pentamethyl-4-prop-2-enoxypiperidine Chemical compound CN1C(C)(C)CC(OCC=C)CC1(C)C WNVSWLWUPQMHQK-UHFFFAOYSA-N 0.000 description 5
• 239000004721 Polyphenylene oxide Substances 0.000 description 5
• 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
• 125000004432 carbon atom Chemical group C* 0.000 description 5
• 239000004417 polycarbonate Substances 0.000 description 5
• 229920000728 polyester Polymers 0.000 description 5
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• 239000000843 powder Substances 0.000 description 5
• 150000005846 sugar alcohols Polymers 0.000 description 5
• QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 5
• 229920002554 vinyl polymer Polymers 0.000 description 5
• KAKZBPTYRLMSJV-UHFFFAOYSA-N vinyl-ethylene Natural products C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 5
• 239000001993 wax Substances 0.000 description 5
• DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 4
• FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 description 4
• 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
• 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
• ZPIRWAHWDCHWLM-UHFFFAOYSA-N 2-dodecylsulfanylethanol Chemical compound CCCCCCCCCCCCSCCO ZPIRWAHWDCHWLM-UHFFFAOYSA-N 0.000 description 4
• CKPKHTKLLYPGFM-UHFFFAOYSA-N 6,6-dimethylheptane-1,1-diol Chemical compound CC(CCCCC(O)O)(C)C CKPKHTKLLYPGFM-UHFFFAOYSA-N 0.000 description 4
• CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
• FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 4
• YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 4
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
• 229920000877 Melamine resin Polymers 0.000 description 4
• 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 description 4
• 229910019032 PtCl2 Inorganic materials 0.000 description 4
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• 238000009835 boiling Methods 0.000 description 4
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• CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 4
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• 230000003197 catalytic effect Effects 0.000 description 4
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• ZEBMSMUPGIOANU-UHFFFAOYSA-N (3,5-ditert-butyl-4-hydroxyphenyl)methylphosphonic acid Chemical compound CC(C)(C)C1=CC(CP(O)(O)=O)=CC(C(C)(C)C)=C1O ZEBMSMUPGIOANU-UHFFFAOYSA-N 0.000 description 2
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