1. Polyethylene naphthalate (PEN) Moni Muraki Heidi Pecoraro CHEM 231 November 28, 2005

2. Esterification Reaction H2OH2O + naphthalene dicarboxylic acid ethylene glycerol

3. Ethylenenaphthalene Monomer naphthalene groupethylene group

4. Condensation Polymerization Same reaction that forms monomer Same reaction that forms monomer Step-growth polymerization – combines two molecules and removes a small molecule Step-growth polymerization – combines two molecules and removes a small molecule –Polyesters are formed by this mechanism Heat (∆) catalyzes the reaction Heat (∆) catalyzes the reaction Not chain-growth polymerization – instead any two reactive molecules can combine Not chain-growth polymerization – instead any two reactive molecules can combine

5. PEN Polymerization H2OH2O H2OH2O

6. PEN: Uses Can be processed into films, fibers, and containers Can be processed into films, fibers, and containers Film: media tapes Film: media tapes Fibers: electrical insulation, cords/cables, tire cord, narrow- and broad-woven fabrics, synthetic molecular membranes Fibers: electrical insulation, cords/cables, tire cord, narrow- and broad-woven fabrics, synthetic molecular membranes Containers: bottles, jars, tableware Containers: bottles, jars, tableware

7. PEN: Commercial Products

8. PEN: A Brief History In the UK, ICI Alkali Division laboratories produced polyethylene in 1935 In the UK, ICI Alkali Division laboratories produced polyethylene in 1935 –Polyethylene has thermoplastic properties that were vital to the development of radar 1953 – DuPont first commercial production of PEN fiber for carpets 1953 – DuPont first commercial production of PEN fiber for carpets Currently >2000 patents for PEN products Currently >2000 patents for PEN products

9. PEN: Health Risks? None found, however: None found, however: –Exposure to high amounts of naphthalene can damage or destroy RBCs and has been shown to cause cancer in rats  Classified as possibly carcinogenic in humans –Ethylene glycol is a suspected toxin in the following systems:  Cardiovascular, developmental, GI, liver, kidney, neurological, reproductive, respiratory, and skin/sense organs

10. PEN: Health Risks? Polyethylene hazards: skin and eye irritation Polyethylene hazards: skin and eye irritation Polyethylene terephthalate (PET) – a close relative of PEN: phthalates (which can act as endocrine disruptors) leach into water or food if the container is heated Polyethylene terephthalate (PET) – a close relative of PEN: phthalates (which can act as endocrine disruptors) leach into water or food if the container is heated

11. PEN: Properties High temperature resistance High temperature resistance –High glass transition temp (unlike PET) High UV resistance High UV resistance Resistant to hydrolysis in alkaline or very hot aqueous conditions Resistant to hydrolysis in alkaline or very hot aqueous conditions Rigid, transparent, colorless Rigid, transparent, colorless Thus, slow degradation Thus, slow degradation

12. PEN: Recycling Commercial recycling firms Commercial recycling firms Bottles and jars – recyclable and reusable Bottles and jars – recyclable and reusable –Containers can be recycled –PEN can be sterilized at high temperatures

13. References E.S. Stevens. 2001. Green Plastics: An introduction to the new science of biodegradable plastics., accessed November 22, 2005. E.S. Stevens. 2001. Green Plastics: An introduction to the new science of biodegradable plastics., accessed November 22, 2005. The History of Plastics. 2005., accessed November 25, 2005 The History of Plastics. 2005., accessed November 25, 2005 Color your carpet. 2005. History of Dyes., accessed November 25, 2005 Color your carpet. 2005. History of Dyes., accessed November 25, 2005 British Petroleum. 2001. Elements: naphthalates from bp-expanding the use of polyesters. 1(1):Summer 2001. British Petroleum. 2001. Elements: naphthalates from bp-expanding the use of polyesters. 1(1):Summer 2001. H. Meimberg, S. Thalhammer, A. Brachmann, B. Muller, L.A. Eichacker, W.M. Heckl, G. Heubl. 2003. Selection of chloroplasts by laser microbeam microdissection for single-chloroplast PCR. Biotechniques 34(6):1238-43. H. Meimberg, S. Thalhammer, A. Brachmann, B. Muller, L.A. Eichacker, W.M. Heckl, G. Heubl. 2003. Selection of chloroplasts by laser microbeam microdissection for single-chloroplast PCR. Biotechniques 34(6):1238-43. M.S.M. Alger (ed). 1989. Polymer science dictionary. Elsevier Science Publishers LTD. 346p. M.S.M. Alger (ed). 1989. Polymer science dictionary. Elsevier Science Publishers LTD. 346p. P.Y. Bruice. 2004. Organic Chemistry. 4th ed. Pearson Education, Inc. 1148p. P.Y. Bruice. 2004. Organic Chemistry. 4th ed. Pearson Education, Inc. 1148p. T. Furatani. 2005. Organic Chemistry Lecture, NSCC. November 23, 2005. T. Furatani. 2005. Organic Chemistry Lecture, NSCC. November 23, 2005. Wikipedia. 2005. Naphthalene., accessed November 18, 2005. Wikipedia. 2005. Naphthalene., accessed November 18, 2005. Scorecard: the pollution information site. 2005. Ethylene glycol., accessed November 18, 2005. Scorecard: the pollution information site. 2005. Ethylene glycol., accessed November 18, 2005. M.L. Berins. 1991. Spi Plastics Engineering Handbook of the Society of the Plastics Industry, Inc., 5th ed. Van Nostrand Reinhold Publisher. 67p. M.L. Berins. 1991. Spi Plastics Engineering Handbook of the Society of the Plastics Industry, Inc., 5th ed. Van Nostrand Reinhold Publisher. 67p. Polymer Science Learning Center. 2005. Polyester., accessed November 25, 2005. Polymer Science Learning Center. 2005. Polyester., accessed November 25, 2005. Sirex. 2005. 3R-Foam, Range of Applications., accessed November 25, 2005. Sirex. 2005. 3R-Foam, Range of Applications., accessed November 25, 2005. Landscape Structures. 2005. Recycled Polyethylene Bench., accessed November 25, 2005. Landscape Structures. 2005. Recycled Polyethylene Bench., accessed November 25, 2005. Plastics resource.com. 2005. Information on plastics and the environment., accessed November 2, 2005. Plastics resource.com. 2005. Information on plastics and the environment., accessed November 2, 2005.