JP2005538230A - 有機材料の安定化 - Google Patents

Info

Publication number

JP2005538230A

JP2005538230A JP2004535223A JP2004535223A JP2005538230A JP 2005538230 A JP2005538230 A JP 2005538230A JP 2004535223 A JP2004535223 A JP 2004535223A JP 2004535223 A JP2004535223 A JP 2004535223A JP 2005538230 A JP2005538230 A JP 2005538230A

Authority

JP

Japan

Prior art keywords

group

carbon atoms

tert

butyl

component

Prior art date

2002-09-11

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.)

Pending

Links

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• 239000011368 organic material Substances 0.000 title claims abstract description 23
• 230000006641 stabilisation Effects 0.000 title description 8
• 238000011105 stabilization Methods 0.000 title description 8
• 239000000203 mixture Substances 0.000 claims abstract description 112
• 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 82
• 239000003381 stabilizer Substances 0.000 claims abstract description 50
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 48
• 150000001875 compounds Chemical class 0.000 claims abstract description 30
• 150000001412 amines Chemical class 0.000 claims abstract description 25
• 230000003647 oxidation Effects 0.000 claims abstract description 17
• 238000007254 oxidation reaction Methods 0.000 claims abstract description 17
• 230000015556 catabolic process Effects 0.000 claims abstract description 11
• 238000006731 degradation reaction Methods 0.000 claims abstract description 11
• AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims abstract description 10
• 150000001408 amides Chemical class 0.000 claims abstract description 8
• 239000002216 antistatic agent Substances 0.000 claims abstract description 6
• SQDFHQJTAWCFIB-UHFFFAOYSA-N n-methylidenehydroxylamine Chemical compound ON=C SQDFHQJTAWCFIB-UHFFFAOYSA-N 0.000 claims abstract description 6
• 229920001059 synthetic polymer Polymers 0.000 claims abstract description 4
• -1 2,4-di-tert-butylphenyl Chemical group 0.000 claims description 194
• 239000004698 Polyethylene Substances 0.000 claims description 32
• 229920000573 polyethylene Polymers 0.000 claims description 31
• 239000000654 additive Substances 0.000 claims description 29
• 229910052757 nitrogen Inorganic materials 0.000 claims description 27
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
• 238000000034 method Methods 0.000 claims description 13
• 239000004743 Polypropylene Substances 0.000 claims description 11
• 239000002253 acid Substances 0.000 claims description 11
• 238000012545 processing Methods 0.000 claims description 11
• 125000002252 acyl group Chemical group 0.000 claims description 9
• 125000003342 alkenyl group Chemical group 0.000 claims description 9
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
• 125000004450 alkenylene group Chemical group 0.000 claims description 8
• 125000002947 alkylene group Chemical group 0.000 claims description 7
• 239000004611 light stabiliser Substances 0.000 claims description 7
• 229920000098 polyolefin Polymers 0.000 claims description 7
• 229920001155 polypropylene Polymers 0.000 claims description 7
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
• 239000002530 phenolic antioxidant Substances 0.000 claims description 5
• OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims description 5
• 239000003760 tallow Substances 0.000 claims description 5
• AIBRSVLEQRWAEG-UHFFFAOYSA-N 3,9-bis(2,4-ditert-butylphenoxy)-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OP1OCC2(COP(OC=3C(=CC(=CC=3)C(C)(C)C)C(C)(C)C)OC2)CO1 AIBRSVLEQRWAEG-UHFFFAOYSA-N 0.000 claims 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 claims description 4
• 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 4
• XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical compound OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 claims description 4
• 230000000087 stabilizing effect Effects 0.000 claims description 4
• ZEFSGHVBJCEKAZ-UHFFFAOYSA-N bis(2,4-ditert-butyl-6-methylphenyl) ethyl phosphite Chemical compound CC=1C=C(C(C)(C)C)C=C(C(C)(C)C)C=1OP(OCC)OC1=C(C)C=C(C(C)(C)C)C=C1C(C)(C)C ZEFSGHVBJCEKAZ-UHFFFAOYSA-N 0.000 claims description 3
• NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 claims description 3
• WGKLOLBTFWFKOD-UHFFFAOYSA-N tris(2-nonylphenyl) phosphite Chemical compound CCCCCCCCCC1=CC=CC=C1OP(OC=1C(=CC=CC=1)CCCCCCCCC)OC1=CC=CC=C1CCCCCCCCC WGKLOLBTFWFKOD-UHFFFAOYSA-N 0.000 claims description 3
• WBWXVCMXGYSMQA-UHFFFAOYSA-N 3,9-bis[2,4-bis(2-phenylpropan-2-yl)phenoxy]-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane Chemical compound C=1C=C(OP2OCC3(CO2)COP(OC=2C(=CC(=CC=2)C(C)(C)C=2C=CC=CC=2)C(C)(C)C=2C=CC=CC=2)OC3)C(C(C)(C)C=2C=CC=CC=2)=CC=1C(C)(C)C1=CC=CC=C1 WBWXVCMXGYSMQA-UHFFFAOYSA-N 0.000 claims description 2
• 125000003545 alkoxy group Chemical group 0.000 claims description 2
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
• 238000002156 mixing Methods 0.000 claims 1
• 239000000126 substance Substances 0.000 abstract description 9
• PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 52
• 229920001577 copolymer Polymers 0.000 description 51
• 229920000642 polymer Polymers 0.000 description 31
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 22
• 239000005977 Ethylene Substances 0.000 description 20
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 17
• VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 16
• 229940048053 acrylate Drugs 0.000 description 16
• KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 15
• 239000000047 product Substances 0.000 description 14
• 229920001400 block copolymer Polymers 0.000 description 13
• NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 12
• 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
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 12
• 239000001527 calcium lactate Substances 0.000 description 12
• 229960002401 calcium lactate Drugs 0.000 description 12
• MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 12
• 239000000463 material Substances 0.000 description 11
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
• 239000004952 Polyamide Substances 0.000 description 10
• 150000002148 esters Chemical class 0.000 description 10
• 229920002647 polyamide Polymers 0.000 description 10
• 229920002857 polybutadiene Polymers 0.000 description 10
• 229920002554 vinyl polymer Polymers 0.000 description 10
• 239000005062 Polybutadiene Substances 0.000 description 9
• 229920000058 polyacrylate Polymers 0.000 description 9
• 239000004417 polycarbonate Substances 0.000 description 9
• 239000002904 solvent Substances 0.000 description 9
• 238000012360 testing method Methods 0.000 description 9
• 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 8
• KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 8
• 239000002270 dispersing agent Substances 0.000 description 8
• 238000001125 extrusion Methods 0.000 description 8
• 229920001684 low density polyethylene Polymers 0.000 description 8
• 239000004702 low-density polyethylene Substances 0.000 description 8
• 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
• 239000002861 polymer material Substances 0.000 description 8
• 229920006324 polyoxymethylene Polymers 0.000 description 8
• NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 7
• 239000004721 Polyphenylene oxide Substances 0.000 description 7
• 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 7
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
• MKJXYGKVIBWPFZ-UHFFFAOYSA-L calcium lactate Chemical compound [Ca+2].CC(O)C([O-])=O.CC(O)C([O-])=O MKJXYGKVIBWPFZ-UHFFFAOYSA-L 0.000 description 7
• 235000011086 calcium lactate Nutrition 0.000 description 7
• 150000001993 dienes Chemical class 0.000 description 7
• 239000000835 fiber Substances 0.000 description 7
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• 239000008187 granular material Substances 0.000 description 7
• 239000004700 high-density polyethylene Substances 0.000 description 7
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• 239000000843 powder Substances 0.000 description 7
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 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
• 229920001903 high density polyethylene Polymers 0.000 description 6
• 239000000155 melt Substances 0.000 description 6
• 239000000178 monomer Substances 0.000 description 6
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• 239000004800 polyvinyl chloride Substances 0.000 description 6
• 229920000915 polyvinyl chloride Polymers 0.000 description 6
• 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 6
• 229920000089 Cyclic olefin copolymer Polymers 0.000 description 5
• 229920003171 Poly (ethylene oxide) Polymers 0.000 description 5
• 150000001252 acrylic acid derivatives Chemical class 0.000 description 5
• WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 5
• 125000003118 aryl group Chemical group 0.000 description 5
• 238000000576 coating method Methods 0.000 description 5
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• 229920001971 elastomer Polymers 0.000 description 5
• WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 5
• 239000007789 gas Substances 0.000 description 5
• 229920001519 homopolymer Polymers 0.000 description 5
• 238000000465 moulding Methods 0.000 description 5
• FTWUXYZHDFCGSV-UHFFFAOYSA-N n,n'-diphenyloxamide Chemical compound C=1C=CC=CC=1NC(=O)C(=O)NC1=CC=CC=C1 FTWUXYZHDFCGSV-UHFFFAOYSA-N 0.000 description 5
• WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 5
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• 238000011925 1,2-addition Methods 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
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• CWGBFIRHYJNILV-UHFFFAOYSA-N (1,4-diphenyl-1,2,4-triazol-4-ium-3-yl)-phenylazanide Chemical compound C=1C=CC=CC=1[N-]C1=NN(C=2C=CC=CC=2)C=[N+]1C1=CC=CC=C1 CWGBFIRHYJNILV-UHFFFAOYSA-N 0.000 description 3
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• FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 3
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