TWI385204B - 光致變色系統的穩定 - Google Patents
光致變色系統的穩定 Download PDFInfo
- Publication number
- TWI385204B TWI385204B TW093129170A TW93129170A TWI385204B TW I385204 B TWI385204 B TW I385204B TW 093129170 A TW093129170 A TW 093129170A TW 93129170 A TW93129170 A TW 93129170A TW I385204 B TWI385204 B TW I385204B
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- Taiwan
- Prior art keywords
- group
- carbon atoms
- alkyl
- phenyl
- groups
- Prior art date
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- 230000006641 stabilisation Effects 0.000 title description 2
- 238000011105 stabilization Methods 0.000 title description 2
- -1 2,2,6,6-tetramethylpiperidinyl Chemical group 0.000 claims description 227
- 125000004432 carbon atom Chemical group C* 0.000 claims description 170
- 125000000217 alkyl group Chemical group 0.000 claims description 143
- 229910052739 hydrogen Inorganic materials 0.000 claims description 78
- 239000000203 mixture Substances 0.000 claims description 75
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 74
- 150000001875 compounds Chemical class 0.000 claims description 73
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 73
- 239000001257 hydrogen Substances 0.000 claims description 69
- 125000002947 alkylene group Chemical group 0.000 claims description 59
- 229920000642 polymer Polymers 0.000 claims description 59
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 52
- 150000002431 hydrogen Chemical class 0.000 claims description 49
- 125000003118 aryl group Chemical group 0.000 claims description 47
- 229920001577 copolymer Polymers 0.000 claims description 40
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 38
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 29
- 239000006096 absorbing agent Substances 0.000 claims description 28
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 27
- 125000003342 alkenyl group Chemical group 0.000 claims description 27
- 150000001412 amines Chemical class 0.000 claims description 27
- 125000003545 alkoxy group Chemical group 0.000 claims description 26
- 229910052736 halogen Inorganic materials 0.000 claims description 26
- 239000000654 additive Substances 0.000 claims description 25
- 229910052799 carbon Inorganic materials 0.000 claims description 25
- 150000002367 halogens Chemical class 0.000 claims description 24
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 20
- 239000000126 substance Substances 0.000 claims description 20
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 17
- 239000003381 stabilizer Substances 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 14
- 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 13
- 229920000728 polyester Polymers 0.000 claims description 13
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 12
- 239000004743 Polypropylene Substances 0.000 claims description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 11
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 11
- 125000004464 hydroxyphenyl group Chemical group 0.000 claims description 11
- 229920000139 polyethylene terephthalate Polymers 0.000 claims description 11
- 239000005020 polyethylene terephthalate Substances 0.000 claims description 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- 239000004417 polycarbonate Substances 0.000 claims description 10
- 239000005038 ethylene vinyl acetate Substances 0.000 claims description 9
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 claims description 9
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 8
- 230000000996 additive effect Effects 0.000 claims description 8
- 239000004611 light stabiliser Substances 0.000 claims description 8
- 239000011159 matrix material Substances 0.000 claims description 8
- 125000001624 naphthyl group Chemical group 0.000 claims description 8
