CA2294795A1 - Electrochrome polymer systems - Google Patents
Electrochrome polymer systems Download PDFInfo
- Publication number
- CA2294795A1 CA2294795A1 CA002294795A CA2294795A CA2294795A1 CA 2294795 A1 CA2294795 A1 CA 2294795A1 CA 002294795 A CA002294795 A CA 002294795A CA 2294795 A CA2294795 A CA 2294795A CA 2294795 A1 CA2294795 A1 CA 2294795A1
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- aryl
- independently
- another
- electrochromic
- Prior art date
- 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.)
- Abandoned
Links
- 229920000642 polymer Polymers 0.000 title claims abstract description 76
- 239000000178 monomer Substances 0.000 claims abstract description 75
- 238000006068 polycondensation reaction Methods 0.000 claims abstract description 9
- -1 tetrafluoroborate Chemical compound 0.000 claims description 72
- 125000001424 substituent group Chemical group 0.000 claims description 30
- 238000006243 chemical reaction Methods 0.000 claims description 29
- 239000001257 hydrogen Substances 0.000 claims description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 27
- 239000000203 mixture Substances 0.000 claims description 26
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 22
- 229910052736 halogen Inorganic materials 0.000 claims description 22
- 150000002367 halogens Chemical class 0.000 claims description 21
- 230000008569 process Effects 0.000 claims description 20
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 19
- 238000006116 polymerization reaction Methods 0.000 claims description 19
- 239000000126 substance Substances 0.000 claims description 16
- 229910052760 oxygen Inorganic materials 0.000 claims description 15
- 238000002360 preparation method Methods 0.000 claims description 13
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 12
- 102100038191 Double-stranded RNA-specific editase 1 Human genes 0.000 claims description 12
- 101000742223 Homo sapiens Double-stranded RNA-specific editase 1 Proteins 0.000 claims description 12
- 101000686491 Platymeris rhadamanthus Venom redulysin 1 Proteins 0.000 claims description 12
- 238000000576 coating method Methods 0.000 claims description 12
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 11
- 238000002835 absorbance Methods 0.000 claims description 10
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
- 238000001228 spectrum Methods 0.000 claims description 10
- 150000001450 anions Chemical class 0.000 claims description 9
- 125000005842 heteroatom Chemical group 0.000 claims description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 9
- 125000004434 sulfur atom Chemical group 0.000 claims description 9
- 239000000010 aprotic solvent Substances 0.000 claims description 8
- 150000004820 halides Chemical class 0.000 claims description 8
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 claims description 8
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 7
- YRIUSKIDOIARQF-UHFFFAOYSA-N dodecyl benzenesulfonate Chemical compound CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 YRIUSKIDOIARQF-UHFFFAOYSA-N 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- LDMOEFOXLIZJOW-UHFFFAOYSA-N 1-dodecanesulfonic acid Chemical compound CCCCCCCCCCCCS(O)(=O)=O LDMOEFOXLIZJOW-UHFFFAOYSA-N 0.000 claims description 5
- 239000006096 absorbing agent Substances 0.000 claims description 5
- NIKBCKTWWPVAIC-UHFFFAOYSA-N butyl benzenesulfonate Chemical compound CCCCOS(=O)(=O)C1=CC=CC=C1 NIKBCKTWWPVAIC-UHFFFAOYSA-N 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 3
- IPZJQDSFZGZEOY-UHFFFAOYSA-N dimethylmethylene Chemical compound C[C]C IPZJQDSFZGZEOY-UHFFFAOYSA-N 0.000 claims description 3
- SSILHZFTFWOUJR-UHFFFAOYSA-N hexadecane-1-sulfonic acid Chemical compound CCCCCCCCCCCCCCCCS(O)(=O)=O SSILHZFTFWOUJR-UHFFFAOYSA-N 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 239000002562 thickening agent Substances 0.000 claims description 3
- 150000007824 aliphatic compounds Chemical class 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 150000001491 aromatic compounds Chemical class 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 238000010526 radical polymerization reaction Methods 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims 18
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 10
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 9
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims 6
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims 6
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims 5
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 4
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 3
- 102100024692 Double-stranded RNA-specific editase B2 Human genes 0.000 claims 3
- 101000686486 Homo sapiens Double-stranded RNA-specific editase B2 Proteins 0.000 claims 3
- 101000686495 Platymeris rhadamanthus Venom redulysin 2 Proteins 0.000 claims 3
- WPPDXAHGCGPUPK-UHFFFAOYSA-N red 2 Chemical compound C1=CC=CC=C1C(C1=CC=CC=C11)=C(C=2C=3C4=CC=C5C6=CC=C7C8=C(C=9C=CC=CC=9)C9=CC=CC=C9C(C=9C=CC=CC=9)=C8C8=CC=C(C6=C87)C(C=35)=CC=2)C4=C1C1=CC=CC=C1 WPPDXAHGCGPUPK-UHFFFAOYSA-N 0.000 claims 3
- RFEBDZANCVHDLP-UHFFFAOYSA-N 3-[(4-cyanophenyl)methylamino]-6-(trifluoromethyl)quinoxaline-2-carboxylic acid Chemical compound OC(=O)C1=NC2=CC=C(C(F)(F)F)C=C2N=C1NCC1=CC=C(C#N)C=C1 RFEBDZANCVHDLP-UHFFFAOYSA-N 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- 230000005670 electromagnetic radiation Effects 0.000 abstract description 4
- 230000035699 permeability Effects 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 84
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 77
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 42
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 36
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 30
- 238000000921 elemental analysis Methods 0.000 description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
- 239000002904 solvent Substances 0.000 description 24
- 239000000047 product Substances 0.000 description 23
- 239000012300 argon atmosphere Substances 0.000 description 22
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 20
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 19
- 239000010410 layer Substances 0.000 description 19
- 239000011521 glass Substances 0.000 description 17
- 239000002244 precipitate Substances 0.000 description 17
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 13
- MWVTWFVJZLCBMC-UHFFFAOYSA-N 4,4'-bipyridine Chemical group C1=NC=CC(C=2C=CN=CC=2)=C1 MWVTWFVJZLCBMC-UHFFFAOYSA-N 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 12
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 12
- 239000011734 sodium Substances 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 11
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 10
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 10
- 230000007717 exclusion Effects 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 9
- 150000002170 ethers Chemical class 0.000 description 9
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 9
- 150000003254 radicals Chemical class 0.000 description 9
- 229910052708 sodium Inorganic materials 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- VEPOHXYIFQMVHW-XOZOLZJESA-N 2,3-dihydroxybutanedioic acid (2S,3S)-3,4-dimethyl-2-phenylmorpholine Chemical compound OC(C(O)C(O)=O)C(O)=O.C[C@H]1[C@@H](OCCN1C)c1ccccc1 VEPOHXYIFQMVHW-XOZOLZJESA-N 0.000 description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 239000013078 crystal Substances 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 238000010521 absorption reaction Methods 0.000 description 7
