84 JOURNAL OF COSMETIC SCIENCE SUSTAINABLE UC/ STABILIZERS BASED ON ISOSORBIDE Michael Jaffe1, Ph.D., A.J. East1, Z. Ophir1, Y. Zhang1, G. Collins1, W. Hammond1 and P. Friedhoff2 1 Medical Device Concept Laboratory, New Jersey Institute of Technology 2 Iowa Corn Promotion Board A new class of sustainable resource derived UV stabilizers, based on the cinnamic acid esters of isosorbide is under investigation. This work is part of a larger program to identify commercially relevant com sugars based chemistries. The Iowa Com Promotion Board (ICPB) is the lead organization that has been supporting research designed to develop cost-effective com based chemistries and processes relevant to the commercial polymer and related industries. ICPB has licensed technology developed at Pacific Northwest National Laboratory (PNNL) to manufacture isosorbide. This research was funded by the Iowa Com Promotion Board, US Department of Agriculture and the US Department of Energy. ICPB has partnered with the New Jersey Institute of Technology (NJIT) to identify and assess potential polymer applications for isosorbide. The project is centered on defining the cost-performance of isosorbide derived compounds that improve the performance characteristics of commercial systems. The work will positively impact the feasibility of fuel production in an existing biomass processing facility by creating applications for high-value chemical building block derivatives co-produced with liquid fuels. The work builds on inventions and concepts of the ICPB-PNNL and ICPB-NJIT partnerships where several patents have been filed and more are pending. Isosorbide is a versatile, GRAS, dianhydrosugar compound, derived from sorbitol, with broad application as a building block for the polymer and pharmaceutical industries. Isosorbide currently sells for about $2.00/pound it is expected that the new process could lead to volume pricing ofless than $1/pound. The properties of isosorbide are summarized in Figure 1. J rbicl� .Ei:.1 �cl Ch�mbiri� : Ch:1mi lll ?wp:1rti:1 Characteristics: GAS No.: 652-67-5 a _x:.:;__�, ")� Molecular formula: Appearance: Melting point: Boiling point: Solubility: Other: C6H10O4 (Mw = 146.14) White crystalline powder, very hygroscopic 61-64°C 16o0c (10mm Hg) OH Soluble in water, alcohol, dioxane ketones. Almost insoluble in hydrocarbons, esters, ethers Very heat stable. Non-toxic, GRAS Figure 1 - Structure and Properties of Isosorbide

2007 ANNUAL SCIENTIFIC MEETING Figure 2 shows the proposed generic reaction route for attaching cinnamic acid moieties to isosorbide. 0 OH J:t:j + HO O COOH ,&' OMe OH DCD DMAP OMe Meo O oco � - ' � HO�coo� ('. 11 Figure 2 85 Preliminary characterization indicates that these compounds are hydrophilic, thermally stable compounds that are compatible with many polymer and cosmetic base materials. A typical UV spectrum is shown in Figure 3. Spectrum/Peak Report Date 11/3/05 Tisne 03:33:01 Page 1 of 1 Iaoaorbide Biaferulate O. 0063, in CH2Cl2 Method file : Intot111ation : untitled. Default Met.4od. Data File : C:\YIZBAN ... 1\ISDF1103.SD Created ll/3/05 J:29:21 Over la.id Spectra: l Name Peaks (mnl Abs IAD) Valleys {ma) Abs (AU) 325.0 296.0 236.0 Report 9enerated by : patelc 2.46010 2,304.70 2.24130 2S9.0 306.0 1.10030 2.19890 ••• End Spectrum/Peak Report ••• Figure 3 t.• 194-fl t� 1&21, -£"' 1'111& Signature: .........••....• It is expected that this family of compounds will effectively absorb both UV A and UVB and be suitable for both cosmetic and polymer applications. We have also developed technology for the controlled monoesterification of isosorbide, leaving the second unreacted hydroxyl as an active site for the addition of compatibilizing, plasticizing or other functionally active moieties. This isosorbide based chemistry then provides a template for "designer" UV stabilizers based on GRAS core material.