- 229920001155 polypropylene Polymers 0.000 claims description 8
- 239000004698 Polyethylene Substances 0.000 claims description 7
- 239000003963 antioxidant agent Substances 0.000 claims description 7
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- 229920000515 polycarbonate Polymers 0.000 claims description 7
- 229920000573 polyethylene Polymers 0.000 claims description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 229920000098 polyolefin Polymers 0.000 claims description 6
- 229920002554 vinyl polymer Polymers 0.000 claims description 6
- 239000004793 Polystyrene Substances 0.000 claims description 5
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 5
- 125000002757 morpholinyl group Chemical group 0.000 claims description 5
- 229920002223 polystyrene Polymers 0.000 claims description 5
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 125000004122 cyclic group Chemical group 0.000 claims description 4
- 125000003700 epoxy group Chemical group 0.000 claims description 4
- 239000003063 flame retardant Substances 0.000 claims description 4
- 150000002430 hydrocarbons Chemical group 0.000 claims description 4
- 230000003287 optical effect Effects 0.000 claims description 4
- 229920000058 polyacrylate Polymers 0.000 claims description 4
- 230000005855 radiation Effects 0.000 claims description 4
- 229910052727 yttrium Inorganic materials 0.000 claims description 4
- KYNSBQPICQTCGU-UHFFFAOYSA-N Benzopyrane Chemical compound C1=CC=C2C=CCOC2=C1 KYNSBQPICQTCGU-UHFFFAOYSA-N 0.000 claims description 3
- 239000004372 Polyvinyl alcohol Substances 0.000 claims description 3
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- 229920002678 cellulose Polymers 0.000 claims description 3
- 238000000576 coating method Methods 0.000 claims description 3
- 125000006612 decyloxy group Chemical group 0.000 claims description 3
- 239000000945 filler Substances 0.000 claims description 3
- 125000001188 haloalkyl group Chemical group 0.000 claims description 3
- 229920005669 high impact polystyrene Polymers 0.000 claims description 3
- 239000004797 high-impact polystyrene Substances 0.000 claims description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
- XMGMFRIEKMMMSU-UHFFFAOYSA-N phenylmethylbenzene Chemical group C=1C=CC=CC=1[C]C1=CC=CC=C1 XMGMFRIEKMMMSU-UHFFFAOYSA-N 0.000 claims description 3
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 claims description 3
- 125000003386 piperidinyl group Chemical group 0.000 claims description 3
- 229920003229 poly(methyl methacrylate) Polymers 0.000 claims description 3
- 229920002451 polyvinyl alcohol Polymers 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- RSPCKAHMRANGJZ-UHFFFAOYSA-N thiohydroxylamine Chemical group SN RSPCKAHMRANGJZ-UHFFFAOYSA-N 0.000 claims description 3
- 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 description 2
- MJPPGVVIDGQOQT-UHFFFAOYSA-N 2-bromo-5-(2-bromo-2-nitroethenyl)furan Chemical compound [O-][N+](=O)C(Br)=CC1=CC=C(Br)O1 MJPPGVVIDGQOQT-UHFFFAOYSA-N 0.000 claims description 2
- JQXYBDVZAUEPDL-UHFFFAOYSA-N 2-methylidene-5-phenylpent-4-enoic acid Chemical compound OC(=O)C(=C)CC=CC1=CC=CC=C1 JQXYBDVZAUEPDL-UHFFFAOYSA-N 0.000 claims description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 2
- 241000237858 Gastropoda Species 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000005264 aryl amine group Chemical group 0.000 claims description 2
- LCIYFINKFGDAHD-UHFFFAOYSA-N azepane;3-nitrobenzoic acid Chemical compound C1CCCNCC1.OC(=O)C1=CC=CC([N+]([O-])=O)=C1 LCIYFINKFGDAHD-UHFFFAOYSA-N 0.000 claims description 2
- 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000002619 bicyclic group Chemical group 0.000 claims description 2
- QYMGIIIPAFAFRX-UHFFFAOYSA-N butyl prop-2-enoate;ethene Chemical compound C=C.CCCCOC(=O)C=C QYMGIIIPAFAFRX-UHFFFAOYSA-N 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 239000011248 coating agent Substances 0.000 claims description 2
- 229920006245 ethylene-butyl acrylate Polymers 0.000 claims description 2
- 238000005562 fading Methods 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- 239000003607 modifier Substances 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
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 claims description 2
- 239000004926 polymethyl methacrylate Substances 0.000 claims description 2
- SCUZVMOVTVSBLE-UHFFFAOYSA-N prop-2-enenitrile;styrene Chemical compound C=CC#N.C=CC1=CC=CC=C1 SCUZVMOVTVSBLE-UHFFFAOYSA-N 0.000 claims description 2
- 230000000087 stabilizing effect Effects 0.000 claims description 2
- 229920000638 styrene acrylonitrile Polymers 0.000 claims description 2
- 150000001656 butanoic acid esters Chemical class 0.000 claims 1
- 238000005352 clarification Methods 0.000 claims 1
- 239000002516 radical scavenger Substances 0.000 claims 1
- 125000003396 thiol group Chemical group [H]S* 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
- 239000000975 dye Substances 0.000 description 19
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 19
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 15
- 239000004615 ingredient Substances 0.000 description 15
- 229920000768 polyamine Polymers 0.000 description 15
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 15
- 239000000463 material Substances 0.000 description 13
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 12
- 239000005977 Ethylene Substances 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 11
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 11
- 239000000460 chlorine Substances 0.000 description 11
- 229910052801 chlorine Inorganic materials 0.000 description 11
- 150000002148 esters Chemical class 0.000 description 11
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 10
- 239000007983 Tris buffer Substances 0.000 description 10
- 150000001721 carbon Chemical group 0.000 description 10
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 10
- 239000011737 fluorine Substances 0.000 description 10
- 229910052731 fluorine Inorganic materials 0.000 description 10
- MEMWNTAFSYIKSU-UHFFFAOYSA-N pyran Chemical compound O1C=CC=C=C1 MEMWNTAFSYIKSU-UHFFFAOYSA-N 0.000 description 10
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 9
- 239000005062 Polybutadiene Substances 0.000 description 9
- 239000004721 Polyphenylene oxide Substances 0.000 description 9
- BJFLSHMHTPAZHO-UHFFFAOYSA-N benzotriazole Chemical compound [CH]1C=CC=C2N=NN=C21 BJFLSHMHTPAZHO-UHFFFAOYSA-N 0.000 description 9
- 239000012964 benzotriazole Substances 0.000 description 9
- 239000010408 film Substances 0.000 description 9
- 229920001684 low density polyethylene Polymers 0.000 description 9
- 239000004702 low-density polyethylene Substances 0.000 description 9
- 229920002857 polybutadiene Polymers 0.000 description 9
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 9
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 8
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 8
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 8
- 125000003277 amino group Chemical group 0.000 description 8
- 239000004305 biphenyl Substances 0.000 description 8
- 150000001993 dienes Chemical class 0.000 description 8
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 8
- 239000000178 monomer Substances 0.000 description 8
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 8
- 238000006116 polymerization reaction Methods 0.000 description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 7
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 7
- 125000003710 aryl alkyl group Chemical group 0.000 description 7
- 239000002585 base 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
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 7
- 239000004700 high-density polyethylene Substances 0.000 description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 7
- 229920006324 polyoxymethylene Polymers 0.000 description 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 6
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 6
- GHKOFFNLGXMVNJ-UHFFFAOYSA-N Didodecyl thiobispropanoate Chemical compound CCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCC GHKOFFNLGXMVNJ-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
- 125000002252 acyl group Chemical group 0.000 description 6
- 125000001931 aliphatic group Chemical group 0.000 description 6
- 235000006708 antioxidants Nutrition 0.000 description 6
- PXXJHWLDUBFPOL-UHFFFAOYSA-N benzamidine Chemical group NC(=N)C1=CC=CC=C1 PXXJHWLDUBFPOL-UHFFFAOYSA-N 0.000 description 6
- FQUNFJULCYSSOP-UHFFFAOYSA-N bisoctrizole Chemical compound N1=C2C=CC=CC2=NN1C1=CC(C(C)(C)CC(C)(C)C)=CC(CC=2C(=C(C=C(C=2)C(C)(C)CC(C)(C)C)N2N=C3C=CC=CC3=N2)O)=C1O FQUNFJULCYSSOP-UHFFFAOYSA-N 0.000 description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
- 229910052794 bromium Inorganic materials 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 239000007859 condensation product Substances 0.000 description 6
- 229920001971 elastomer Polymers 0.000 description 6
- 125000005843 halogen group Chemical group 0.000 description 6
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- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 6
- 229920003023 plastic Polymers 0.000 description 6
- 239000004033 plastic Substances 0.000 description 6
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- 229920000915 polyvinyl chloride Polymers 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 5
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 5
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 5
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
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- 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
- 125000004430 oxygen atom Chemical group O* 0.000 description 5
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 5
- 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
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 5
- 229920001707 polybutylene terephthalate Polymers 0.000 description 5
- 229920000570 polyether Polymers 0.000 description 5
- 229920006380 polyphenylene oxide Polymers 0.000 description 5
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- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 5
- 235000013772 propylene glycol Nutrition 0.000 description 5
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 5
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 125000006527 (C1-C5) alkyl group Chemical group 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
- IHWDSEPNZDYMNF-UHFFFAOYSA-N 1H-indol-2-amine Chemical class C1=CC=C2NC(N)=CC2=C1 IHWDSEPNZDYMNF-UHFFFAOYSA-N 0.000 description 4
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 4
- RXFCIXRFAJRBSG-UHFFFAOYSA-N 3,2,3-tetramine Chemical compound NCCCNCCNCCCN RXFCIXRFAJRBSG-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
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 229920000877 Melamine resin Polymers 0.000 description 4
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- 239000004299 sodium benzoate Substances 0.000 description 1
- 229940074404 sodium succinate Drugs 0.000 description 1
- ZDQYSKICYIVCPN-UHFFFAOYSA-L sodium succinate (anhydrous) Chemical compound [Na+].[Na+].[O-]C(=O)CCC([O-])=O ZDQYSKICYIVCPN-UHFFFAOYSA-L 0.000 description 1
- IJRHDFLHUATAOS-DPMBMXLASA-N sodium;(z,12r)-12-hydroxyoctadec-9-enoic acid Chemical compound [Na+].CCCCCC[C@@H](O)C\C=C/CCCCCCCC(O)=O IJRHDFLHUATAOS-DPMBMXLASA-N 0.000 description 1
- 239000006076 specific stabilizer Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical group O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 229920005613 synthetic organic polymer Polymers 0.000 description 1
- 150000000000 tetracarboxylic acids Chemical class 0.000 description 1
- NZNAAUDJKMURFU-UHFFFAOYSA-N tetrakis(2,2,6,6-tetramethylpiperidin-4-yl) butane-1,2,3,4-tetracarboxylate Chemical compound C1C(C)(C)NC(C)(C)CC1OC(=O)CC(C(=O)OC1CC(C)(C)NC(C)(C)C1)C(C(=O)OC1CC(C)(C)NC(C)(C)C1)CC(=O)OC1CC(C)(C)NC(C)(C)C1 NZNAAUDJKMURFU-UHFFFAOYSA-N 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- YONPGGFAJWQGJC-UHFFFAOYSA-K titanium(iii) chloride Chemical compound Cl[Ti](Cl)Cl YONPGGFAJWQGJC-UHFFFAOYSA-K 0.000 description 1
- 229960000984 tocofersolan Drugs 0.000 description 1
- AOBORMOPSGHCAX-DGHZZKTQSA-N tocofersolan Chemical compound OCCOC(=O)CCC(=O)OC1=C(C)C(C)=C2O[C@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C AOBORMOPSGHCAX-DGHZZKTQSA-N 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- 235000019149 tocopherols Nutrition 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 150000003628 tricarboxylic acids Chemical class 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005590 trimellitic acid group Chemical group 0.000 description 1
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- CNUJLMSKURPSHE-UHFFFAOYSA-N trioctadecyl phosphite Chemical compound CCCCCCCCCCCCCCCCCCOP(OCCCCCCCCCCCCCCCCCC)OCCCCCCCCCCCCCCCCCC CNUJLMSKURPSHE-UHFFFAOYSA-N 0.000 description 1
- 229940036248 turpentine Drugs 0.000 description 1
- 229920001862 ultra low molecular weight polyethylene Polymers 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 229920001866 very low density polyethylene Polymers 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
- 150000007934 α,β-unsaturated carboxylic acids Chemical class 0.000 description 1
- 239000002076 α-tocopherol Substances 0.000 description 1
- 235000004835 α-tocopherol Nutrition 0.000 description 1
- 239000011590 β-tocopherol Substances 0.000 description 1
- 235000007680 β-tocopherol Nutrition 0.000 description 1
- 239000002478 γ-tocopherol Substances 0.000 description 1
- QUEDXNHFTDJVIY-UHFFFAOYSA-N γ-tocopherol Chemical class OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-UHFFFAOYSA-N 0.000 description 1
- QUEDXNHFTDJVIY-DQCZWYHMSA-N γ-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-DQCZWYHMSA-N 0.000 description 1
- 239000002446 δ-tocopherol Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K9/00—Tenebrescent materials, i.e. materials for which the range of wavelengths for energy absorption is changed as a result of excitation by some form of energy
- C09K9/02—Organic tenebrescent materials
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
- C08K5/3477—Six-membered rings
- C08K5/3492—Triazines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP03103587 | 2003-09-29 |
Publications (2)
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|---|---|
| TW200512281A TW200512281A (en) | 2005-04-01 |
| TWI385204B true TWI385204B (zh) | 2013-02-11 |
Family
ID=34384662
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW093129170A TWI385204B (zh) | 2003-09-29 | 2004-09-27 | 光致變色系統的穩定 |
Country Status (12)
| Country | Link |
|---|---|
| US (2) | US20070064195A1 (enExample) |
| EP (1) | EP1709114A1 (enExample) |
| JP (1) | JP4764822B2 (enExample) |
| KR (1) | KR101099452B1 (enExample) |
| CN (1) | CN1860167B (enExample) |
| AU (1) | AU2004275997B2 (enExample) |
| BR (1) | BRPI0414852A (enExample) |
| CA (1) | CA2538031C (enExample) |
| MY (1) | MY149850A (enExample) |
| RU (1) | RU2405793C2 (enExample) |
| TW (1) | TWI385204B (enExample) |
| WO (1) | WO2005030856A1 (enExample) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102005041952A1 (de) * | 2005-09-03 | 2007-03-08 | Bayer Materialscience Ag | Zusammensetzungen enthaltend Polycarbonat und neuartige UV-Absorber |
| ATE406413T1 (de) * | 2006-01-27 | 2008-09-15 | Ems Chemie Ag | Photochrome formmassen und daraus hergestellte gegenstände |
| CN100389168C (zh) * | 2006-04-04 | 2008-05-21 | 吉林大学 | 基底诱导同一染料分子发不同颜色荧光的方法 |
| US7667285B2 (en) | 2006-12-14 | 2010-02-23 | Motorola, Inc. | Printed electronic substrate havine photochromic barrier layer |
| BRPI0807143A2 (pt) * | 2007-02-06 | 2014-04-15 | Basell Polyolefine Gmbh | Itens fotocrômicos flexíveis e/ou rígidos para embalar itens sensíveis à luz |
| DE102007011069A1 (de) | 2007-03-07 | 2008-09-11 | Bayer Materialscience Ag | Polycarbonatzusammensetzung enthaltend UV-Absorber |
| EP2022820B1 (de) | 2007-07-25 | 2016-08-24 | Ems-Patent Ag | Photochrome formmassen und daraus hergestellte gegenstände |
| US8609300B2 (en) * | 2009-06-25 | 2013-12-17 | Sabic Innovative Plastics Ip B.V. | Method of making holographic recording materials and articles formed thereby |
| JP2013035877A (ja) * | 2009-12-10 | 2013-02-21 | Tokuyama Corp | フォトクロミック組成物 |
| WO2011139319A1 (en) * | 2010-05-03 | 2011-11-10 | Kent State University | Smart photochromic chiral nematic liquid crystal window |
| US8715887B2 (en) | 2010-07-30 | 2014-05-06 | Sabic Innovative Plastics Ip B.V. | Complex holograms, method of making and using complex holograms |
| EP2447236A1 (de) | 2010-10-12 | 2012-05-02 | Bayer MaterialScience AG | Spezielle UV-Absorber für härtbare UV-Schutz Beschichtungen |
| US9187668B2 (en) | 2011-10-27 | 2015-11-17 | Chromatic Technologies, Inc. | Photochromic inks |
| US8871424B2 (en) * | 2012-01-20 | 2014-10-28 | Cryovac, Inc. | Laser imageable polyolefin film |
| CN102898791A (zh) * | 2012-09-21 | 2013-01-30 | 江西科为薄膜新型材料有限公司 | 具有变色功能的pet薄膜 |
| JP5693689B2 (ja) * | 2012-09-24 | 2015-04-01 | 富士フイルム株式会社 | セルロースアシレートフィルム、それを用いた偏光板および液晶表示装置 |
| CN103275509A (zh) * | 2013-06-21 | 2013-09-04 | 苏州新区特氟龙塑料制品厂 | 一种变色塑料 |
| CN103911877B (zh) * | 2014-04-17 | 2016-01-13 | 傅科杰 | 一种用于纺织面料的变色剂 |
| US10253164B2 (en) * | 2014-05-15 | 2019-04-09 | Basf Se | Highly effective stabilizer |
| WO2017008974A1 (en) | 2015-07-14 | 2017-01-19 | Unilever Plc | Antimicrobial composition |
| WO2017047745A1 (ja) * | 2015-09-16 | 2017-03-23 | 三井化学株式会社 | 光学材料用重合性組成物、該組成物から得られる光学材料およびプラスチックレンズ |
| KR102063056B1 (ko) * | 2016-02-01 | 2020-01-07 | 주식회사 엘지화학 | 점착제 조성물, 그 조성물의 경화물을 포함하는 봉지층을 포함하는 태양전지용 봉지재 시트 및 상기 봉지재 시트를 포함하는 태양전지 모듈 |
| CN107828407A (zh) * | 2017-11-30 | 2018-03-23 | 天津工业大学 | 一种固态囊芯的变色微纳胶囊及其制备方法 |
| TWI754807B (zh) * | 2019-04-10 | 2022-02-11 | 財團法人紡織產業綜合研究所 | 聚酯光變色組成物以及聚酯光變色纖維的製備方法 |
| TWI754918B (zh) * | 2020-04-20 | 2022-02-11 | 財團法人紡織產業綜合研究所 | 光變色聚丙烯纖維及其製備方法 |
| TWI798707B (zh) | 2021-05-28 | 2023-04-11 | 財團法人紡織產業綜合研究所 | 光變色阻熱纖維和其製備方法 |
| CN113416516B (zh) * | 2021-06-18 | 2022-11-11 | 北京天山新材料技术有限公司 | 丙烯酸酯厌氧胶、用于形成其的组合物及应用 |
| WO2025225708A1 (ja) * | 2024-04-26 | 2025-10-30 | 株式会社クラレ | フォトクロミックフィルム、樹脂膜、及び積層体 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997040409A1 (en) * | 1996-04-19 | 1997-10-30 | Transitions Optical, Inc. | Photochromic naphthopyran compositions of improved fatigue resistance |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3485764A (en) * | 1964-05-22 | 1969-12-23 | American Cyanamid Co | Polymeric photochromic compositions stabilized with ultraviolet light absorbers |
| US5200116A (en) * | 1990-07-23 | 1993-04-06 | Ppg Industries, Inc. | Photochromic chromene compounds |
| KR100187320B1 (ko) * | 1991-02-21 | 1999-04-01 | 월터 클리웨인 | 광, 산소 및 열에 대해 안정화된 도료 |
| JPH06184355A (ja) * | 1992-12-16 | 1994-07-05 | Sumitomo Chem Co Ltd | フォトクロミック性能を有する樹脂組成物 |
| US5556973A (en) * | 1994-07-27 | 1996-09-17 | Ciba-Geigy Corporation | Red-shifted tris-aryl-s-triazines and compositions stabilized therewith |
| EP1213283B1 (en) * | 1995-03-15 | 2009-04-29 | Ciba Holding Inc. | Biphenyl-substituted triazines as light stabilisers |
| US6255483B1 (en) * | 1995-03-15 | 2001-07-03 | Ciba Specialty Chemicals Corporation | Biphenyl-substituted triazines |
| BE1012529A3 (fr) * | 1996-09-13 | 2000-12-05 | Ciba Sc Holding Ag | Melange de triaryltriazines et son utilisation pour la stabilisation de materiaux organiques. |
| ES2205268T3 (es) * | 1996-11-20 | 2004-05-01 | Ciba Specialty Chemicals Holding Inc. | Derivados de triacina simetricos. |
| IT1292461B1 (it) * | 1997-07-03 | 1999-02-08 | Great Lakes Chemical Italia | Composti fotocromatici,procedimento per la loro preparazione e loro utilizzo in materiali polimerici |
| ITMI980366A1 (it) * | 1998-02-25 | 1999-08-25 | Ciba Spec Chem Spa | Preparazione di eteri amminici stericamente impediti |
| GB2382348B (en) | 2000-07-26 | 2004-04-21 | Ciba Sc Holding Ag | Polyolefin film for protected environment |
| CO5231248A1 (es) * | 2000-07-26 | 2002-12-27 | Ciba Sc Holding Ag | Articulos transparentes de polimero de baja consistencia |
| US6547390B1 (en) * | 2000-09-11 | 2003-04-15 | Exxene Corporation | Top stabilized photochromic lens system |
| JP3922873B2 (ja) * | 2000-09-29 | 2007-05-30 | 株式会社トクヤマ | 硬化性組成物 |
| ZA200301683B (en) * | 2002-03-04 | 2004-09-06 | Ciba Sc Holding Ag | Synergistic combinations of UV absorbers for pigmented polyolefins. |
-
2004
- 2004-09-17 MY MYPI20043803A patent/MY149850A/en unknown
- 2004-09-20 US US10/572,154 patent/US20070064195A1/en not_active Abandoned
- 2004-09-20 CN CN2004800282267A patent/CN1860167B/zh not_active Expired - Fee Related
- 2004-09-20 KR KR1020067005755A patent/KR101099452B1/ko not_active Expired - Fee Related
- 2004-09-20 RU RU2006114602/05A patent/RU2405793C2/ru not_active IP Right Cessation
- 2004-09-20 JP JP2006530247A patent/JP4764822B2/ja not_active Expired - Fee Related
- 2004-09-20 BR BRPI0414852-5A patent/BRPI0414852A/pt not_active Application Discontinuation
- 2004-09-20 CA CA2538031A patent/CA2538031C/en not_active Expired - Fee Related
- 2004-09-20 EP EP04787170A patent/EP1709114A1/en not_active Withdrawn
- 2004-09-20 WO PCT/EP2004/052238 patent/WO2005030856A1/en not_active Ceased
- 2004-09-20 AU AU2004275997A patent/AU2004275997B2/en not_active Ceased
- 2004-09-27 TW TW093129170A patent/TWI385204B/zh not_active IP Right Cessation
-
2009
- 2009-07-24 US US12/508,641 patent/US8262945B2/en not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997040409A1 (en) * | 1996-04-19 | 1997-10-30 | Transitions Optical, Inc. | Photochromic naphthopyran compositions of improved fatigue resistance |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2538031A1 (en) | 2005-04-07 |
| JP2007507569A (ja) | 2007-03-29 |
| US8262945B2 (en) | 2012-09-11 |
| RU2405793C2 (ru) | 2010-12-10 |
| KR20060090811A (ko) | 2006-08-16 |
| MY149850A (en) | 2013-10-31 |
| WO2005030856A8 (en) | 2006-08-03 |
| US20090289236A1 (en) | 2009-11-26 |
| BRPI0414852A (pt) | 2006-11-21 |
| RU2006114602A (ru) | 2007-11-20 |
| AU2004275997A1 (en) | 2005-04-07 |
| WO2005030856A1 (en) | 2005-04-07 |
| CN1860167B (zh) | 2011-01-26 |
| AU2004275997B2 (en) | 2010-07-22 |
| TW200512281A (en) | 2005-04-01 |
| CA2538031C (en) | 2015-03-17 |
| JP4764822B2 (ja) | 2011-09-07 |
| CN1860167A (zh) | 2006-11-08 |
| EP1709114A1 (en) | 2006-10-11 |
| US20070064195A1 (en) | 2007-03-22 |
| KR101099452B1 (ko) | 2011-12-28 |
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| MM4A | Annulment or lapse of patent due to non-payment of fees |