Biotech Forum February 9, 2011 Improved Performance Sugar-Based Chemistries for Biomedical Applications BPA Replacement Water Uptake High Use Temperature Polyesters Low Molar Mass Designer Compounds M. Jaffe, A. J. East, W. Hammond, X. Feng, P. Saini New Jersey Institute of Technology Improved Performance Sugar-Based Chemistries for Biomedical Applications BPA Replacement Water Uptake High Use Temperature Polyesters Low Molar Mass Designer Compounds M. Jaffe, A. J. East, W. Hammond, X. Feng, P. Saini New Jersey Institute of Technology

2 Medical Device Concept Laboratory Overview Isosorbide Backbone Modification Coatings and Adhesives Isosorbide was developed as a polyester backbone modifier: Raises Tg, lowers dX/dt in PET for next generation package (Hoechst, DuPont) Thermosets isosorbide diglycidyl ether for bis-A free epoxies Low molar mass Cosmetic and Polymer Additives UV Stabilizers, Plasticizers, humectants, anti- oxidants Thermoplastics Polyesters Polycarbonates Polyamides Polyurethanes New Monomers and polymers New AB Monomers with controlled stereochemistry Tm=61°C, Tb=160°C, GRAS, 8 kilo soluble 1 liter water Medical Adhesives, soluble drugs, Performance biomaterials

3 Medical Device Concept Laboratory Isosorbide Chemistry Isosorbide reactivity and stereochemistry is complex but can be exploited  Unequal reactivity of pendent hydroxyls (endo-exo) allows asymmetric substitution with stereochemical control oNew stereoregular AB monomers –New stereoregular polyesters oNew approach to ester backbone modification oLow molar mass multifunctional “designer” compounds  Isosorbide thermodynamics allow for epimerization reaction to isoidide (exo-exo) Isosorbide is a precursor to isoidide stereochemistry  Glucose  isosorbide, other sugars not investigated (yet)  Strong IP position Fast Slow IsosorbideIsoidide

4 Medical Device Concept Laboratory Isosorbide-based Epoxy Replace BPA Dry mechanical properties similar to Bis A epoxy Water uptake 50% Water soluble before crosslinking

5 Medical Device Concept Laboratory Isosorbide Compounds Water Uptake Observations  Isosorbide-based epoxy networks are capable of significant water uptake oCurrent data ranges from 50% –Target is application dependent but < 1% is often desired oReacting free OH with isocyanates to produce polyoxazolidones significantly lowers water uptake  Isosorbide based polyesters are not noticeably hydroscopic oLarge PEIT database oAB monomers oStereochemically controlled PisosT. PisoiT  Cinnamic acid esters, fatty acid esters, hydroxy acids are not noticeably hydroscopic Conclusion: Isosorbide water uptake is a function of the local chemical environment and is controllable High Water Uptake Low Water Uptake Medical Adhesive PEG Replacement

6 Medical Device Concept Laboratory Isosorbide - Thermoplastics Polycarbonates  Replace bis-phenol A  Improve thermal performance Polyesters  Improved performance for commodity polyesters, Raise Tg  New stereoregular polymers  New LCPs with renewable disrupters, mesogens Polyurethanes

7 Medical Device Concept Laboratory Controlled Stereochemistry Isosorbide/Isoidide Monomers and Polymers Poly(isoidide phenyl ether) Advantages  Controlled stoichiometry, stereochemistry  New group of high performance semicrystalline polyesters oTg>150 °C, Tm>300 °C oLow water uptake  Will works with all condensation polymers tp increase Tg oReduced sublimation, reduced color  Biocompatible, Resorbable compositions  New patent platform

8 Medical Device Concept Laboratory Commercial Polymer Backbone Modification with Isosorbide: Next generation New High Use Temperature Homopolymers, Tg > 150 C, Tm ~ 300C+  Controlled stereochemistry based on AB monomers  Esters or ether ester backbones Modify PET To Increase Tg  TA + EG + AB  Transesterify PET + AB  Poly(AB) + PET  Control modifier Stereochemistry Modify PLLA To Increase Tg  Isosorbide based AB monomer  Decouple backbone relaxations to increase Tg  Raise IV to increase toughness New LCPs  Disrupters  Mesogens PLLA (calculated)

9 Medical Device Concept Laboratory Low molar mass compounds Bis compounds  UVA, UVB absorbers  Plasticizers  Anti-oxidants  Thermoset monomers Asymmetric substituted (“designer”) compounds  UVA-UVB  UVA-plasticizer  Plasticizer-Cl scavenger  Limited by utility  All new compositions of matter Not water soluble Stable to 300 °C+

10 Medical Device Concept Laboratory Support Companies  Food packaging  Surfactants and solvents for personal care  UV absorbers for cosmetics  High performance polyesters (in progress)  BPA free low water uptake epoxies (in progress)  Improved polyester fiber Agencies  Sustainable liquid crystalline polymers

11 Medical Device Concept Laboratory Conclusions Sugar derived compounds possess unique, exploitable stereochemistry Isosorbide provides a ubiquitous platform of cost- effective chemistries for biomedical applications and  Isosorbide isomers A proprietary technology platform is being created IsosorbideIsoidide