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(12) United States Patent (10) Patent No.: US 7,525,717 B2 Byker Et Al

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(12) United States Patent (10) Patent No.: US 7,525,717 B2 Byker Et Al US007525717B2 (12) United States Patent (10) Patent No.: US 7,525,717 B2 Byker et al. (45) Date of Patent: Apr. 28, 2009 (54) MULTI-LAYER LIGAND EXCHANGE (56) References Cited THERMOCHROMC SYSTEMS U.S. PATENT DOCUMENTS (75) Inventors: Harlan J. Byker, West Olive, MI (US); 2,710,274 A 6, 1955 Kuehl Frederick A. Millett, Grand Haven, MI (Continued) (US); Paul H. Ogburn, Jr., Hudsonville, FOREIGN PATENT DOCUMENTS MI (US); Douglas A. Vander Griend, Grand Rapids, MI (US); Brad S. EP 0356116 2, 1990 Veldkamp, Zeeland, MI (US); Derick D. (Continued) Winkle, Holland, MI (US) OTHER PUBLICATIONS Kirk-Othmer Encyclopedia of Chemical Technology. Third Edition, (73) Assignee: Pleotint, L.L.C., West Olive, MI (US) vol. 6, "Chromogenic Materials (Electro-. Thermo-) Electrochromic (*) Notice: Subject to any disclaimer, the term of this and Thermochromic,” pp. 129-142, John Wiley & Sons (1979). patent is extended or adjusted under 35 (Continued) U.S.C. 154(b) by 0 days. Primary Examiner David N Spector (74) Attorney, Agent, or Firm Thompson Hine LLP (21) Appl. No.: 11/849,659 (57) ABSTRACT (22) Filed: Sep. 4, 2007 Ligand exchange of thermochromic, LETC, systems exhib (65) Prior Publication Data iting a reversible change in absorbance of electromagnetic radiation as the temperature of the system is reversibly US 2008/O1 OO903 A1 May 1, 2008 changed are described. The described LETC systems include one or more than one transition metalion, which experiences Related U.S. Application Data thermally induced changes in the nature of the complexation (60) Provisional application No. 60/841,827, filed on Sep. or coordination around the transition metal ion(s) and, 1, 2006. thereby, the system changes its ability to absorb electromag netic radiation as the temperature changes. (51) Int. Cl. In accordance with one aspect of the present invention, a GO2F IMOI (2006.01) thermochromic device is disclosed comprising at least two GO2F I/00 (2006.01) thermochromic layers when each thermochromic layer G09G 3/34 (2006.01) includes a polymer, at least one transition metal ion, at least CO7F 15/04 (2006.01) one HeL ligand capable of forming a HeMLC with the tran sition metal ion and at least one LeL ligand capable of form (52) U.S. Cl. ....................... 359/288; 35.9/321; 34.5/106; ing an LeMLC with the transition metal ion. In accordance 54.6/10 with yet another aspect of the present invention, the thermo chromic device further includes a separator between the first (58) Field of Classification Search ................. 250/330; and second thermochromic layers to prevent intermixing of 345/106; 359/288,321; 54.6/10; 556/37 the contents of the layers. See application file for complete search history. 19 Claims, 9 Drawing Sheets Influence of AS' on Absorbance vs. Temperature 5 AS'=160 AS'=140 4 - AS=180 : 3 - AH = 60 kJ/mole e(LeMLC) = 1 5. g(HMLC) = 280 2 b = 0.075cm MeT = 0.2 HeLT = 1.6 LeLT = 2.5 O O 100 200 300 400 500 600 Temperature (C) US 7,525,717 B2 Page 2 U.S. PATENT DOCUMENTS Srivastava, J. et al., “Synthesis of Polyacrylic Acid Based Thermochromic Polymers.” Proc. of SPIE, vol. 5062, pp. 111-115 3, 192,101 A 6/1965 Koenig (2003). 3,236,651 A 2f1966 Marks et al. Kojima, K. et al., “Pressure and Temperature Effects on Octahedral 3,445,291 A 5, 1969 Stein Tetrahedral Equilibria in Pyridine Solutions of Some Cobalt(II) 3,723,349 A 3, 1973 Heseltine et al. Halides.” Bull. Chem. Soc. Jpn., vol. 56, No. 3, pp. 684-688 (Mar. 3,816,335 A 6, 1974 Evans 1983). 4.575,259 A 3, 1986 Bacci et al. Griffiths, T.R. et al., “Effects of Cations upon Absorption Spectra Part 4,970,315 A 11, 1990 Schmidhalter 4.-Octahedral-Tetrahedral Equilibria between Chloro-nickel(II) 5,159,057 A 10/1992 Perry Complexes in Ethylene Glycol and Glycerol.” Trans. Faraday Soc., 5,240,897 A 8, 1993 Braun et al. 6,084,702 A 7/2000 Byker et al. 65, pp. 3179-3 186 (1969). 6,362,303 B1 3/2002 Byker et al. Griffiths, T.R. et al., “Effects of Cations upon Absorption Spectra Part 6,446,402 B1 9/2002 Byker et al. 2.-Formation of Tetrahedral Tetrachloronickelate(II) in Aqueous 6,620,872 B2 9, 2003 Fisher Solution.” Trans. Faraday Soc., 65, pp. 1727-1733 (1969). 6,665,107 B2 12/2003 Forgette et al. Gill, Naida S. et al., "Complex Halides of the Transition Metals. Part 6,737,159 B2 5, 2004 Garrett et al. I. Tetrahedral Nickel Complexes,” J. Chem. Soc., pp. 3397-4007 6,737.418 B2 5/2004 Hogenkamp et al. (1959). 6,998,072 B2 2/2006 Welch et al. Sunamoto, J. et al., “Solvochromism and Thermochromism of 7,179,535 B2 2, 2007 Fisher Cobalt(II) Complexes Solubilized in Reversed Micelles.” Bulletin of 7,226,966 B2 * 6/2007 Kambe et al. ............... 524/432 the Chemical Society of Japan, vol. 51, No. 11, pp. 3130-3135 (Nov. 7,256.296 B2 8, 2007 Diamond et al. 1978). 2006, O159874 A1 7/2006 Koran et al. Marinkovic, M. et al., “Thermochromic complex compounds in 2008/0100902 A1* 5/2008 Byker et al. ................ 359,288 phase change materials: Possible application in an agricultural green 2008/0105851 A1* 5/2008 Byker et al. ... ... 252/408.1 house.” Solar Energy Materials and Solar Cells, 51, pp. 401-411 2008/0106781 A1* 5/2008 Byker et al. ................ 359,288 (1998). Arutunjan, R.E. et al., “Thermochromic Glazing for Zero Net FOREIGN PATENT DOCUMENTS Energy House.” Glass Processing Days, Conference Proceedings, JP 2004-3596.23 12, 2004 pp. 299-301, Eighth International Conference (Jun. 15-18, 2003). WO WO 2008028128 A1 * 3, 2008 Rozova, K.B. et al., Abstract for "Sun screening thermochromic glazing materials.” TsNIIEP, USSR. Svetotekhnika (1986), (10), OTHER PUBLICATIONS 12-14. CODEN: SVETAGISSN: 0.039-7067. Journal written in Rus International Search Report of the International Searching Authority Sian. CAN 107:30324 AN 1987:43.0324 CAPLUS. regarding International Application No. PCT/US2007/077385 (Feb. Greenberg, C. “Chromogenic Materials (Thermochromic).” Kirk 4, 2008). Othmer Encyclopedia of Chemical Technology 4th Edition, vol. 6,pp. Written Opinion of the International Searching Authority regarding 337-343, John Wiley & Sons. International Application No. PCT/US2007/077385 (Feb. 24, 2008). Sone, K. et al., Inorganic Thermochromism, pp. 1-71, Springer Long, G.J. et al., “Transition Metal Chemistry of Quinuclidinone Verlag (1987). Containing Ligands. III. Electronic and Structural Properties of Sev Angell, C.A., “Octahedral-Tetrahedral Coordination Equilibria of eral Transition Metal Complexes Containing trans-2-(2'- Nickel (II) and Copper (II) in Concentrated Aqueous Electrolyte Quinolyl)methylene-3-quinuclidinone.” Inorganic Chemistry, vol. Solutions,” Journal of the American Chemical Society,88 (22), pp. 13, No. 2, pp. 270-278 (XP-002465696) (1974). 5192-5198 (Nov. 20, 1966). Kuroiwa, K. et al., “Heat-Set Gel-like Networks of Lipophilic Co(II) Day, J.H., “Thermochromism of Inorganic Compounds.” Chemical Triazole Complexes in Organic Media and Their Thermochromic Reviews, vol. 68, No. 6, pp. 649-657 (Nov. 25, 1968). Structural Transitions,” Journal of the American Chemical Society, Scaife, D.E. et al., “Influence of Temperature on Some Octahedral vol. 126, pp. 2016-2021 (XP-002465697) (2004). Tetrahedral Equilibria in Solution.” Inorganic Chemistry, vol. 6, No. Arutunjan, R. et al., “Smart Thermochromic Glazing for Energy Saving Window Applications.” Poster Session Abstract8, The Fourth 2, pp. 358-365 (Feb. 1967). International Conference on Advanced Optical Materials and Sunamoto, J. et al., “Formation of Polynuclear Cupric Halides in Devices, Tartu, Estonia (Jul. 6-9, 2004). Cationic Reversed Micelles.” Inorganic Chemisry, vol. 19, No. 12, Kojima, K. et al., “Pressure and Temperature Effects on Octahedral pp. 3668-3673 (1980). Tetrahedral Equilibria in Pyridine Solutions of Some Cobalt(II) Sunamoto, J. et al., “Reversed Micelles to Mimic the Active Site of Halides. II.” Bull. Chem. Soc. Jpn. vol. 57, No. 3, pp. 879-880 (Mar. Metalloenzymes.” Inorganica Chimica Acta, 92, pp. 159-163 (1984). 1984). Katzin, L.I., “Energy Value of the Octahedral-Tetrahedral Coordina Yanush, O.V. et al., “Laminated Glass with Variable Transmission for tion Change.” The Journal of Chemical Physics, vol. 35. No. 2, pp. Daylight Regulation.” Glass Processing Days, Conference Proceed 467-472 (Aug. 1961). ings, pp. 815-817. Seventh International Conference (Jun. 18-21. Sestili, L. et al., “Formation Equilibria of Pseudotetrahedral Co (II) 2001). Halogenocomplexes in Acetonitrile.” J. Inorg. Nucl. Chem. No. 32. Halopenen, I. et al., “Smart Laminated Glasses for Regulation of pp. 1997-2008 (1970). Lighting.” Glass Processing Days, Conference Proceedings, pp. 324 326, Sixth International Conference (Jun. 13-16, 1999). * cited by examiner U.S. Patent Apr. 28, 2009 Sheet 1 of 9 US 7,525,717 B2 4 Figure 2 3 2 1 O 950 1050 1 150 350 450 550 65 o 750 850 950 1050. 1150 Figure 4 950 1050 1 150 350 450 550 65 o 750 850 950 1050. 1150 350 450 550 650 T50 850 950 1050 1 150 4 Figure 7 4 Figure 8 3. 3 2 2 1. 1 O O 35 45 iss 65 is 85 9 5 15 115 35 45 is is 6s is 85 9 5 15 115 U.S. Patent Apr. 28, 2009 Sheet 2 of 9 US 7,525,717 B2 350. 450 550 650 T50 850 950 1050 1 150 350 450 550 650 750 85 O 950 1 0.5 O 1150 Figure 11 Figure 12 350 450 550 650 is 850 95 O 10s 0 1 150 950 Oso so 950 1 0.5 O 1150 Figure 15 Figure 16 95 is so 95 5 so U.S.
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