AU735970B2 - Electrochromic polymer systems - Google Patents
Electrochromic polymer systems Download PDFInfo
- Publication number
- AU735970B2 AU735970B2 AU83390/98A AU8339098A AU735970B2 AU 735970 B2 AU735970 B2 AU 735970B2 AU 83390/98 A AU83390/98 A AU 83390/98A AU 8339098 A AU8339098 A AU 8339098A AU 735970 B2 AU735970 B2 AU 735970B2
- Authority
- AU
- Australia
- Prior art keywords
- alkyl
- independently
- another
- aryl
- hydrogen
- 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.)
- Ceased
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- 229920000642 polymer Polymers 0.000 title claims abstract description 79
- 239000000178 monomer Substances 0.000 claims abstract description 75
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 22
- 238000006068 polycondensation reaction Methods 0.000 claims abstract description 9
- -1 (CI-C 1 8 )-alkyl Chemical group 0.000 claims description 71
- 229910052739 hydrogen Inorganic materials 0.000 claims description 36
- 239000001257 hydrogen Substances 0.000 claims description 35
- 125000001424 substituent group Chemical group 0.000 claims description 31
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 30
- 238000006243 chemical reaction Methods 0.000 claims description 28
- 239000000203 mixture Substances 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 26
- 229910052736 halogen Inorganic materials 0.000 claims description 24
- 150000002367 halogens Chemical class 0.000 claims description 24
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 23
- 230000008569 process Effects 0.000 claims description 19
- 239000000126 substance Substances 0.000 claims description 16
- 238000002360 preparation method Methods 0.000 claims description 14
- 229910052796 boron Inorganic materials 0.000 claims description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 12
- 238000000576 coating method Methods 0.000 claims description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
- 238000002835 absorbance Methods 0.000 claims description 11
- 238000001228 spectrum Methods 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 150000001450 anions Chemical class 0.000 claims description 9
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 9
- 125000005842 heteroatom Chemical group 0.000 claims description 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
- 239000000010 aprotic solvent Substances 0.000 claims description 8
- 150000004820 halides Chemical class 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 125000004434 sulfur atom Chemical group 0.000 claims description 7
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 claims description 6
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims description 6
- 239000006096 absorbing agent Substances 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 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
- YRIUSKIDOIARQF-UHFFFAOYSA-N dodecyl benzenesulfonate Chemical compound CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 YRIUSKIDOIARQF-UHFFFAOYSA-N 0.000 claims description 5
- 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 description 5
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- LDMOEFOXLIZJOW-UHFFFAOYSA-N 1-dodecanesulfonic acid Chemical compound CCCCCCCCCCCCS(O)(=O)=O LDMOEFOXLIZJOW-UHFFFAOYSA-N 0.000 claims description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 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
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 4
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims 3
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 2
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 claims 1
- MWVTWFVJZLCBMC-UHFFFAOYSA-P 4-pyridin-1-ium-4-ylpyridin-1-ium Chemical compound C1=[NH+]C=CC(C=2C=C[NH+]=CC=2)=C1 MWVTWFVJZLCBMC-UHFFFAOYSA-P 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- 229950000688 phenothiazine Drugs 0.000 claims 1
- 102200096026 rs104894064 Human genes 0.000 claims 1
- 230000005670 electromagnetic radiation Effects 0.000 abstract description 4
- 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 72
- 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 33
- 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 26
- 239000002904 solvent Substances 0.000 description 24
- 239000000047 product Substances 0.000 description 23
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 20
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 20
- 239000012300 argon atmosphere Substances 0.000 description 20
- 239000010410 layer Substances 0.000 description 19
- 239000011521 glass Substances 0.000 description 17
- 239000002244 precipitate Substances 0.000 description 17