- 238000004587 chromatography analysis Methods 0.000 description 7
- 239000011248 coating agent Substances 0.000 description 7
- GUVUOGQBMYCBQP-UHFFFAOYSA-N dmpu Chemical compound CN1CCCN(C)C1=O GUVUOGQBMYCBQP-UHFFFAOYSA-N 0.000 description 7
- 238000011049 filling Methods 0.000 description 7
- 238000001556 precipitation Methods 0.000 description 7
- 238000000926 separation method Methods 0.000 description 7
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000000853 adhesive Substances 0.000 description 6
- 230000001070 adhesive effect Effects 0.000 description 6
- 239000004020 conductor Substances 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 238000005956 quaternization reaction Methods 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 238000007789 sealing Methods 0.000 description 6
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 5
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 5
- 230000008859 change Effects 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- 239000008096 xylene Substances 0.000 description 5
- FZQMJOOSLXFQSU-UHFFFAOYSA-N 3-[3,5-bis[3-(dimethylamino)propyl]-1,3,5-triazinan-1-yl]-n,n-dimethylpropan-1-amine Chemical compound CN(C)CCCN1CN(CCCN(C)C)CN(CCCN(C)C)C1 FZQMJOOSLXFQSU-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- FMRHJJZUHUTGKE-UHFFFAOYSA-N Ethylhexyl salicylate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1O FMRHJJZUHUTGKE-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 238000010276 construction Methods 0.000 description 4
- OKVJWADVFPXWQD-UHFFFAOYSA-N difluoroborinic acid Chemical compound OB(F)F OKVJWADVFPXWQD-UHFFFAOYSA-N 0.000 description 4
- ZTOMUSMDRMJOTH-UHFFFAOYSA-N glutaronitrile Chemical compound N#CCCCC#N ZTOMUSMDRMJOTH-UHFFFAOYSA-N 0.000 description 4
- 238000002955 isolation Methods 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- 229940078552 o-xylene Drugs 0.000 description 4
- 239000004033 plastic Substances 0.000 description 4
- 229920003023 plastic Polymers 0.000 description 4
- 229920000728 polyester Polymers 0.000 description 4
- 125000006850 spacer group Chemical group 0.000 description 4
- ULTHEAFYOOPTTB-UHFFFAOYSA-N 1,4-dibromobutane Chemical compound BrCCCCBr ULTHEAFYOOPTTB-UHFFFAOYSA-N 0.000 description 3
- SLBOQBILGNEPEB-UHFFFAOYSA-N 1-chloroprop-2-enylbenzene Chemical compound C=CC(Cl)C1=CC=CC=C1 SLBOQBILGNEPEB-UHFFFAOYSA-N 0.000 description 3
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 3
- IVURTNNWJAPOML-UHFFFAOYSA-N 5,10-dihydrophenazine Chemical class C1=CC=C2NC3=CC=CC=C3NC2=C1 IVURTNNWJAPOML-UHFFFAOYSA-N 0.000 description 3
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 229910052804 chromium Inorganic materials 0.000 description 3
- 239000011651 chromium Substances 0.000 description 3
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 229920006332 epoxy adhesive Polymers 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 229940052308 general anesthetics halogenated hydrocarbons Drugs 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 238000005342 ion exchange Methods 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- WOFDVDFSGLBFAC-UHFFFAOYSA-N lactonitrile Chemical compound CC(O)C#N WOFDVDFSGLBFAC-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 3
- 229920002120 photoresistant polymer Polymers 0.000 description 3
- 229920002635 polyurethane Polymers 0.000 description 3
- 239000004814 polyurethane Substances 0.000 description 3
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 3
