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WO 2008/028128 Al (12) INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property Organization International Bureau (43) International Publication Date PCT (10) International Publication Number 6 March 2008 (06.03.2008) WO 2008/028128 Al (51) International Patent Classification: 49460 (US). VELDKAMP, Brad, S. [US/US]; 28-1/2 C09K 9/02 (2006.01) C07F 15/06 (2006.01) West Cherry Avenue, Zeeland, MI 49464 (US). C07F 15/04 (2006.01) (74) Agents: LEVY, Mark, P. et al.; Thompson Hine LLP, Intellectual Property Group, Post Office Box 8801, Dayton, (21) International Application Number: OH 45401-8801 (US). PCT/US2007/077385 (81) Designated States (unless otherwise indicated, for every (22) International Filing Date: 3 1 August 2007 (31.08.2007) kind of national protection available): AE, AG, AL, AM, AT,AU, AZ, BA, BB, BG, BH, BR, BW, BY,BZ, CA, CH, (25) Filing Language: English CN, CO, CR, CU, CZ, DE, DK, DM, DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, HN, HR, HU, ID, IL, (26) Publication Language: English IN, IS, JP, KE, KG, KM, KN, KP, KR, KZ, LA, LC, LK, LR, LS, LT, LU, LY,MA, MD, ME, MG, MK, MN, MW, (30) Priority Data: MX, MY, MZ, NA, NG, NI, NO, NZ, OM, PG, PH, PL, 60/841,827 1 September 2006 (01.09.2006) US PT, RO, RS, RU, SC, SD, SE, SG, SK, SL, SM, SV, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, (71) Applicant (for all designated States except US): ZM, ZW PLEOTINT, L.L.C. [US/US]; 7705 West Olive Road, (84) Designated States (unless otherwise indicated, for every West Olive, MI 49460 (US). kind of regional protection available): ARIPO (BW, GH, GM, KE, LS, MW, MZ, NA, SD, SL, SZ, TZ, UG, ZM, (72) Inventors; and ZW), Eurasian (AM, AZ, BY, KG, KZ, MD, RU, TJ, TM), (75) Inventors/Applicants (for US only): VANDER European (AT,BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, GRIEND, Douglas, A. [US/US] ; 808 Chippewa Drive SE, FR, GB, GR, HU, IE, IS, IT, LT,LU, LV,MC, MT, NL, PL, Grand Rapids, MI 49506 (US). OGBURN, Paul, H., Jr. PT, RO, SE, SI, SK, TR), OAPI (BF, BJ, CF, CG, CI, CM, [US/US]; 4370 Sunnyslope Drive, Hudsonville, MI 49426 GA, GN, GQ, GW, ML, MR, NE, SN, TD, TG). (US). MILLETT, Frederick, A. [US/US]; 13684 Forest Park Drive, Grand Haven, MI 49417 (US). MILLETT, Published: Frederick, C. [US/US]; 13684 Forest Park Drive, Grand — with international search report Haven, MI 49417 (US). WINKLE, Derick, D. [US/US]; — before the expiration of the time limit for amending the 1365 Heather Drive, Holland, MI 49423 (US). BYKER, claims and to be republished in the event of receipt of Harlan, J. [US/US]; 17383 Lake Road, West Olive, MI amendments (54) Title: LIGAND EXCHANGE THERMOCHROMIC, (LETC), SYSTEMS (57) Abstract: Ligand exchange of thermochromic, LETC, systems exhibiting a reversible change in absorbance of electromagnetic radiation as the temperature of the system is reversibly changed are described. The described LETC systems include one or more than one transition metal ion, which experiences thermally induced changes in the nature of the complexation or coordination around the transition metal ion(s) and, thereby, the system changes its ability to absorb electromagnetic radiation as the temperature changes. 350 450 550 650 750 850 950 1050 1150 Attorney Docket No. 562272-00007 LIGAND EXCHANGE THERMOCHROMIC, (LETC), SYSTEMS Definition of terms/abbreviations (4-MeOPh^P(V = bis(4-methoxyphenyl)phosphinate 18-crown-6 = 1,4,7,10,13, 16-hexaoxacyclooctadecane 1-EtBIMZ = 1-ethyl- lH-benzimidazole 1-MeBIMZ = 1-methyl- lH-benzimidazole 4-(3-PhPr)Pyr = 4-(3-phenylpropyl)pyridine) acac = acetylacetonate BIMZ = benzimidazole B113PO = tributylphosphine oxide CF3COOLi = lithium trifluoroacetate Di-TMOLP = di-trimethylolpropane DMSO = dimethylsulphoxide DP = dipyridyl = 2,2'-bipyridine EG = ethylene glycol EXM = Exchange Metal ΗεL = high molar absorption coefficient ligand = high epsilon ligand ΗεMLC = high molar absorption coefficient MLC = high epsilon MLC LETC = ligand exchange thermochromic(s) LεL = low molar absorption coefficient ligand = low epsilon ligand LεMLC = low molar absorption coefficient MLC = low epsilon MLC m = molal = moles of solute per kilogram of solvent M = molar = moles of solute per liter of solution Me = metal ion MLC = metal - ligand complex N-Bu-di(l-MeBIMZ-2-yl-methyl)amine = N,N-bis[(l-methyl-l H- benzimidazol-2-yl)methyl]butanamine ΝIR = near infrared nm = nanometer NPG = neopentyl glycol = 2,2-dimethylpropane-l,3-diol N-Pr-dipicolylamine = N,N-bis(pyridine-2-ylmethyl)propan- 1-amine Ν-Pr-DPamine = -propyl- N-pyridin-2-ylpyridin-2-amine PI13P = PPI13 = triphenylphosphine PVB = poly(vinyl butyral) R/O = Ring Opening TC Compound SRT™ = sunlight responsive thermochromic TBABr = tetrabutylammonium bromide TBACl = tetrabutylammonium chloride TBAI = tetrabutylammonium iodide TC = thermochromic(s) TEACl H2O = tetraethylammonium chloride monohydrate TMEDA = Ν,Ν,Ν ',Ν '-tetramethylethylenediamine TMOLP = trimethylolpropane = 2-ethyl-2-(hydroxymethyl)propane-l,3-diol TTCTD = 1,4,8,1 l-tetrathiacyclotetradecane UV = ultraviolet Y = % white light transmission based on 2° exposure of a D65light source ε = molar absorption coefficient = molar absorptivity, in liters/(mole*cm) γ-BL = gamma-butyrolactone λ = wavelength in nanometers Background Many chromogenic phenomena are known in which a change in color or a change in light absorption results from some action or stimulus exerted on a system. The most common chromogenic phenomena are electrochromics, (EC), photochromies, (PC), and thermochromics, (TC). Many phenomena are also known in which optical changes, like light scattering or diffuse reflection changes, take place as a result of some action or stimulus exerted on a system. Unfortunately, referring to these as chromic phenomena has led to a fair amount of confusion in the past. We prefer to distinguish light scattering systems from chromogenic systems by referring to the light scattering phenomena as a phototropic, thermotropic or electrotropic phenomena. This distinction and other distictions are elaborated on below. In general, and especially for the sake of the patent application, the terms used for an optical phenomena, should relate to the direct, primary action causing the phenomena. For example, modern day electrochromic systems generally involve electrochemical oxidation and reduction reactions. Thus an electrical process directly causes materials to change their light absorbing or light reflecting properties. Alternatively, electrical energy can also be used to generate heat or light and this heat or light, in turn, may be used to affect a thermochromic or a photochromic change. However, the indirect use of electricity should not make these electrochromic phenomena. For example, a thermochromic layer may increase in temperature and light absorption when in contact with a transparent conductive layer which is resistively heated by passing electricity through the transparent conductive layer. However, in accordance with the terminology used herein, this is still a thermochromic device and should not be called an electrochromic device. Also, just because an electric light produced UV radiation that caused a color change by a phototchemical reaction, like the ring opening of a spirooxazine compound, that would not make such a procedure a demonstration of electrochromics. A similar distinction should be made with a thermochromic layer that is responsive to sunlight as described in US Patents 6,084,702 and 6,446,402. The thermochromic layer may be heated by absorbing sunlight or being in contact with another layer that absorbs sunlight. Here sunlight exposure changes the color and/or the amount of light absorbed by the thermochromic layer. However, this is still a thermochromic phenomenon because a heat induced temperature change causes the chromogenic change and the same change takes place when the layer is heated by other means. The absorbed photons from the sun are only converted to heat and do not directly cause a photochromic change. Accordingly, the term photochromies should be reserved for systems in which the absorption of a photon directly causes a photochemical or photophysical reaction which gives a change in color or a change in the system's ability to absorb other photons. In addition to chromogenic systems, there are a variety of systems with reversible changes in light scattering. The more widely studied light scattering systems include: (1) lower critical solution temperature, LCST, polymeric systems; (2) polymer dispersed liquid crystal, PDLC, systems; (3) polymer stabilizer cholesteric texture, PSCT, systems and (4) thermoscattering, TS, systems. Additional description of these and other light scattering phenomena may be found in US Patent 6,362,303. In the past, several of these phenomena have been called thermochromic and even electrochromic. From our standpoint these phenomena are neither thermochromic nor electrochromic since the word chroma relates to color and the intensity and quality of color. These are better termed thermotropic or electrotropic to help indicate the change in state that takes place. Definitions rarely cover every eventuality, especially when it comes to borderline cases. Hence electrochemical systems that change from colorless and non-light scattering to specularly reflecting are still generally termed electrochromic because of the electrochemical nature of these processes. Also, some thermochromic systems involve changes between liquid and solid phases and could conceivably be called thermotropic systems. But these systems have dramatic changes in light absorption and are still termed thermochromic. On the other side, some reversible light scattering systems may have some spectral selectivity to the light scattering and hence give rise to some color appearance. Yet the primary change is between light scattering and non-light scattering states. Even the change in some systems from colorless and non-light scattering to a frosted, diffusely reflecting and white appearance might suggest a color change to the color white. However, we still term these tropic and not chromic changes.
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