- IVURTNNWJAPOML-UHFFFAOYSA-N 5,10-dihydrophenazine Chemical class C1=CC=C2NC3=CC=CC=C3NC2=C1 IVURTNNWJAPOML-UHFFFAOYSA-N 0.000 description 13
- 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
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- 230000007717 exclusion Effects 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
- 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
- 239000011734 sodium Substances 0.000 description 10
- 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
- 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
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 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 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
- 229910052708 sodium Inorganic materials 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
- FMRHJJZUHUTGKE-UHFFFAOYSA-N Ethylhexyl salicylate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1O FMRHJJZUHUTGKE-UHFFFAOYSA-N 0.000 description 6
- 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
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 6
- 239000004020 conductor Substances 0.000 description 6
- 239000000463 material Substances 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
- 230000008859 change Effects 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 238000005956 quaternization reaction Methods 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
- 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
- 238000010276 construction Methods 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
- 238000003756 stirring Methods 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
- 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
- 239000002253 acid Substances 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 229910052804 chromium Inorganic materials 0.000 description 3
- 239000011651 chromium Substances 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 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
- 125000005843 halogen group Chemical group 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 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
- HJNHUFQGDJLQRS-UHFFFAOYSA-N 2-(3-bromopropoxy)oxane Chemical compound BrCCCOC1CCCCO1 HJNHUFQGDJLQRS-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
- OOWFYDWAMOKVSF-UHFFFAOYSA-N 3-methoxypropanenitrile Chemical compound COCCC#N OOWFYDWAMOKVSF-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
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
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- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
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- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 102100026459 POU domain, class 3, transcription factor 2 Human genes 0.000 description 2
- 239000004698 Polyethylene Substances 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
- 150000007513 acids Chemical class 0.000 description 2
- 239000000654 additive Substances 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
- 229910052794 bromium Inorganic materials 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
- 230000000295 complement effect Effects 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- JQZRVMZHTADUSY-UHFFFAOYSA-L di(octanoyloxy)tin Chemical compound [Sn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O JQZRVMZHTADUSY-UHFFFAOYSA-L 0.000 description 2
- 239000012975 dibutyltin dilaurate Substances 0.000 description 2
- OKVJWADVFPXWQD-UHFFFAOYSA-N difluoroborinic acid Chemical compound OB(F)F OKVJWADVFPXWQD-UHFFFAOYSA-N 0.000 description 2
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000012039 electrophile Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 230000005484 gravity Effects 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- SSILHZFTFWOUJR-UHFFFAOYSA-N hexadecane-1-sulfonic acid Chemical compound CCCCCCCCCCCCCCCCS(O)(=O)=O SSILHZFTFWOUJR-UHFFFAOYSA-N 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
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- 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)
- Plural Heterocyclic Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Electrochromic Elements, Electrophoresis, Or Variable Reflection Or Absorption Elements (AREA)
- Pyridine Compounds (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Polyesters Or Polycarbonates (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Liquid Crystal Substances (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
- Polymerisation Methods In General (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19728876 | 1997-07-07 | ||
| DE19728876 | 1997-07-07 | ||
| DE19801638 | 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 (2)
| Publication Number | Publication Date |
|---|---|
| AU8339098A AU8339098A (en) | 1999-02-08 |
| AU735970B2 true AU735970B2 (en) | 2001-07-19 |
Family
ID=26038069
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU83390/98A Ceased AU735970B2 (en) | 1997-07-07 | 1998-06-24 | Electrochromic polymer systems |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US6569361B1 (https=) |
| EP (1) | EP1027397B1 (https=) |
| JP (1) | JP2002511096A (https=) |
| KR (1) | KR100564863B1 (https=) |
| AT (1) | ATE342947T1 (https=) |
| AU (1) | AU735970B2 (https=) |
| BR (1) | BR9811668A (https=) |
| CA (1) | CA2294795A1 (https=) |
| DE (1) | DE59813775D1 (https=) |
| ES (1) | ES2275308T3 (https=) |
| WO (1) | WO1999002621A1 (https=) |
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| 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 |
| AU770559B2 (en) * | 1999-10-11 | 2004-02-26 | University College Dublin | Electrochromic device |
| 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 |
| US6955806B2 (en) | 2001-01-18 | 2005-10-18 | 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 |
| US7855821B2 (en) * | 2004-11-15 | 2010-12-21 | Gentex Corporation | Electrochromic compounds and associated media and devices |
| US7428091B2 (en) * | 2004-11-15 | 2008-09-23 | 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 |
| CN101341190A (zh) * | 2005-07-11 | 2009-01-07 | 西门子公司 | 聚合物4,4′－联吡啶结构、用于电致变色活性层的制剂及用于后者的用途 |
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| 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 |
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| 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 |
| US9738140B2 (en) | 2014-08-04 | 2017-08-22 | Gentex Corporation | Electrochromic devices |
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| 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 |
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Citations (3)
| 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 |
| EP0196497A1 (en) * | 1985-03-08 | 1986-10-08 | Sumitomo Electric Industries Limited | Functional elastomer |
| EP0319156A1 (en) * | 1987-11-30 | 1989-06-07 | Minnesota Mining And Manufacturing Company | Polypyridiniums |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| 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 |
| US5140455A (en) | 1989-11-29 | 1992-08-18 | Donnelly Corporation | High performance electrochemichromic solutions and devices thereof |
| US5818636A (en) * | 1990-02-26 | 1998-10-06 | Molecular Displays, Inc. | Complementary surface confined polmer electrochromic materials, systems, and methods of fabrication therefor |
| US5457564A (en) * | 1990-02-26 | 1995-10-10 | Molecular Displays, Inc. | Complementary surface confined polymer electrochromic materials, systems, and methods of fabrication therefor |
| EP0612826B1 (en) * | 1993-02-26 | 2000-10-04 | Donnelly Corporation | Electrochromic polymeric solid films, manufacturing electrochromic devices using such solid films, and processing 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 DE DE59813775T patent/DE59813775D1/de not_active Expired - Fee Related
- 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 AT AT98933640T patent/ATE342947T1/de not_active IP Right Cessation
- 1998-06-24 JP JP50805499A patent/JP2002511096A/ja not_active Ceased
- 1998-06-24 US US09/462,045 patent/US6569361B1/en not_active Expired - Fee Related
- 1998-06-24 AU AU83390/98A patent/AU735970B2/en not_active Ceased
- 1998-06-24 CA CA002294795A patent/CA2294795A1/en not_active Abandoned
- 1998-06-24 WO PCT/EP1998/003862 patent/WO1999002621A1/de not_active Ceased
- 1998-06-24 KR KR1020007000084A patent/KR100564863B1/ko not_active Expired - Fee Related
- 1998-06-24 EP EP98933640A patent/EP1027397B1/de not_active Expired - Lifetime
Patent Citations (3)
| 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 |
| EP0196497A1 (en) * | 1985-03-08 | 1986-10-08 | Sumitomo Electric Industries Limited | Functional elastomer |
| EP0319156A1 (en) * | 1987-11-30 | 1989-06-07 | Minnesota Mining And Manufacturing Company | Polypyridiniums |
Also Published As
| Publication number | Publication date |
|---|---|
| AU8339098A (en) | 1999-02-08 |
| ES2275308T3 (es) | 2007-06-01 |
| KR100564863B1 (ko) | 2006-03-28 |
| KR20010021526A (ko) | 2001-03-15 |
| EP1027397A1 (de) | 2000-08-16 |
| DE59813775D1 (de) | 2006-11-30 |
| JP2002511096A (ja) | 2002-04-09 |
| BR9811668A (pt) | 2000-09-19 |
| EP1027397B1 (de) | 2006-10-18 |
| ATE342947T1 (de) | 2006-11-15 |
| WO1999002621A1 (de) | 1999-01-21 |
| CA2294795A1 (en) | 1999-01-21 |
| US6569361B1 (en) | 2003-05-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FGA | Letters patent sealed or granted (standard patent) | ||
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |