PT1896550E - Meios eletrocrómicos estabilizados - Google Patents
Meios eletrocrómicos estabilizados Download PDFInfo
- Publication number
- PT1896550E PT1896550E PT67773820T PT06777382T PT1896550E PT 1896550 E PT1896550 E PT 1896550E PT 67773820 T PT67773820 T PT 67773820T PT 06777382 T PT06777382 T PT 06777382T PT 1896550 E PT1896550 E PT 1896550E
- Authority
- PT
- Portugal
- Prior art keywords
- hydroxy
- tetramethyl
- hydroxypiperidinium
- citrate
- carbon atoms
- Prior art date
Links
- 239000000203 mixture Substances 0.000 claims abstract description 46
- 150000002443 hydroxylamines Chemical class 0.000 claims abstract description 33
- 239000000654 additive Substances 0.000 claims abstract description 24
- 238000000034 method Methods 0.000 claims abstract description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 124
- 125000000217 alkyl group Chemical group 0.000 claims description 102
- -1 sulphoxides Chemical class 0.000 claims description 70
- 239000002904 solvent Substances 0.000 claims description 47
- 150000001875 compounds Chemical class 0.000 claims description 37
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 30
- CSGAUKGQUCHWDP-UHFFFAOYSA-N 1-hydroxy-2,2,6,6-tetramethylpiperidin-4-ol Chemical compound CC1(C)CC(O)CC(C)(C)N1O CSGAUKGQUCHWDP-UHFFFAOYSA-N 0.000 claims description 23
- KMEUSKGEUADGET-UHFFFAOYSA-N 1-hydroxy-2,2,6,6-tetramethylpiperidin-4-one Chemical compound CC1(C)CC(=O)CC(C)(C)N1O KMEUSKGEUADGET-UHFFFAOYSA-N 0.000 claims description 22
- YYTYIUAYFBFKHX-UHFFFAOYSA-N n-(1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl)acetamide Chemical compound CC(=O)NC1CC(C)(C)N(O)C(C)(C)C1 YYTYIUAYFBFKHX-UHFFFAOYSA-N 0.000 claims description 19
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 18
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 18
- 239000007983 Tris buffer Substances 0.000 claims description 17
- CRGBPDJWOLULDY-UHFFFAOYSA-N (1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl) acetate Chemical compound CC(=O)OC1CC(C)(C)N(O)C(C)(C)C1 CRGBPDJWOLULDY-UHFFFAOYSA-N 0.000 claims description 15
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 15
- 230000000996 additive effect Effects 0.000 claims description 15
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims description 12
- QPCDCPDFJACHGM-UHFFFAOYSA-K pentetate(3-) Chemical compound OC(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CCN(CC(O)=O)CC([O-])=O QPCDCPDFJACHGM-UHFFFAOYSA-K 0.000 claims description 11
- 229940124543 ultraviolet light absorber Drugs 0.000 claims description 11
- XLXPBRSBVHQNAU-UHFFFAOYSA-N 1-hydroxypiperidin-1-ium 2-hydroxypropane-1,2,3-tricarboxylate Chemical compound C(CC(O)(C(=O)[O-])CC(=O)[O-])(=O)[O-].O[NH+]1CCCCC1.O[NH+]1CCCCC1.O[NH+]1CCCCC1 XLXPBRSBVHQNAU-UHFFFAOYSA-N 0.000 claims description 10
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 10
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 claims description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 239000012965 benzophenone Substances 0.000 claims description 8
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 claims description 8
- 150000008366 benzophenones Chemical class 0.000 claims description 7
- 229920005862 polyol Polymers 0.000 claims description 7
- 150000003077 polyols Chemical class 0.000 claims description 7
- QDNPLNOHUNPYHZ-UHFFFAOYSA-N 1-hydroxy-2,2,6,6-tetramethyl-4-propoxypiperidine Chemical compound CCCOC1CC(C)(C)N(O)C(C)(C)C1 QDNPLNOHUNPYHZ-UHFFFAOYSA-N 0.000 claims description 6
- KRNWYBIEWUXCOB-UHFFFAOYSA-N 1-hydroxy-4-methoxy-2,2,6,6-tetramethylpiperidine Chemical compound COC1CC(C)(C)N(O)C(C)(C)C1 KRNWYBIEWUXCOB-UHFFFAOYSA-N 0.000 claims description 6
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 claims description 6
- ZCILGMFPJBRCNO-UHFFFAOYSA-N 4-phenyl-2H-benzotriazol-5-ol Chemical class OC1=CC=C2NN=NC2=C1C1=CC=CC=C1 ZCILGMFPJBRCNO-UHFFFAOYSA-N 0.000 claims description 6
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 claims description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 6
- 150000001408 amides Chemical class 0.000 claims description 6
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 claims description 6
- GAEKPEKOJKCEMS-UHFFFAOYSA-N gamma-valerolactone Chemical compound CC1CCC(=O)O1 GAEKPEKOJKCEMS-UHFFFAOYSA-N 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 claims description 6
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 6
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 6
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 claims description 6
- GAOMYAAENOAIMT-UHFFFAOYSA-N 1-(1-hydroxy-2,2,6,6-tetramethylpiperidin-1-ium-4-yl)oxy-3-methoxypropan-2-ol;acetate Chemical compound CC([O-])=O.COCC(O)COC1CC(C)(C)[NH+](O)C(C)(C)C1 GAOMYAAENOAIMT-UHFFFAOYSA-N 0.000 claims description 5
- TXXNVPVRPSACBM-UHFFFAOYSA-N 2-hydroxypropane-1,2,3-tricarboxylic acid;1-hydroxy-2,2,6,6-tetramethylpiperidin-4-ol Chemical compound CC1(C)CC(O)CC(C)(C)[NH+]1O.CC1(C)CC(O)CC(C)(C)[NH+]1O.CC1(C)CC(O)CC(C)(C)[NH+]1O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O TXXNVPVRPSACBM-UHFFFAOYSA-N 0.000 claims description 5
- FPPLREPCQJZDAQ-UHFFFAOYSA-N 2-methylpentanedinitrile Chemical compound N#CC(C)CCC#N FPPLREPCQJZDAQ-UHFFFAOYSA-N 0.000 claims description 5
- WSGYTJNNHPZFKR-UHFFFAOYSA-N 3-hydroxypropanenitrile Chemical compound OCCC#N WSGYTJNNHPZFKR-UHFFFAOYSA-N 0.000 claims description 5
- CMJLMPKFQPJDKP-UHFFFAOYSA-N 3-methylthiolane 1,1-dioxide Chemical compound CC1CCS(=O)(=O)C1 CMJLMPKFQPJDKP-UHFFFAOYSA-N 0.000 claims description 5
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 claims description 5
- ZTOMUSMDRMJOTH-UHFFFAOYSA-N glutaronitrile Chemical compound N#CCCCC#N ZTOMUSMDRMJOTH-UHFFFAOYSA-N 0.000 claims description 5
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 claims description 5
- 150000002576 ketones Chemical class 0.000 claims description 5
- 150000002825 nitriles Chemical class 0.000 claims description 5
- 229940116351 sebacate Drugs 0.000 claims description 5
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 claims description 5
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims description 5
- 150000003457 sulfones Chemical class 0.000 claims description 5
- ZZXUZKXVROWEIF-UHFFFAOYSA-N 1,2-butylene carbonate Chemical compound CCC1COC(=O)O1 ZZXUZKXVROWEIF-UHFFFAOYSA-N 0.000 claims description 4
- DOIAXYYFHLZFJT-UHFFFAOYSA-N 1-hydroxy-2,2,6,6-tetramethyl-4-propoxypiperidin-1-ium;acetate Chemical compound CC([O-])=O.CCCOC1CC(C)(C)[NH+](O)C(C)(C)C1 DOIAXYYFHLZFJT-UHFFFAOYSA-N 0.000 claims description 4
- OMLXPSWZYGQPCR-UHFFFAOYSA-N 1-hydroxy-2,2,6,6-tetramethylpiperidin-1-ium-4-one;acetate Chemical compound CC([O-])=O.CC1(C)CC(=O)CC(C)(C)[NH+]1O OMLXPSWZYGQPCR-UHFFFAOYSA-N 0.000 claims description 4
- NIPVMEKAVWIWRO-UHFFFAOYSA-N 1-hydroxy-4-methoxy-2,2,6,6-tetramethylpiperidin-1-ium;acetate Chemical compound CC([O-])=O.COC1CC(C)(C)[NH+](O)C(C)(C)C1 NIPVMEKAVWIWRO-UHFFFAOYSA-N 0.000 claims description 4
- SNJKFAANXLYUMC-UHFFFAOYSA-N 1-hydroxypiperidin-1-ium acetate Chemical compound ON1CCCCC1.C(C)(=O)O SNJKFAANXLYUMC-UHFFFAOYSA-N 0.000 claims description 4
- BNICBIMYAXBRQY-UHFFFAOYSA-N 1-hydroxypiperidine;hydrochloride Chemical compound [Cl-].O[NH+]1CCCCC1 BNICBIMYAXBRQY-UHFFFAOYSA-N 0.000 claims description 4
- IMNZCNLFZBWMDI-UHFFFAOYSA-N 2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate;1-hydroxy-2,2,6,6-tetramethylpiperidin-1-ium-4-ol Chemical compound CC1(C)CC(O)CC(C)(C)[NH+]1O.CC1(C)CC(O)CC(C)(C)[NH+]1O.CC1(C)CC(O)CC(C)(C)[NH+]1O.CC1(C)CC(O)CC(C)(C)[NH+]1O.[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O IMNZCNLFZBWMDI-UHFFFAOYSA-N 0.000 claims description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- 150000001735 carboxylic acids Chemical class 0.000 claims description 4
- 150000005676 cyclic carbonates Chemical class 0.000 claims description 4
- 125000004122 cyclic group Chemical group 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims description 4
- 229910052710 silicon Inorganic materials 0.000 claims description 4
- 239000010703 silicon Substances 0.000 claims description 4
- LWWWYUBIKPGGGT-UHFFFAOYSA-N 1-(1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl)oxy-3-methoxypropan-2-ol Chemical compound COCC(O)COC1CC(C)(C)N(O)C(C)(C)C1 LWWWYUBIKPGGGT-UHFFFAOYSA-N 0.000 claims description 3
- VXBXRPKTLUBAHQ-UHFFFAOYSA-N 2-[bis(carboxylatomethyl)amino]acetate;1-hydroxy-2,2,6,6-tetramethylpiperidin-1-ium-4-ol Chemical compound CC1(C)CC(O)CC(C)(C)[NH+]1O.CC1(C)CC(O)CC(C)(C)[NH+]1O.CC1(C)CC(O)CC(C)(C)[NH+]1O.[O-]C(=O)CN(CC([O-])=O)CC([O-])=O VXBXRPKTLUBAHQ-UHFFFAOYSA-N 0.000 claims description 3
- ZGDIZLYJGRHLDL-UHFFFAOYSA-N 2-[bis(carboxylatomethyl)amino]acetate;n-(1-hydroxy-2,2,6,6-tetramethylpiperidin-1-ium-4-yl)acetamide Chemical compound [O-]C(=O)CN(CC([O-])=O)CC([O-])=O.CC(=O)NC1CC(C)(C)[NH+](O)C(C)(C)C1.CC(=O)NC1CC(C)(C)[NH+](O)C(C)(C)C1.CC(=O)NC1CC(C)(C)[NH+](O)C(C)(C)C1 ZGDIZLYJGRHLDL-UHFFFAOYSA-N 0.000 claims description 3
- OMQHDIHZSDEIFH-UHFFFAOYSA-N 3-Acetyldihydro-2(3H)-furanone Chemical compound CC(=O)C1CCOC1=O OMQHDIHZSDEIFH-UHFFFAOYSA-N 0.000 claims description 3
- SCJBEZKWVYBIRT-UHFFFAOYSA-N CC1(C)CC(=O)CC(C)(C)[NH+]1O.CC1(C)CC(=O)CC(C)(C)[NH+]1O.CC1(C)CC(=O)CC(C)(C)[NH+]1O.[O-]C(=O)CN(CC([O-])=O)CC([O-])=O Chemical compound CC1(C)CC(=O)CC(C)(C)[NH+]1O.CC1(C)CC(=O)CC(C)(C)[NH+]1O.CC1(C)CC(=O)CC(C)(C)[NH+]1O.[O-]C(=O)CN(CC([O-])=O)CC([O-])=O SCJBEZKWVYBIRT-UHFFFAOYSA-N 0.000 claims description 3
- 150000001449 anionic compounds Chemical group 0.000 claims description 3
- 150000001450 anions Chemical class 0.000 claims description 3
- VEZXCJBBBCKRPI-UHFFFAOYSA-N beta-propiolactone Chemical compound O=C1CCO1 VEZXCJBBBCKRPI-UHFFFAOYSA-N 0.000 claims description 3
- BQGQSQPCMIWNFQ-UHFFFAOYSA-N carbonic acid;2-(oxiran-2-ylmethoxymethyl)oxirane Chemical class OC(O)=O.C1OC1COCC1CO1 BQGQSQPCMIWNFQ-UHFFFAOYSA-N 0.000 claims description 3
- 150000001768 cations Chemical class 0.000 claims description 3
- WBYWAXJHAXSJNI-UHFFFAOYSA-N cinnamic acid Chemical class OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 claims description 3
- 229940071106 ethylenediaminetetraacetate Drugs 0.000 claims description 3
- 125000005647 linker group Chemical group 0.000 claims description 3
- 150000002891 organic anions Chemical group 0.000 claims description 3
- 229960000380 propiolactone Drugs 0.000 claims description 3
- 150000003873 salicylate salts Chemical class 0.000 claims description 3
- IJVRPNIWWODHHA-UHFFFAOYSA-N 2-cyanoprop-2-enoic acid Chemical class OC(=O)C(=C)C#N IJVRPNIWWODHHA-UHFFFAOYSA-N 0.000 claims description 2
- FAAXXEHCRYLVDZ-UHFFFAOYSA-N 2-hydroxypropane-1,2,3-tricarboxylic acid;(1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl) acetate Chemical compound OC(=O)CC(O)(C([O-])=O)CC([O-])=O.CC(=O)OC1CC(C)(C)[NH+](O)C(C)(C)C1.CC(=O)OC1CC(C)(C)[NH+](O)C(C)(C)C1 FAAXXEHCRYLVDZ-UHFFFAOYSA-N 0.000 claims description 2
- YWBXOXPKPRNECI-UHFFFAOYSA-N 2-hydroxypropane-1,2,3-tricarboxylic acid;1-hydroxy-2,2,6,6-tetramethylpiperidin-4-ol Chemical compound CC1(C)CC(O)CC(C)(C)[NH+]1O.CC1(C)CC(O)CC(C)(C)[NH+]1O.OC(=O)CC(O)(C([O-])=O)CC([O-])=O YWBXOXPKPRNECI-UHFFFAOYSA-N 0.000 claims description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 2
- 150000001558 benzoic acid derivatives Chemical class 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
- 150000002531 isophthalic acids Chemical class 0.000 claims description 2
- 150000002690 malonic acid derivatives Chemical class 0.000 claims description 2
- 125000004043 oxo group Chemical group O=* 0.000 claims description 2
- 150000002989 phenols Chemical class 0.000 claims description 2
- RAIYODFGMLZUDF-UHFFFAOYSA-N piperidin-1-ium;acetate Chemical compound CC([O-])=O.C1CC[NH2+]CC1 RAIYODFGMLZUDF-UHFFFAOYSA-N 0.000 claims description 2
- 150000003504 terephthalic acids Chemical class 0.000 claims description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 2
- CMBOOIMONIXIMV-UHFFFAOYSA-K 1,1-dihydroxy-2,2,6,6-tetramethylpiperidin-1-ium;2-hydroxypropane-1,2,3-tricarboxylate Chemical compound CC1(C)CCCC(C)(C)[N+]1(O)O.CC1(C)CCCC(C)(C)[N+]1(O)O.CC1(C)CCCC(C)(C)[N+]1(O)O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O CMBOOIMONIXIMV-UHFFFAOYSA-K 0.000 claims 2
- RCWLUQYIUNVIQO-UHFFFAOYSA-N ON.O=N Chemical class ON.O=N RCWLUQYIUNVIQO-UHFFFAOYSA-N 0.000 claims 2
- ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical compound COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- PEJBSSCKFNBGFO-UHFFFAOYSA-L 2-(carboxymethyl)-2-hydroxybutanedioate;1,1-dihydroxy-2,2,6,6-tetramethylpiperidin-1-ium Chemical compound CC1(C)CCCC(C)(C)[N+]1(O)O.CC1(C)CCCC(C)(C)[N+]1(O)O.OC(=O)CC(O)(C([O-])=O)CC([O-])=O PEJBSSCKFNBGFO-UHFFFAOYSA-L 0.000 claims 1
- WQFZLUAKGBOQEN-UHFFFAOYSA-N 2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate;1-hydroxy-2,2,6,6-tetramethylpiperidin-1-ium-4-one Chemical compound CC1(C)CC(=O)CC(C)(C)[NH+]1O.CC1(C)CC(=O)CC(C)(C)[NH+]1O.CC1(C)CC(=O)CC(C)(C)[NH+]1O.CC1(C)CC(=O)CC(C)(C)[NH+]1O.[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O WQFZLUAKGBOQEN-UHFFFAOYSA-N 0.000 claims 1
- CAZAXTALZNYAGA-UHFFFAOYSA-N 2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate;n-(1-hydroxy-2,2,6,6-tetramethylpiperidin-1-ium-4-yl)acetamide Chemical compound CC(=O)NC1CC(C)(C)[NH+](O)C(C)(C)C1.CC(=O)NC1CC(C)(C)[NH+](O)C(C)(C)C1.CC(=O)NC1CC(C)(C)[NH+](O)C(C)(C)C1.CC(=O)NC1CC(C)(C)[NH+](O)C(C)(C)C1.[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O CAZAXTALZNYAGA-UHFFFAOYSA-N 0.000 claims 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 claims 1
- NZIPTDMFVXCSMQ-UHFFFAOYSA-N 2-hydroxypropane-1,2,3-tricarboxylate;n-(1-hydroxy-2,2,6,6-tetramethylpiperidin-1-ium-4-yl)acetamide Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.CC(=O)NC1CC(C)(C)[NH+](O)C(C)(C)C1.CC(=O)NC1CC(C)(C)[NH+](O)C(C)(C)C1.CC(=O)NC1CC(C)(C)[NH+](O)C(C)(C)C1 NZIPTDMFVXCSMQ-UHFFFAOYSA-N 0.000 claims 1
- SFPQDYSOPQHZAQ-UHFFFAOYSA-N 2-methoxypropanenitrile Chemical compound COC(C)C#N SFPQDYSOPQHZAQ-UHFFFAOYSA-N 0.000 claims 1
- XCKPLVGWGCWOMD-YYEYMFTQSA-N 3-[[(2r,3r,4s,5r,6r)-6-[(2s,3s,4r,5r)-3,4-bis(2-cyanoethoxy)-2,5-bis(2-cyanoethoxymethyl)oxolan-2-yl]oxy-3,4,5-tris(2-cyanoethoxy)oxan-2-yl]methoxy]propanenitrile Chemical compound N#CCCO[C@H]1[C@H](OCCC#N)[C@@H](COCCC#N)O[C@@]1(COCCC#N)O[C@@H]1[C@H](OCCC#N)[C@@H](OCCC#N)[C@H](OCCC#N)[C@@H](COCCC#N)O1 XCKPLVGWGCWOMD-YYEYMFTQSA-N 0.000 claims 1
- DCWQZPJHHVLHSV-UHFFFAOYSA-N 3-ethoxypropanenitrile Chemical compound CCOCCC#N DCWQZPJHHVLHSV-UHFFFAOYSA-N 0.000 claims 1
- CLXHHCOBXLEKGO-UHFFFAOYSA-N C=C.CC1(C)CC(=O)CC(C)(C)N1O.CC1(C)CC(=O)CC(C)(C)N1O.CC1(C)CC(=O)CC(C)(C)N1O.CC1(C)CC(=O)CC(C)(C)N1O Chemical group C=C.CC1(C)CC(=O)CC(C)(C)N1O.CC1(C)CC(=O)CC(C)(C)N1O.CC1(C)CC(=O)CC(C)(C)N1O.CC1(C)CC(=O)CC(C)(C)N1O CLXHHCOBXLEKGO-UHFFFAOYSA-N 0.000 claims 1
- 150000001299 aldehydes Chemical class 0.000 claims 1
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 abstract description 6
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 abstract description 5
- 238000006731 degradation reaction Methods 0.000 abstract description 5
- 230000000087 stabilizing effect Effects 0.000 abstract description 5
- 238000004383 yellowing Methods 0.000 abstract description 5
- 230000015556 catabolic process Effects 0.000 abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 46
- 239000001257 hydrogen Substances 0.000 description 44
- 150000002431 hydrogen Chemical group 0.000 description 31
- 125000002947 alkylene group Chemical group 0.000 description 24
- QPCDCPDFJACHGM-UHFFFAOYSA-N N,N-bis{2-[bis(carboxymethyl)amino]ethyl}glycine Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(=O)O)CCN(CC(O)=O)CC(O)=O QPCDCPDFJACHGM-UHFFFAOYSA-N 0.000 description 21
- 229960003330 pentetic acid Drugs 0.000 description 21
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Classifications
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- 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
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/92—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with a hetero atom directly attached to the ring nitrogen atom
- C07D211/94—Oxygen atom, e.g. piperidine N-oxide
-
- 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
- C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
- C08K5/3432—Six-membered rings
- C08K5/3435—Piperidines
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/15—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on an electrochromic effect
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- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/165—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on translational movement of particles in a fluid under the influence of an applied field
- G02F1/166—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on translational movement of particles in a fluid under the influence of an applied field characterised by the electro-optical or magneto-optical effect
- G02F1/167—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on translational movement of particles in a fluid under the influence of an applied field characterised by the electro-optical or magneto-optical effect by electrophoresis
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- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/1033—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with oxygen
-
- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F2201/00—Constructional arrangements not provided for in groups G02F1/00 - G02F7/00
- G02F2201/08—Constructional arrangements not provided for in groups G02F1/00 - G02F7/00 light absorbing layer
- G02F2201/086—UV absorbing
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nonlinear Science (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Polymers & Plastics (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Molecular Biology (AREA)
- Electrochemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Electrochromic Elements, Electrophoresis, Or Variable Reflection Or Absorption Elements (AREA)
- Cosmetics (AREA)
- Polymerisation Methods In General (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US69535605P | 2005-06-30 | 2005-06-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PT1896550E true PT1896550E (pt) | 2013-09-24 |
Family
ID=36917270
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PT67773820T PT1896550E (pt) | 2005-06-30 | 2006-06-21 | Meios eletrocrómicos estabilizados |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US7718096B2 (https=) |
| EP (1) | EP1896550B1 (https=) |
| JP (1) | JP5112305B2 (https=) |
| KR (1) | KR101296096B1 (https=) |
| DK (1) | DK1896550T3 (https=) |
| ES (1) | ES2435525T3 (https=) |
| PT (1) | PT1896550E (https=) |
| TW (1) | TWI395808B (https=) |
| WO (1) | WO2007003508A1 (https=) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009019957A1 (ja) * | 2007-08-07 | 2009-02-12 | Konica Minolta Holdings, Inc. | 表示素子 |
| JP5458484B2 (ja) * | 2007-09-18 | 2014-04-02 | コニカミノルタ株式会社 | 表示素子 |
| JP5287726B2 (ja) * | 2007-11-12 | 2013-09-11 | コニカミノルタ株式会社 | 表示素子 |
| JP5568990B2 (ja) * | 2008-02-06 | 2014-08-13 | コニカミノルタ株式会社 | 表示素子 |
| WO2009099185A1 (ja) * | 2008-02-07 | 2009-08-13 | Konica Minolta Holdings, Inc. | 表示素子 |
| WO2009116353A1 (ja) * | 2008-03-18 | 2009-09-24 | コニカミノルタホールディングス株式会社 | 電気化学的表示素子 |
| US10571772B2 (en) | 2011-01-11 | 2020-02-25 | Ajjer, Llc | Added feature electrooptical devices and automotive components |
| EP2514800B2 (de) * | 2011-04-21 | 2018-03-07 | Merck Patent GmbH | Verbindungen und flüssigkristallines Medium |
| SG11201703031PA (en) | 2014-10-14 | 2017-05-30 | Ecolab Usa Inc | Reducing polymer fouling and agglomeration in acrylate/methacrylate processes |
| CA2979828C (en) | 2015-03-18 | 2023-08-29 | Ecolab Usa Inc. | The use of stable lipophilic hydroxylamine compounds for inhibiting polymerization of vinyl monomers |
| US9957209B2 (en) | 2015-03-31 | 2018-05-01 | Ecolab Usa Inc. | Use of quinone methides as antipolymerants for vinylic monomers |
| CA2982465C (en) | 2015-04-20 | 2024-05-14 | Ecolab Usa Inc. | Sterically hindered hydroquinones as antifoulants for unsaturated monomers |
| US11695089B2 (en) | 2019-12-31 | 2023-07-04 | Industrial Technology Research Institute | Solar cell modules |
| US12584064B2 (en) | 2022-04-21 | 2026-03-24 | Vitro Flat Glass Llc | Electrochromic devices and compositions including anodic components as cathodic component counter-anions |
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| US4247175A (en) | 1978-10-31 | 1981-01-27 | Research Frontiers Incorporated | Light valve containing improved light valve suspension |
| US4407565A (en) | 1981-01-16 | 1983-10-04 | Research Frontiers Incorporated | Light valve suspension containing fluorocarbon liquid |
| US4590231A (en) * | 1983-10-11 | 1986-05-20 | Ciba-Geigy Corporation | Polyolefin compositions stabilized against degradation using hydroxylamine derivatives |
| US4691015A (en) * | 1984-07-23 | 1987-09-01 | Ciba-Geigy Corporation | Hydroxylamines derived from hindered amines |
| US4772103A (en) | 1985-06-10 | 1988-09-20 | Research Frontiers Incorporated | Light valve containing an improved suspension, and liquids therefor |
| US4902108A (en) | 1986-03-31 | 1990-02-20 | Gentex Corporation | Single-compartment, self-erasing, solution-phase electrochromic devices, solutions for use therein, and uses thereof |
| US5204473A (en) * | 1987-09-21 | 1993-04-20 | Ciba-Geigy Corporation | O-substituted N-hydroxy hindered amine stabilizers |
| US5239406A (en) * | 1988-02-12 | 1993-08-24 | Donnelly Corporation | Near-infrared reflecting, ultraviolet protected, safety protected, electrochromic vehicular glazing |
| US5096950A (en) * | 1988-10-19 | 1992-03-17 | Ciba-Geigy Corporation | Polyolefin compositions stabilized with NOR-substituted hindered amines |
| US5140455A (en) | 1989-11-29 | 1992-08-18 | Donnelly Corporation | High performance electrochemichromic solutions and devices thereof |
| JPH0726096B2 (ja) * | 1991-07-22 | 1995-03-22 | 大蔵省印刷局長 | フォトクロミック組成物 |
| US5239405A (en) * | 1991-09-06 | 1993-08-24 | Donnelly Corporation | Electrochemichromic solutions, processes for preparing and using the same, and devices manufactured with the same |
| US5467217A (en) | 1991-11-01 | 1995-11-14 | Research Frontiers Incorporated | Light valve suspensions and films containing UV absorbers and light valves containing the same |
| JPH05224343A (ja) * | 1992-02-13 | 1993-09-03 | Nissan Motor Co Ltd | フォトクロミック合わせガラス |
| US5780160A (en) | 1994-10-26 | 1998-07-14 | Donnelly Corporation | Electrochromic devices with improved processability and methods of preparing the same |
| ES2308783T3 (es) | 1996-03-13 | 2008-12-01 | Huntsman Advanced Materials (Switzerland) Gmbh | Combinacion de estabilizadores. |
| US6178034B1 (en) * | 1996-04-10 | 2001-01-23 | Donnelly Corporation | Electrochromic devices |
| US6020987A (en) | 1997-04-02 | 2000-02-01 | Gentex Corporation | Electrochromic medium capable of producing a pre-selected color |
| US5770114A (en) * | 1997-08-06 | 1998-06-23 | Gentex Corporation | UV stabilized compositions with improved solubility |
| DE19735732A1 (de) | 1997-08-18 | 1999-02-25 | Bayer Ag | UV-geschützte elektrochrome Lösung |
| DE19748358A1 (de) | 1997-11-03 | 1999-05-06 | Bayer Ag | Elektrochromes System |
| US6753999B2 (en) | 1998-03-18 | 2004-06-22 | E Ink Corporation | Electrophoretic displays in portable devices and systems for addressing such displays |
| DE19824126A1 (de) * | 1998-05-29 | 1999-12-02 | Bayer Ag | UV-geschützte elektrochrome Anordnung auf Basis von Poly-(3,4-ethylendioxy-thiophen)-Derivaten |
| KR100550224B1 (ko) * | 1998-12-14 | 2006-02-08 | 시바 스폐셜티 케미칼스 홀딩 인코포레이티드 | 입체장애 아민 화합물 |
| US6599326B1 (en) | 1999-01-20 | 2003-07-29 | Ciba Specialty Chemicals Corporation | Inhibition of pulp and paper yellowing using hydroxylamines and other coadditives |
| US6271377B1 (en) * | 1999-02-25 | 2001-08-07 | Ciba Specialty Chemicals Corporation | Hydroxy-substituted N-alkoxy hindered amines and compositions stabilized therewith |
| US6392041B1 (en) * | 1999-02-25 | 2002-05-21 | Ciba Specialty Chemicals Corporation | Hydroxy-substituted N-alkoxy hindered amines and compositions stabilized therewith |
| US6355756B1 (en) * | 1999-05-18 | 2002-03-12 | International Business Machines Corporation | Dual purpose electroactive copolymers, preparation thereof, and use in opto-electronic devices |
| JP2001115134A (ja) * | 1999-10-14 | 2001-04-24 | Nippon Mitsubishi Oil Corp | イオン伝導性物質 |
| US6614578B2 (en) | 1999-12-03 | 2003-09-02 | Gentex Corporation | Ultraviolet stabilizing materials having a solublizing moiety |
| US6710906B2 (en) | 1999-12-03 | 2004-03-23 | Gentex Corporation | Controlled diffusion coefficient electrochromic materials for use in electrochromic mediums and associated electrochromic devices |
| JP4572445B2 (ja) * | 2000-05-29 | 2010-11-04 | 住友化学株式会社 | 高分子組成物 |
| DE60212337T2 (de) * | 2001-01-16 | 2007-06-14 | Ciba Speciality Chemicals Holding Inc. | Tintenstrahldrucktinte und -aufzeichnungsmaterial |
| DE60205734T2 (de) * | 2001-03-20 | 2006-03-09 | Ciba Speciality Chemicals Holding Inc. | Flammhemmende zusammensetzungen |
| JP4888987B2 (ja) * | 2001-05-08 | 2012-02-29 | 株式会社Ａｄｅｋａ | 水系塗料組成物 |
| JP4061863B2 (ja) | 2001-06-20 | 2008-03-19 | 富士ゼロックス株式会社 | 画像表示装置及び表示駆動方法 |
| TW520478B (en) | 2001-06-29 | 2003-02-11 | Inventec Corp | System with automatic transmission and fax management and method therefor |
| JP2003121883A (ja) * | 2001-10-11 | 2003-04-23 | Dainippon Printing Co Ltd | エレクトロクロミック素子 |
| EP1456296A1 (de) * | 2001-12-20 | 2004-09-15 | AMI Agrolinz Melamine International GmbH | Additiv zur inhibierung von photolytischen abbaureaktionen in aminoplasten |
| JP4594727B2 (ja) * | 2002-05-02 | 2010-12-08 | チバ ホールディング インコーポレーテッド | 安定化ボディケア製品、家庭用品、織物材料及び織物 |
| US6778034B2 (en) * | 2002-05-07 | 2004-08-17 | G.M.W.T. (Global Micro Wire Technology) Ltd. | EMI filters |
| WO2004024810A2 (en) * | 2002-09-11 | 2004-03-25 | Ciba, Specialty Chemicals Holding Inc. | Stabillization of organic materials |
| US7384464B2 (en) * | 2004-03-25 | 2008-06-10 | Ciba Specialty Chemicals Corporation | Ink jet and recording material |
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2006
- 2006-06-21 ES ES06777382T patent/ES2435525T3/es active Active
- 2006-06-21 KR KR1020087002522A patent/KR101296096B1/ko not_active Expired - Fee Related
- 2006-06-21 WO PCT/EP2006/063381 patent/WO2007003508A1/en not_active Ceased
- 2006-06-21 EP EP06777382.0A patent/EP1896550B1/en not_active Not-in-force
- 2006-06-21 PT PT67773820T patent/PT1896550E/pt unknown
- 2006-06-21 JP JP2008518790A patent/JP5112305B2/ja not_active Expired - Fee Related
- 2006-06-21 DK DK06777382.0T patent/DK1896550T3/da active
- 2006-06-27 US US11/475,699 patent/US7718096B2/en not_active Expired - Fee Related
- 2006-06-29 TW TW095123634A patent/TWI395808B/zh not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| ES2435525T3 (es) | 2013-12-20 |
| EP1896550A1 (en) | 2008-03-12 |
| US20070002423A1 (en) | 2007-01-04 |
| US7718096B2 (en) | 2010-05-18 |
| JP5112305B2 (ja) | 2013-01-09 |
| DK1896550T3 (da) | 2013-11-18 |
| TWI395808B (zh) | 2013-05-11 |
| KR101296096B1 (ko) | 2013-08-19 |
| KR20080030070A (ko) | 2008-04-03 |
| TW200704764A (en) | 2007-02-01 |
| JP2009500647A (ja) | 2009-01-08 |
| WO2007003508A1 (en) | 2007-01-11 |
| EP1896550B1 (en) | 2013-08-14 |
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