JP4764822B2 - 光互変系の安定化 - Google Patents

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Publication number

JP4764822B2

JP4764822B2 JP2006530247A JP2006530247A JP4764822B2 JP 4764822 B2 JP4764822 B2 JP 4764822B2 JP 2006530247 A JP2006530247 A JP 2006530247A JP 2006530247 A JP2006530247 A JP 2006530247A JP 4764822 B2 JP4764822 B2 JP 4764822B2

Authority

JP

Japan

Prior art keywords

group

carbon atoms

tert

butyl

alkyl

Prior art date

2003-09-29

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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• 230000006641 stabilisation Effects 0.000 title description 3
• 238000011105 stabilization Methods 0.000 title description 3
• 125000004432 carbon atom Chemical group C* 0.000 claims description 422
• 125000000217 alkyl group Chemical group 0.000 claims description 125
• 239000000203 mixture Substances 0.000 claims description 58
• 229920000642 polymer Polymers 0.000 claims description 56
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 44
• 125000003118 aryl group Chemical group 0.000 claims description 30
• 239000006096 absorbing agent Substances 0.000 claims description 28
• 229910052799 carbon Inorganic materials 0.000 claims description 28
• 239000000654 additive Substances 0.000 claims description 27
• 125000003342 alkenyl group Chemical group 0.000 claims description 25
• 150000001412 amines Chemical class 0.000 claims description 23
• 239000000463 material Substances 0.000 claims description 16
• VMRIVYANZGSGRV-UHFFFAOYSA-N 4-phenyl-2h-triazin-5-one Chemical compound OC1=CN=NN=C1C1=CC=CC=C1 VMRIVYANZGSGRV-UHFFFAOYSA-N 0.000 claims description 15
• 238000000034 method Methods 0.000 claims description 15
• 239000003381 stabilizer Substances 0.000 claims description 14
• 239000002253 acid Substances 0.000 claims description 13
• 239000002861 polymer material Substances 0.000 claims description 13
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
• 239000004611 light stabiliser Substances 0.000 claims description 8
• 239000011159 matrix material Substances 0.000 claims description 7
• 238000012545 processing Methods 0.000 claims description 7
• 230000008569 process Effects 0.000 claims description 6
• 239000003963 antioxidant agent Substances 0.000 claims description 5
• 239000003795 chemical substances by application Substances 0.000 claims description 5
• 238000010348 incorporation Methods 0.000 claims description 4
• 230000000087 stabilizing effect Effects 0.000 claims description 4
• 239000000945 filler Substances 0.000 claims description 3
• 239000003063 flame retardant Substances 0.000 claims description 3
• AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 claims description 3
• 238000005562 fading Methods 0.000 claims description 2
• XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical class OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 claims description 2
• 239000000049 pigment Substances 0.000 claims description 2
• RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 claims 1
• 241001648319 Toronia toru Species 0.000 claims 1
• -1 N-methyl-piperidinyl group Chemical group 0.000 description 224
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 72
• 125000002947 alkylene group Chemical group 0.000 description 71
• 150000001875 compounds Chemical class 0.000 description 58
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 53
• PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical class C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 46
• 229920001577 copolymer Polymers 0.000 description 44
• 125000003545 alkoxy group Chemical group 0.000 description 32
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 28
• 125000003884 phenylalkyl group Chemical group 0.000 description 24
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 22
• 150000001721 carbon Chemical group 0.000 description 20
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 19
• 125000001931 aliphatic group Chemical group 0.000 description 18
• 125000002993 cycloalkylene group Chemical group 0.000 description 18
• 239000000975 dye Substances 0.000 description 18
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 17
• 125000005843 halogen group Chemical group 0.000 description 16
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
• VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 15
• 239000005977 Ethylene Substances 0.000 description 15
• MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 15
• 125000004093 cyano group Chemical group *C#N 0.000 description 14
• 229910052757 nitrogen Inorganic materials 0.000 description 13
• 125000004430 oxygen atom Chemical group O* 0.000 description 13
• NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 12
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
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• 239000004952 Polyamide Substances 0.000 description 12
• 125000003277 amino group Chemical group 0.000 description 12
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 12
• 239000010408 film Substances 0.000 description 12
• 229920002647 polyamide Polymers 0.000 description 12
• 125000002252 acyl group Chemical group 0.000 description 11
• 229910052801 chlorine Inorganic materials 0.000 description 11
• 125000001309 chloro group Chemical group Cl* 0.000 description 11
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• 239000004702 low-density polyethylene Substances 0.000 description 11
• 239000004417 polycarbonate Substances 0.000 description 11
• 229920000728 polyester Polymers 0.000 description 11
• 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 11
• 239000004743 Polypropylene Substances 0.000 description 10
• 125000002723 alicyclic group Chemical group 0.000 description 10
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 10
• 125000000000 cycloalkoxy group Chemical group 0.000 description 10
• 150000002148 esters Chemical class 0.000 description 10
• 229910052731 fluorine Inorganic materials 0.000 description 10
• 125000001153 fluoro group Chemical group F* 0.000 description 10
• GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 10
• OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 9
• 125000004450 alkenylene group Chemical group 0.000 description 9
• 125000000732 arylene group Chemical group 0.000 description 9
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 9
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 9
• 125000002768 hydroxyalkyl group Chemical group 0.000 description 9
• 229920000139 polyethylene terephthalate Polymers 0.000 description 9
• 239000005020 polyethylene terephthalate Substances 0.000 description 9