- 125000004076 pyridyl group Chemical group 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 3
- 229910001887 tin oxide Inorganic materials 0.000 description 3
- 229910052724 xenon Inorganic materials 0.000 description 3
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- CBQBPHBGFCZSGG-UHFFFAOYSA-N 1,2-dihydrophenazine;sodium Chemical compound [Na].[Na].C1=CC=C2N=C(C=CCC3)C3=NC2=C1 CBQBPHBGFCZSGG-UHFFFAOYSA-N 0.000 description 2
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 2
- HTQFQWJJHDJUOU-UHFFFAOYSA-N 3-[10-(3-hydroxypropyl)phenazin-5-yl]propan-1-ol Chemical compound C1=CC=C2N(CCCO)C3=CC=CC=C3N(CCCO)C2=C1 HTQFQWJJHDJUOU-UHFFFAOYSA-N 0.000 description 2
- OOWFYDWAMOKVSF-UHFFFAOYSA-N 3-methoxypropanenitrile Chemical compound COCCC#N OOWFYDWAMOKVSF-UHFFFAOYSA-N 0.000 description 2
- CMJLMPKFQPJDKP-UHFFFAOYSA-N 3-methylthiolane 1,1-dioxide Chemical compound CC1CCS(=O)(=O)C1 CMJLMPKFQPJDKP-UHFFFAOYSA-N 0.000 description 2
- BODSVJALBQPJQA-UHFFFAOYSA-N 4-[2-(4-hydroxyphenyl)propan-2-yl]phenol;potassium Chemical compound [K].[K].C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 BODSVJALBQPJQA-UHFFFAOYSA-N 0.000 description 2
- XKVQOPLKMBUCCC-UHFFFAOYSA-N 5-(4-bromobutyl)-10-phenylphenazine Chemical compound C12=CC=CC=C2N(CCCCBr)C2=CC=CC=C2N1C1=CC=CC=C1 XKVQOPLKMBUCCC-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- 239000004822 Hot adhesive Substances 0.000 description 2
- 229910021577 Iron(II) chloride Inorganic materials 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 2
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 239000004411 aluminium Substances 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
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- 238000007639 printing Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000006479 redox reaction Methods 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 238000007790 scraping Methods 0.000 description 1
- 238000006748 scratching Methods 0.000 description 1
- 230000002393 scratching effect Effects 0.000 description 1
- 238000005204 segregation Methods 0.000 description 1
- KYKFCSHPTAVNJD-UHFFFAOYSA-L sodium adipate Chemical compound [Na+].[Na+].[O-]C(=O)CCCCC([O-])=O KYKFCSHPTAVNJD-UHFFFAOYSA-L 0.000 description 1
- 239000001601 sodium adipate Substances 0.000 description 1
- 235000011049 sodium adipate Nutrition 0.000 description 1
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Inorganic materials [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- WDFTWKQHSSVVJK-UHFFFAOYSA-N tert-butyl benzenesulfonate Chemical compound CC(C)(C)OS(=O)(=O)C1=CC=CC=C1 WDFTWKQHSSVVJK-UHFFFAOYSA-N 0.000 description 1
- 150000005621 tetraalkylammonium salts Chemical class 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical class CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- MYOWBHNETUSQPA-UHFFFAOYSA-N tetradecane-1-sulfonic acid Chemical compound CCCCCCCCCCCCCCS(O)(=O)=O MYOWBHNETUSQPA-UHFFFAOYSA-N 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- UZPUXLRDLVOKTB-UHFFFAOYSA-N trifluoromethyl benzenesulfonate Chemical compound FC(F)(F)OS(=O)(=O)C1=CC=CC=C1 UZPUXLRDLVOKTB-UHFFFAOYSA-N 0.000 description 1
- 238000010792 warming Methods 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
-
- 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
- G02F1/1503—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 caused by oxidation-reduction reactions in organic liquid solutions, e.g. viologen solutions
-
- 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
- G02F1/1514—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 characterised by the electrochromic material, e.g. by the electrodeposited material
- G02F2001/15145—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 characterised by the electrochromic material, e.g. by the electrodeposited material the electrochromic layer comprises a mixture of anodic and cathodic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Nonlinear Science (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Plural Heterocyclic Compounds (AREA)
- Electrochromic Elements, Electrophoresis, Or Variable Reflection Or Absorption Elements (AREA)
- Polyesters Or Polycarbonates (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Liquid Crystal Substances (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Pyridine Compounds (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Polymerisation Methods In General (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19728876 | 1997-07-07 | ||
| DE19728876.6 | 1997-07-07 | ||
| DE19801638.7 | 1998-01-17 | ||
| DE19801638A DE19801638A1 (de) | 1998-01-17 | 1998-01-17 | Elektrochrome Polymersysteme |
| PCT/EP1998/003862 WO1999002621A1 (de) | 1997-07-07 | 1998-06-24 | Elektrochrome polymersysteme |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2294795A1 true CA2294795A1 (en) | 1999-01-21 |
Family
ID=26038069
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002294795A Abandoned CA2294795A1 (en) | 1997-07-07 | 1998-06-24 | Electrochrome polymer systems |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US6569361B1 (enExample) |
| EP (1) | EP1027397B1 (enExample) |
| JP (1) | JP2002511096A (enExample) |
| KR (1) | KR100564863B1 (enExample) |
| AT (1) | ATE342947T1 (enExample) |
| AU (1) | AU735970B2 (enExample) |
| BR (1) | BR9811668A (enExample) |
| CA (1) | CA2294795A1 (enExample) |
| DE (1) | DE59813775D1 (enExample) |
| ES (1) | ES2275308T3 (enExample) |
| WO (1) | WO1999002621A1 (enExample) |
Families Citing this family (66)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19906655A1 (de) * | 1999-02-18 | 2000-11-16 | Bayer Ag | Elektrochrome Vorrichtung mit verbesserter Lichtechtheit |
| DE19914304A1 (de) * | 1999-03-29 | 2000-10-05 | Bayer Ag | Elektrochrome Kontrastplatte |
| DE60017440T2 (de) * | 1999-10-11 | 2006-03-02 | University College Dublin | Elektrochrome vorrichtung |
| 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 |
| CA2434693A1 (en) | 2001-01-18 | 2002-10-17 | Genzyme Corporation | Ionene polymers and their use as antimicrobial agents |
| US6635194B2 (en) | 2001-08-28 | 2003-10-21 | Gentex Corporation | Electrochromic medium having a self-healing cross-linked polymer gel and associated electrochromic device |
| US7595011B2 (en) | 2004-07-12 | 2009-09-29 | Ciba Specialty Chemicals Corporation | Stabilized electrochromic media |
| US7428091B2 (en) * | 2004-11-15 | 2008-09-23 | Gentex Corporation | Electrochromic compounds and associated media and devices |
| US7855821B2 (en) * | 2004-11-15 | 2010-12-21 | Gentex Corporation | Electrochromic compounds and associated media and devices |
| DE102005032081A1 (de) * | 2005-05-31 | 2007-02-15 | Siemens Ag | Elektrochromes Material, Verwendung davon und Display |
| JP2009500677A (ja) * | 2005-07-11 | 2009-01-08 | シーメンス アクチエンゲゼルシヤフト | ポリマー４，４′−ビピリジニウム構造体、エレクトロクロミック活性層用配合物及びそのための使用 |
| KR100701646B1 (ko) * | 2005-11-10 | 2007-04-06 | 한양대학교 산학협력단 | 단분산성 고분자 입자의 표면 기능기에 비올리진을결합시킨 반사형 전기변색 표시소자와 이의 제조방법 |
| US7414770B2 (en) | 2006-05-03 | 2008-08-19 | Gentex Corporation | Contollably dissolving spacing member and associated electrochromic device and method for manufacturing the same |
| RU2464607C2 (ru) * | 2007-03-13 | 2012-10-20 | Государственное Учебно-Научное Учреждение Физический Факультет Московского Государственного Университета Им.М.В.Ломоносова | Однослойное секционное электрохромное устройство, включающее в себя электрохромный материал полимерного типа |
| US8345345B2 (en) | 2007-06-27 | 2013-01-01 | Gentex Corporation | Electrochromic device having an improved fill port plug |
| WO2014022681A1 (en) | 2012-08-01 | 2014-02-06 | Gentex Corporation | Assembly with laser induced channel edge and method thereof |
| US8928966B1 (en) | 2012-08-08 | 2015-01-06 | Gentex Corporation | Electrochromic polyelectrolyte gel medium having improved creep resistance and associated electrochromic device |
| US9758099B2 (en) | 2013-03-15 | 2017-09-12 | Gentex Corporation | Display system and method thereof |
| US9057925B2 (en) | 2013-03-15 | 2015-06-16 | Gentex Corporation | Fill port plugs for electrochromic devices |
| US9354470B2 (en) | 2013-09-24 | 2016-05-31 | Gentex Corporation | Electro-optic device |
| JP6221686B2 (ja) * | 2013-11-27 | 2017-11-01 | 株式会社リコー | エレクトロクロミック化合物及び表示素子 |
| AT516080B1 (de) | 2014-07-28 | 2016-04-15 | Zizala Lichtsysteme Gmbh | Abdeckung für eine Leuchteneinrichtung |
| EP3177962B1 (en) | 2014-08-04 | 2020-07-08 | Gentex Corporation | Electrochromic devices |
| KR20170134472A (ko) | 2015-03-09 | 2017-12-06 | 젠텍스 코포레이션 | 플라스틱 기판을 가지는 전기 화학적 장치 |
| WO2016209323A1 (en) | 2015-06-25 | 2016-12-29 | Gentex Corporation | Electrochromic thermoplastics, devices, and composites |
| CN108025675A (zh) | 2015-09-18 | 2018-05-11 | 金泰克斯公司 | 用于后视镜组件的拨动机构 |
| WO2017062698A1 (en) | 2015-10-09 | 2017-04-13 | Gentex Corporation | Electro-optic mirror having user-adjustable dimming with visual feedback |
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| WO2017087019A1 (en) | 2015-11-20 | 2017-05-26 | Gentex Corporation | Protic-soluble organic electrochromic compounds |
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| CN108367712B (zh) | 2015-12-14 | 2022-04-29 | 金泰克斯公司 | 具有光学开关的双模态机构 |
| US10769434B2 (en) | 2015-12-22 | 2020-09-08 | Gentex Corporation | Mirror assembly incorporating a scanning apparatus |
| US10105006B2 (en) | 2016-04-07 | 2018-10-23 | Electrolux Home Products, Inc. | Cooking appliance with indicators formed using electrochromic material |
| US10459307B2 (en) | 2016-04-22 | 2019-10-29 | Gentex Corporation | Flame retardancy of electrochromic devices |
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| US9694042B1 (en) * | 2016-05-23 | 2017-07-04 | Kaeco Group, Inc. | Mastic gum top dressing for the prevention of gastrointestinal distress in horses and other species |
| CN109690395B (zh) | 2016-09-30 | 2021-06-15 | 金泰克斯公司 | 电致变色装置中的色彩偏移缓解 |
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| CN110326293A (zh) | 2017-03-22 | 2019-10-11 | 金泰克斯公司 | 并入图像传感器的显示组件 |
| CN110582721B (zh) | 2017-05-01 | 2022-09-20 | 金泰克斯公司 | 具有可切换的白天和夜晚模式的成像装置 |
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| WO2019130275A1 (en) | 2017-12-29 | 2019-07-04 | Gentex Corporation | Polarized electrochromic device |
| WO2020012340A1 (en) | 2018-07-12 | 2020-01-16 | Gentex Corporation | Mirror assembly incorporating a scanning apparatus |
| US11066046B2 (en) | 2018-09-25 | 2021-07-20 | Getex Corporation | Authentication concealment and alignment systems |
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| CN113168515A (zh) | 2018-12-10 | 2021-07-23 | 金泰克斯公司 | 用于减小视场搜索空间的扫描设备 |
| WO2020121201A1 (en) | 2018-12-13 | 2020-06-18 | Gentex Corporation | Alignment apparatus for vehicle authentication system |
| US10929698B2 (en) | 2018-12-17 | 2021-02-23 | Gentex Corporation | Advanced features for vehicle authentication system |
| US11479185B2 (en) | 2019-02-01 | 2022-10-25 | Gentex Corporation | Active infrared illumination for enhancing rear vision from a vehicle |
| EP3948414B1 (en) | 2019-03-29 | 2025-05-07 | Gentex Corporation | Electro-optic sub-assemblies and assemblies having an electrochromic gel layer |
| US11692065B2 (en) * | 2019-03-29 | 2023-07-04 | Cornell University | Phenazine copolymers and uses thereof |
| US11906866B2 (en) | 2019-06-27 | 2024-02-20 | Gentex Corporation | Electrochromic films and methods of forming and using |
| US12134351B2 (en) | 2020-09-18 | 2024-11-05 | Gentex Corporation | Concealment panel with asymmetric reflectance |
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| US12600300B2 (en) | 2022-03-22 | 2026-04-14 | Gentex Corporation | Full display mirror assembly with through bezel infrared illumination |
| CN223919212U (zh) | 2022-03-28 | 2026-02-17 | 金泰克斯公司 | 具有盲点检测系统的全显示镜组件 |
| WO2024074987A1 (en) | 2022-10-03 | 2024-04-11 | Gentex Corporation | Rearview mirror assembly |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59217789A (ja) * | 1983-05-25 | 1984-12-07 | Japan Electronic Ind Dev Assoc<Jeida> | エレクトロクロミツク材料 |
| JPS59217791A (ja) * | 1983-05-25 | 1984-12-07 | Japan Electronic Ind Dev Assoc<Jeida> | エレクトロクロミツク材料 |
| JPS61204224A (ja) * | 1985-03-08 | 1986-09-10 | Sumitomo Electric Ind Ltd | 機能性エラストマ− |
| 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 |
| US4841021A (en) * | 1987-11-30 | 1989-06-20 | Minnesota Mining And Manufacturing Company | Polypyridinium |
| US5140455A (en) | 1989-11-29 | 1992-08-18 | Donnelly Corporation | High performance electrochemichromic solutions and devices thereof |
| US5457564A (en) * | 1990-02-26 | 1995-10-10 | Molecular Displays, Inc. | Complementary surface confined polymer electrochromic materials, systems, and methods of fabrication therefor |
| US5818636A (en) * | 1990-02-26 | 1998-10-06 | Molecular Displays, Inc. | Complementary surface confined polmer electrochromic materials, systems, and methods of fabrication therefor |
| EP1004649A3 (en) * | 1993-02-26 | 2000-07-26 | Donnelly Corporation | Electrochromic polymeric solid films, manufacturing electrochromic devices using such solid films, and processes for making such solid films and devices |
| DE4325591A1 (de) | 1993-07-30 | 1995-02-02 | Hoechst Ag | Dihydrophenazinpolymere |
| US5679283A (en) * | 1994-07-22 | 1997-10-21 | Gentex Corporation | Electrochromic layer and devices comprising same |
| EP1041425A4 (en) * | 1997-12-19 | 2007-05-02 | Nippon Mitsubishi Oil Corp | ELECTROCHROMIC ELEMENT |
-
1998
- 1998-06-24 WO PCT/EP1998/003862 patent/WO1999002621A1/de not_active Ceased
- 1998-06-24 CA CA002294795A patent/CA2294795A1/en not_active Abandoned
- 1998-06-24 AT AT98933640T patent/ATE342947T1/de not_active IP Right Cessation
- 1998-06-24 JP JP50805499A patent/JP2002511096A/ja not_active Ceased
- 1998-06-24 DE DE59813775T patent/DE59813775D1/de not_active Expired - Fee Related
- 1998-06-24 AU AU83390/98A patent/AU735970B2/en not_active Ceased
- 1998-06-24 EP EP98933640A patent/EP1027397B1/de not_active Expired - Lifetime
- 1998-06-24 ES ES98933640T patent/ES2275308T3/es not_active Expired - Lifetime
- 1998-06-24 BR BR9811668-1A patent/BR9811668A/pt not_active IP Right Cessation
- 1998-06-24 US US09/462,045 patent/US6569361B1/en not_active Expired - Fee Related
- 1998-06-24 KR KR1020007000084A patent/KR100564863B1/ko not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| ATE342947T1 (de) | 2006-11-15 |
| US6569361B1 (en) | 2003-05-27 |
| JP2002511096A (ja) | 2002-04-09 |
| EP1027397A1 (de) | 2000-08-16 |
| KR100564863B1 (ko) | 2006-03-28 |
| WO1999002621A1 (de) | 1999-01-21 |
| AU735970B2 (en) | 2001-07-19 |
| ES2275308T3 (es) | 2007-06-01 |
| KR20010021526A (ko) | 2001-03-15 |
| EP1027397B1 (de) | 2006-10-18 |
| AU8339098A (en) | 1999-02-08 |
| DE59813775D1 (de) | 2006-11-30 |
| BR9811668A (pt) | 2000-09-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |