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Warwick Effect Polymers Ltd

Warwick Effect Polymers (WEP) is a leading company in the field of polymer innovation. With a focus on controlled free radical polymerization and Cu(I) mediated living radical polymerization, WEP offers a range of advanced polymers with diverse applications. The company's current technology partners include leading companies in hair-spray/gel and controlled release of agrochemicals. WEP's strategy includes exploiting existing intellectual property, providing polymer expertise through short-term contracts, and developing new IP in polymers for healthcare. With a strong management team and significant expansion opportunities, WEP is poised for further growth.

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Warwick Effect Polymers Ltd

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  1. Warwick Effect Polymers Ltd Innovation in Polymers Elementis Nov. 18th, 2004

  2. Papers on TM mediated living radical polymerisation

  3. Cu (I) Mediated LRP – mechanism?

  4. Cu (I) Mediated LRP • Very Good Technique for control over Molecular weight • Inert to many Functional Groups • Applicable to a wide range of Monomers • Very robust Method Only really sensitive to oxygen Allowing a wide range of operating conditions • Contamination of product by Cu • Catalyst is not recycled

  5. Ligands for Copper Mediated Polymerisation

  6. ABA Tri-block AB Di-block Taperedblock Alternatingblock Alternatingcopolymer Graft Advanced polymers

  7. Controlled Free Radical Polymerization and Warwick Effect Polymers • Fast-growing area of new technology • WEP has worldwide patents protecting platform/generic technology (US and Europe) • Several blue-chip customers • Significant expansion opportunities • Diverse market potential

  8. Management • Chairman Michael Penington • CEO Fergal O’Brien (May 2004) • CTO David Haddleton • B Dev (US) Thomas Neenan • Director Phil Stern

  9. Science Advisory Board • Craig Hawker, IBM, Almaden, (UCSB) • Mitsuo Sawamoto, Kyoto University • Tom Davis, University of New South Wales

  10. Strategy • Exploit existing IP for the development and supply of new polymers to meet specific customer needs. • Provide polymer expertise via short term contracts to develop customer base and provide revenue. • Develop new IP in polymers for healthcare.

  11. Current WEP technology Partners • Company A • Hair-spray/Gel • Company B • Controlled release of Agrochemicals • Companies C,D,E …. • PolyPEG™ for Healthcare

  12. Scale-up • WEP able to manufacture up to 10 kg in house • Close relationship with scale up partner. • Successful scale up to 100 kg (1000 kg by Q1 05). • WEP open to alternative scale-up options

  13. 160 kg Pilot Plant Scale up

  14. Mn 10,500 PDI 1.15 Copper level by ICP None detected

  15. Survey of Applications • Solution Modifiers • Surface and Fabric Modifiers • Pigment and Dye Modifiers • Biological • New PEG technology • Mucoadhesives • Polymers for diagnostics

  16. Preparation of PDMS macroinitiators

  17. Tri-block copolymers from di-functional PDMS initiators

  18. Critical micelle concentration by fluorimetry CMC = 0.1 g / L

  19. pH = 3.60 sigmoidal fit 1st derivative 2nd derivative CAC = 0.16 g•L-1

  20. sigmoidal fit 1st derivative 2nd derivative CAC = 1.59 g•L-1

  21. Hydrophobic Fluorinated Initiator PMMA PMMA - Di Fluoroinitiator

  22. Microcapsule Synthesis

  23. SEM Image of a 21-arm Polystyrene Star • Film formation in CS2 • Relative humidity 70% • Temperature 19°C • Regular hexagonal distribution of pores ~2 µm

  24. Novel Effect Polymers- Polymeric Inks • Cu (I) mediated LRP enables us to tailor the property of functional molecules e.g. solubility, wet fastness and light fastness. • Disperse Red 1- insoluble in water, but hydroxy functionalised

  25. Initiator Synthesis Initiator Disperse Red 1

  26. Synthesis Water Soluble Polymeric Inks

  27. Synthesis Water Soluble Diblocks P(DMAEMA) Mn= 5020 g /mol Mw /Mn = 1.14 P(DMAEMA) MMA diblock Mn = 7450 g/mol Mw /Mn = 1.34

  28. UV determination for Molar Extinction Coefficient’s emax / L mol-1 cm-1 Effect molecule = 32700 Initiator = 32300 PDMAEMA = 30200 PMMA = 29500

  29. Synthesis of Disperse Red 1 Monomer • The monomer derived from the effect molecule can be copolymerised with methacrylates using standard living free radical initiators such as ethyl-2- bromoisobutyrate. • The effect monomer can be used in small amounts ranging up to 10 %. • These polymers were synthesised to improve light-fastness properties.

  30. Conversions and polydispersities of polymerisation of statistical copolymer of MMA (95 %) and DR1 monomer (5%) with ethyl-2-bromoisobutyrate

  31. Polymeric Inks from Living Radical Polymerization Gibbet Bond Paper Xerox Acid Paper

  32. Light-fastness Comparisons Before and After 50 Hours UV exposure PDMAEMA PDEAEMA Before After

  33. Anthroquinone dyes

  34. Phthalocyanines

  35. Fluorescent initiator with DMAEMA

  36. Protein Based Drugs • Insulin, Interferon • Diabetes, Osteoporosis, Inflam. Bowel disease • A need for Oral delivery • Longer stability to enzyme degradation • Enhanced absorption across the GI tract • Optimised hydrophilic/hydrophobic balance

  37. Mntheo Mnexp PDi 6,200 4,000 1.056,400 4,100 1.06 6,300 4.200 1.06  ● t GPC ResultsNHS-Poly(PEGMA) NHS-Poly(PEGMA)  Propyl ligand in toluene solutionEthyl ligand in anisole solutionPropyl ligand in anisole solution ● t

  38. POLY PEG + POLY PEG™

  39. Multifunctional Initiators Multifunctional 3, 5 and 8 based on 1,3,5-trihydroxybenzene, glucose and lactose.

  40. POLYFUNCTIONAL INITIATORS lmax 439 nm Application: P-PEG(475)-methacrylate, toluene (50%) • Room temperature • Good control: PDI=1.10, Mn = 5300 • “-N=N-” group compatible with the conditions employed

  41. DMAEMA/BMA (35/65 wt%) Random Copolymer by AIBN Presumed yield: 100% Copolymer Cost/Kg: $4.50 kg

  42. DMAEMA/BMA (4KDa/7.5 KDa) by CFRP Presumed Yield: 90% Block Copolymer Cost/Kg: $6.31

  43. Conclusion/Discussion • CFRP offers some unique advantages with respect to control of structure • WEP has scaled technology to >100 kg; 1000 kg by Q1 ‘05 • Cost of technology versus performance • WEP is open to a partnership in various technology areas; wide variety of deal structures/interactions possible

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