• 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 9
• 229920002554 vinyl polymer Polymers 0.000 description 9
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 8
• VCMLCMCXCRBSQO-UHFFFAOYSA-N 3h-benzo[f]chromene Chemical compound C1=CC=CC2=C(C=CCO3)C3=CC=C21 VCMLCMCXCRBSQO-UHFFFAOYSA-N 0.000 description 8
• KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 8
• 229910052751 metal Inorganic materials 0.000 description 8
• 239000002184 metal Substances 0.000 description 8
• 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 8
• 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 8
• 229920002857 polybutadiene Polymers 0.000 description 8
• 239000005062 Polybutadiene Substances 0.000 description 7
• 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 7
• 125000003710 aryl alkyl group Chemical group 0.000 description 7
• 125000004429 atom Chemical group 0.000 description 7
• 239000003054 catalyst Substances 0.000 description 7
• QZHPTGXQGDFGEN-UHFFFAOYSA-N chromene Chemical compound C1=CC=C2C=C[CH]OC2=C1 QZHPTGXQGDFGEN-UHFFFAOYSA-N 0.000 description 7
• 150000001993 dienes Chemical class 0.000 description 7
• 239000005038 ethylene vinyl acetate Substances 0.000 description 7
• 239000004700 high-density polyethylene Substances 0.000 description 7
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 7
• 239000010410 layer Substances 0.000 description 7
• 239000000178 monomer Substances 0.000 description 7
• 229920006324 polyoxymethylene Polymers 0.000 description 7
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 6
• NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 6
• 229920000089 Cyclic olefin copolymer Polymers 0.000 description 6
• GHKOFFNLGXMVNJ-UHFFFAOYSA-N Didodecyl thiobispropanoate Chemical compound CCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCC GHKOFFNLGXMVNJ-UHFFFAOYSA-N 0.000 description 6
• 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
• 239000004721 Polyphenylene oxide Substances 0.000 description 6
• 239000007983 Tris buffer Substances 0.000 description 6
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 6
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 6
• 125000005724 cycloalkenylene group Chemical group 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
• 229920001971 elastomer Polymers 0.000 description 6
• 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 6
• 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 6
• 229920001903 high density polyethylene Polymers 0.000 description 6
• 239000004615 ingredient Substances 0.000 description 6
• 125000001624 naphthyl group Chemical group 0.000 description 6
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 6
• 125000002071 phenylalkoxy group Chemical group 0.000 description 6
• 229920003023 plastic Polymers 0.000 description 6
• 239000004033 plastic Substances 0.000 description 6
• 229920001707 polybutylene terephthalate Polymers 0.000 description 6
• 229920001155 polypropylene Polymers 0.000 description 6
• 239000004814 polyurethane Substances 0.000 description 6
• 239000004800 polyvinyl chloride Substances 0.000 description 6
• 229920000915 polyvinyl chloride Polymers 0.000 description 6
• DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 5
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 5
• ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 5
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
• 0 CCC(CC)(*(C(*(C1(CC(CNN)(*(C)C2(C)NC)NC)C2N)N)=O)[N+]1[O-])N Chemical compound CCC(CC)(*(C(*(C1(CC(CNN)(*(C)C2(C)NC)NC)C2N)N)=O)[N+]1[O-])N 0.000 description 5
• 239000004698 Polyethylene Substances 0.000 description 5
• 229910052796 boron Inorganic materials 0.000 description 5
• 125000004181 carboxyalkyl group Chemical group 0.000 description 5
• 238000009472 formulation Methods 0.000 description 5
• 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 description 5
• 229920001519 homopolymer Polymers 0.000 description 5
• 229910052740 iodine Inorganic materials 0.000 description 5
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 5
• DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 5
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
• 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 5
• SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 5
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• 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 5
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• 150000005846 sugar alcohols Polymers 0.000 description 5
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
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• ZPIRWAHWDCHWLM-UHFFFAOYSA-N 2-dodecylsulfanylethanol Chemical compound CCCCCCCCCCCCSCCO ZPIRWAHWDCHWLM-UHFFFAOYSA-N 0.000 description 4
• RXFCIXRFAJRBSG-UHFFFAOYSA-N 3,2,3-tetramine Chemical compound NCCCNCCNCCCN RXFCIXRFAJRBSG-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
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• 229920000877 Melamine resin Polymers 0.000 description 4
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
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• ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 4
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• 230000000996 additive effect Effects 0.000 description 4
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• 125000004183 alkoxy alkyl group Chemical group 0.000 description 4
• 125000004453 alkoxycarbonyl group Chemical group 0.000 description 4
• 125000005037 alkyl phenyl group Chemical group 0.000 description 4
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• QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 4
• 239000012964 benzotriazole Substances 0.000 description 4
• 125000005518 carboxamido group Chemical group 0.000 description 4
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• 239000000806 elastomer Substances 0.000 description 4
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• XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 4
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• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 4
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• 238000002156 mixing Methods 0.000 description 4
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• 150000007513 acids Chemical class 0.000 description 3
• 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 3
• 125000004423 acyloxy group Chemical group 0.000 description 3
• 125000005250 alkyl acrylate group Chemical group 0.000 description 3
• 229920001585 atactic polymer Polymers 0.000 description 3
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